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A Grand Tour of Italy

This sample two week (14 nights) itinerary covers some of Italy's most loved destinations: Amalfi Coast, Rome, Florence, Cinque Terre, Milan, and Venice. The services we provide as part of our comprehensive packages include accommodations, train tickets, transfers (airport and train station) and city tours. In addition to the tours included we can arrange a number of excursions based on your own interests. All of our tours are custom, and this is just a sample meant to give an idea for what our trips are like, and the opportunities our destinations provide. One of our team in the region will be available to you during and leading up to the trip to answer any questions and arrange local services. You will receive access to your Guest Page, with its information on the best these destinations have to offer, including things to see and do, and other inside tips from restaurant recommendations to tipping advice. Upon arrival we will provide you with a local cell phone that you can use to contact our employee (who you will meet in person) throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 accommodation options, including boutique hotels, charming B&Bs, and spacious apartments. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambience.
Route for Naples, Positano, Rome, Florence, Monterosso Al Mare, Milan, Venice tour

Day Stop in Naples

Day Stop in Naples

1 days in Naples

Day Stop in Naples

To call Naples rough around the edges would be quite the understatement. Yet amidst the chaos and beneath the grime is one of Italy's true gems. It's the third-largest city in the country, home to over three million people. An important port city for all the civilizations that have existed there, Naples is the original melting pot. Founded as Neapolis (literally "new city") by the Greeks in the 7th century B.C., Naples has many layers of history for you to discover.

To call Naples rough around the edges would be quite the understatement. Yet amidst the chaos and beneath the grime is one of Italy's true gems. It's the third-largest city in the country, home to over three million people. An important port city for all the civilizations that have existed there, Naples is the original melting pot. Founded as Neapolis (literally "new city") by the Greeks in the 7th century B.C., Naples has many layers of history for you to discover.

Day 1 - Day Stop in Naples

Day 1 - Day Stop in Naples

A rugged south-facing coastline with five fishing villages. In contrast to Cinque Terre, its counterpart in the north of Italy, the Amalfi villages can all be reached by road. We will arrange for a driver to pick you up in Naples Airport and take you to your accommodation on the Amalfi coast. Along the way, for a extra fee, we can arrange for a stop in Pompeii, or our recommendation, the much less crowded yet at least as interesting Herculaneum, part of the same UNESCO listing as Pompeii. A visit to the rim of the crater of Vesuvius is another option en route. The vehicle used for your transfer will be a standard sedan, station wagon or minivan. We can arrange for an upgrade to a more luxurious class of vehicle for an extra fee.

3 Nights in Positano

3 Nights in Positano

4 days in Positano

3 Nights in Positano

Of the five towns that constitute the Amalfi Coast, Positano is almost certainly the most photographed. A cascade of color rolling down steep hillsides towards the sea. The Amalfi Coast road snakes through the town, providing the main means of connectivity to the outside world. The only other option is by boat and there are regular ferries to the other Amalfi Coast towns and to Capri island in the Bay of Naples, so day tripping is definitely a possibility. Positano's coarse-grain sand public beaches can fill up fast on sunny days but there are quieter stretches to be found and a water taxi ride will take you to somewhere more secluded. Positano is at one end of the Path of the Gods, a demanding hiking trail that will take you inland to the town of Agerola, but the journey is its own reward, with some killer views along the way.

Of the five towns that constitute the Amalfi Coast, Positano is almost certainly the most photographed. A cascade of color rolling down steep hillsides towards the sea. The Amalfi Coast road snakes through the town, providing the main means of connectivity to the outside world. The only other option is by boat and there are regular ferries to the other Amalfi Coast towns and to Capri island in the Bay of Naples, so day tripping is definitely a possibility. Positano's coarse-grain sand public beaches can fill up fast on sunny days but there are quieter stretches to be found and a water taxi ride will take you to somewhere more secluded. Positano is at one end of the Path of the Gods, a demanding hiking trail that will take you inland to the town of Agerola, but the journey is its own reward, with some killer views along the way.

Day 1

Day 1 - Arrival in Positano

Your driver will bring you straight to your accommodation on the Amalfi Coast.

Day 2

Day 2 - Your First Full Day in Positano

Amalfi Coast Private Day Trip from Positano

Amazing Amalfi

Included in your vacation package price.

The Amalfi Coast is your oyster today. We'll arrange for an English-speaking driver to pick you up in the morning and remain at your disposal for the whole day, so you can explore at your own pace and really make the most of your time in one of the prettiest parts of Italy.


Activity Level : Moderate
Duration : 8 hours

Soak up the Capri Sun

Suggested activities for an additional cost, depending on your choice

There are several ferries a day to and from the island of Capri, taking around between 50 and 70 minutes, depending whether you're starting from Positano or Amalfi, making this an easy self-guided day trip. Once you arrive at Marina Grande you could hop in an open-top taxi or take the funicular to visit the town of Capri for some shopping. The quieter town of Anacapri is more suitable if you're looking for a laid-back kind of place. From both spots you'll be able to admire the views over the island and over the Bay of Naples. Another popular option is to take a boat to the island's most famous sight, the Blue Grotto. Just be sure to get back to the port in time for your ferry back to the Amalfi Coast.


One great way to enjoy both the island and the water is a boat trip from Sorrento on the Amalfi coast. This is available as a group tour on the ferry, a small group tour with a small boat, or as a private tour.

Capri & Anacapri Group Tour

Capri & Anacapri Group Tour

Suggested activities for an additional cost, depending on your choice

Don't miss the opportunity to see the best of the Italian Riviera. Meet your guide and group in Marina Piccola in Sorrento and depart for a pleasant boat ride to Capri. During the crossing, the breathtaking sight of the Sorrento Coast will unfold before your eyes. When you land in Capri you'll hop aboard a minibus for a guided tour of the island. You'll stop at Anacapri to visit the Villa St. Michele, built by the Swedish doctor and writer Axel Munthe on the remains of Roman ruins. The area offers a wonderful view of the island from its beautiful shady garden. Next you'll go from Anacapri to Capri by private minibus. After lunch you can visit the Garden of Augustus, which has a wonderful view of the famous “Faraglioni.” The main square here, Piazza Umberto I, has a pretty white church and several open-air cafes where you can sit and watch the world drift by. You'll have plenty of free time for shopping in the elegant and exclusive island boutiques before heading back to your accommodation.


Activity Level : Light
Duration : 9-10 hours

Private Excursion to Capri and Anacapri

Private Excursion to Capri and Anacapri

Suggested activities for an additional cost, depending on your choice

On this tour you'll be exploring the wonders of Capri and Anacapri. You'll be driven to Sorrento port from where you will set out by boat. When you arrive at the port of Capri your guide will accompany you to a car for the drive to Anacapri. Then you'll have a walking tour of Anacapri with free time to visit Villa San Michele. After driving to the center of Capri, you'll have a one-hour guided walking tour, effectively going from one side of the island to the other, through its narrow streets and nooks and crannies. Following the walking tour you'll have free time for lunch and shopping. Then you'll head to the port for the trip back to your accommodation in Positano. We recommend wearing comfortable shoes, and don't forget your camera!


Activity Level : Moderate
Duration : 10 hours

Day 3

Day 3 - Your Second Full Day in Positano

Pompeii and Herculaneum

Suggested activities for an additional cost, depending on your choice

Mount Vesuvius erupted in 79 A.D., spewing lava and volcanic ash for days, devastating the Ancient Roman towns of Pompeii and Herculaneum. Pompeii certainly draws all the crowds but Herculaneum is well worth taking the time to see. The effects of the eruption were different in this smaller town populated mostly by the wealthy, rather than by the common-folk as Pompeii was, so you'll see different aspects of the history of the period and the way people lived by visiting both sites. The volcano itself can be seen from far away, and can be visited in combination with Pompeii on a group day trip. If you want to see all three sites, which is just about achievable, we suggest having a private driver for the day. But we recommend to dedicate enough time to Mount Vesuvius, which includes visiting a family-run winery and having a cooking class, and one of the two sites in one day, especially with hot weather and if you're stay in Positano, due to the distance.

Pompeii & Herculaneum Group Tour from Amalfi

Pompeii & Herculaneum Group Tour from Amalfi

Suggested activities for an additional cost, depending on your choice

On this special tour you'll be seeing Pompeii and Herculaneum, two historic cities that were destroyed by the volcano Vesuvius. You'll be picked up from your accommodation and taken to Pompeii, where you'll have a guided tour of the ruins. Next you'll head to Herculaneum, a more rural city. You'll have an expert guide the whole time so you'll get full insight into the history of the area. This really is a fascinating excursion for history buffs or anyone who wants to learn more about the history of Italy. At the end of the day you'll be driven back to your accommodation. You'll be doing a lot of walking, so please wear comfortable clothes and shoes.


Activity Level : Moderate
Duration : 8 hours

Pompeii Private Day Trip with Cooking Class and Wine Tasting on Mount Vesuvius

Pompeii Private Day Trip with Cooking Class and Wine Tasting on Mount Vesuvius

Suggested activities for an additional cost, depending on your choice

On this eight-hour excursion to Vesuvius and Pompeii, you're sure to enjoy one of the best days of your holiday in Italy. You'll set off in the morning when your driver picks you up at your accommodation. Your destination is the Sorrentino Vini winery on the slopes of Vesuvius. You'll get to explore this beautiful landscape, then enjoy a cooking class, lunch and wine tasting overlooking the bay, with the volcano at your back. After driving to Pompeii you'll have a two-hour guided tour that will make the past come to life. Afterwards, the driver will take you back to your accommodation. We suggest wearing comfortable shoes, and don't forget your camera!


Activity Level : Moderate
Duration : 8 hours

Day 4

Day 4 - Traveling to Rome by Private Transfer

Today you're off to magnificent Rome. First, our driver will pick you up from your accommodation in Amalfi and drive you to Naples Train Station. The car ride should take about an hour. Once you arrive in Naples, you'll catch one of the many high-speed train services linking Naples and Rome. We'll arrange for Premium class seats. The journey time is a little over an hour.

You can upgrade your transfer

Rome by Private Transfer

Upgrade for an additional cost
We also offer the following excursions in Positano

Pompei and Mount Vesuvius Private Day Trip from Positano
Moderate8 hours
Positano and Amalfi Small Group Cruise
Moderate10 hours
Private Day Trip to Capri
Moderate8 hours
Private Day Trip to Ischia and Procida Islands
Moderate10 hours

3 Nights in Rome

3 Nights in Rome

4 days in Rome

3 Nights in Rome

The capital of Italy is a vibrant, energetic and stylish city. While thoroughly modern in sensibility, Rome is also home to some of the world’s most important works of classic art and architecture. This city has been an epicenter for culture, politics and religion for more than 2,500 years. From the Spanish Steps to the Vatican, there are more than enough sights to keep even the most active tourists busy and even somewhere as popular as Rome you can find places just off the tourist trail and bustling with locals. But it’s also nice to slow down and enjoy Rome’s famous cafes and restaurants, which can be just as beguiling as the buildings. Lounge with an espresso on the Campo de Fiori and watch the changing light on the fountains and the facades. Visit the Vatican and explore some of the world’s most beautiful churches. Rome really comes alive at night, when restaurants and wine bars bring a renewed vitality to the city. You’ll also have opportunities for day trips to local vineyards, olive groves, and other places producing regional delicacies. No matter what your interests, or what kind of holiday you’re looking for, Rome will be an enjoyable destination.

The capital of Italy is a vibrant, energetic and stylish city. While thoroughly modern in sensibility, Rome is also home to some of the world’s most important works of classic art and architecture. This city has been an epicenter for culture, politics and religion for more than 2,500 years. From the Spanish Steps to the Vatican, there are more than enough sights to keep even the most active tourists busy and even somewhere as popular as Rome you can find places just off the tourist trail and bustling with locals. But it’s also nice to slow down and enjoy Rome’s famous cafes and restaurants, which can be just as beguiling as the buildings. Lounge with an espresso on the Campo de Fiori and watch the changing light on the fountains and the facades. Visit the Vatican and explore some of the world’s most beautiful churches. Rome really comes alive at night, when restaurants and wine bars bring a renewed vitality to the city. You’ll also have opportunities for day trips to local vineyards, olive groves, and other places producing regional delicacies. No matter what your interests, or what kind of holiday you’re looking for, Rome will be an enjoyable destination.

Day 4

Day 4 - Arrival in Rome

Upon arriving to Roma Termini train station, we'll arrange for our driver to pick you up from the terminal and take you to your centrally located accommodation.

Rome Twilight Walk with Gelato Group Tour

Get Acquainted with Rome on a twilight tour

Please ask your travel advisor for the cost to add this to your package

We think the ideal introduction to Rome's historic (but not ancient) center is to take a small group late afternoon walking tour. Over the course of two and a half hours your expert guide will show you the key sights of the historic center of Rome. The Spanish Steps, Piazza Navona, the Pantheon and the Trevi Fountain are all covered. You'll get insider tips and tricks to help you in your time as a temporary Roman and enjoy some homemade gelato too.


Activity Level : Light
Duration : 2.5 hours

Day 5

Day 5 - Your First Full Day in Rome

Colosseum & Roman Forum Private Tour

Focus on Ancient Rome with a group or private tour

Included in your vacation package price.

Rome's origin story unfolds when you visit the Colosseum and the adjacent Roman Forum. Hear about life in ancient Rome and soak in the grandeur of these testaments to a lost civilisation. We will arrange for a private guide to take you on a three hour tour to explain how the Colosseum was built and what happened to it in the years since. Afterwards the tour proceeds to the Roman Forum, the center of political life of the city and ultimately the Empire, finding out the different purposes of the buildings whose columns and porticos still stand today.


Activity Level : Moderate
Duration : 3 Hours

The Gourmet Experience in Rome

Suggested activities for an additional cost, depending on your choice

There's no better way to explore Italian cuisine than by taking gourmet tours which will give you a deep cultural experience. You can learn how to make gelato and tiramisu, enjoy a luxury gourmet dinner with a wine tasting in a private cellar, or be part of a small group food crawl. Choose any of these experiences and we can guarantee you'll want more.

Group Gelato & Tiramisu Class in a Professional Kitchen in Campo de' Fiori

Group Gelato & Tiramisu Class in a Professional Kitchen in Campo de' Fiori

Suggested activities for an additional cost, depending on your choice

If you've got a sweet tooth you're in the right city, and this is the right excursion for you. In a small group you'll work with an expert chef to make delicious tiramisu and gelato. You'll have all the ingredients and instruction you need to make a sweet masterpiece, then sit down to enjoy it!


Activity Level : Easy
Duration : 1.5 hours

Luxury Gourmet Dinner with Wine Tasting In Rome and Aperitif in Private Cellar Group Tour

Luxury Gourmet Dinner with Wine Tasting In Rome and Aperitif in Private Cellar Group Tour

Suggested activities for an additional cost, depending on your choice

This 2.5-hour tour and degustation is perfect for foodies. In the cellar of a very special restaurant, you'll start with an aperitif as you soak up the atmosphere. Then you'll head upstairs for dinner, enjoying sumptuous Roman specialties while you get the special treatment from the owners of the restaurant. We can't think of a better way to enjoy a Roman dinner!


Activity Level : Easy
Duration : 2.5 hours

Small Group Food Tour - Campo de' Fiori, Jewish Ghetto, Trastevere

Small Group Food Tour - Campo de' Fiori, Jewish Ghetto, Trastevere

Suggested activities for an additional cost, depending on your choice

Food lovers, here's your chance to experience Rome’s enchanting squares and neighborhoods while tasting your way through some of the city’s best shops, restaurants, and markets, discovering the secrets of Italian cuisine. Meet your friendly, local expert food connoisseur in the city center, and get ready to stroll through a number of neighborhoods to visit the most famous food markets, groceries, coffee shops, ice cream shops, and restaurants. Taste some of the delicious food and wines the city is famous for, including pizza bianca, mortadella, gelato, and supplì. From fried artichokes or zucchini flowers in the Jewish ghetto to spices and vegetables in Campo de Fiori, you'll ignite your senses and burn some calories while you enjoy walking amongst the beauty around you.


Activity Level : Light
Duration : 3.5 hours

Day 6

Day 6 - Your Second Full Day in Rome

Rome and Catholicism

Suggested activities for an additional cost, depending on your choice

It's hard to miss the dome of St Peter's, and it's the first thing you see when arriving in Rome by plane. It really is an ever-present reference point on the city's skyline. Vatican City is the spiritual and administrative center of the Roman Catholic Church. Technically a separate state and surrounded by stone walls, the Vatican is a must-see.


We offer a range of option to suit your specific preferences: private tours, small group tours and even tours with experienced scholars who can offer unique insight to the area.

Vatican Museums and Sistine Chapel Private Tour

Vatican Museums and Sistine Chapel Private Tour

Suggested activities for an additional cost, depending on your choice

On this special excursion you'll be seeing one of the most impressive highlights in Rome: the Vatican. You'll skip the lines and have your own private guide to explain the history and significance of this amazing building and the works of art it contains. On this 3-hour excursion you'll be astounded by the wonderful spiritual and artistic experience that you'll have upon visiting this historic and religious site.


Activity Level : Light
Duration : 3 Hours

The Complete Vatican Group Tour with Vatican Museums, Sistine Chapel and St. Peter's Basilica

The Complete Vatican Group Tour with Vatican Museums, Sistine Chapel and St. Peter's Basilica

Suggested activities for an additional cost, depending on your choice

If you're going to see the most famous highlights in Rome, you'll want to do it on this tour with an expert guide. You'll explore the Sistine Chapel, the Vatican Museums, St. Peter's Basilica, St. Peter's tomb, and more. This is the complete Vatican experience. You'll skip the lines and have your own private guide to explain the history and significance of these amazing buildings and the works of art they contain.


Activity Level : Light
Duration : 3.5 hours

Day 7

Day 7 - Traveling to Florence by Train

Today it's time to bid arriverderci to the Eternal City. You're headed to Italy's art palace, Florence. The high speed train service gets you there in just over an hour and a half. We've included standard class tickets in your package but can upgrade these to business class for an extra fee. We will also arrange for a driver to take you to Roma Termini station in plenty of time for your departing train.

You can upgrade your transfer

Florence by Private Transfer with a stop in Orvieto

Upgrade for an additional cost
We also offer the following excursions in Rome

4 Day Private Gourmet Tour - Guide and Driver
Light4 Days
Colosseum, Roman Forum and Palatine Hill Group Tour
Moderate3 Hours
Cooking Class in the Jewish District Group Tour
Easy3 hours
Eating in the Monti Neighborhood: A Pizza Tour Close to the Colosseum
Light2.5 hours

2 Nights in Florence

2 Nights in Florence

3 days in Florence

2 Nights in Florence

Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.

Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.

Day 7

Day 7 - Arrival in Florence

Upon arriving to Florence's main station, Santa Maria Novella, we'll arrange for our driver to pick you up from the platform and take you to your centrally located accommodation.

Florence in a Day Private Tour

The Best of Florence in a Day

Included in your vacation package price.

An experienced private guide will spend most of the day with you, combining guided visits to the Accademia to see Michaelangelo's famous David, the Uffizi Gallery to admire the must-see works of the Renaissance and a walking tour of the historical center. After the Accademia visit in the morning you'll have a lunch break , then continue the walking tour to the Uffizi visit, where your tour ends.


Activity Level : Moderate
Duration : 6 hours

Day 8

Day 8 - Your First Full Day in Florence

Explore Tuscany: San Gimignano, Siena and Chianti

Suggested activities for an additional cost, depending on your choice

One of the best things about Florence is how easy it is to get into the Tuscan countryside to explore this fabulous part of Italy. Unless you have your own car, a group excursion departing from Florence in the morning provides the perfect opportunity to cover a lot of ground without spending too much money.


A splendid excursion recommended for those without many days to dedicate to the region includes San Gimignano, aka the "Medieval Manhattan," thanks to its 14 towers, and the splendid Siena, famed for its horse race that takes place on the main square. No visit to Tuscany is complete without a visit to a winery and this is where you can have lunch and taste some of the local wine.

For a more active and exciting experience, a Vespa or E-bike are just perfect on the scenic rolling hills.

San Gimignano, Siena and Chianti Group Tour

San Gimignano, Siena and Chianti Group Tour

Suggested activities for an additional cost, depending on your choice

This full-day tour will show you some of the most beautiful sights in Italy. An expert local guide will show you all the secrets and stories to famous sights including San Gimignano, Siena and Chianti. You'll set out from the city and learn about the history and culture that have made Italy so special today. Wear comfortable clothing and shoes, and don't forget your camera!


Activity Level : Light
Duration : 11.5 hours

Vespa and Chianti Small Group Tour

Vespa and Chianti Small Group Tour

Suggested activities for an additional cost, depending on your choice

This group Vespa tour through Chianti is a interesting way to see this beloved countryside. You'll zip along the deserted roads that wind through the hills and vineyards. It's a great way to get out of the city and do something different while visiting Italy. You'll look just like a local! Meet the group at the appointed time and place and set out. You're going to have a great time!


Activity Level : Moderate
Duration : 8.5 Hours

Florence in a Day Private Tour

Florence in a Day Private Tour

Suggested activities for an additional cost, depending on your choice

This is the perfect tour for first-time visitors to Florence, or anyone who wants to see more of the city while learning about its historic culture. Along with an expert guide you'll visit the Academia and Uffizi galleries, with an interesting walking tour of the city between. Your guide will meet you at your accommodation at the agreed-upon time. At the end of the tour you'll have a chance to linger in the Uffizi gallery to discover more artistic wonders at your own pace.


Activity Level : Moderate
Duration : 6 hours

Cooking Class: From the Market to the Table

Cook with a local chef

Please ask your travel advisor for the cost to add this to your package

What better way to get to know a region than by cooking some of its local dishes? If you're of a culinary bent or just curious about how Italian food is so tasty, we have the perfect activity for you. A small group market tour and cooking class will teach you a lot more about the local cuisine than eating in a restaurant. Start the day with a tour of Florence's Central Market with an Italian chef, choosing the ingredients to prepare today's lunch with. After that you'll head up to the kitchen and get to work. Over the next few hours you'll prepare a full four course Italian meal, from appetiser to dessert. When you sit down to enjoy the fruit of your labors with some wine or soft drink you will feel both satisfied and educated, coming away from the class with some recipes to impress the folks back home with.


Activity Level : Light
Duration : 6 Hours

Day 9

Day 9 - Traveling to Monterosso Al Mare by Train

Your time in Florence has drawn to a close but there's more classic Italian beauty ahead, this time of the coastal variety. We have included standard class train tickets. You'll need to change trains in La Spezia and the total journey time is around 2 and a half hours. We'll arrange for our driver to pick you up from the accommodation and take you to the train station.

You can upgrade your transfer

Cinque Terre by Private Transfer

Upgrade for an additional cost
We also offer the following excursions in Florence

Accademia Gallery Private Tour
Light3 hours
Chianti Half-day Afternoon Group Tour
Moderate5.5 hours
Cinque Terre Group Excursion
Light14 hours
Cinque Terre Private Day Trip
Light10 Hours

2 Nights in Monterosso Al Mare

2 Nights in Monterosso Al Mare

3 days in Monterosso Al Mare

2 Nights in Monterosso Al Mare

As the northern-most of the Cinque Terre villages, Monterosso-al-Mare (literally the red mountain by the sea) is the most accessible of five. Road, rail and ferry links, and a wide choice of hotels make this an excellent base for visiting all the other villages and neighboring towns as well. This choice and accessibility comes at a price – it is the least pretty of the five. Yet that will hardly seem to matter when you're looking out to sea, or hiking the steep trail to Vernazza, the next village. Monterosso has the largest and best equipped beach of all the Cinque Terre villages so if some sun worship is on your vacation agenda, this is the perfect spot. As well as the opportunity to hike in the Cinque Terre national park between some of the villages you can also take the regular trains or if seas allow, the ferry service to the other villages. Private and boat day trips provide another way to admire the villages from their most natural aspect, the sea.

As the northern-most of the Cinque Terre villages, Monterosso-al-Mare (literally the red mountain by the sea) is the most accessible of five. Road, rail and ferry links, and a wide choice of hotels make this an excellent base for visiting all the other villages and neighboring towns as well. This choice and accessibility comes at a price – it is the least pretty of the five. Yet that will hardly seem to matter when you're looking out to sea, or hiking the steep trail to Vernazza, the next village. Monterosso has the largest and best equipped beach of all the Cinque Terre villages so if some sun worship is on your vacation agenda, this is the perfect spot. As well as the opportunity to hike in the Cinque Terre national park between some of the villages you can also take the regular trains or if seas allow, the ferry service to the other villages. Private and boat day trips provide another way to admire the villages from their most natural aspect, the sea.

Day 9

Day 9 - Arrival in Monterosso Al Mare

We will provide instructions on how to reach your accommodation from the train station.

Day 10

Day 10 - Your First Full Day in Monterosso Al Mare

Cinque Terre Small Group Morning Boat Tour

Explore Cinque Terre on foot, by train or by sea

Included in your vacation package price.

During this tour you will explore and learn from the sea the marvellous breathtaking panoramas of the Cinque Terre, a beautiful UNESCO World Heritage Site that will astound you..As you float along the waters your guide will tell you everything you need to know about the area. Sailing in the Gulf of the Poets, between the crystal clear waters, the first village that you will admire is to Portovenere, so beloved by the english poet Lord Byron, and, subsequently, the villages of the Cinque Terre, five picturesque villages by coloured houses, suspended on the hills from the terraced vineyards close to the sea. Bring your camera because this is one of the most picturesque parts of Italy!


Activity Level : Light
Duration : 2.5 Hours

Cinque Terre Private Hiking Tour

Hiking trails in Cinque Terre

Please ask your travel advisor for the cost to add this to your package

Hiking in Cinque Terre is demanding but rewarding. Only for people in good physical conditions and equipped with good hiking boots and comfortable outfit plus sun hat, sunscreen, extra water. It takes around 3 hours for the Monterosso to Vernazza leg and the same for Vernazza to Corniglia. Note that the scenic and easy walk "Via dell’Amore" (the love road) between Riomaggiore and Manarola is interrupted and won’t be restored soon.


Activity Level : Strenuous
Duration : 6 hours

Day 11

Day 11 - Traveling to Milan by Train

It's time to get to the capital of fashion - Milan. We'll book you standard class tickets from Cinque Terre to Milan. Depending on where you're staying, you might need to change trains once. The whole journey takes around 2 hours 30 minutes. If necessary your hotel will be able to arrange a taxi to the train station.

You can upgrade your transfer

Milan by Private Transfer

Upgrade for an additional cost
We also offer the following excursions in Monterosso Al Mare

Cinque Terre Private Tour by Train
Moderate6 hours
Cinque Terre by Kayak Group Tour from Monterosso
Moderate5 hours (3 hours of paddling)
Fishing the Cinque Terre Private Tour from Monterosso
Light2.5 hours
Lunch Boat Cinque Terre Small Group Tour
Light5 hours

2 Nights in Milan

2 Nights in Milan

3 days in Milan

2 Nights in Milan

Italy’s fashion and business hub, Milan fizzes with energy. But don't let the city's professional side fool you: this is a place that prides itself on history and culture, and the locals always seems to be having a good time. Milan's signature building is the Duomo, an imposing Gothic cathedral that sits in the heart of this former Roman capital. The combination of its size and beauty make it a must-see sight. You can also look forward to elegant evenings at the legendary La Scala opera, charming cafes and restaurants, great shopping opportunities, and breathtaking art and architecture. Home to Da Vinci's Last Supper, Milan is also rich in art galleries, from the old masters to contemporary art. This being Italy, you'll find delicious cuisine here too, and the "aperitivo" is one of the most interesting traditions of Milan gastronomy. At many of the city's cafes and bars in the early evening you can pay a slightly higher price for a drink and get your pick from a free buffet. It's one of the best ways to experience the different flavors of Milanese cooking. The compact city center means that one or two days should be enough to satisfy your curiosity.

Italy’s fashion and business hub, Milan fizzes with energy. But don't let the city's professional side fool you: this is a place that prides itself on history and culture, and the locals always seems to be having a good time. Milan's signature building is the Duomo, an imposing Gothic cathedral that sits in the heart of this former Roman capital. The combination of its size and beauty make it a must-see sight. You can also look forward to elegant evenings at the legendary La Scala opera, charming cafes and restaurants, great shopping opportunities, and breathtaking art and architecture. Home to Da Vinci's Last Supper, Milan is also rich in art galleries, from the old masters to contemporary art. This being Italy, you'll find delicious cuisine here too, and the "aperitivo" is one of the most interesting traditions of Milan gastronomy. At many of the city's cafes and bars in the early evening you can pay a slightly higher price for a drink and get your pick from a free buffet. It's one of the best ways to experience the different flavors of Milanese cooking. The compact city center means that one or two days should be enough to satisfy your curiosity.

Day 11

Day 11 - Arrival in Milan

Upon arriving to Milan's main station, Milano Centrale, we'll arrange for our driver to pick you up from the platform and take you to your centrally located accommodation.

Grand Group Tour of Milan

Grand Group Tour of Milan

Included in your vacation package price.

This special 3.5-hour tour of Milan is simply the best way to get to know the spectacular art, architecture and history of this splendid city. Your guide will show you some of the most amazing spots in the city and you'll also get a chance to see Leonardo da Vinci's The Last Supper, one of the most famous paintings in the world. In just a few hours you'll come to a better appreciation of this unique destination.


Activity Level : Light
Duration : 3.5 hours

Day 12

Day 12 - Your First Full Day in Milan

Leonardo da Vinci Private Walking Tour

Leonardo da Vinci and his Milanese Masterpieces

Please ask your travel advisor for the cost to add this to your package

Leonardo da Vinci spent many years in Milan, where some of his works are still kept. Start at the Pinacoteca Ambrosiana, a treasure chest that displays "The Portrait of a Musician" and "The Atlantic Codex." You can see "The Last Supper" in the Convent of Santa Maria delle Grazie. Tickets are very hard to get, and the official website is sold out a year in advance. We recommend booking a tour with our expert local guide.


Activity Level : Light
Duration : 3 hours

The Splendid villas & Gorgeous Landscapes of the Stars: a Day on Lake Como

Suggested activities for an additional cost, depending on your choice

Lake Como is the best known of the Northern Italian lakes and has attracted celebrities like George Clooney, who has a holiday villa by the shore. To make for an easy visit you can take a group excursion that will get you transported to and from the lake and includes a guided tour of the town of Como itself, time for shopping and lunch as well as some time to visit Bellagio. It's a full day with an early start but you should be back in Milano for some aperitivo.

Lake Como & Bellagio Group Day Trip

Lake Como & Bellagio Group Day Trip

Suggested activities for an additional cost, depending on your choice

Lake Como is famous around the world for a reason: it is simply a stunning landscape you'll love to explore. This full-day tour gives you an in-depth experience of the lake and all it has to offer. From a guided walking tour of Como to a cruise on the blue waters of the lake, you'll see some of the most beautiful areas and villas, and hear all about the history of the region, it's wealth and its silk production.


Activity Level : Light
Duration : 10 hours

Best of Como Lakeside Private Tour from Milan

Best of Como Lakeside Private Tour from Milan

Suggested activities for an additional cost, depending on your choice

This is the perfect way to explore the opulence of Lake Como while you're staying in Milan. With an expert local guide you'll hop on and off a water taxi to see some of the most impressive villas on the lake as well as several of the charming lakeside towns, all of which have amazing architecture and histories. You'll be picked up at your accommodation in the morning and dropped off there after the tour. The entire excursion takes about 9 hours. Have fun!


Activity Level : Light
Duration : 9 hours

Day 13

Day 13 - Traveling to Venice by Train

Today you're headed to the city on the lagoon. The marvels of Venice await! By far the quickest and most convenient way to get from Milan to Venice is by direct high-speed train, with a journey time of just two and a half hours. We'll arrange for second class tickets, with an upgrade to first class available for an extra fee. Our driver will pick you up from your accommodation and take you to Milan Train Station.

You can upgrade your transfer

By Private Transfer to Venice

Upgrade for an additional cost
We also offer the following excursions in Milan

Best of Como Lakeside Private Tour by Train from Milan
Moderate9 hours
Best of Milan Private Tour in a Vintage Fiat 500
Light2 hours
Easy Entrance Duomo, Underground, and Terrace Small Group Tour
Light2.5 hours
In The Footsteps of Da Vinci Group Walking Tour
Light3 hours

2 Nights in Venice

2 Nights in Venice

3 days in Venice

2 Nights in Venice

Venice is a legendary city with a charm and atmosphere all its own. The city was constructed on more than 100 islands connected by a series of canals, most of which are lined with gorgeous palaces, beautiful churches, and all sorts of impressive architecture. While the city isn’t huge, it is packed with pedestrian-only streets and quaint, winding alleys that will keep you exploring for days. The city is very popular with tourists year-round, so you certainly won’t be the only travelers walking through the streets with camera in hand. This being Italy, the cuisine in Venice is delicious, and we can especially recommend the Cicchetti of Venice tour. Cicchetti are Venetian tapas, and this tour will introduce you to some of the city’s most iconic eateries and its most delicious recipes. If it’s your first time in Venice, we can organize a tour to show you all the most important sites. And since no trip to the city of canals is complete without a boat ride, we offer a number of ways for you to get a new point of view of the city and its magnificent architecture. It’s easy to while away your time in Venice, discovering new secrets around every corner.

Venice is a legendary city with a charm and atmosphere all its own. The city was constructed on more than 100 islands connected by a series of canals, most of which are lined with gorgeous palaces, beautiful churches, and all sorts of impressive architecture. While the city isn’t huge, it is packed with pedestrian-only streets and quaint, winding alleys that will keep you exploring for days. The city is very popular with tourists year-round, so you certainly won’t be the only travelers walking through the streets with camera in hand. This being Italy, the cuisine in Venice is delicious, and we can especially recommend the Cicchetti of Venice tour. Cicchetti are Venetian tapas, and this tour will introduce you to some of the city’s most iconic eateries and its most delicious recipes. If it’s your first time in Venice, we can organize a tour to show you all the most important sites. And since no trip to the city of canals is complete without a boat ride, we offer a number of ways for you to get a new point of view of the city and its magnificent architecture. It’s easy to while away your time in Venice, discovering new secrets around every corner.

Day 13

Day 13 - Arrival in Venice

Start your Venetian experience off in style by arriving in a private water taxi. We'll arrange a transfer by boat from Santa Lucia train station to your hotel in the city.

Murano and Burano

Suggestion to explore on your own

Today we suggest going off the beaten path and onto a boat to cross the water and explore two islands which are not islands at all. Murano and Burano are tiny archipelagos, collections of islands linked by numerous bridges. On Murano, the stately architecture is stunning but the main attraction here is the collection of incredible glassblowers, whose works in progress you can see at Murano’s many ateliers

. Burano is also an archipelago in northern Venice, consisting of four islands linked by many bridges. What you’ll notice first are the brightly painted houses, which make the island glow with an energy all its own. Largely inhabited by artists, it’s a great place to poke around and explore, including the Church of San Martino, which houses a classic Tiepolo painting from the 18th century. We can arrange tickets for a group boat trip but you might prefer exploring on your own.

Day 14

Day 14 - Your First Full Day in Venice

First Time in Venice Private Tour

Introducing Venice: A Private Tour

Included in your vacation package price.

Venice is a magical city, and today you’ll discover the best it has to offer, with a private three-hour tour with your own personal guide. You’ll get a feel for the layout of the city and appreciate some of its legendary landmarks. After being picked up at your accommodation, you’ll head toward the elegant Piazza San Marco, which is enclosed by buildings from the ancient republic. The shining gold of the Byzantine St. Mark church is sure to impress you. Later you’ll wind your way through the Castello district, including the large campo Santa Maria Formosa. Before reaching the famous Rialto bridge you’ll stop by the square of San Giovanni e Paolo and the Marco Polo House. From the top of the bridge you’ll be able to take in the wonders of the Grand Canal. At this point you’ll be right in the market, which is a lovely place to enjoy a glass of wine along with local recipes. Here you’ll conclude your tour in true Italian style.


Activity Level : Light
Duration : 3 hours

Cicchetti and Wine Small Group Tour of Venice

Venetian Tapas and Wine Tour

Please ask your travel advisor for the cost to add this to your package

You're in Italy so good food isn't too far away if you know where to look. One of our favorite ways to get to know a city is by taking a food tour. We can highly recommend taking part in this small group tour and getting your culinary bearings set with an afternoon sampling cicchetti, the Venetian version of tapas, accompanied by wine at Venice's best Bacari wine bars.


Activity Level : Easy
Duration : 2.5 hours

Day 15

Day 15 - Departure Day

It's time to bid arrivederci to Venice but you'll get a good last look at the city as your private water taxi captain takes you to the airport for your departing flight.

We also offer the following excursions in Venice

Cortina and the Dolomites Day Group Tour
Moderate8 Hours
Dolomites and Cortina d'Ampezzo Private Car Tour
Moderate9 hours
Grand Canal Boat Group Tour
Easy1 hour
Group Walking Tour of Venice
Light1.5 hour

What's Included

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.

Naples

Naples - Amalfi Private Transfer

Positano

3 Nights Accommodation
Breakfast (hotels only)
Amalfi Coast Private Day Trip
Amalfi Coast - Naples Private Transfer
Naples - Rome Premium Class Train Ticket

Rome

3 Nights Accommodation
Breakfast (hotels only)
Rome Train Station Transfer
Colosseum & Roman Forum Private Tour
Rome Train Station Transfer
Rome - Florence Standard Class Train Tickets

Florence

2 Nights Accommodation
Breakfast (hotels only)
Florence Train Station Transfer
Florence in a Day Private Tour
Florence - Cinque Terre Standard Class Train Tickets
Florence Train Station Transfer

Monterosso Al Mare

2 Nights Accommodation
Breakfast (hotels only)
Cinque Terre Small Group Morning Boat Tour
Cinque Terre - Milan Standard Train Tickets

Milan

2 Nights Accommodation
Breakfast (hotels only)
MIlan Train Station Transfer
Grand Group Tour of Milan
Milan - Venice Standard Class Train Tickets
MIlan Train Station Transfer

Venice

2 Nights Accommodation
Breakfast (hotels only)
Venice Water Taxi Santa Lucia Train Station Transfer
First Time in Venice Private Tour
Venice Marco Polo Airport Transfer
The package excludes:

  • Flights to and from Europe.
  • Tips for Tour Guides, Drivers and Local Reps.
  • Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
  • Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
  • Travel Insurance. See the insurance link on our website

Benefits of Traveling with JayWay

A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.

A Travel Advisor who speaks your language
We will make sure that all your requirements and interests are taken into account in preparing your itinerary.
A totally tailored itinerary for your vacation
Your trip is customized for you by  an experienced trip planner and an expert on the region.
A choice of hand-picked hotels and excursions
We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.
Detailed pre-trip preparation to make the most of every day
Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.
On-trip Concierge Service to smooth out any bumps in the road
Our local staff are at your service throughout your journey via the local prepaid cellphone which we provide.
Personalized Guest Page to make sure you're not missing out
Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of vacation packages including these destinations
Review by Julia & Kirk

Julia & Kirk

Colorado

Love the friendly people you interact with either on the phone, or via email. The Guest Page is so easy to use with loads of great information. JayWay Travel makes it very easy to build a great completely customized vacation trip.

Love the friendly people you interact with either on the phone, or via email. The Guest Page is so easy to use with loads of great information. JayWay Travel makes it very easy to build a great completely customized vacation trip.

Year : 2019
Visited : Italy
Itinerary : Venice, Bologna, Milan, Levanto, Florence, Siena, Rome
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Venice, Bologna, Milan, Levanto, Florence, Siena, Rome
Rating :
5 / 5
Review by Holly, Andy, Jacqueline & Anthony

Holly, Andy, Jacqueline & Anthony

New York

The best Travel Agency. They are a well oiled team of professionals. You will always feel like they are with you during the duration of your trip. Accessible at all times prior to as well as during your trip.

The best Travel Agency. They are a well oiled team of professionals. You will always feel like they are with you during the duration of your trip. Accessible at all times prior to as well as during your trip.

Year : 2018
Visited : Italy
Itinerary : Milan, Lake Como, Milan, Venice, Bologna, Florence, Castellina in Chianti, Pisa, Monterosso Al Mare
Rating :
5 / 5
Year : 2018
Visited : Italy
Itinerary : Milan, Lake Como, Milan, Venice, Bologna, Florence, Castellina in Chianti, Pisa, Monterosso Al Mare
Rating :
5 / 5
Review by Jon & Carly

Jon & Carly

California

Curated experiences for the mid-range and high-end budget traveler.

Curated experiences for the mid-range and high-end budget traveler.

Year : 2018
Visited : Italy
Itinerary : Venice, Milan, Lake Como, Milan, Castellina in Chianti, Florence, Naples, Capri, Naples, Rome
Rating :
4.6 / 5
Year : 2018
Visited : Italy
Itinerary : Venice, Milan, Lake Como, Milan, Castellina in Chianti, Florence, Naples, Capri, Naples, Rome
Rating :
4.6 / 5

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