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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

Today you're headed out of Naples and to one of the most famous parts of coastline in the world, the Amalfi Coast. 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 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 in Positano.

Day 2

Day 2 - Your First Full Day in Positano

Amalfi Coast Private Day Trip from Positano

Amalfi Coast Private Day Trip from Positano

Included in your vacation package price.

Don't miss opportunity to tour the gorgeous Amalfi and/or Sorrentino Coast. We'll arrange for an experienced 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 on the Italian Riviera. This is an eight-hour tour, so you'll have plenty of time to explore, and your driver knows just where to go. We recommend wearing comfortable shoes, and don't forget your camera!


Activity Level : Moderate
Duration : 8 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 eruption of Mt. 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.


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 an hour, 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 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 Positano 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 standard class seats but we ca upgrade to higher class for additional fee. 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
Private Day Trip to Capri
Moderate8 hours
Private Mozzarella di Bufala Experience with an Excursion to Paestum
Moderate8 hours
Small Group Boat Excursion to Capri with Private Transfers from Positano
Moderate9-10 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.

Take a Twilight Tour

Suggested activities for an additional cost, depending on your choice

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. You can also take advantage of nighttime for a more intimate tour of the Colosseum, visiting areas not usually opened to the general public, without the usual daytime crowds.

Rome Twilight Walk with Gelato Group Tour

Rome Twilight Walk with Gelato Group Tour

Suggested activities for an additional cost, depending on your choice

This is an intimate Rome walking tour helping you to get your bearings at the start of your trip to the Eternal City. You’ll visit the top sights and enjoy a gelato tasting. You’ll visit the Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona and even see some Ancient Roman ruins along the way. Traveling in small groups of 15 people or fewer with an expert local tour guide you can ask questions, get recommendations and really get a feel for the city on this short, relaxed tour.


Activity Level : Light
Duration : 2.5 hours

VIP Colosseum Underground and Arena Floor at Night Group Tour

VIP Colosseum Underground and Arena Floor at Night Group Tour

Suggested activities for an additional cost, depending on your choice

Enter the Colosseum at night, avoiding the crowds, and accessing special areas usually closed to the public. During this tour you will visit the surroundings of the Colosseum, starting from the Teatro Marcello and the interior and underground spaces of the Colosseum. You will walk in the arena floor, where gladiators used to fight and where you can admire the silence of general access areas. You will then explore the real underground part with just your tour guide and group.


Activity Level : Light
Duration : 2.45 hours

Day 5

Day 5 - Your First Full Day in Rome

Pristine Sistine Early Entrance Small Group Vatican Tour

Pristine Sistine Early Entrance Small Group Vatican Tour

Included in your vacation package price.

Standing in the Sistine Chapel and marvelling at Michelangelo's masterpieces is a memory that will stay with you forever but to enjoy it this moment to its fullest the best way is by entering the Vatican a full hour before the general public. It'll be an early start for this VIP small group tour but totally worth it. Your guide will tell you the story of the chapel, before continuing to explore the Vatican Museums and St Peter's Basilica.


Activity Level : Light
Duration : 3.45 hours

Gourmet Experiences

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 : Light
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

Colosseum, Roman Forum and Palatine Hill Group Tour

Colosseum, Roman Forum and Palatine Hill Group Tour

Included in your vacation package price.

Hear stories of lions, gladiators & emperors on this thorough exploration of Ancient Rome. There's no waiting in line as we've included express entry at the Colosseum, Roman Forum & Palatine Hill. Your expert guide will takae you in a group of no more than 15 people for an intimate and fun tour of three of the most significant sites of Ancient Rome.


Activity Level : Moderate
Duration : 3 Hours

Borghese Gallery Group Tour: With Bernini, Caravaggio, and Raphael

Renaissance Masters Up Close

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

If you're itching to delve into Rome's high culture in a quiet, peaceful gallery, we offer a private tour of the Borghese Gallery, stuffed with works from Renaissance masters. This tour takes you inside one of the most spellbinding art museums in the world. Located in the 17th century home of Cardinal Borghese, it houses the art of the Cardinal himself - collected, commissioned (and even stolen!) during his lifetime. Since this is a private residence and not a sprawling palace, the Borghese Gallery is particularly manageable.


Activity Level : Easy
Duration : 2.5 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 Private Tour
Moderate3 Hours
Cooking Class in the Jewish District Group Tour
Easy3 hours
Crypts, Bones and Catacombs - Rome Group Walking Tour
Light3 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 train station and take you to your centrally located accommodation.

Hike the Florence Greenway for the Best Views

Suggestion to explore on your own

Some of the best views of Florence aren’t to be found in the city. Hiking along the city’s new green urban trail, Greenway Florence, will reward you. Start from Via dei Bardi number 1 and visit the splendid 19th century garden named after its founder, the antiques collector and dealer Stefano Bardini. You could easily spend quite a bit of time admiring this ornate oasis of flowers and statues along with the view of Florence. Then push onwards to Michelangelo Square on top of the hill for another breathtaking view of the city and a visit to the Romanesque San Miniato church.

Day 8

Day 8 - Your First Full Day in Florence

Florence City Private Walking Tour

Florence City Private Walking Tour

Included in your vacation package price.

Sometimes Florence feels like an outdoor museum. There's so much to see in every direction, it can be a little overwhelming. That's why this three-hour city walking tour is so great: in a short time you'll explore the most important bridges, alleys, medieval markets and Renaissance palaces, so you can appreciate the best of this unique city. You'll be picked up from you accommodation and your guide will lead you through the city streets.


Activity Level : Moderate
Duration : 3 Hours

Cooking Class: From the Market to the Table Small Group Tour

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. An upgrade to a higher class is possible for an extra fee. 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
Cinque Terre Private Day Trip
Light10 Hours
Cinque Terre Small Group Tour
Moderate11 hours
Dinner in Chianti Vineyards Group Tour
Light5.5 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.

Swim in Splendid Waters

Suggestion to explore on your own

If you like swimming, you have more than a few options on the coast. In warmer weather we recommend the tiny harbor of Vernazza and Riomaggiore. The only equipped beach nearby is in Monterosso, and this one is suitable for families as well. So grab your towel and maybe a focaccia and a drink or gelato. As usual, the best suggestion is follow the locals!

Day 10

Day 10 - Your First Full Day in Monterosso Al Mare

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

Sunset Cinque Terre Small Group Boat Tour

Sunset Cinque Terre Small Group Boat Tour

Included in your vacation package price.

Ready to relax? Hop aboard a local skipper's boat and soak up the last rays of the sunset as they cast their spell. Then sip a tasty aperitif and watch the beautiful coast slip by as you float along the waves! What a way to get a new point of view on the Cinque Terre, one of the most beautiful parts of Italy.


Activity Level : Easy
Duration : 3 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. An upgrade to a higher class is possible for an extra fee. 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
Moderate4 hours (3 hours of paddling)
Lunch Boat Cinque Terre Small Group Tour
Light4,5 hours
Private Excursion to Genoa by Train
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.

Shop in the Fashion Quarter and the Navigli Neighborhood

Suggestion to explore on your own

Milan is home to the most prestigious designers and renowned fashion labels in the world. There's a bedazzling concentration of luxury shops around via Montenapoleone. If you like shopping, you've come to the right place. The "quadrilatero" is the heart of the shopping area, and consists of four streets: Via Montenapoleone, Via della Spiga, Via Manzoni and Corso Venezia. Your local JayWay contact will recommend several places to visit in this area, both shops and eateries, and can also recommend places in another area known for its vintage fashion.

Day 12

Day 12 - Your First Full Day in Milan

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

In The Footsteps of Da Vinci Group 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, which includes the entrance ticket.


Activity Level : Light
Duration : 3 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 standard 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 Como Lakeside Private Tour from Milan
Light9 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

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 the closest possible point to your hotel in Venice.

Please note that porter assistance from the water taxi to the hotel is not included but can be arranged at extra charge.

Cicchetti and Wine Small Group Tour of Venice

Cicchetti and Wine Small Group Tour of Venice

Take your taste buds on a delicious adventure with this tour of Venice's Bacari wine bars and their famous cicchetti dishes. These small tapas-style dishes are ideal for teaming with Italian wine, so tour the city's famous bars and try everything from fried olives to wedges of cheesy polenta. With the chance to learn about the history along the way, this is one Venice tour no food lover can miss. This three-hour tour is a pure delight for all your senses. You'll love it!


Activity Level : Light
Duration : 2.5 hours

Day 14

Day 14 - Your First Full Day in Venice

First Time in Venice Private Tour

First Time in Venice Private Tour

Included in your vacation package price.

Discover Venice with this unique walking tour, which unfolds through the elegant Piazza San Marco, surrounded by the governmental buildings of the ancient Republic. You'll enter the beautiful Saint Mark church, then stroll through the Castello district including the large campo Santa Maria Formosa. The square of San Giovanni e Paolo will be your next stop. Before reaching Rialto you'll pass by the Marco Polo house. From the top of the famous Rialto bridge you'll encounter all the splendours of the Grand Canal.


Activity Level : Light
Duration : 3 hours

Royal Culture: Doge’s Palace and the Peggy Guggenheim Collection

Suggestion to explore on your own

Two of the more unique attractions in Venice are the Doge’s Palace and the Peggy Guggenheim Collection. We recommend seeing both while you’re in the city.

The Doge's Palace is a stunning palace built in Venetian Gothic style and one of the most conspicuous landmarks in Venice. The Doge of Venice, the highest ruling authority of the former Republic of Venice, once used the palace as his house. Situated on the Grand Canal, the palace opened as a museum in 1923.
The Peggy Guggenheim Collection is a rich art museum that has more than enough to keep you busy for an afternoon. The personal collection of the legendary philanthropist, the museum gives you a chance to see excellent works of 20th century international avant-garde art, all in a stunning palace right along the Grand Canal.

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. Your private boat will dock at the closest possible point to your hotel.

We also offer the following excursions in Venice

Cortina and the Dolomites Day Group Tour
Moderate8 Hours
Dolomites Day Private Tour
Moderate8 hours
Dolomites and Cortina d'Ampezzo Private Car Tour
Moderate9 hours
Grand Canal Small Group Boat Tour
Easy1 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 - Positano Private Transfer

Positano

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

Rome

3 Nights Accommodation
Breakfast (hotels only)
Rome Train Station Transfer
Pristine Sistine Early Entrance Small Group Vatican Tour
Colosseum, Roman Forum and Palatine Hill Group Tour
Rome Train Station Transfer
Rome - Florence Standard Class Train Tickets

Florence

2 Nights Accommodation
Breakfast (hotels only)
Florence Train Station Transfer
Florence City Private Walking Tour
Florence - Monterosso Standard Class Train Tickets
Florence Train Station Transfer

Monterosso Al Mare

2 Nights Accommodation
Breakfast (hotels only)
Sunset Cinque Terre Small Group Boat Tour
Monterosso - 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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