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Magical Italian Exploration

Two weeks exploring some of Italy's highest highlights, Rome, the Amalfi Coast, Tuscany, Florence, Venice. Truly magical! The services we provide as part of our comprehensive packages include accommodations, train tickets, transfers (airport, train station and some long distance) and several city tours. This 2 week Italy itinerary with Amalfi coast is the ideal sampler for a country you'll want to visit again and again. In addition to the tours included we can arrange a number of excursions based on your own interests. There is also an option to travel between cities by private car or van transfers at an extra cost. 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 Rome, Positano, Naples, Florence, Castellina in Chianti, Florence, Venice tour

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 1

Day 1 - Arrival in Rome

After you land at Rome's Fiumicino airport you will be met in the arrivals hall by a driver holding a sign with your name on. The journey to your accommodation in the center of Rome should take around an hour.

Our representative will then meet with you to answer any questions you have and to get you settled for the rest of your trip.

Rome Twilight Walk with Gelato Small Group Tour

Rome Twilight Walk with Gelato Group Tour

Included in your vacation package price.

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

Day 2

Day 2 - Your First Full Day in Rome

Colosseum, Roman Forum and Palatine Hill Group Tour

Focus on Ancient Rome with a Group or Private Tour

Included in your vacation package price.

Today you'll be joining a small group tour and learning all about Ancient Rome on a three hour tour of some of the city's most significant sights from the days of the Roman Empire. Priority entry tickets will be provided for you and an expert guide will regale you with the fascinating history of the Colosseum, the Roman Forum and Palatine Hill. You'll hear about more than just gladiators and lions as the Roman Forum was the epicenter of the political life of the city and ultimately the Empire.


Activity Level : Moderate
Duration : 3 Hours

World War II Historic Sites

Suggestion to explore on your own

Rome and its surroundings were the battleground for some of the fiercest and most famous events of World War II. If you're interested, there are plenty of sites to explore, including The Anzio BeachHead Museum, the Allied cemeteries, and memorials for Nazi atrocities. You could go on your own or with a guide, let us know if you would like us to arrange one for a day or half day. If you have relatives or friends who fought in Italy, the guide can pinpoint where they fought and tailor-make your tour according to your specific interest and timeframe.

Day 3

Day 3 - Your Second 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 4

Day 4 - Traveling to Positano by Train

Today you're off to the beautiful Amalfi Coast. The fastest and most economic way to get there is to take a 1h train from Rome to Naples and then have our driver pick you up from the platform and take you directly to your accommodation in Positano. We've included standard class tickets in your package but an upgrade to a higher class is possible for an extra fee.

You can upgrade your transfer

Positano by Private Transfer

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

(FOR PRIVATE GROUP) Full Day Rome Colosseum and Walking Tour
Light8 Hours
(FOR PRIVATE GROUP) Rome Lunch / Dinner
Easy1.5 - 2 Hours
(FOR PRIVATE GROUP) Vatican and Sistine Chapel Private Tour
Light4 Hours
2 Hours Private Photo Session
Easy2 hours

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 4

Day 4 - Arrival in Positano

Our driver will bring you directly to your accommodation in Amalfi Coast.

Kayak and Swim in Secluded Coves

Suggestion to explore on your own

Kayaking is a great way to enjoy this beautiful area, and you can rent kayaks on Spiaggia Grande, Positano's main beach. Go on your own or join a guided tour to explore the beaches, caves and coves that make it unique. You can also stop to swim on an isolated beach, away from the crowd, to snorkel or dive. Excursions at sunset are particularly pleasant, and highly recommended.

Day 5

Day 5 - Your First Full Day in Positano

Amazing Amalfi

Suggested activities for an additional cost, depending on your choice

The first thing you'll want to do on the Amalfi Coast is take some photos and there are some truly stunning vistas to be found. There are numerous ways to explore the coastline, by foot if you're up to hiking the arduous Sentiero degli Dei (the Path of the Gods), by sea kayak, by boat using the ferries that shuttle between the towns and villages on the coast, or by road, either using the local bus services, on a rented scooter, or for the utmost convenience, with a private driver which we can arrange for you, or even a private guide.

Amalfi Coast Private Day Trip from Positano

Amalfi Coast Private Day Trip from Positano

Suggested activities for an additional cost, depending on your choice

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

Path of the Gods Private Hiking Tour

Path of the Gods Private Hiking Tour

Suggested activities for an additional cost, depending on your choice

Travel to the small village of Nocelle, near Positano, where you'll start a 3-hour hike. With your guide, you’ll then set off to explore the Path of the Gods, a stunning trail named after the Roman temples that once lined the route. The trail hugs the cliffs of the Amalfi Coast, setting you up for impressive panoramas that stretch over craggy gorges and sleepy hamlets, down to the sea. Keep your camera handy as you walk along the trail to Bomerano and then back again.


Activity Level : Strenuous
Duration : 5 hours

Day 6

Day 6 - Your Second Full Day in Positano

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

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

Day 7

Day 7 - Traveling to Florence by Private Transfer & Train, via Naples

Today it is time to leave Positano towards Naples but there can be more discoveries 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.

We also offer the following excursions in Positano

Kayak Group Tour
Moderate3 hours
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

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 7 - Day Stop in Naples

Day 7 - Day Stop in Naples

Your driver will take you to Napoli Centrale station in plenty of time for you to get to your departing train.

Today you're headed for one of Italy's cultural highlights of Italy, Florence, capital of Tuscany. The journey by high speed train takes around three hours and there are trains throughout the day. We'll arrange for standard class tickets for you, but we haven't included a train station transfer service as a taxi will work out much cheaper, your hotel reception can call the taxi for you, and let you know what time it's necessary to leave.

Day Stop in Florence

Day Stop in Florence

1 days in Florence

Day Stop 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's works 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's works 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 Stop in Florence

Day 7 - Day Stop in Florence

Upon arriving to Florence's main station, Santa Maria Novella, we will arrange for a driver to meet you.

It's time to leave a hustle and bustle of Florence and head for the hills. We will arrange for a driver to pick you up at your accommodation in Florence and transfer you through the scenic countryside to your next overnight destination. 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.

4 Nights in Castellina in Chianti

4 Nights in Castellina in Chianti

5 days in Castellina in Chianti

4 Nights in Castellina in Chianti

We have chosen Castellina as one of our key destinations in Tuscany as this small town or large village offers all the facilities most visitors need while allowing them to enjoy the countryside location as well. Public transport is limited so you will definitely need a driver or rental car while you're here. On the edge of a village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings. Close by you'll find San Gimignano, a 'medieval Manhattan' well worthy of a day trip and the walled town of Monteriggioni is even closer.

We have chosen Castellina as one of our key destinations in Tuscany as this small town or large village offers all the facilities most visitors need while allowing them to enjoy the countryside location as well. Public transport is limited so you will definitely need a driver or rental car while you're here. On the edge of a village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings. Close by you'll find San Gimignano, a 'medieval Manhattan' well worthy of a day trip and the walled town of Monteriggioni is even closer.

Day 7

Day 7 - Arrival in Castellina in Chianti

Your driver will bring you to your accommodation in Castellina center or in the scenic countryside nearby, depending on your choice of accommodation.

Day 8

Day 8 - Your First Full Day in Castellina in Chianti

Explore Chianti's Hills on Foot and Wheels

Suggestion to explore on your own

The rolling hills around Castellina offer many possibilities for splendid short or day-long trips. Your hotel and the local tourist office located in the main street close to Palazzo Squarcialupi will offer plenty of suggestions and maps for hiking and cycling. On the edge of the village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings in style.

Day 9

Day 9 - Your Second Full Day in Castellina in Chianti

Private Cooking Class with Professional Chef in Castellina in Chianti

Private Cooking Class with Professional Chef in Castellina in Chianti

Included in your vacation package price.

This three-hour cooking class is perfect for pasta lovers. With an expert Italian chef you'll learn the secrets of world-class cuisine, then sit down to eat what you've prepared. And it all takes place in a professional kitchen in the gorgeous hills of Chianti. What could be better?


Activity Level : Light
Duration : 3 hours

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti

This tour has been designed to give you a taste of authentic Tuscany. You'll be driven through the beautiful countryside south of Siena, where you'll have the possibility to stop for some wine tasting. Your first stop, Montalcino, is famous for its Brunellos. You'll also visit Montepulciano, which is known for its Vino Nobile wines. Please let us know if you wish to visit a winery so we can book it for you.

Along the way you'll have some delicious local foods too. This is a gastronomic extravaganza and you'll love every minute of it!


Activity Level : Light
Duration : 7 hours

Day 10

Day 10 - Your Third Full Day in Castellina in Chianti

Siena and San Gimignano Full-day Private Tour from Castellina

Siena and San Gimignano Full-day Private Tour from Castellina

This full-day tour is simply fantastic. Start with a two-hour guided tour of Siena, then you'll have an hour to enjoy lunch on your own. After the lunch break, you'll continue your journey to San Gimignano, where you will have a two-hour guided tour. The journey to San Gimignano takes about one hour. After your visit in San Gimignano your driver will take you to your accommodation. The journey to Castellina will take about one hour. The entire tour lasts about 8 hours.  


Activity Level : Moderate
Duration : 8 hours

Day 11

Day 11 - Traveling to Venice by Private Transfer & Train, via Florence

It's time to leave the Tuscan countryside behind but you're not going too far. We will arrange for a driver to meet you at your accommodation to transfer you to the capital of the Tuscany region, Florence. The journey will take between 45 and 90 minutes depending on where in Tuscany you choose to stay. 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.

We also offer the following excursions in Castellina in Chianti

Off-Road Tuscan Wine Private Tour
Moderate5 hours
Private Day Trip to Florence
Light8 hours
Siena Half-day Private Tour from Castellina
Moderate4 hours
Truffle Hunt and Wine Tasting Private Tour
Moderate4 hours

Day Stop in Florence

Day Stop in Florence

1 days in Florence

Day Stop 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's works 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's works 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 11 - Day Stop in Florence

Day 11 - Day Stop in Florence

Upon reaching Florence your driver will take you to the main railway station Santa Maria Novella, where you'll store your bags and meet your Florence guide. After a walking tour and some time on your own to explore Florence, you'll continue your journey to Venice.

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

Your time in Florence has drawn to a close but there's plenty more Italian splendor ahead of you as you push north to the magnificent maritime city of Venice. We have included standard class train tickets for the high speed train service which takes around two hours.

You can upgrade your transfer

Venice by Private Transfer

Upgrade for an additional cost

3 Nights in Venice

3 Nights in Venice

4 days in Venice

3 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 11

Day 11 - 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.

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 12

Day 12 - 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

Murano and Burano

Suggested activities for an additional cost, depending on your choice

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 or a private one of you would like.

Murano, Burano & Torcello Group Tour

Murano, Burano & Torcello Group Tour

Suggested activities for an additional cost, depending on your choice

This tour takes you to three must-see islands of the Venetian Lagoon: Murano, Burano, and Torcello. Murano has been famous for its glassmaking since the 10th century, which we'll help you explore. Then you'll see the colorful island of Burano, which is famous for its brightly colored houses, fishing industry and lacemaking. Third is Torcello, known as the “Mother of Venice.” You will have the chance to visit its basilica, one of the Lagoon's oldest churches, and home to beautiful mosaics, although you can instead focus on the island's museum, or just spend your time strolling about the enchanting, historic island.


Activity Level : Light
Duration : 4 hours

Murano, Burano & Torcello Private Tour

Murano, Burano & Torcello Private Tour

Suggested activities for an additional cost, depending on your choice

This tour takes you to three must-see islands of the Venetian Lagoon: Murano, Burano, and Torcello. Murano has been famous for its glassmaking since the 10th century, which we'll help you explore. Then you'll see the colorful island of Burano, which is famous for its brightly colored houses, fishing industry and lacemaking. Third is Torcello, known as the “Mother of Venice.” You will have the chance to visit its basilica, one of the Lagoon's oldest churches, and home to beautiful mosaics, although you can instead focus on the island's museum, or just spend your time strolling about the enchanting, historic island.


Activity Level : Light
Duration : 4 hours

Day 13

Day 13 - Your Second Full Day in Venice

Venetian Tapas and Wine Tours

Suggested activities for an additional cost, depending on your choice

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, Venetian tapas, accompanied by wine at Venice's best Bacari, traditional wine bars.

Cicchetti and Wine Small Group Tour of Venice

Cicchetti and Wine Small Group Tour of Venice

Suggested activities for an additional cost, depending on your choice

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

Venice Food & Wine Group Tour

Venice Food & Wine Group Tour

Suggested activities for an additional cost, depending on your choice

See Venice from a local's point of view! this tour explores the Santa Croce and Dorsoduro districts, areas normally untouched by the tourist crowds. This is a perfect chance to follow the same bar route that Venetians do after work, or during special celebrations. This tour's food tasting takes place in "Bacari," traditional bars that offer the best selection of local dishes and cicchetti (tapas), often containing delicious fish cooked in traditional yet creative ways. Every food sample is accompanied with a drink: a true Venetian experience calls for prosecco, wine, and grappa!


Activity Level : Moderate
Duration : 3 hours

Dolomites Day Private Tour

Dolomites Day Private Tour

This Dolomites Day Group Tour includes the most famous towns and lakes in the dramatic Dolomite Mountains: Pieve di Cadore, Tre Cime, Cortina, Lake Misurina, Lake Auronzo. Enjoy a memorable day tour discovering Europe’s most beautiful mountains, the Italian Dolomites. These natural wonders will amaze you and will also give you a chance to get out of the city to see another side of Italy.


Activity Level : Moderate
Duration : 8 hours

Day 14

Day 14 - 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

(FOR PRIVATE GROUP) Venice Full Day Private Tour
Moderate9 hours
(FOR PRIVATE GROUP) Venice Lunch / Dinner
Easy1.5 - 2 hours
(FOR PRIVATE GROUP) Verona Full Day Private Tour
Light7 hours
Cortina and the Dolomites Day Group Tour
Moderate8 Hours

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.

Rome

3 Nights Accommodation
Breakfast (hotels only)
Rome Fiumicino Airport Transfer
Rome Twilight Walk with Gelato Group Tour
Colosseum, Roman Forum and Palatine Hill Group Tour
Pristine Sistine Early Entrance Small Group Vatican Tour
Rome - Naples Standard Class Train Ticket
Rome Train Station Transfer
Naples - Positano Private Transfer

Positano

3 Nights Accommodation
Breakfast (hotels only)
Positano - Naples Private Transfer

Naples

Naples - Florence Standard Class Train Ticket

Florence

Florence - Castellina Private Transfer

Castellina in Chianti

4 Nights Accommodation
Breakfast (hotels only)
Private Cooking Class with Professional Chef in Castellina in Chianti
Castellina - Florence Private Transfer

Florence

Florence City Private Walking Tour
Florence - Venice Standard Class Train Tickets

Venice

3 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 Mike & Kirsten

Mike & Kirsten

Nebraska

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :
5 / 5
Review by James & Jan

James & Jan

Texas

JayWay Travel plans your trip down to the smallest detail according to your wishes. Big time travel without the big group.

JayWay Travel plans your trip down to the smallest detail according to your wishes. Big time travel without the big group.

Year : 2019
Visited : Italy, Slovenia, Croatia
Itinerary : Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Zadar, Split, Korcula, Dubrovnik, Rome
Rating :
5 / 5
Year : 2019
Visited : Italy, Slovenia, Croatia
Itinerary : Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Zadar, Split, Korcula, Dubrovnik, Rome
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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