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A Week in Central Italy

This sample week-long itinerary combines some time in Italy's magnificent capital Rome, a drive to Castellina in Chianti, a quintessential Tuscan hilltop town where you'll enjoy a couple of days in the countryside before heading to the last stop on your tour, Florence. The services we provide as part of our comprehensive packages include accommodations, transfers (airport, long distance) and city tours. 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, Castellina in Chianti, Florence 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.

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 Small Group Tour

Rome Twilight Walk with Gelato Small 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, on this relaxed tour with 15 other people at most.


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 2

Day 2 - Your First 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

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 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

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 4

Day 4 - Traveling to Castellina in Chianti by Private Transfer

It's time to bid arrivederci to the eternal city as you're headed for the hills of Tuscany, one of the loveliest parts of Italy. Your driver will pick you up from your accommodation in Rome and you will head north on the highway, taking a small detour at around halfway, to visit UNESCO-listed Orvieto, a medieval gem famed for its gothic cathedral and stunning frescoes. You'll have a couple of hours of free time here to sight-see before continuing your journey to your accommodation in Tuscany. The journey till the first stop takes about 2 hours. After your stop in Orvieto you will continue your way to Tuscany. The journey takes around 6 hours.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.

Castellina in Chianti by Private Transfer with a stop in Orvieto
We also offer the following excursions in Rome

2 Hour Private Photo Session
Easy2 hours
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

2 Nights in Castellina in Chianti

2 Nights in Castellina in Chianti

3 days in Castellina in Chianti

2 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 4

Day 4 - 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.

Time-Travelling in Monteriggioni

Suggestion to explore on your own

Monteriggioni represents one of the most important walled castles in the area. Its structure has been preserved intact, as if time had never passed on the hill from which it elegantly dominates the surrounding landscape. This particular castle is famous for being cited by the “Supreme Poet” Dante Alighieri in his most famous work, The Divine Comedy.

The perfectly circular castle was built by the Sienese between 1213 and 1219 for defensive purposes: its strategic location atop a hill overlooking the Cassia Road allowed the castle to control the cities of the Val d’Elsa and Staggia and be on the lookout for any armies approaching Siena.

The intact fortified wall presents 14 towers, protecting the village. Now, it's an ideal lunch spot along the renowned "Via Francigena" hiking trail, which crosses central Italy from Rome to the Alps and beyond.

Time-Travelling in Monteriggioni

Day 5

Day 5 - Your First Full Day in Castellina in Chianti

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

Siena Half-day Private Tour from Castellina

Siena Half-day Private Tour from Castellina

Included in your vacation package price.

There's no better way to explore the beautiful city of Siena than with a private local guide. A half-day trip is the perfect amount of time for this excursion. You'll tour the city and see the most impressive buildings and monuments while your guide fills you in on the history and most interesting stories from the city's past. This being Italy, there are plenty of opportunities for delicious local cuisine, and you'll get a chance to stop for a sumptuous lunch along the way. To conclude this five-hour excursion you'll be driven back to you accommodation.


Activity Level : Moderate
Duration : 4 hours

Day 6

Day 6 - Traveling to Florence by Private Transfer

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 Cooking Class with Professional Chef in Castellina in Chianti
Light3 hours
Private Day Trip to Florence
Light8 hours
Siena and San Gimignano Full-day Private Tour from Castellina
Moderate8 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'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 6

Day 6 - Arrival in Florence

Upon reaching Florence your driver will take you as close as possible to your accommodation. As the city has several pedestrian only areas so you may need to walk a short way to your accommodation, depending on its location.

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

Day 7

Day 7 - Your First Full Day in Florence

Uffizi Gallery Private Tour

The Cradle of the Renaissance

Included in your vacation package price.

This three-hour guided tour of the Uffizi Gallery is a great way to experience the rich artistic culture and history of Florence. You'll meet your guide at your hotel or at the gallery, then walk through the gallery together. There are numerous world-famous masterpieces on display that you're sure to recognize. After the tour you can stay in the museum to admire the art on your own.


Activity Level : Light
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 8

Day 8 - Departure Day

A driver will pick you up at your accommodation based on your flight time and transfer you to Florence airport for your departure.

We also offer the following excursions in Florence

Accademia Gallery Private Tour
Light3 hours
Buildings on the Arno Private Photo Tour
Light4 hours
Cinque Terre Private Day Trip
Light10 Hours
Cinque Terre Small Group Tour
Moderate11 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
Colosseum, Roman Forum and Palatine Hill Group Tour
Pristine Sistine Early Entrance Small Group Vatican Tour
Rome - Tuscany Private Transfer with a stop in Orvieto

Castellina in Chianti

2 Nights Accommodation
Breakfast (hotels only)
Siena Half-day Private Tour from Castellina
Castellina - Florence Private Transfer

Florence

2 Nights Accommodation
Breakfast (hotels only)
Florence City Private Walking Tour
Uffizi Gallery Private Tour
Florence 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 Linda, Robert, William & Carmen

Linda, Robert, William & Carmen

Colorado

If you want a worry-free vacation, choose JayWay Travel. They go the "extra mile" to make your vacation so enjoyable and so memorable!

If you want a worry-free vacation, choose JayWay Travel. They go the "extra mile" to make your vacation so enjoyable and so memorable!

Year : 2019
Visited : Italy
Itinerary : Rome, Cruise, Rome, Siena, Florence, Lake Como
Rating :
5 / 5
Year : 2019
Visited : Italy
Itinerary : Rome, Cruise, Rome, Siena, Florence, Lake Como
Rating :
5 / 5
Review by Megan & Jason

Megan & Jason

Missouri

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :
4.8 / 5
Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :
4.8 / 5

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