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 of what our trips are like, and the opportunities our destinations provide.
One of our team members in the region will be available to you leading up to and during your 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 SIM that you can use to reach your local JayWay contact (who you will meet in person) throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 star 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.
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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
Castellina in Chianti
Florence
package excludes:
- Flights from and to your home country.
- 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
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 destination-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
Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.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.3 Nights in Rome
3 Nights 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.
Cinematic Night
To start off your Rome adventure, we suggest an easy introduction of an aperitivo or bar on a short walk. Bar San Calisto is where La Grande Bellezza movie was shot and its a very famous bar of Trastevere - make sure to try their amazing granita di caffe with panna! If you're a fan of The Talented Mr. Ripley you'll find these locations look familiar: Cafe Latino in Rome (The Vesuvio nightclub) and the cafe where Freddie turns up, on Piazza Navona opposite Bernini's Fountain of the Four Rivers. Huge hit Eat, Pray, Love was partially shot in Rome, and if you want to follow the food footsteps of the movie, here is a short guide: San Crispino (gelato), Vechio Orso and Santa Lucia trattorias.
Day 2
Day 2 - Your First Full Day in Rome

Premium Colosseum, Roman Forum and Palatine Hill Group Tour
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.
Gourmet Experiences
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.

Guided Group Wine & Food Pairing Dinner Near the Pantheon
This 2.5-hour tour and degustation is perfect for foodies. You'll start with an aperitif as you soak up the atmosphere. Then you'll head 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!

Group Food Tour - Campo de' Fiori, Jewish Ghetto, Trastevere
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.
Day 3
Day 3 - Your Second Full Day in Rome

Vatican Early Morning Small Group Tour
Your semi-private early morning Vatican tour begins near the entrance of the Vatican Museums, where you will meet your expert guide. Explore the Pinecone Courtyard, Octagonal Courtyard, and galleries filled with masterpieces, including the Laocoön, Apollo Belvedere, and the Belvedere Torso. Visit the Sistine Chapel, where you can admire Michelangelo’s breathtaking ceiling frescoes and “The Last Judgement” before the crowds arrive. The tour continues through the Raphael Rooms and St. Peter’s Basilica, where you will see Michelangelo’s Pietà, Bernini’s Baldacchino, and the grandeur of Piazza San Pietro.

Welcome to Rome - Group City Stroll with Gelato Tasting
Join an intimate Rome walking tour designed to acquaint you with the Eternal City at the outset of your journey. Explore the foremost attractions while savoring a delightful gelato tasting experience. Wander through the Pantheon, Trevi Fountain, Spanish Steps, Piazza Navona, and encounter remnants of Ancient Roman history along this leisurely excursion, limited to just 15 fellow travelers.
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 Castellina in Chianti. The whole journey takes around 6 hours. Please note that this is a non guided transfer.

2 Nights in Castellina in Chianti
2 Nights 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
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 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.

Day 5
Day 5 - Your First Full Day in Castellina in Chianti

Siena Half-day Private Tour from Castellina
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.
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 accommodations to transfer you to the capital of the Tuscany region, Florence. The journey will take about 1 hour. If you'd like to make a day of out it, for an additional fee we can arrange some stops on the way in the Tuscan hills.
2 Nights in Florence
2 Nights 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
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.
Day 7
Day 7 - Your First Full Day in Florence

The Cradle of the Renaissance
Get to know some of Florence's most spectacular treasures with the help of a private guide at the Uffizi Gallery. Your knowledgeable guide will explain the works of the greatest artists from the Middle Ages to the Renaissance: Cimabue, Giotto, Botticelli, Leonardo da Vinci, Michelangelo, Raphael, Titian, and many more. You'll see world-famous paintings that you've seen on television and in advertisements. Looking at the most famous artworks of the period, you'll understand why Florence is the birthplace of the Renaissance.

Homemade Pasta Group Cooking Class
Learn to make fresh pasta in the heart of Florence with a fun and authentic Italian experience. Join this hands-on cooking class along the Arno River, where expert chefs will guide you in crafting ravioli, fettuccine, and tortelli from scratch. Discover the secrets of perfect sauces like classic Pommarola and rich Burro e Salvia, then sit down to enjoy your homemade pasta paired with organic Tuscan wine from a family farm. With personal attention, this immersive experience will give you the skills and confidence to recreate authentic Italian dishes at home.
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.
Glowing Reviews from Our Guests
Average of our Guest's Ratings of tour packages including these destinations

The whole trip was so well done 👍. Cost versus quality was right on
– David, Donna, Daniela, BRIAN, Rose, Jason & Dana, West Virginia
Visited : Italy
Itinerary : Rome, Florence, Venice
Rating :

You planned a perfect trip for us thank you everyone we dealt with were great the guides Georgina was so helpful it really was planned well
– Victoria & Angela, Massachusetts
Visited : Italy
Itinerary : Rome, Florence, Sorrento, Rome
Rating :

Using JayWay travel takes the guesswork and stress out of the planning with no anxiety for transfers, excursions and experiences. They made our trip seamless. I can't imagine making this journey with out them.
– Patty & Brian, Georgia
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Ischia, Naples
Rating :