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One Week Rome & Tuscany Tour

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. Our Destination Manager in the region provides assistance before and during your travels. They will be available to you leading up to the trip to answer any questions and arrange local services. You will be provided with information on the best these destinations have to offer including things to see and do, restaurants, entertainment and other insider tips. Upon arrival we will provide you with a local cell phone that you can use to contact our Destination Manager throughout your trip. In all of our destinations we offer a variety of accommodation options including boutique style hotels, charming B&Bs and spacious apartments ranging from a three to five star level. From our first hand experience we can ensure they are all clean, comfortable and centrally located. We generally discourage chain hotels but provide accommodations with unique features or an authentic feel.
Italy
• Rome
• Castellina in Chianti
• Florence

Itinerary


3 Nights in Rome

Day 1

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.

Included : Rome Fiumicino Airport Transfer

Day 2

First Time in Rome
You'll be introduced to the layout and history of Rome today. Riding comfortable Brompton city bikes through the picturesque cobbled streets of the historical center of Rome flanked by beautifully built aristocratic palazzi, our eyes will be enchanted by the white travertino marble churches and they will feast on the famous variety of colours that make Rome unique. This tour is designed to get you oriented in the city and the main sights in the great center of Rome without duplicating the city's signature attractions such as the Colosseum and Roman Forum and the Vatican. On this tour you'll learn all about Villa Borghese, Piazza di Spagna and the Spanish Steps, the Pantheon, Piazza Farnese and Piazza Navona as well as getting a little outside the obvious and crossing over the Tiber to the Trastevere neighborhood.

The Might of Rome Private Bike Tour
The Might of Rome Private Bike Tour
Maximum group size : 4
Duration : 3 Hours
Activity level : Moderate
Included in your
vacation package
Optional: Get Acquainted with Rome on a twilight tour
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.

Rome Twilight Walk with Gelato Group Tour
Rome Twilight Walk with Gelato Group Tour
Duration : 2.5 hours
Activity level : Light
Included : The Might of Rome Private Bike Tour

Day 3

Optional: Focus on Ancient Rome with a group or private tour
Rome's origin story unfolds when you visit the Colosseum and the adjacent Roman Forum. Hear about life in ancient Rome and soak in the grandeur of these testaments to a lost civilisation. We can arrange for a private guide to explain how the Colosseum was built and what happened to it in the years since. Afterwards the tour proceeds to the Roman Forum, the center of political life of the city and ultimately the Empire, finding out the different purposes of the buildings whose columns and porticos still stand today. If you'd prefer the atmosphere of a group tour, which for parties of 4 or fewer can also save some money, we can instead arrange for spaces on a tour by a reputable group tour company.

Colosseum & Roman Forum Private Tour
Colosseum & Roman Forum Private Tour
Maximum group size : 12
Duration : 3 Hours
Activity level : Moderate
Colosseum, Roman Forum and Palatine Hill Group Tour
Colosseum, Roman Forum and Palatine Hill Group Tour
Duration : 3 Hours
Activity level : Moderate
Optional: Rome and Catholicism
It's hard to miss the dome of St Peter's, and it's the first thing you see when arriving in Rome by plane. It really is an ever-present reference point on the city's skyline. Vatican City is the spiritual and administrative center of the Roman Catholic Church. Technically a separate state and surrounded by stone walls, the Vatican is a must-see.

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

Vatican Private Tour
Vatican Private Tour
Maximum group size : 12
Duration : 3 Hours
Activity level : Light
The Complete Vatican Group Tour with Vatican Museums, Sistine Chapel and St. Peters Basilica
The Complete Vatican Group Tour with Vatican Museums, Sistine Chapel and St. Peters Basilica
Duration : 3.5 hours
Activity level : Light

Day 4

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 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.
Included : Rome - Tuscany Private Transfer with a stop in Orvieto
Rome

A little about 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.

2 Nights in Castellina in Chianti

Day 1

Your driver will bring you to your accommodation in the Tuscan countryside.

Day 2

Optional: See Siena with a Private Guide
Besides Florence, the second most important city in Tuscany is Siena. Famed for the Palio di Siena, a twice yearly horserace that pits neighbor against neighbor, this historic hilltop town is packed with things to see. To ensure you don't miss anything, we can arrange for a private guide to meet you and spend a couple of hours explaining the history of the town and its surroundings. Once you book your trip you'll find suggestions of some of our favorite Siena eateries in your guest page too.

Siena Private Walking Tour
Siena Private Walking Tour
Duration : 2 hours
Activity level : Light
Optional: Montalcino, Montepulciano and Pienza
Spend a day exploring the Tuscan countryside south of Siena, with a couple of winery visits in the the renowned denominations of Montalcino, famous for its Brunellos and Montepulciano, known for its Vino Nobile wines. Between the two you'll find Pienza, an idyllic Tuscan village synonymous with Pecorino cheese. With all these gastronomic delights you're bound to have a delicious day. If you'd prefer not to do the driving we can arrange for a private driver to take you around and open a few doors in places that are even more authentic.

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Trequanda
Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Trequanda
Duration : 7 hours
Activity level : Light

Day 3

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.
Included : Castellina - Florence Private Transfer
Castellina in Chianti

A little about 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.

2 Nights in Florence

Day 1

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 get to see all of the most iconic buildings and works of art in Florence. You'll be picked up from you accommodation and your guide will lead you through the city streets. The tour will either conclude at the Academy Museum or at the Uffizi Gallery, where you'll admire some of the most famous works of art in the world. We recommend wearing walking shoes, and don't forget your camera!
Florence City Private Walking Tour
Florence City Private Walking Tour
Duration : 3 Hours
Activity level : Moderate
Included in your
vacation package

Included : Florence City Private Walking Tour

Day 2

Optional: Cook with a local chef
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.

Market Tour and Cooking Class Small Group Tour
Market Tour and Cooking Class Small Group Tour
Duration : 5.5 Hours
Activity level : Light
Optional: Florence Museums, the Cradle of the Renaissance
Florence hosts some of the most interesting and popular museums in the world. The Accademia is most famous for Michaelangelo's David, and the Uffizi Gallery has must-see works from the Renaissance. Both are worth a visit. Thanks to the quality and amount of artwork in each museum, we suggest visiting one per day, ideally with a private guide (which will also allow you to skip the long lines) in combination with a walking tour of the historical center.

Other great museums include the Palazzo Pitti, a magnificent Renaissance complex, and the largest museum complex in Florence. It contains the interesting Museum of Costume and Fashion. The Jewish Museum documents the history of the Jews in Florence over the centuries and their relationship with the city. The collection includes furniture, textile, and silver used for ceremonies between the end of the sixteenth and nineteenth centuries.

Accademia Gallery Private Tour
Accademia Gallery Private Tour
Duration : 3 hours
Activity level : Light
Uffizi Gallery Private Tour
Uffizi Gallery Private Tour
Duration : 3 hours
Activity level : Light

Day 3

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

A little about Florence

Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci are here too, at some of the city’s other amazing galleries. 

But there’s more to do in Florence than admire art. It’s a beautiful and very romantic place, and even a stroll through the streets is charming. Add a handful of world-class restaurants, delectable local wine and cuisine, and that warm Tuscan welcome, and you have a destination unlike any other. Visiting Florence also perfectly situates you for exploring Tuscany. There are many easy day trips that will take you through picturesque landscapes of hills and vineyards in the heart of Italy.

What's Included

Below you will find all the services provided as part of your complete vacation package.

Should you wish to add any optional tours and excursions listed on the Itinerary tab, please let us know.


  • 3 Nights Accommodation in Rome
  • Rome Fiumicino Airport Transfer
  • The Might of Rome Private Bike Tour
    Duration : 3 Hours
    Includes : Guide, Brompton city bike hire, Helmet
    Excludes : Tip for a guide
  • Rome - Tuscany Private Transfer with a stop in Orvieto
  • 2 Nights Accommodation in Castellina in Chianti
  • Castellina - Florence Private Transfer
  • 2 Nights Accommodation in Florence
  • Florence City Private Walking Tour
    Duration : 3 Hours
    Includes : English-speaking guide
    Excludes : Tip for the guide
  • Florence Airport Transfer
  • Pre-trip assistance of the JayWay Destination Manager.
  • On-trip assistance from local JayWay Representatives.
  • A pre-paid local cell phone for all destinations.
  • Excursion booking advice and assistance.
  • Access to your personalized Guest Page, containing detailed destination information and tips on the best that these cities can offer.


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