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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.

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.

Day 2

Day 2 - Your First Full Day in Rome

Focus on Ancient Rome with a group or private tour

Included in your vacation package price.

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.


Activity Level : Moderate
Duration : 3 Hours

Get Acquainted with Rome on a twilight tour

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

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.


Activity Level : Light
Duration : 2.5 hours

Day 3

Day 3 - Your Second Full Day in Rome

Rome and Catholicism

Suggested activities for an additional cost, depending on your choice

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 Museums and Sistine Chapel Private Tour

Suggested activities for an additional cost, depending on your choice

On this special excursion you'll be seeing one of the most impressive highlights in Rome: the Vatican. You'll skip the lines and have your own private guide to explain the history and significance of this amazing building and the works of art it contains. On this 3-hour excursion you'll be astounded by the wonderful spiritual and artistic experience that you'll have upon visiting this historic and religious site.


Activity Level : Light
Duration : 3 Hours

The Complete Vatican Group Tour with Vatican Museums, Sistine Chapel and St. Peter's Basilica

Suggested activities for an additional cost, depending on your choice

If you're going to see the most famous highlights in Rome, you'll want to do it on this tour with an expert guide. You'll explore the Sistine Chapel, the Vatican Museums, St. Peter's Basilica, St. Peter's tomb, and more. This is the complete Vatican experience. You'll skip the lines and have your own private guide to explain the history and significance of these amazing buildings and the works of art they contain.


Activity Level : Light
Duration : 3.5 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 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 Rome

4 Day Private Gourmet Tour - Guide and Driver
Light4 Days
Colosseum & Roman Forum Private Tour
Moderate3 Hours
Cooking Class in the Jewish District Group Tour
Easy3 hours
Eating in the Monti Neighborhood: A Pizza Tour Close to the Colosseum
Light2.5 hours

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 the Tuscan countryside.

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.


Activity Level : Moderate
Duration : 4 hours

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 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

Private Cooking Class with Professional Chef in Castellina in Chianti
Light3 hours
Siena and San Gimignano Full-day Private Tour from Castellina
Moderate8 hours

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 are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.

Florence is the capital of Tuscany and home to the region’s greatest Renaissance art and architecture. The Renaissance actually started here, and today the city’s numerous cathedrals and art galleries show the evidence of this rich and inspiring period. You’ll want to see the Duomo Cathedral and the Galleria dell’Accademia, which houses Michelangelo’s “David.” Botticelli and Da Vinci are here too, at some of the city’s other amazing galleries. But there’s more to do in Florence than simply admire the art. It’s a beautiful, romantic place, and even a stroll through the streets is charming. Add world-class restaurants, delectable local wine and cuisine, and a warm Tuscan welcome, and you have a destination unlike any other. Florence is also an ideal base for exploring Tuscany, with its picturesque hills and vineyards in the heart of Italy.

Day 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

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 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!


Activity Level : Moderate
Duration : 3 Hours

Day 7

Day 7 - Your First Full Day in Florence

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

Florence Museums, the Cradle of the Renaissance

Suggested activities for an additional cost, depending on your choice

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

Suggested activities for an additional cost, depending on your choice

This three-hour guided tour of the Academia Gallery is a great way to experience the rich artistic culture and history of Florence. You'll meet your guide at your hotel, then walk for an hour in the beautiful Florence city centre and then to the gallery. The statue of David is definitely the most famous work on display, but it's certainly not the only thing worth seeing. Have your questions at the ready! After the tour you can stay in the museum to admire the art on your own.


Activity Level : Light
Duration : 3 hours

Uffizi Gallery Private Tour

Suggested activities for an additional cost, depending on your choice

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. Have your questions at the ready! After the tour you can stay in the museum to admire the art on your own.


Activity Level : Light
Duration : 3 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

Chianti Half-day Afternoon Group Tour
Moderate5.5 hours
Cinque Terre Group Excursion
Light14 hours
Cinque Terre Private Day Trip
Light10 Hours
Dinner in Chianti Vineyards Group Tour
Light5.5 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
Rome - Tuscany Private Transfer with a stop in Orvieto

Castellina in Chianti

2 Nights Accommodation
Breakfast (hotels only)
Castellina - Florence Private Transfer

Florence

2 Nights Accommodation
Breakfast (hotels only)
Florence City Private Walking 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.

Holly & Michael

Boston, MA

JayWay made our honeymoon planning so carefree: once we got to Croatia we knew everything was already taken care of! We enjoyed all of the extra excursions and insider knowledge suggested to us as well as all of the hotels and apartments we stayed at. To think of planning a trip of this magnitude while also planning my wedding was overwhelming. I am so very thankful for JayWay and the team that helped make our honeymoon so memorable.

JayWay made our honeymoon planning so carefree: once we got to Croatia we knew everything was already taken care of! We enjoyed all of the extra excursions and insider knowledge suggested to us as well as all of the hotels and apartments we stayed at. To think of planning a trip of this magnitude while also planning my wedding was overwhelming. I am so very thankful for JayWay and the team that helped make our honeymoon so memorable.

Year : 2013
Visited : Croatia
Itinerary : Dubrovnik, Korcula, Hvar, Trogir
Rating :
5 / 5
Year : 2013
Visited : Croatia
Itinerary : Dubrovnik, Korcula, Hvar, Trogir
Rating :
5 / 5

Marjorie & Eric

Virginia

Everything was seamless. That's the way we like it. Also, we prefer to explore on our own, and JayWay provided the information we needed to do that. Everyone responded when we needed them, including Jay.

Everything was seamless. That's the way we like it. Also, we prefer to explore on our own, and JayWay provided the information we needed to do that. Everyone responded when we needed them, including Jay.

Year : 2015
Visited : Czech Republic, Austria, Hungary
Itinerary : Prague, Vienna, Budapest
Rating :
5 / 5
Year : 2015
Visited : Czech Republic, Austria, Hungary
Itinerary : Prague, Vienna, Budapest
Rating :
5 / 5

Nicholas & Elizabeth

Missouri

Worry free perfect way to organize a trip in an unfamiliar place.

Worry free perfect way to organize a trip in an unfamiliar place.

Year : 2018
Visited : Croatia
Itinerary : Dubrovnik, Split, Hvar, Split
Rating :
5 / 5
Year : 2018
Visited : Croatia
Itinerary : Dubrovnik, Split, Hvar, Split
Rating :
5 / 5

Dave and Family

Indiana

Interest and response of staff to questions and requests was outstanding.  Very friendly and helpful.  Their communications with drivers, etc. enabled seamless transportation and transfers. City tours of 1.5 - 2 hours were the right length with good informative content.  Recommendation for travel-day stops were very good. JayWay applies their knowledge of the country to help guide an outstanding trip.  Services and transfers arranged by their attentive staff are executed easily and on-time, making the travel experience easy and pleasant.

Interest and response of staff to questions and requests was outstanding.  Very friendly and helpful.  Their communications with drivers, etc. enabled seamless transportation and transfers. City tours of 1.5 - 2 hours were the right length with good informative content.  Recommendation for travel-day stops were very good. JayWay applies their knowledge of the country to help guide an outstanding trip.  Services and transfers arranged by their attentive staff are executed easily and on-time, making the travel experience easy and pleasant.

Year : 2016
Visited : Croatia
Itinerary : Dubrovnik, Dubrovnik, Hvar, Split, Pag, Plitvice, Zagreb
Rating :
4.8 / 5
Year : 2016
Visited : Croatia
Itinerary : Dubrovnik, Dubrovnik, Hvar, Split, Pag, Plitvice, Zagreb
Rating :
4.8 / 5

Alan, Barbara, Cynthia & John

Connecticut

JayWay Travel created a wonderful itinerary with great service, great local guides, great accommodations, at a great price. We will definitely recommend JayWay Travel, which we chose after careful internet research.

JayWay Travel created a wonderful itinerary with great service, great local guides, great accommodations, at a great price. We will definitely recommend JayWay Travel, which we chose after careful internet research.

Year : 2018
Visited : Poland
Itinerary : Krakow, Wroclaw, Poznan, Gdansk, Warsaw
Rating :
5 / 5
Year : 2018
Visited : Poland
Itinerary : Krakow, Wroclaw, Poznan, Gdansk, Warsaw
Rating :
5 / 5

Patricia & Roberta

California

The staff person who helped us plan the itinerary, was enormously helpful, knowledgeable about how to plan the trip; how long to stay in certain places, etc. He was also very patient when we made changes to our itinerary and/or our accommodations. We literally couldn't have planned the trip without him. An enormously helpful, informative, travel service that is essential for anyone traveling to countries they are not familiar with.

The staff person who helped us plan the itinerary, was enormously helpful, knowledgeable about how to plan the trip; how long to stay in certain places, etc. He was also very patient when we made changes to our itinerary and/or our accommodations. We literally couldn't have planned the trip without him. An enormously helpful, informative, travel service that is essential for anyone traveling to countries they are not familiar with.

Year : 2018
Visited : Croatia, Italy
Itinerary : Dubrovnik, Korcula, Hvar, Split, Trogir, Plitvice, Rovinj, Venice
Rating :
5 / 5
Year : 2018
Visited : Croatia, Italy
Itinerary : Dubrovnik, Korcula, Hvar, Split, Trogir, Plitvice, Rovinj, Venice
Rating :
5 / 5

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