Tuscany

Explore the Cities and Towns of Tuscany

Licensed & Certified

We work exclusively with accredited guides and professional chauffeurs across Italy.

Local Knowledge

Our team lives and works here, offering insight beyond the landmarks.

Tailored for You

Every itinerary is thoughtfully crafted around your pace, from private dawn tours to intimate vineyard tastings.

Overview

Tuscany is among the most beautiful regions of Italy. The gentle curves and slopes of the land will enchant you. Tuscany is as famous for its wine and cuisine as it is for its landscapes. Wine production focuses on red wines like Chianti, San Giovese, Rosso di Montalcino, Rosso di Montepulciano, Bolgheri, and others.

Food is prepared with seasonal ingredients and enjoyed quietly by charming views. There are many medieval towns and castles, and in each of them you can find a treasure or two; it can be a painting by a famous artist hidden in an unusual church, a meal prepared by a passionate cook, or a great conversation with a local - whatever it is, for sure will be genuine.

Journeying through the hills and valleys, discovering the beauty of the land and the calm within yourself has attracted seekers of life and love to beautiful Tuscany for many years. The tradition continues to this day, and Tuscany welcomes them with her open arms. Major attractions: small and bigger medieval towns including Siena, San Gimignano, Monteriggioni, Volterra, Certaldo, Greve in Chianti, Montalcino, Montepulciano, Cortona, Pienza, and many others. Major festivals and events: Siena's Palio horse race, Puccini's Summer Opera Festival in Torre del Lago, Arezzo's Saracen Joust, Estate Fiesolana Music Festival, Cortona music and food festival, other local festivals.)

Gallery

Wonderful Val DOrcia Tuscany

Experience the Decadence of Tuscany

Tuscany Countryside, Italy

Experience the Incredible Val DOrcia in Tuscany

Southern Tuscany landscape in Spring

Castiglion Fiorentino

Terme di San Filippo - San Filippo Natura Hot Springs, Tuscany

Val D'Orcia

Viareggio

Volterra

Arrezzo Bagno Vignoni Barga Carrara Castiglion Fiorentino Chianciano Terme Chianti Cortona Elba Island Fiesole Florence Livorno Lucca Maremma Montalcino Montecatini Montepulciano Monteriggioni Monticchiello Pienza Pietrasanta Pisa Porto Santo Stefano San Gimignano San Miniato Saturnia Siena Terme di San Filippo - San Filippo Natura Hot Springs, Tuscany Val D'Orcia Viareggio Volterra

Our Multi-Day Holidays Tours

TUR-02137

Christmas in Rome & Maremma: A Spa and Shopping Escape

Experience the best of Rome and Tuscany on this 10-day holiday tour. Shop the festive streets of Rome, explore iconic sights, and visit Christmas markets. Then relax in Maremma’s luxury spa resorts, enjoy wine tastings, and discover charming Tuscan v...

Private

10 Days / 9 Nights

PRICING

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TUR-01985

The Best of Florence & Tuscany

"This is a fantastic option for those who wish to explore Florence and Tuscany without the hassle of driving. We take care of everything from the beginning to the end, ensuring that you get to see some of the most stunning locations in this beautiful...

Private

6 Days / 5 Nights

STARTING FROM

€2,550 per person

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TUR-02034

New Year's Eve in Florence

Experience the magic of Florence this New Yearâ€™s Eve with a luxurious 5-day getaway. From private transfers to exclusive tours and unforgettable celebrations...

Private

5 Days / 4 Nights

PRICING

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TUR-01200

Treasures of Tuscany & Gourmet Delights of Emilia Romagna Educational Trip

This is an educational tour designed for travel agents, travel writers, and other travel professionals. The tour is centered around exploring a unique area in Tuscany called Maremma, which is known for its beautiful hot springs. Along with the lesser...

Private

8 Days / 7 Nights

STARTING FROM

€1,580 per person

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TUR-01659

Absolute Italy Escorted Tour, October 25th - November 5, 2025

Absolute Italy includes The Amalfi Coast, Capri, Pompeii, Rome, Tuscany, Florence & Venice. It's a fantastic way to see the best of Italy in comfort and style with private transfers and a mix of private and small group tours.

Small Group

12 Days / 11 Nights

STARTING FROM

€4,990 per person

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TUR-01435

Absolute Italy from Venice to the Amalfi Coast including Florence, Tuscany, Rome, Vatican City, Pompeii and Capri

This tour is a once-in-a-lifetime experience in Italy that starts in Venice and ends on the stunning Amalfi Coast. The tour has an array of highlights, including visits to the islands in the Venetian Lagoon, art galleries in Florence, a private tour...

Semi-Private

11 Days / 10 Nights

STARTING FROM

€4,500 per person

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TUR-01425

Florence, Tuscany and the Italian Riviera

A classic introduction to the must-see sites of Tuscany and Cinque Terre. From the wine-growing lands of Chianti and Val d'Orcia to the Renaissance splendour and the museums of Florence, the tour ends in the incredible natural beauty of the Italian...

Private

10 Days / 9 Nights

STARTING FROM

€5,450 per person

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TUR-01383

Treasures of the Etruscans: Undiscovered Central Ital: November 15 - 21, 2023

During this educational experience we offer for travel professionals, you will travel from the very heart of the Roman Empire, center of the Catholic faith into the volcanic, wine-producing regions that were once the homelands of the ancient Etruscan...

Private

7 Days / 6 Nights

STARTING FROM

€1,530 per person

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TUR-01522

11 days in Italy: from Venice to the Amalfi Coast

Experience the art, history, and beauty of Venice, Florence, and Rome with group tours and private accommodations, followed by private tours of the natural splendor of the Amalfi Coast and the island of Capri - 10 incredible nights.

Private

11 Days / 10 Nights

PRICING

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TUR-01352

Absolute Italy: Mostly Private Tour of Italy including the Amalfi Coast - Capri - Pompeii - Rome - Tuscany - Florence and Venice

Private

11 Days / 10 Nights

PRICING

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TUR-01333

Wine Estates, Culture and Fun in Tuscany and the Cinque Terre!

This 9 night/10 day tour begins in Rome and includes some of Italy's most incredible Etruscan towns, hot-springs and forgotten (though incredibly beautiful) coastal areas that few visitors to Italy ever experience. Highlights of the tour include sta...

Private

10 Days / 9 Nights

STARTING FROM

€2,960 per person

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TUR-01971

Tuscany Mini-Stay

A brief retreat to Tuscany promises a delightful blend of Renaissance art, rolling vineyards, and charming medieval towns. This mini holiday in Tuscany provides a perfect taste of the region's art, culture, and culinary delights in just a few memorab...

Private

3 Days / 2 Nights

PRICING

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Our Private and Small Group Tours

TUR-01743

The Best of the Chianti: Radda, Panzano, Greve and Castellina in Chianti with Optional Wine Tastings

The Chianti region of Tuscany is truly glorious and best experienced with a local, licensed driver who knows the area.

Private

PRICING

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TUR-01585

Private Half Day tour of Florence

Would you like a personalized private tour of Florence?

Private

3 Hours

PRICING

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TUR-01034

Private Full Day Tour of Tuscany from Rome

This is a private, full-day tour of Tuscany from Rome and it is one of the very best and most comfortable ways to see Tuscany from Rome.

Private

11 Hours

PRICING

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TUR-00553

Piety and Patronage Tour

Itinerary: Convent of San Marco, Cenacolo di Sant'Apollonia and the Chiostro dello Scalzo. If you are interested to see how friars and nuns lived in Renaissance Florence and to explore museums off the beaten path, then this is the tour for you. Explo...

Private

3 Hours

STARTING FROM

€240 per person

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TUR-01612

Private Tour of the Uffizi Gallery in Florence

Experience the art of Renaissance like never before with our exclusive private tour. Get special VIP entrance tickets and immerse yourself in the greatest collection of Renaissance art ever assembled. Don't miss this once-in-a-lifetime opportunity to...

Private

3.5 Hours

STARTING FROM

€240 per person

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TUR-01413

Gourmet Tuscany: Truffle Hunting Followed by Cooking Class and Lunch

A wonderful morning of truffle hunting, cooking and wine tasting in the beautiful Tuscan countryside.

Semi-Private

4 Hours

STARTING FROM

€210 per person

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TUR-02140

Montalcino Cooking Experience

Join us in the heart of the Brunello di Montalcino region for a refined culinary immersion on a historic vineyard estate. Beginning with a guided tour of the cellar and vineyards, you will then don your apron to create classic Tuscan dishes — working...

Semi-Private

PRICING

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TUR-02125

The Original Florence Street Food & Local Market Tour

Step into Florence the way locals doâ€”with food as your guide and the streets as your dining room. The Florence Morning Street Food Tour is a three-hour journey through bustling markets...

Small Group

3 Hours

PRICING

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TUR-00990

Tuscany: Siena & San Gimignano from Florence or Livorno

This tour of Tuscany begins in either Livorno or Florence and includes a visit to two of Tuscany's most beautiful towns Siena and San Gimignano which are right in the heart of the beautiful Tuscan countryside inside the Chianti wine territory. Over t...

Private

8 Hours

STARTING FROM

€220 per person

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TUR-01615

Private Half Day Tour of Florence with the Accademia Gallery

Discover the Florence of the Medici family with a skip-the-line entrance ticket to see Michelangelo's David sculpture.

Private

3 Hours

PRICING

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TUR-01437

Bagnoreggio and Orvieto Shore Excursion

This is a wonderful tour for those looking for an alternative to Rome during their shore excursion from Civitavecchia. In the comfort of a luxury vehicle visit Civita di Bagnoreggion and Orvieto, two of Italy's most ancient Etruscan settlements, and...

Private

7 Hours

STARTING FROM

€200 per person

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TUR-01110

Experience the Best of Central Italy's Coastal Towns with Cooking and Wine Estate Visit from Civitavecchia

This is an awesome tour we have put together that takes passengers arriving off of the cruise at Civitavecchia north along the Tuscan coast to the beautiful sea-side town of Porto Santo Stefano which is a gorgeous sea-side town with spectacular views...

Private

9 Hours

STARTING FROM

€175 per person

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Our Featured Properties

Italy,Tuscany,Cortona

Villa

La locanda del gelsomino

9 Beds 12/18

Air Conditioning +5 more

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Italy,Tuscany,Val D\'Orcia

Villa

Villa Dolce Vita Pienza Tuscany

6 Beds 6 Baths 12

Air Conditioning +13 more

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Italy,Tuscany,Chianti

Villa

Villa Castrum

5-7 Beds 10-14

Air Conditioning +4 more

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Italy,Tuscany,Montepulciano

Apartment

Casa Divina

2 Beds 2 Baths 4

Air Conditioning +9 more

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Italy,Tuscany,San Gimignano

Estate

Apartment Virgo

1 Beds 1 Baths 3

Air Conditioning +7 more

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Italy,Tuscany,Livorno

Villa

Villa Bellissimo Palazzo

10 Beds Yes Baths 20

Air Conditioning +15 more

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Italy,Tuscany,Livorno

Villa

Villa Giovanile

8 Beds 8 Baths 16

Elevator (Lift) +10 more

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Italy,Tuscany,Montepulciano

Apartment

Giardino Blu

2 Beds 1 Baths 5

Air Conditioning +8 more

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Italy,Tuscany,Bagno Vignoni

Villa

Villa in Val D'Orcia

8 Beds 21

BBQ +10 more

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Italy,Tuscany,Pienza

Villa

Villa Pienza

4 Beds 10

BBQ +10 more

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Italy,Tuscany,Arrezzo

Villa

La Dimora Regale 2

2 Beds 2 Baths 4+2

Air Conditioning +11 more

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Italy,Tuscany,Florence

Apartment

Casa delle Brezze

2 Beds 2 Baths 4

Air Conditioning +12 more

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Popular Transfer Routes in Tuscany

Most requested private transfer services across the region

Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Tuscany and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.

Florence Rome

Private Transfer

Florence Siena

Private Transfer

Florence Pisa

Private Transfer

Florence Lucca

Private Transfer

Don't see your route? We cover all of Italy.

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“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS team took a huge burden off of me! I would like to start of by saying "THANK YOU" both for the amazing job you did on our trip. There was n”

[Read More] Ann Brownell, KHM Travel Group

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and flying to Rome where honestly 4 days is NOT enough. They keep saying to spend more time and we could not agree more! You need to spend more ti”

[Read More] Robin and Kumi Bruun, Tokyo Japan

“The trip was great; we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details, in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.”

[Read More] Leon and Michele

“I traveled with JoAnn West through your services, guided by Giuseppe, in July of this year. What a wonderful experience; your service is really top notch! If I return to Italy for a tour, I will absolutely use your services again and recommend you to my friends!”

[Read More] Lucretia Brower

“As a travel agent, but also a traveler to Italy, thee is no other company I would recommend than the Italy Vacation Specialists. Not only do they really care about what they are doing, they also really know Italy and try to educate many people about ways they can best see the country and not fall into tourist traps. I have been on 4 trips with the IVS team, firstly when they did my first 2 trips f”

[Read More] Laura Chomiak, Travel Agent

“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve high praise for the quality and efficiency of your work. BTW, Guiseppe was an absolute delight. We enjoyed his informative and effervescent per”

[Read More] Jo Ann West

“I am a travel agent with All About Honeymoons and I would highly recommend Italy Vacation Specialists. Jessica was wonderful in helping us plan in a last minute anniversary vacation during high season without any issues. She even checked on our clients while on vacation to make sure things were going well. I plan on using them again soon for all my future bookings!”

[Read More] Tammy Joyce, All About Honeymoons

“We're home now from the most amazing trip to Italy! I can't thank you enough for your efforts and coordination of what was without question the finest vacations I've been on to date.”

[Read More] Carol Carson

“This company really knows their stuff and recommended our family to stay longer in each location. We didn't listen to them, but wished we had in every single place we went. They recommended Sestri Levante over the Cinque Terre which was our favourite destination on our entire trip. We visited Rome where we stayed in the outstanding Hotel Locorno where they know the owner there, like in every place”

[Read More] Sean & Veet Chapman, CGA

“Dear Guiseppe and Jesse, We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future. Hotels 1. Hotel Sovestro in San Gimignano was wonderful. The staff were very friendly and helpful and made the first portion of our journey very stress free. They made us feel like we were p”

[Read More] Ron and Deb Crosby