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-01656

Wines & Food of Piedmont, Cinque Terre & Tuscany

This exclusive small group tour offers you the opportunity to discover some of Northern Italyâ€™s top wine makers and tour their centuries old wineries. An experience designed to delight both the most knowledgeable wine connoisseur or the novice.

Private

10 Days / 9 Nights

PRICING

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TUR-01512

Honor Your Beauty in Italy: A Wellness Experience with full access to the most beautiful spas of central Italy: December 1-10, 2025

10 days of relaxation, ancient wisdom, thermal waters and culinary traditions in the spas of Lazio and Tuscany that will leave you refreshed and rejuvenated.

Small Group

9 Days / 8 Nights

STARTING FROM

€4,650 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-01314

Best Life Ever Tuscany: A continuation of Best Life Ever Amalfi Coast - Almost All Inclusive October 16-22, 2024

Best Life Ever Tuscany is an Epic experience we offer for those who want to enjoy a unique experience focused on fun, health and connecting with others who are focusing on what it means to live their best life! Through genuine connections with other...

Small Group

8 Days / 7 Nights

STARTING FROM

€4,750 per person

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TUR-01344

Luxury Spas of Italy: Private Tour of Central Italy Winter & Spring Healing Package

Did you know that Italy is home to hundreds of natural hot-springs and makes a wonderful winter destination? These natural springs are located all over Italy, though most particularly in central Italy. In the winter time, not only does submerging y...

Private

8 Days / 7 Nights

PRICING

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TUR-00919

Flavors of Fall in Tuscany: Cooking, Truffle Hunting, Chocolate, Olive Oil and Wine Therapy on private 100% Tuscan owned organic estate with weekly departures in October and November 2024

This is an exclusive package we offer during the olive harvest and truffle festivals, which take place all over Tuscany during the month of November when the flavors of fall are at their finest. Experience daily cooking, wine tastings, and incredible...

Private

7 Days / 6 Nights

STARTING FROM

€4,650 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-01520

Italy's Art Capitals: 8-days in Rome, Florence & Venice

7 incredible nights experiencing the art, history and beauty of Venice, Florence and Rome with group tours and private accommodation.

Semi-Private

8 Days / 7 Nights

PRICING

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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-01667

Cooking with Valentina Harris in Tuscany: Intensive Immersion Program

In this unique cooking immersion experience with Valentina Harris, we stay at the gorgeous Villa Amore, just outside of beautiful Lucca. Surrounded by vineyards, olive groves and gardens this villa is a dream property with an enormous kitchen that m...

Small Group

8 Days / 7 Nights

PRICING

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TUR-01439

Highlights of Tuscany: Gourmet Food and Wine Package

This is a unique tour that visits some of the most beautiful areas in Tuscany as well as Umbria which is the region next door. The tour departs from Rome with an option to extend the tour in Florence and covers the beautiful Orcia valley, Siena, Cort...

Private

7 Days / 6 Nights

STARTING FROM

€3,205 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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Our Private and Small Group Tours

TUR-01680

Private Tour of Volterra and Her Incredible Landscapes including San Gimignano

Volterra occupies an incredible position overlooking an amazing, often unbelievable landscape in all directions. It is one of the highest towns in Tuscany and offers visitors a step back through time into Etruria and a look at the Etruscans, though i...

Private

PRICING

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TUR-00302

Full Day Tour of Florence from the Port of Livorno

Escape the crowded 50 person cruise line tours on this Best of Florence shore excursion. With a private tour you will enjoy a very personalized experience that differs greatly from the 50 plus person tours offered by the cruise lines.

Private

PRICING

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TUR-01430

Truffle Hunting & Cooking Class in the Heart of Tuscany

If you're spending your holidays in Tuscany, or even just passing through, do not miss the opportunity to learn more about one of the most mysterious ingredients of Italian cuisine: The Truffle! Have fun hunting in the woods with the truffle-dogs, t...

Semi-Private

5 Hours

STARTING FROM

€190 per person

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TUR-01240

Cooking class with Silvia at the Relais Il Falconiere

Add a luxury cooking class to your Tuscan vacation, complete with a tour of this incredible property along with some wonderful food and wine.

Private

3 Hours

PRICING

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TUR-01584

Private Tour of Tuscany's Chianti Region, including Siena

Chianti, located in Tuscany, is famous for its medieval towns and red wines. A private tour allows you to customize your itinerary for a unique experience. Explore the region's beauty whether you're a wine connoisseur, history buff or just want to se...

Private

7 Hours

PRICING

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TUR-01741

Private Wine Tour of the Orcia Valley

The Orcia Velley in south-eastern Tuscany is one of the most beautiful regions in Tuscany and a world renowned UNESCO World Heritage site. Known for the golf-course-like hills of green and gold (depending on what season you visit), this area is fam...

Private

PRICING

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TUR-01356

Private Full day tour of Florence, its Hills and its great Museums

This full day tour of Florence is a great option for those who have little time in Florence and want to experience the very best of what Florence has to offer in one day. On this tour, we meet you at 09:00 AM or earlier if possible at either your hot...

Private

8 Hours

STARTING FROM

€144 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-00934

Experience Florence: Accademmia, Duomo and the Loggia dei Lanzi

A pleasant walk in Florence is just what you need to be introduced to the city and its splendor and secular heritage! This tour is born to be the smartest walking tour of the city center at the best price.We hear tantalizing...

Small Group

4 Hours

STARTING FROM

€45 per person

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TUR-01638

Private Tour of Siena

Explore the art and history of one of Tuscany's most charming towns with the help of a knowledgeable local guide who will bring the medieval streets to life.

Private

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-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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Our Featured Properties

Italy,Tuscany,Pienza

Villa

Villa Pienza

4 Beds 10

BBQ +10 more

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Italy,Tuscany,Lucca,Camaiore

Villa

Luxury villa near Lucca

8 Beds 16

Air Conditioning +12 more

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Italy,Tuscany,San Gimignano

Villa

Villa near San Gimignano

5 Beds 10

Air Conditioning +14 more

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Italy,Tuscany,Florence,San Casciano in Val di Pesa

Villa

Villa Nicola in Chianti

5 Beds 10

BBQ +12 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa San Martino Cortona

3 Beds 5 Baths 12

BBQ +10 more

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Italy,Tuscany,Val D'Orcia

Villa

Villa Gabriella

8 Beds 8 Baths 16

Bathroom with Shower +15 more

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Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 more

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Italy,Tuscany,Lucca

Villa

Villa Amore: Great Villa for Groups in Tuscany Walking Distance from Town with full Yoga Studio

15 Beds 15 Baths 30

Air Conditioning +15 more

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Italy,Tuscany,Cortona

Villa

La locanda del gelsomino

9 Beds 12/18

Air Conditioning +5 more

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Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 more

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Italy,Tuscany,Florence

Apartment

La Casa Fiorita

4 Beds 4 Baths 4/8

Air Conditioning +11 more

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Italy,Tuscany,Montepulciano

Apartment

Eleganza Spaziosa

2 Beds 2 Baths 6

Air Conditioning +8 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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“I am a travel agent from Lebanon and have organized several group tours as well as individual tours of Italy with Italy Vacation Specialists. I highly recommend them as one of the very best tour operators in Italy to work with, given their professionalism and work ethic which I feel is second-to-none in the travel industry. All of the staff, the guides, the coaches and even the meals we enjoyed we”

[Read More] Nicole Haddad, Lebanese Travel Agent

“Jesse & Giuseppe, Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever.”

[Read More] Bob & Sandy

“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

“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 have traveled to Italy 2x with the IVS for my own pleasure trips and 2x for business with IVS. These guys really pay attention and make your trip go like clockwork. Italy is nuts, just saying! There are so many rules and restrictions now, so we did not want to drive ourselves. Having traveled with them many times and done business on several occasions, most definitely USE this company. They know”

[Read More] JoAnne Beaudoin, Retired Nurse

“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

“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

“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 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

“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

Experience a New Kind of Luxury in Italy. Reclaim Your Time, Space, and Energy 💜 👓 💜

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Tuscany

Uncover the beauty of Italy

Private Journeys Across Italy, Designed by Local Experts

Expert drivers, local guides, and seamless travel across every region of Italy.

Tuscany

Explore the Cities and Towns of Tuscany

Our Local Expertise

Licensed & Certified

Local Knowledge

Tailored for You

Overview

Gallery

Multi-Day Holidays Tours

Private and Small Group Tours

Hotels

Villas

Apartment

Gallery

Explore Towns and Cities in Tuscany

Our Multi-Day Holidays Tours