Tuscany

Overview

Discover Tuscany: Private Tours, Experiences & Custom Travel

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.)

Plan Your Experience

Explore Tuscany

Tuscany in pictures

Gallery

A few frames from our own trips. The rest are in the gallery below.

Wonderful Val DOrcia Tuscany

Experience the Decadence of Tuscany

Tuscany Countryside, Italy

Experience the Incredible Val DOrcia in Tuscany

Southern Tuscany landscape in Spring

Multi-Day Holidays Tours

Whole journeys, planned end to end

Exclusive & Private: Rome, Florence & Venice

This is an exclusive tour of Italy's Art Capitals including Rome, Florence and Venice. We include the finest accommodations, private tours, private transfers and first class rail. Top guides, VIP tickets and the very best guides throughout the progra...

Private

8 Days / 7 Nights

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

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

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

Let's Travel and Cruise Exclusive for Women by Women: Rome - Amalfi Coast - Tuscan Spas - Italian Riviera - Lake Como to Venice May 23 - June 5, 2024

This is a unique adventure through Italy put together for women by women where we will be focusing on the regional cuisine and wines of Italy as well as the natural thermal springs. Over the course of 2 weeks we will experience Rome, Vatican City, t...

Private

14 Days / 13 Nights

Tuscany & Umbria: Exclusive Small Group Tour Including Florence

This deluxe small group (or private tour ) through Tuscany and Umbria in central Italy offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence. There are many highlights on this tour including a...

Semi-Private

7 Days / 6 Nights

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

Italy for Lovers: Private Tour of Italy including the Amalfi Coast, Capri, Rome, Florence, Tuscany & Venice

Italy is one of the world's most romantic destinations - from historic cities to stunning nature, every day you will build beautiful new memories together that will last a lifetime. Whether you are looking for a honeymoon, wedding anniversary or a ve...

Private

11 Days / 10 Nights

Exclusive: Rome - Florence - Tuscany - Milan - Lake District & Venice

This is an exclusive tour that we offer which covers Rome, Florence, Tuscany, Milan, the incredible Lake District and Venice. It is perfect for those who want to sit back, relax and enjoy the very best of what Italy has to offer without having to wor...

Private

10 Days / 9 Nights

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

This is the Italy you have always pictured, seen properly. Over eleven days you travel from the cliffs of the Amalfi Coast to the ruins of Pompeii, from the timeless streets of Rome to the vineyards of Tuscany, the art of Florence, and the quiet cana...

Private

11 Days / 10 Nights

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

Full day Off beaten sites discovering Tuscany & Umbria

South from Florence, north from Rome, Tuscany & Umbria are Italy's green heart & the geographic centre of the country. A long way from either coast, what is to be enjoyed in Tuscany and Umbria is the rolling sea of green..

Private

1 Days

Italy's Northern Wine Country: Fine Wines, Food and Incredible Landscapes in Piedmont, Cinque Terre and Tuscany (Personalized Experiences)

This exclusive small group tour allows you to discover some of Northern Italy's top winemakers and tour their centuries-old wineries and experience designed to delight both the most knowledgeable wine connoisseur and the novice.

Private

10 Days / 9 Nights

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

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

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

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

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

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

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

A Tuscan & Umbrian Christmas Journey

Celebrate Christmas in Italy with this 12-day tour through Florence, Siena, and Perugia. Explore historic landmarks, festive markets, and enjoy local cuisine, wine, and chocolate tastings. Immerse yourself in the holiday spirit and charm of Tuscany a...

Private

12 Days / 11 Nights

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

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

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

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

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

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

Bella Italia: Luxury Private Tour of Italy's Must-See Locations

Visit Italy's top tourist spots in luxury. Stay at some of our favourite hotels, visit the cities with expert private guides and enjoy 1st class transportation from Venice all the way to Amalfi!

Private

15 Days / 14 Nights

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

Wedding in Tuscany on Organic Farm

Experience an unforgettable, affordable, and uniquely romantic wedding on a stunning Tuscan farm in Italy. Every ingredient, wine, and flower arrangement used in the wedding is produced organically on the farm. This exclusive venue has remained undis...

Private

4 Days / 3 Nights

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

Private & Small Group Tours in Tuscany

Days out with people who know the way

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

Florence by Night

The best way to discover Florence and its landmarks during the quieter and cooler evening hours.

Private

2 Hours

The Italian Riviera: Portofino - Santa Margherita Liguria

When your cruise ship docks in Genoa, enjoy a private shore excursion to Rapallo, Portofino and Santa Margherita Ligure. Your private driver will take you to the world know seas resort town of Rapallo, Rapalloâ€™s long list of attractions begins with...

Private

5 Hours

Tuscan Wine Tour from Livorno

This tour is a perfect tour for foodies and wine lovers who want to get the most out of their time in Tuscany from the port of Livorno. Chianti is a large wine producing zone in the Tuscany region of Italy and is home to some of Italy's most notable...

Private

12 Hours

Music and Wine in the Val D'Orcia

If you want to experience the genuine beauty of the Tuscan countryside, taste the great wines produced there and learn how they are made, try out the traditional dishes and learn how to cook them, enjoy a wellness session with your loved one, or simp...

Private

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

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

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

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

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

San Gimignano Morning Tour with Full Tuscan Lunch and Multiple Wine Tastings

North west of Siena, on the hills of Val d'Elsa, stands the medieval town of San Gimignano. Defined as the town "with a hundred towers", owing to the presence of these impressive buildings symbolising power and wealth, till the thirteenth century the...

Small Group

8 Hours

Pisa and Lucca Full Day Private Tour

The leaning tower of Pisa is perhaps one of the most iconic symbols of Italy and known the world over as one of Italy's major tourist attractions. No doubt, you will find a lot of tourists coming to Pisa. At first, you may think that's a turn-off,...

Private

7 Hours

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

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

Private Tour of the Orcia Valley, with optional wine tastings

If you're looking for a perfect escape to the stunning Val d'Orcia, then visiting three of Tuscany's most picturesque towns should be on your bucket list. Not only are these towns known for their breathtaking beauty, but also for their incredible win...

Private

7 Hours

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

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

Pisa, Volterra, San Gimignano

This is one of our favorite private tours in the Tuscany region, exclusively offered by Italy Vacation Specialists. We can pick you up from your hotel in Florence, cruise ship in Livorno, or villa in Tuscany to begin this tour. During the tour, you w...

Private

8 Hours

Pienza, Montepulciano and Tuscany's Beautiful Orcia Valley

The Orcia Valle or Val D`Orcia located in South Eastern Tuscany is an area of Tuscany very infrequently visited by tourists, although it is one of Italy`s most beautiful landscapes to behold and we highly recommend if you have the time that you disco...

Private

8 Hours

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

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

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

The Leaning Tower of Pisa & Florence from Livorno with Wine Tastings in Montecarlo

This is a great option for those coming into the port in Livorno who want to see Florence and Pisa, two very important cities in Italy. Our English speaking driver-guide will pick you up at your ship at approximately 08:30 AM (depending on the arriv...

Private

8 Hours

Florence in a Day Shore Excursion

Discover the heart of Renaissance Italy from your cruise ship by spending a magical day exploring the wonders of this magnificent destination.

Private

10 Hours

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

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

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

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

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

Fall Ball in Florence

Be prepared to be delighted. This fall, for the first time ever we are hosting Italy's "FALL BALL" in Florence Italy. An event not to be missed - gentlmen get your tuxedos on and ladies - full gowns. Proceeds of this event are going to "Teachers Wit...

Private

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

Private Half Day tour of Florence

Would you like a personalized private tour of Florence?

Private

3 Hours

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

Hotels

Rooms we would happily sleep in again

Italy,Tuscany,Chianti,Greve in Chianti

Hotel

Castello Vicchiomaggio

★ ★ ★ ★

Castello Vicchiomaggio is a historic castle dating back to the 1400s. Just outside Greve, it produce...

Business Centre +5 more

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Italy,Tuscany,Florence

Hotel

Gallery Art Hotel Florence

★ ★ ★ ★

Gallery Hotel Art is a luxurious design hotel created by Florentine architect Michele Bonan. Set in...

Buffet Breakfast +10 more

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Italy,Tuscany,Florence

Hotel

Hotel Adriatico Florence

★ ★ ★ ★

The hotel Adriatico is situated in the historical centre of Florence and combines warm Florentine h...

ATM +12 more

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Italy,Tuscany,Montalcino

Hotel

Hotel Dei Capitani

★ ★ ★

Situated in part of the eighteenth-century "Catasto Leopoldino" in the historic centre of Montalcino...

Luggage Storage +4 more

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Italy,Tuscany,Florence

Hotel

Hotel Lungarno Florence

★ ★ ★ ★

The exclusive and stylish Hotel Lungarno, is one of the only hotels in Florence situated directly on...

Airport Shuttle +17 more

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Italy,Tuscany,Siena

Hotel

Hotel Santa Caterina

★ ★ ★

Santa Caterina Hotel in Siena, housed in a renovated 18th-century patrician villa, is a small and co...

Island of Ponza +4 more

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Italy,Tuscany,Florence

Hotel

Hotel Tornabuoni Beacci Florence

★ ★ ★ ★

The Bechi Family is happy to welcome you to the site of the Hotel Tornabuoni Beacci to discover this...

Concierge +8 more

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Italy,Tuscany,Chianti

Hotel

Relais Vignale

★ ★ ★ ★

Situated in the heart of the Chianti Classico region, halfway between Florence and Siena. The hotel...

Ostia +5 more

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Italy,Tuscany

Hotel

Relais Villa Poggiano

★ ★ ★ ★ ★

Villa Poggiano nestles amid 6 hectares of parkland, on a crest above the gentle hills of Val dÃ¢â‚¬â...

Business Centre +14 more

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Italy,Tuscany,Siena,Montepulciano

Hotel

Villa Cicolina

★ ★ ★ ★

Located just outside the stunning medieval town of Montepulciano, Villa Cicolina it ideally situated...

Parking +2 more

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Italy,Tuscany,Florence (FI),Greve in Chianti

Hotel

Villa Rignana

★ ★ ★ ★

Surrounded by vineyards and nestling in the heart of the Chianti Classico region, Villa Rignana is a...

Gym

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Italy,Tuscany,Chianti,Greve in Chianti

Hotel

Villa Vignamaggio

★ ★ ★ ★

Used as the set for famous costume films and supposed birthplace of Mona Lisa, Vignamaggio offers un...

Business Centre +9 more

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Villas

Private homes with stories of their own

Italy,Tuscany,Grosseto,Montemerano

Villa

Bella Villa di Campagna

11 Beds 12 Baths 26

Air Conditioning +17 more

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Italy,Tuscany,Cortona

Villa

Cottage near Cortona

2 Beds 6

Air Conditioning +10 more

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Italy,Tuscany,Lucca

Villa

Gorgeous villa near Lucca

3 Beds 6

Balcony +11 more

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Italy,Tuscany,Arrezzo

Villa

Il Nascondiglio Verde

2 Beds 2 Baths 4

Air Conditioning +11 more

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Italy,Tuscany,Arrezzo

Villa

La Dimora Regale 1

1 Beds 1 Baths 2

Air Conditioning +11 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,Cortona

Villa

La locanda del gelsomino

9 Beds 12/18

Air Conditioning +5 more

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Italy,Tuscany,Arrezzo

Villa

La Masseria

2 Beds 2 Baths 4

Air Conditioning +11 more

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Italy,Tuscany,Arrezzo,Arezzo

Villa

Luxury Villa in Arezzo

10 Beds 20

Air Conditioning +12 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,Volterra

Villa

Luxury villa near Volterra

4 Beds 11

Air Conditioning +13 more

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Italy,Tuscany,Cortona

Villa

Stunning Villa near Cortona

4 Beds 8

Balcony +12 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,Livorno

Villa

Villa Bellissimo Palazzo

10 Beds Yes Baths 20

Air Conditioning +15 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Buccelletti: Great Option for Small Families, Couples of Group of Friends

4 Beds 4 Baths 10

BBQ +10 more

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Italy,Tuscany

Villa

Villa Casavecchia

12 Beds 26

Air Conditioning +8 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,Val D\'Orcia

Villa

Villa Dolce Vita Pienza, Tuscany

6 Beds 6 Baths 12

Air Conditioning +13 more

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Italy,Tuscany,Florence

Villa

Villa Fiori d'Arte

8 Beds 8 Baths 16-18

Air Conditioning +13 more

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Italy,Tuscany,San Gimignano

Villa

Villa for families between Florence and Siena

7 Beds 10-18

Air Conditioning +13 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,Livorno

Villa

Villa Giovanile

8 Beds 8 Baths 16

Elevator (Lift) +10 more

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Italy,Tuscany,Florence,Montaione

Villa

Villa in Iano with breathtaking view

4 Beds 9

Air Conditioning +13 more

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Italy,Tuscany,Siena

Villa

Villa in Siena for 7 people

4 Beds 7

BBQ +8 more

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Italy,Tuscany,Siena

Villa

Villa in Siena for 8 People

4 Beds 8

Balcony +10 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,Arrezzo

Villa

Villa Medievale Rosa 1

3 Beds 3 Baths 6

Air Conditioning +11 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,Pistoia

Villa

Villa Pattoni

13 Beds 12 Baths 26

Air Conditioning +10 more

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Italy,Tuscany,Pienza

Villa

Villa Pienza

4 Beds 10

BBQ +10 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,Grosseto

Villa

Villa Serenissima

9 Beds 9 Baths 18

Air Conditioning +12 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Stefano: Ideal Property for Artists, Families & Large Groups in Tuscany

7 Beds 6 Baths 16

BBQ +11 more

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Italy,Tuscany,Montepulciano

Villa

Villa Tanoak

Swimming Pool +1 more

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Italy,Tuscany,Arrezzo

Villa

Villa Vinaia

5 suite rooms and 3 apartments Beds 5 Baths 18 + 6

Air Conditioning +9 more

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Apartments

A local address to call your own

Apartment Virgo apartment rental in Tuscany

Italy,Tuscany,San Gimignano

Estate

Apartment Virgo

1 Beds 1 Baths 3

Air Conditioning +7 more

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Italy,Tuscany,Montepulciano

Apartment

Apartments Montepulciano (Tranquillo)

2 Beds 2 Baths 5

Air Conditioning +11 more

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Italy,Tuscany,Montepulciano

Apartment

Apartments Montepulciano (Uliveto)

1 Beds 1 Baths 4

Air Conditioning +9 more

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Italy,Tuscany,Florence

Apartment

Casa della Acacia

2 Beds 2 Baths 4

Air Conditioning +11 more

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Italy,Tuscany,Florence

Apartment

Casa della Quiete

2 Beds 2 Baths 4

Air Conditioning +12 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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Italy,Tuscany,Montepulciano

Apartment

Casa Divina

2 Beds 2 Baths 4

Air Conditioning +9 more

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Italy,Tuscany,Florence

Apartment

Central Apartment in Florence with frescoed ceiling

3 Beds 7

Air Conditioning +10 more

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Cottage Fienile apartment rental in Tuscany

Italy,Tuscany,Siena (SI),Castellina in Chianti

Estate

Cottage Fienile

Air Conditioning +10 more

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Cottage Riccio apartment rental in Tuscany

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Riccio

Air Conditioning +7 more

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Cottage Talluri apartment rental in Tuscany

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 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,Montepulciano

Apartment

Eleganza Spaziosa

2 Beds 2 Baths 6

Air Conditioning +8 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,Florence

Apartment

La Casa Fiorita

4 Beds 4 Baths 4/8

Air Conditioning +11 more

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Italy,Tuscany,Siena

Apartment

La Dimora del Gazebo

3 Beds 2 Baths 6

Air Conditioning +16 more

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Italy,Tuscany,Montepulciano

Apartment

Tuscan Eclipse

1 Beds 1 Baths 2

Bathroom with Shower +8 more

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Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool apartment rental in Tuscany

Italy,Tuscany,Castiglion Fiorentino

Estate

Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool

16 Beds 16 Baths 26

BBQ +11 more

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Italy,Tuscany,Montepulciano

Apartment

Vista Collina

1 Beds 1 Baths 2

Air Conditioning +8 more

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Italy,Tuscany,Montepulciano

Apartment

Wonders Room

1 Beds 1 Baths 2

Air Conditioning +6 more

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Photo Gallery

View from Pienza in the Val DOrcia, Tuscany

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 Featured Properties

Stays we picked one by one

Giardino Blu featured rental property in Tuscany

Italy,Tuscany,Montepulciano

Apartment

Giardino Blu

2 Beds 1 Baths 5

Air Conditioning +8 more

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La Casa Fiorita featured rental property in Tuscany

Italy,Tuscany,Florence

Apartment

La Casa Fiorita

4 Beds 4 Baths 4/8

Air Conditioning +11 more

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Italy,Tuscany,Florence

Villa

Villa Fiori d'Arte

8 Beds 8 Baths 16-18

Air Conditioning +13 more

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Cottage Talluri featured rental property in Tuscany

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 more

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Casa delle Brezze featured rental property in Tuscany

Italy,Tuscany,Florence

Apartment

Casa delle Brezze

2 Beds 2 Baths 4

Air Conditioning +12 more

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Italy,Tuscany

Villa

Villa Casavecchia

12 Beds 26

Air Conditioning +8 more

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Italy,Tuscany,Arrezzo

Villa

Villa Medievale Rosa 1

3 Beds 3 Baths 6

Air Conditioning +11 more

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La Masseria featured rental property in Tuscany

Italy,Tuscany,Arrezzo

Villa

La Masseria

2 Beds 2 Baths 4

Air Conditioning +11 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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Duetto Classico featured rental property in Tuscany

Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 more

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Italy,Tuscany,Siena

Villa

Villa in Siena for 8 People

4 Beds 8

Balcony +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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Popular Transfer Routes in Tuscany

The rides our guests ask for most, with a driver who knows the way.

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

Florence San Gimignano

Private Transfer

Florence Arezzo

Private Transfer

Florence Orvieto

Private Transfer

Florence Cortona

Private Transfer

Florence Montepulciano

Private Transfer

Florence Venice

Private Transfer

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In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“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 w…”
Leon and Michele Read their story

“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…”
Nicole Haddad, Lebanese Travel Agent Read their story

“My husband and I just took a two week trip to Italy that was planned for us by Eleanor Kinchin-Smith. It was a fantastic trip and we could not have been more thrilled. We worked together with Ele to let her know about our interests and our style of travel. She…”
Emily and David Davison Read their story

“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 o…”
Tammy Joyce, All About Honeymoons Read their story

“In August 2018, my family of four and myself travelled from Vancouver, BC to Rome Italy and spent 3 weeks touring Italy with IVS. This company had come highly recommended by many friends and associates of ours who had used them before and indeed to say they do…”
Vijaya Sunil CPA, CGA Read their story

“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 fl…”
Robin and Kumi Bruun, Tokyo Japan Read their story