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-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-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-00640

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

STARTING FROM

€1,700 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-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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TUR-01567

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

PRICING

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TUR-01575

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

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-01677

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

PRICING

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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-01322

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

PRICING

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Our Private and Small Group Tours

TUR-00991

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

STARTING FROM

€220 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-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-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-00997

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

STARTING FROM

€180 per person

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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-01601

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

STARTING FROM

€120 per person

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TUR-00295

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

STARTING FROM

€200 per person

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TUR-01642

Florence by Night

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

Private

2 Hours

PRICING

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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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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-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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Our Featured Properties

Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 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,Siena

Villa

Villa in Siena for 7 people

4 Beds 7

BBQ +8 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,Siena

Villa

Villa in Siena for 8 People

4 Beds 8

Balcony +10 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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Italy,Tuscany,Montepulciano

Apartment

Casa Divina

2 Beds 2 Baths 4

Air Conditioning +9 more

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Italy,Tuscany

Villa

Villa Casavecchia

12 Beds 26

Air Conditioning +8 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,Arrezzo

Villa

Villa Medievale Rosa 1

3 Beds 3 Baths 6

Air Conditioning +11 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,Livorno

Villa

Villa Giovanile

8 Beds 8 Baths 16

Elevator (Lift) +10 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

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“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

“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

“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

“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

“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

“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

“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

“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

“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

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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