Tuscany
Explore the Cities and Towns of Tuscany
Our Local Expertise
Over 20 years of crafting exceptional journeys across 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
Multi-Day Holidays Tours
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 si...
Flavors of Fall in Tuscany: Cooking, Truffle Hunting, Chocolate, Olive Oil and Wine Therapy on priva...
This is an exclusive package we offer during the olive harvest and truffle festivals, which take place all over Tuscany...
New Year's Eve in Florence
Experience the magic of Florence this New Year’s Eve with a luxurious 5-day getaway. From private transfers to exclusi...
Exclusive & Private: Rome, Florence & Venice
This is an exclusive tour of Italy's Art Capitals including Rome, Florence and Venice. We include the finest accommodati...
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 natu...
Tuscany Mini-Stay
A brief retreat to Tuscany promises a delightful blend of Renaissance art, rolling vineyards, and charming medieval town...
Italy for Lovers: Private Tour of Italy including the Amalfi Coast, Capri, Rome, Florence, Tuscany &...
Italy is one of the world's most romantic destinations - from historic cities to stunning nature, every day you will bui...
Let's Travel and Cruise Exclusive for Women by Women: Rome - Amalfi Coast - Tuscan Spas - Italian R...
This is a unique adventure through Italy put together for women by women where we will be focusing on the regional cuisi...
Honor Your Beauty in Italy: A Wellness Experience with full access to the most beautiful spas of cen...
10 days of relaxation, ancient wisdom, thermal waters and culinary traditions in the spas of Lazio and Tuscany that will...
Wedding in Tuscany on Organic Farm
Experience an unforgettable, affordable, and uniquely romantic wedding on a stunning Tuscan farm in Italy. Every ingredi...
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 a...
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...
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 g...
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 E...
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...
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 cent...
Best Life Ever Tuscany: A continuation of Best Life Ever Amalfi Coast - Almost All Inclusive October...
Best Life Ever Tuscany is an Epic experience we offer for those who want to enjoy a unique experience focused on fun, he...
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 Va...
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 Ve...
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 for...
A Tuscan & Umbrian Christmas Journey
Celebrate Christmas in Italy with this 12-day tour through Florence, Siena, and Perugia. Explore historic landmarks, fes...
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...
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...
Wines & Food of Piedmont, Cinque Terre & Tuscany
This exclusive small group tour offers you the opportunity to discover some of Northern Italy’s top wine makers and to...
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...
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, follo...
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 ca...
Absolute Italy from Venice to the Amalfi Coast including Florence, Tuscany, Rome, Vatican City, Pomp...
This tour is a once-in-a-lifetime experience in Italy that starts in Venice and ends on the stunning Amalfi Coast. The t...
Italy's Northern Wine Country: Fine Wines, Food and Incredible Landscapes in Piedmont, Cinque Terre...
This exclusive small group tour allows you to discover some of Northern Italy’s top winemakers and tour their centurie...
Absolute Italy: Mostly Private Tour of Italy including the Amalfi Coast - Capri - Pompeii - Rome - T...
Absolute Italy includes The Amalfi Coast, Capri, Pompeii, Rome, Tuscany, Florence & Venice. It's a fantastic way to see...
Private and Small Group Tours
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 c...
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 wil...
Montalcino Cooking Experience
Join us in the heart of the Brunello di Montalcino region for a refined culinary immersion on a historic vineyard estate...
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.
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....
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 abo...
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 h...
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 p...
Florence by Night
The best way to discover Florence and its landmarks during the quieter and cooler evening hours.
Experience the Best of Central Italy's Coastal Towns with Cooking and Wine Estate Visit from Civitav...
This is an awesome tour we have put together that takes passengers arriving off of the cruise at Civitavecchia north alo...
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 v...
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 Tu...
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 an...
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.
Piety and Patronage Tour
Itinerary: Convent of San Marco, Cenacolo di Sant'Apollonia and the Chiostro dello Scalzo. If you are interested to see...
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 ma...
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 en...
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 Wo...
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 o...
Bagnoreggio and Orvieto Shore Excursion
This is a wonderful tour for those looking for an alternative to Rome during their shore excursion from Civitavecchia. I...
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 won...
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.
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! Th...
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 touri...
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...
Private Half Day tour of Florence
Would you like a personalized private tour of Florence?
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 to...
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. A...
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...
The Original Florence Street Food & Local Market Tour
Step into Florence the way locals do—with food as your guide and the streets as your dining room. The Florence Morning...
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...
Pisa, Volterra, San Gimignano
This is one of our favorite private tours in the Tuscany region, exclusively offered by Italy Vacation Specialists. We c...
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...
Hotels
Hotel Adriatico Florence
The hotel Adriatico is situated in the historical centre of Florence and combines warm Florentine h...
Hotel Lungarno Florence
The exclusive and stylish Hotel Lungarno, is one of the only hotels in Florence situated directly on...
Hotel Santa Caterina
Santa Caterina Hotel in Siena, housed in a renovated 18th-century patrician villa, is a small and co...
Hotel Tornabuoni Beacci Florence
The Bechi Family is happy to welcome you to the site of the Hotel Tornabuoni Beacci to discover this...
Relais Vignale
Situated in the heart of the Chianti Classico region, halfway between Florence and Siena. The hotel...
Relais Villa Poggiano
Villa Poggiano nestles amid 6 hectares of parkland, on a crest above the gentle hills of Val dâ€â...
Villa Cicolina
Located just outside the stunning medieval town of Montepulciano, Villa Cicolina it ideally situated...
Villa Rignana
Surrounded by vineyards and nestling in the heart of the Chianti Classico region, Villa Rignana is a...
Villas
Villa Amore: Great Villa for Groups in Tuscany Walking Distance from Town with full Yoga Studio
Villa Buccelletti: Great Option for Small Families, Couples of Group of Friends
Villa Stefano: Ideal Property for Artists, Families & Large Groups in Tuscany
Apartment
Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool
Gallery
Explore Towns and Cities in Tuscany
Discover the charming cities and towns that make Tuscany unique
Our Multi-Day Holidays Tours
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...
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...
New Year's Eve in Florence
Experience the magic of Florence this New Year’s Eve with a luxurious 5-day getaway. From private transfers to exclusive tours and unforgettable celebrations...
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...
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...
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...
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...
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...
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.
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...
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.
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..
Our Private and Small Group Tours
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 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.
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...
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.
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, Rapallo’s long list of attractions begins with...
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...
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...
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...
Florence by Night
The best way to discover Florence and its landmarks during the quieter and cooler evening 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 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 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.
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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.
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Stories That Stay With You
Here's what our guests share about their unforgettable journeys
“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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