Historical Immersion Tour of Stunning Tuscany

Church of San Biagio in Montepulciano, Italy

What to expect on this itinerary

Your customizable 10-day historical tour of Tuscany will lead you from Florence to Siena and from Chianti to the Val d’Orcia. This tour immerses you in celebrated artworks, notable grape varietals, antique defensive walls, and dramatic cathedral facades. Discover the authentic beauty of the countryside among rows of cypress trees and uncover the secrets of crafting handmade pasta.

Countries Visited

Italy

Places Visited

Florence, Chianti, Lucca, Val d’Orcia

Suggested Duration

10 Days

Customizable Itinerary

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Day 1

Florence – Fabulous Introductory Tour

Florence is a majestic city that is steeped in history. Your private transfer will greet you at Florence Peretola Airport upon your arrival in Tuscany and escort you to the comforts of your gorgeous hotel in the heart of the city. After settling into your accommodation, you will meet your guide in the lobby and set out on an introductory tour of Florence’s captivating history. This tour will lead you from the famous Ponte Vecchio to the renowned Duomo. The unreinforced brick dome stands at 376 feet tall.

What's Included:

Transfer
Accommodation
Day 2

Florence – Renaissance History and Art

Day 3

Chianti – Wine Tour of Chianti

Day 4

Chianti – The History of Siena

Day 5

Val d’Orcia – Private Cooking Class

Day 6

Val d’Orcia – The Hilltop Villages of Val d’Orcia

Day 7

Lucca – Artisan Charm and Beauty at Volterra

Day 8

Lucca – The Architecture of Lucca

Day 9

Lucca – Venture to Pisa and Livorno

Day 10

Lucca – Departure

Trip Highlights

  • Embrace the sensational detail and impressive design of Michelangelo’s David when visiting the Galleria dell’Accademia
  • Witness the exceptional collection of artwork that is featured at the Uffizi Gallery, such as Titian’s Venus of Urbino
  • Wander among the dramatic architectural design of the Cattedrale di Pisa, which blends Pisan Romanesque and Gothic designs
  • Discover the history of Tuscan cuisine and the importance of continued culinary heritage during a cooking class with a master chef
  • Delight in the traditions of wines that have been crafted in the Chianti and Val d’Orcia regions
  • Find marvelous Etruscan remains and paintings from the 1st century BC inside the Town Museum of Montepulciano
  • Learn the preserved art of Alabaster carving during a private demonstration and workshop in the medieval town of Volterra
  • Enjoy an exclusive tour of the Bargello Museum to view the marvelous galleries that host work from master artists, including Donatello

Detailed Description

You will embrace remarkable heritage and culture during this 10-day historical Tuscany tour. With private transfers, luxurious accommodations, and specialist guides, this tour will immerse you in the elaborate past of one of Italy’s most iconic regions. You will have the ultimate experience of exploring secluded villages, charming landscapes, and opulent cityscapes. You will also experience the overlooked canals of Livorno, the celebrated wines of Montepulciano, the renowned list of Pisa’s Leaning Tower, and the ways in which the masters of Renaissance art in Florence continue to reflect the history of the city and greater Italy.

Your historical tour of Tuscany will begin with your arrival at Florence’s international airport, where your private transfer will meet you at baggage claim. You will have two nights in Florence, and your knowledgeable guide will provide an introductory tour of the majestic city that is known for its art, architecture, and culture. You will traverse the famous Uffizi and Accademia museums to view the work of master artists, such as Botticelli and Michelangelo. Two nights in the Chianti region will highlight the splendors of the Tuscan countryside, beginning by unveiling the specific flavors of Chianti wine that has made it popular over the centuries.

You will continue to the Val d’Orcia for two nights. You will learn the art of crafting handmade pasta under the guidance of a chef who is experienced in the traditions of Tuscany’s Cucina Povera. Outside of Pienza, you will visit a local farm to learn the steps to making the special cheese of the preserved town before partaking in an artisan workshop that will teach you about the preservation of local traditions.

Three nights in Lucca will begin with an artisan demonstration of carving alabaster before a guided tour has you traversing the ancient city of Volterra. A full-day tour of Lucca will take you along the famous walls and through the winding cobblestone lanes that surround the Torre Guinigi. Venturing to Pisa will highlight the beauty of Gothic and Romanesque designs in the former naval powerhouse, and your time exploring Livorno will shine a light on the grandeur of the seaside city.

Starting Price

$4,500 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.

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Verified Traveler Reviews

Based on 696 reviews

Italy Anniversary Tour Review: 2 Weeks

Our first trip to Italy was a romantic anniversary celebration, and thanks to Zicasso’s travel specialist and our travel company, it became one of the most extraordinary and meaningful travel experiences of our lives. It was everything we had dreamed of, and so much more!

From our very first conversations, she took the time to understand who we are as travelers: our love of art, architecture, history, culture, food, wine, and lifelong learning. She translated those passions into an imaginative, beautifully personalized journey through Rome, Tuscany, Florence, and Venice.

One of her greatest gifts is her intuitive understanding of the rhythm of travel. We wanted days filled with discovery, learning, and new experiences, but also leisurely afternoons and evenings to wander cobblestone streets, linger over wonderful meals, and simply absorb the atmosphere of Italian life. She struck that balance perfectly. Our itinerary was wonderfully rich, yet never rushed or overscheduled.

The private guides she selected were exceptional: not simply knowledgeable, but gifted teachers and storytellers who brought centuries of Italian history, art, architecture, and culture vividly to life. In Florence, for example, our guide helped us explore the Renaissance through fascinating stories of the Medici family, Michelangelo’s creative process, and the philosophy of Humanism. Our visits to the great museums and historic landmarks became intellectually stimulating and deeply engaging experiences.

She also introduced us to Italy’s living traditions: a fabulous food tour in Rome, wine tasting in Tuscany, explorations of enchanting medieval towns and villages, and boat excursions to Murano and Burano, where we discovered the centuries-old artistry of glassblowing and lacemaking. These experiences gave us a wonderful sense of the richness and continuity of Italian culture.

Her choices of accommodations were equally inspired. Each was distinctive, beautifully located, and full of character, from a charming, peaceful boutique hotel near the Pantheon in Rome, to a magical stay in a medieval Tuscan village, an elegant Art Deco hotel in Florence, and a fairytale suite in Venice. Every setting added another layer of romance and delight to our anniversary celebration. And the cuisine was heavenly! Every meal was memorable, culminating in a dreamy farewell dinner beside a Venetian canal.

Behind all this magic was the travel specialist’s impeccable planning, extraordinary attention to detail, and genuinely proactive care. Every transition, from airports and private transfers to trains and boats, was seamlessly coordinated.

One small example perfectly captures her approach. When our train from Florence to Venice was delayed, we contacted the travel specialist to let her know. She immediately reassured us that she was already monitoring our train and had informed our guide in Venice of the delay. There was nothing for us to do but relax, enjoy the ride, and look forward to the magnificence of Venice! That kind of thoughtful anticipation gave us complete peace of mind throughout our travels.

Equally special was her warmth and genuine personal connection. She was always accessible, and we found ourselves exchanging messages most days, not because anything needed fixing, but simply because it was such a pleasure sharing our experiences with her. She combines exceptional professionalism, creativity, and meticulous organization with kindness, generosity of spirit, and a contagious passion for sharing the beauty of her country. By the end of our journey, we felt we had gained not only an extraordinary travel advisor, but also a wonderful new friend.

Italy opened our minds, elevated our souls, and deeply touched our hearts. Our travel specialist didn’t simply organize a magnificent vacation; she opened the door to a country and culture we have now fallen completely in love with.

We cannot recommend our travel specialist and travel company highly enough. For anyone seeking a thoughtfully curated, culturally immersive, deeply personal, and truly unforgettable Italian journey, she is an exceptional choice.

We are already dreaming of returning to explore Sicily and Sardinia with our family, and there is absolutely no question who we will call!

Thank you for giving us far more than a beautiful vacation. You gave us an extraordinary gift: memories, discoveries, and connections we will treasure for the rest of our lives.

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Italy Trip Review: Tuscany, Florence, Lucca, Cinque Terre, Chianti, Cooking Class, Biking, Hiking, Local Cuisine, 1 Week

Zicasso’s travel agent was accommodating and helpful for our trip to Tuscany. Since there were so many of us, people had different needs. She was able to accommodate our differences and work out plans the best she could. We enjoyed all of the selections that she gave us, especially the dinner in the Chianti vineyard. Everyone loved that. We definitely recommend this travel company!

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Italy Travel Review: Tuscany, Cinque Terre, Florence, Sunset Cruise, Truffle Hunting, Hiking, Cooking Classes, Olive Oil Mill, Wine Tasting, Museums, 10 Nights

We can't say enough good things about the trip planned for us in Tuscany and Cinque Terre. It was the perfect balance of cultural (museums, artwork, architecture), historical (tours of towns, churches), food (culinary classes, olive oil mill, winemaking/vineyards), and outdoor activities (hiking, truffle hunting, sunset boating cruise). The uniqueness of some of the activities made this vacation one of the best European vacations we have ever experienced.

The guidance of Zicasso's travel specialists was so appreciated and was spot on for planning meals and when to leave open time. The guides and drivers they provided were extremely knowledgeable, helpful, and very friendly. Even when we had major air travel issues getting to Italy, they immediately came to our rescue when we had to arrive in Florence instead of Pisa.

Also, all of the accommodations which they booked for us were comfortable, spacious, and within easy walking distance of local attractions. We highly recommend Zicasso. We are looking forward to being able to plan our next Italian adventure with them.

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Italy Travel Review: Tuscany, Siena, Montepulciano, Pienza, San Gimignano, Florence, Farm-to-Table Experience, 6 Nights

We had a fantastic trip, all thanks to our travel specialist. We spent a few days in Siena, touring different Tuscan towns like Montepulciano, Pienza, and San Gimignano, and then we spent a couple of nights in Florence. All of our drivers and guides were very thoughtful that we had my two-year-old nephew with us.

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Italy Trip Review: Rome, Florence, Tuscany, Cinque Terre, Venice, Pizza-Making Class, 2 Weeks

We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.

The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.

The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.

One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.

Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.

While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!

Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.

Every experience felt personal, meaningful, and special.

This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!

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Italy Vacation Review: Florence, Pisa, Chianti, Rome, Cooking Class, Wine Tasting, 1 Week

My girlfriends and I had a wonderful trip to Florence, Pisa, Radda in Chianti, and Rome. Zicasso’s travel specialist was so great to work with! Her planning made our travel a seamless experience. Our local contact provided timely updates and contact information throughout the duration of our trip. I would definitely work with them again!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

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