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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I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.

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The trip was absolutely beautiful and well planned. Zicasso's travel expert did a fantastic job and she was on top of everything. She texted me every night with the next day's plans. The only negative aspect of the trip was that the Sorrento hotel had no air conditioning. The rooms and lobby were extremely hot, hovering around 80° day and night.

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My husband and I had utilized the services of Zicasso for prior journeys to Italy, Southeast Asia, and Australia/New Zealand. For our recent trip to Matera and Puglia, I requested an agency located in Italy that specializes in travel to Italy. We selected a company that was on a magazine’s A-list of travel advisors.

Our travel consultant listened to and respected my requests for certain activities (private food, historical and boat tours, wine tastings, cheese making) and types of accommodations (properties that offered a shaded area to relax and read). She also emailed answers to my numerous detail-oriented questions (the curse of having personally worked as a tour guide). She sent a lovely gift to our first hotel and called halfway through our vacation to check in with us. Communication via text with WhatsApp was convenient and used frequently. Most importantly, when we had a problem with one of our accommodations, she followed up (even after our trip had ended) and graciously offered some compensation.

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Italy’s beauty is legendary—its rolling landscapes, vibrant culture, incredible cuisine, and deep history are truly one of a kind. But what made our trip truly extraordinary was the care, creativity, and attention to detail that the Zicasso travel company team brought to every part of our journey.

Our 12-day family adventure—with three teenagers!—was the perfect balance of guided exploration, fun hands-on experiences, and thoughtfully chosen hidden gems. Every stop offered something special for each of us, which is no small feat when traveling with a group of different interests.

While we’re fairly seasoned travelers, having the added support of your concierge service via WhatsApp was a game-changer. Any small questions or needs were handled quickly, warmly, and with a level of professionalism that gave us total peace of mind.

And the hotels—just wow. Every property was not only comfortable and welcoming, but also perfectly located, making it easy for us to explore and enjoy each destination to the fullest.

A heartfelt thank you to the entire travel company team for creating such a seamless and memorable experience. We can’t wait to plan our next adventure with you.

Grazie mille and arrivederci for now!

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We just got back from an amazing two-week vacation with our children and our eight-year-old granddaughter. The travel specialists at Zicasso's tour company were incredibly knowledgeable, responsive, and professional. They took all of my ideas and managed to incorporate them seamlessly into our itinerary. I had quite a few requests and even made some last-minute changes, which they accommodated without any hesitation. One specialist, in particular, was exceptionally kind and helpful!

The organization of the trip was smooth and effortless. The transportation, drivers, and guides were all top-notch! We traveled in clean and well-maintained Mercedes vans, with well-dressed and personable drivers. The local guides were not only knowledgeable, but also spoke English clearly, sharing fascinating insights that allowed us to dive deeper into the history and culture. The hotels we stayed at ranged from good to very good. If I were to plan this again, I might choose a different location in Rome; the area was a bit congested and the hotel could use some upgrades, but it was conveniently situated.

The wine tastings were enjoyable and dinner at the vineyard was truly magical! Our standout activities were the cooking classes in Florence and Rome. The chefs were professional and imparted a lot of knowledge, giving us valuable skills to take home.

The highlight of our trip was definitely the private boat charter in Capri! We had a perfect day on a brand-new yacht, with an experienced captain and crew who took us to hidden caves away from the crowds, allowing us to swim in stunning locations. It was an absolutely fantastic trip!

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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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