7-Day Off the Beaten Path Tuscany Vacation

Panoramic view of the Val Di Chiana in Tuscany, Italy.

What to expect on this itinerary

Indulge in the beauty of rolling hills and iconic rows of cypress trees that lead to charming medieval towns during this custom-tailored 7-day Tuscany tour. Whether sampling the remarkable flavors of local wines or basking in spectacular views, you will travel away from the trodden path to immerse yourself in authentic towns, unique traditions, and customary flavors that have been preserved through time.

Countries Visited

Italy

Places Visited

Siena, Florence

Suggested Duration

7 Days

Customizable Itinerary

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Day 1

Siena – Culinary Introduction to Tuscany

Your flight will land at Florence Peretola International Airport, where your private transfer will meet you upon your arrival. You will arrive in Siena with time to settle into the comforts of your luxurious accommodation. The 12th-century tower of Torre del Mangia reaches nearly 289 feet tall and looms over the main square of Piazza del Campo. You can visit a traditional garden, where the residents tend to vegetables, goats, geese, and chickens. Here, the chefs create traditional local cuisine using only local and seasonal flavors, providing you with a fabulous introduction.

What's Included:

Transfer
Accommodation
Day 2

Siena – Enjoy Art and Medieval Towns

Day 3

Siena – Murlo, Arezzo, and Val di Chiana Aretina

Day 4

Siena – The Coastal Wine and Olive Oil Route

Day 5

Siena – Monticchiello, Pitigliano, and Sorano

Day 6

Florence – Off-the-Beaten-Path Tour of Florence

Day 7

Florence – Departure

Trip Highlights

  • Embrace the gorgeous flavors of traditional Chianti Classico when sampling wines around the medieval town of Montefioralle
  • Discover the marvels of Florence from a different perspective and uncover the hidden gems of the city
  • Uncover Etruscan artifacts when visiting the Val di Chiana Aretina
  • Sample the marvelous wines known as Super Tuscans in the hilltop town of Bolgheri
  • Bask in the beautiful canals and charming café culture of the seaside town of Livorno
  • Embrace the marvelous and historic tastes of a Jewish dessert known as sfratto dei goym
  • Witness the striking plays of the Teatro Povero when visiting the town of Monticchiello

Detailed Description

You will have an immersive experience during this 7-day Tuscany tour. This off-the-beaten-path adventure provides you with luxury, specialist guides, and private drivers. Tuscany possesses an abundance of hidden gems that are often overlooked for the more famous destinations. Traveling away from the known cities and worn paths will provide you with pleasant surprises, such as authentic cuisine, cobblestone lanes that have remained unchanged since medieval times, unique canals, and natural wine cellars.

Your Tuscany tour will begin with your arrival at Florence’s international Airport, where your private transfer will escort you to the city of Siena. You will have time to get acquainted with the medieval city before embarking on an introductory tour that will lead you to a dinner of delicious fare. You will have five nights in the city, and you will use it as a base to explore the larger variety of Tuscany’s landscape and culture. Your private driver will lead you to old towns near the edges of Florence to find incredible artwork and heritage that has been hidden in the shadows of Tuscany’s capital. In the hilltop town of Montefioralle, you can wander along the cobblestone paths and sample the incredible flavors of Chianti Classico.

The following day, you will find the pre-Roman history of Tuscany on display beneath the medieval foundations of the towns of Murlo and Arezzo. Spending time on the Etruscan Coast will take you from Livorno to Piombino, where you can sample the elegant flavors of Super Tuscans and savor the distinctive flavors of local olive oils.

The medieval towns of Monticchiello, Pitigliano, and Sorano will offer unique insights into the culture and history of Tuscany, ranging from a historic theater to a unique Jewish heritage. You will then transfer to Florence, where a private tour of the city will reveal art and culture outside of the famous museums.

Starting Price

$2,600 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.

4.8

Verified Traveler Reviews

Based on 150 reviews

Travel Review: Memorable Vacation to Italy, Florence, Tuscany, Siena, Antinori Winery Tour, Rome, Vatican Tour
Giuliana of this Italy travel company guided us every step of the way and created one of our most memorable vacations. The most impressive thing at the outset was how quickly she responded to our initial inquiry. We had never been to Italy, had not done a great deal of research, and had only a general idea of what we wanted beyond the dates (mid-May) and the cities we wanted to visit (Florence and Rome). Within a day, Giuliana submitted a detailed proposed itinerary based on a recent client request similar to ours. The proposal included various options that provided a great starting point for further discussion. She asked many questions, including our hotel preferences (small boutique, high-rise, how many stars, etc.) and suggested a number of venues that would expose us to Italy’s remarkable history and culture. The result was a vacation specifically suited to our personal tastes and interests. We spent four days in Florence and three in Rome. In Florence, we stayed at the Hotel Lungarno on the Arno River, a lovely small hotel in the heart of the city within walking distance to everything of interest, including the Uffizi and Academy museums, and the famous Duomo. It rained two nights, but we didn’t have far to go for a great dinner. The hotel restaurant was superb. One of the highlights of the Florence leg of the trip was a day tour of the Tuscany wine region that included a stopover in the historic town of Siena. We had lunch at the Osteria di Passignano, a restaurant at the Antinori vineyards where we were treated to a four course lunch and wine tasting and a tour of the winery. Fabulous. In Rome, we stayed at the Hotel Saint George. Another small, well appointed, boutique hotel, centrally located near the Tiber River, it provided access to all the essential venues, including the Vatican, Coliseum, Spanish Steps, etc. As in Florence, everything was in walking distance, including fine dining restaurants, pizzerias, espresso bars, and gelateria—and lots of places to shop. The hotel was comfortable, attractive, with a friendly and efficient staff, but we would not recommend the hotel restaurant. It was nice enough (although too brightly lit) but was virtually empty the night we were there and the food was just O.K. That wasn’t Giuliana’s fault since the hotel restaurant was not on her recommended list. We were just tired (it was our first night) and thought we’d give it a try. The hotel concierge made up for it, however, by recommending two great nearby restaurants for the remaining two nights. Neither was on Guiliana’s list, but they were terrific. A word about the logistical aspects of the trip: we viewed this as critical to the success of a customized tour with multiple venues and connections. We couldn’t have been more pleased. On arriving at Rome’s Fiumicino Airport, we were greeted by Aldo who drove us to the high-speed train to Florence. After sharing an espresso with us in the station café, he made sure we got on the right train, helped us with our bags, and took us to our seats. Similar service greeted us at every connection point during the trip. Our personal tour guides, Enza (Florence), Andrea (Tuscany), and Sylvia (Rome), were exceptionally knowledgeable, personable, and fluent in English. Giuliana telephoned us at several points during the trip to confirm that we had arrived at our destination, that the drivers were on time, and that the accommodations met our expectations. Very reassuring to know she was keeping such close tabs on things. In short, all elements of transportation and personal service were impeccable. Would we visit Italy again? Without doubt. The trip simply whetted our appetites. Would we use this company? We wouldn’t consider any other service. Next time, however, we’ll make more of an effort to visit the restaurants recommended by Giuliana.

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Italy Tour Review: Siena, Florence, Chianti, San Gimignano, Private Wine Tasting, Nine-Day Trip
Overall, our trip was very nice. The accommodations in Siena and Florence were very good, except the Florence hotel had very thin walls and you could hear the tenants in the next room. However, the room, amenities, daily breakfast buffet, and central location, especially to the train station, were very good.

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Travel Review: Anniversary Vacation in Italy, Florence, Siena, Tuscany, History, Hiking, Cooking Lesson, Hiking

We had a wonderful trip. "Tuscany in Winter" was my husband's idea to experience this beautiful  part the world beating summer crowds. We visited the lovely ancient city of Siena the historic Florence and the Tuscany countryside for a few days in between. We were able to enjoy the galleries, restaurants and other popular sites pretty much on our own and were welcomed very warmly in cold weather by all.

Our guide and driver were very professional and pleasant. They were very concerned about all aspects of the responsibility of providing the very best service possible.

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Italy Trip Review: Florence, Siena, Talamone, Montepulciano, Saturnia
The trip was absolutely fabulous. We stayed mostly in the smaller cities. The only large City we visited was Florence but that was perfect. I didn't want the usual. I wanted to visit the smaller towns to meet the locals and enjoy real Italian life. It was a great mixture of Big City, small city, farms, oceanside, and vineyards. We visited small cities around Siena, Talamone, Montepulciano and many other towns along the way.We had a personal driver take us to all the different destinations. That was great! There is no way I could have navigated the winding narrow roads much less find my way around. The drivers were dressed in suits and super friendly.  After a long day of wine tasting, the driver taught us how to sing "That's Amore" in Italian. Then direct us to our BnB as we stubbled down the cobbled street.It was a dream trip that now after it is over, seems like a dream. Thank God for pictures.Thank you Ziacsso for planning a once in a life time trip. 

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Travel Review: Luxury Anniversary Italy Vacation, Rome, Florence, Siena, Chianti, Amalfi Coast, Capri Boat Tour, Cooking Class

My brothers and I asked our agent to plan a 50th Wedding Anniversary trip to Italy for our parents who had never been to Italy (or Europe, for that matter).  The trip was absolutely perfect.  Our parents are not big travelers, so we wanted them to be "hand held" a bit and our agent arranged just that.  They were picked up at the airport by a driver, so they did not have to worry about a taxi or finding their way to their hotel.  The trip was a 12 day trip starting out in Rome where they spent 4 days.  They stayed in a lovely boutique hotel (with a great location) with a fantastic roof top bar that was perfect setting for sharing a glass of processo while enjoying the views of this gorgeous city.  When they toured the Vatican, there were only 6 people in their party (including themselves).  They loved the small group size.  They were able to ask questions and hear everything the tour guide said.  We had a private driver take them for a day trip to the village where our father's dad came from.  Our agent was really able to personalize this trip for them.  From Rome, it was off to Florence where they stayed in another lovely hotel centrally located with amazing views of the city.  They also took a cooking class nearby and loved every minute of it.  They spent another day enjoying wine tasting in Siena and Chianti.  Every single excursion was well laid out and extremely well planned.  They ended their trip by spending 4 days on the Almafi coast taking another cooking class (just the two of them) and enjoying a private boat ride to the island of Capri.  It was definitely a trip of a lifetime and we were all pleased with the outcome.  I would highly recommend this agency to anyone who wants a trip tailored to meet all their needs and wants.

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Luxury Italy Group Tour Review: Rome, Tuscany, Chianti, Montepulciano, Montalcino, Siena, Florence, Pisa, Lucca, San Gimignano

THE BEST VACATION EVER!!!!

I must admit that I was somewhat uncomfortable arranging a group tour to Italy with someone I communicated with only via the Internet and telephone.  However, after my first communication with our agent -- I knew that she “had it.”  She understood exactly what we wanted to do.  She was right-on in both concept and execution.

Our ten-day adventure in Italy began with a private transfer with an English speaking local driver from the Rome airport to our fantastic 3 star boutique hotel located right in the historical center of Rome.  During our three days in Rome, we had fantastic private tours of Ancient Rome, the Coliseum, and the Vatican Museums.  Extremely knowledgeable, English-speaking guides led all of our tours.  Sense of Italy had arranged for VIP, skip the line, priority entrance for all tours -- saving us from long waits in long lines.

After our busy 3 days in Rome, we departed via private van transfer from our hotel in Rome to the Chianti Region of Tuscany.  The transfer included stops on the Val D’ Orcia to visit the amazing Villages of Montalcino and Montepulciano.  The “light lunch” and wine tasting we enjoyed in Montalcino was one of the highlights of our trip.  In Tuscany we stayed 7 Nights in a beautiful, historic villa located on one of the best wine estates of Chianti (Villa Le Corti near San Casciano) where we were met with a fantastic welcome dinner. During our time in Tuscany we were transported by private van from our villa to private tours of Siena, San Gimignano, Florence, Pisa and Lucca.  On each of our stops we were met by knowledgeable English speaking guides that clearly were proud of the history of their country, and were anxious to share it.  Interspersed in all of this activity were numerous exceptional meals with opportunities to taste (and drink) very fine Italian wines.

When we finally were forced to leave Italy, our agent arranged for private transport accommodating our varying departure times from the Florence airport and train station.

Thanks to this travel company and our agent for designing the perfect vacation for our group.  The only complaint that I heard was that we ate too much — wow was all the food delicious.  I really don’t know how she did it.  All of the tours were great — the van drivers friendly and helpful, the guides knowledgeable, and the sites spectacular.  Our stay in the villa was a great experience.  We were treated royally everywhere.  We all marveled at our agent's ability to get us, the vans, the guides, the food and wine, etc. all at the right place at the right time.  She is a genius!!!!

Jeff E

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Customizable Itinerary

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

28,000+ Verified Traveler Reviews