Tuscany is one of the great destinations of Italy and, indeed, of the entire world. The beautiful scenery comes from the large tracts of agricultural land placed on rolling hills, dotted with cypress trees, and crossed with the famous strada bianchi or white-colored dirt roads. The architecture and artwork of the region just add the dreamlike ambiance.
In addition to its beauty, Tuscany is known for its wine. Famous wines from the region include Chianti, Brunello di Montalcino, Vino Nobile di Montepulciano, and Vernaccia di San Gimignano. We’ll try them all, visiting cellars both grandiose and off the beaten path. We even spend a day touring wineries of nearby Umbria, which has excellent wines but is much less known.
We visit major Tuscan cities including Florence, Chianti, Arezzo, Assisi, and Montepulciano. Our main focus is the wine but we supplement this with visits to local food producers and cultural highlights.
Tuscany is a spectacular region for a vacation and there is no better way to visit than to focus on the wine.
Related blog posts:
- Taste the region’s wines: Brunello di Montalcino, Chianti, Nobile de Montepulciano, Super Tuscans
- Visit 10 different Italian wineries, ranging from large and modern to very small scale
- Try your hand at the art of pasta making during a class with a local chef
- Walk the stunning streets of Florence and learn about local history
- Tour a local pecorino (sheep’s cheese) farm in Pienza followed by a picnic
- Learn about the art of coffee roasting and chocolate making at a cafe in Arezzo
- Sample small-batch family made olive oil
- Location: Tuscany (and Umbria)
- Private Tour Only: June 26 – July 2, 2023
- Trip Price Per Person: $4,250
- Single supplement: $800
- Minimum: 6 people
- Host: Giovanni Ramaccioni or other Italian host
- Meals: See below under What Is Included for specifics
"What a fantastic trip we had in Tuscany! I can't thank you and Giovanni enough for your kindness, flexibility, and support. It makes for a more relaxing and enjoyable experience." - Dane M.
As is with every Taste Vacation tour, the attention to detail is incredible. Everything from ensuring that participants have enough wine, tasting spectacular wines, visiting exclusive wineries, dining on great food, touring beautiful vineyards, plenty of activities to keep us busy, and enjoying unique restaurants is covered.Elizabeth & Jake
I was concerned about the limitations of being on a guided tour as well as having to spend the entire time with a group of strangers. What I found was that the tours were extremely well planned and the accommodations, meals, wine tastings, and activities were perfect! And at the end of the trip, the people that began the tour not knowing each other, parted as a group of forever friends planning another adventure together with TasteAlice T.
We meet at our Florence hotel in the early afternoon and set off with our certified local Florence guide who will take you on a wonderful historical walk of the city. (If you wish to visit the David or any of the other impressive historical sites, you should plan on arriving to Florence a day early.) You will then have free time on your own to do as you like. That evening, you’ll meet your host for the week (Giovanni) for an aperitif and orientation.
We’ll then make our way to a quaint family-owned restaurant for a lovely welcome meal. After dinner, we head back to the hotel and rest up for tomorrow’s adventures – our first full food and wine day in Tuscany.
After breakfast, we’ll leave the city and head out into the countryside to one of the most famous wine regions with one of the most famous wine styles in Italy: Chianti. Our first stop is the estate of Marchesi Antinori, a family winemaking business now in its 26th generation! This major Italian winemaking family has multiple estates and we visit one of its newest properties, yet tied to its history in Chianti dating back to 1385. After a tour and tasting, we continue to the picturesque city of San Gimignano, a small medieval walled town famous for its dozen or so towers sticking up into the sky. After exploring the town on foot, we’ll head to the local Fattoria Poggio Alloro, a combination rural farm and vineyard, for a lunch of food products, such as the Chianina brand of beef and the saffron spice which has been locally grown since the 13th century. We’ll pair this with the estate grown Vernacciadi, which although it is the most famous white wine from the region is relatively unknown internationally.
After, we will check into our charming historic villa out in the countryside before visiting one more winery for the day: the 900-hectare Castello di Albola wine and olive oil producing estate in the hills of Chianti. Our dinner will be back at our excellent countryside hotel.
This morning we check out of our villa and transfer to Arezzo to visit Vestri Cioccolato, a chocolate maker that has been producing delicious chocolate for 30 years, owns a farm in the Dominican Republic which provides product, and roasts their own coffee. We’ll learn about the chocolate-making and roasting processes and, of course, sample a few of their creations. We then transfer to the center of this lovely small city where you can explore the various cafes and restaurants for lunch on your own.
After lunch, we visit Fattoria di Gratena, a winery located on the outskirts of Arezzo. This organic winery is most interesting because of its creation of a new clone, unique to the property, called Gratena Nero.
After the wine tasting we’ll head to our hotel in Città di Castello, a lovely town in the northern part of Umbria. Tonight is a “make your own” dinner, as we will be making our own pasta at a private cooking class with Chef and Owner of Ristorante Fiorentino, Alessia Uccellini. Store-bought pasta will be disappointing forever more.
Today is our day to visit Umbria and its outstanding wineries. We at Taste Vacations love Umbria because it is as scenic as Tuscany and yet much less visited. We start with a visit to Arnoldo Caprai winery, the leading winery of the region and leading producer of its most famous local grape, the Sagrantino di Montefalco. We will learn all about and taste wines made from the Sangrantino grape, grown in this area for over 400 years.
We then travel to Bevagna, a medieval Umbrian village renowned for its beautiful landscapes, some Ancient Rome mosaic floorings, but most of all for being the center of production for Sagrantino di Montefalco. There, we will visit Agricola Mevante, a brand new winery that will give us a much different viewpoint from the large Arnoldo Caprai. You’ll be able to wander the historic town of Bevagna and find lunch on your own.
For Dinner, we will visit the local brewery, Birrificio Altotevere, for an opportunity to try local craft beer and burgers the Italian way.
This morning begins with a visit to the very small and local olive oil mill of our friend Emanuele Ragani and his family. Emanuele will not only show us how the mill, with an actual grist stone, operates but will fire up a wood oven, heat up bread, and pour delicious olive oil on top for a tasting. The olive oil makes a great souvenir from Italy but it is the local experience, watching Emanuele and his family as they continue to run a business serving the locals, who bring their olives by for pressing year after year.
We then head to Assisi, the city made famous by St. Francis, for a tour of the city and the church where he is buried. Assisi’s church is impressive but you will equally enjoy the many winding streets, the views over the valley below, and the multitude of shops and restaurants. We are on our own here for lunch, allowing you to pick your dining option at leisure.
After our morning of Italian culture, it is back to the wine (and back to Tuscany) with a visit to Azienda Agricola Leuta. This is a relatively new winery in a new region, which only recent has been identified as having good terroir for wine grapes. Leuta specializes in Syrah and Cabernet Franc, two grapes we will not have tried much up until now on this tour. After a tasting, we continue to the nearby city of Cortona, made famous by the book Under the Tuscan Sun, our home for the evening. We’ll check into our hotel where you will then have free time to take in the sights and sound of this beautiful town before reconvening for a delicious dinner at a local gem.
Our first stop of the morning is at Avignonesi, a winery located just outside the quiet village of Valiano di Montepulciano. The old winery (comprised of nine vineyard plots, a villa, a chapel and the historic wine cellars) has a new owner, Belgium transplant Virginie Saverys, who has brought biodynamic winemaking and organic wines to the property. Virginie’s daughter is involved and the winery has an Australian (female) winemaker on staff. We will learn about the property and taste the local wines before heading to the highlight region of the day – the Val d’Orcia.
The Val d’Orcia is one of the most beautiful sections of Tuscany, which is one of the most beautiful provinces of Italy, which is one of the most beautiful countries in the world. We are in a good place!
We’ll start our Val d’Orcia tour by visiting the city of Pienza, perched high above the valley and designated a UNESCO World Heritage Site. (The entire valley is designated a World Cultural Landscape.) After a quick historical walking tour of the city, we’ll head to a local farm that specializes in making pecorino, the ubiquitous local sheep’s cheese. We’ll learn about the process, have a taste of the fresh cheese, and eat a nice picnic lunch right on the farm.
It is then on to Montepulciano, another famous hilltop town, where you will have an hour to wander the streets on your own. We then gather together again to visit Cantine Gattavecchi for a tour of their barrel room (underground cellars) and a tasting of the local wine, the outstanding Vino Nobile di Montepulciano. This is a family-owned, fourth generation business that is a pillar of the local wine community.
Heading back to Cortona, we’ll share a final meal together at the Locanda al Pozzo Antico, a fine dining establishment run by the owner Paola where we’ll try to outdo our previous successes with Tuscan cuisine.
We’ll take a post-breakfast walk of Cortona, as Giovanni will point out some of the important sites that featured in Under the Tuscan Sun. You are then free to take the train or a shuttle onwards to Florence or Rome (Check out Extend Your Stay: What To Do in Italy). Or perhaps you’ll follow the theme of the book and decide to stay in Tuscany permanently?
Night 1: Il Guelfo Bianco, Florence: This boutique hotel is housed in a restored building dating back to the 15th century. It’s perfect central location is near the Cathedral of Santa Maria del Fiore, the Accademia Gallery and the Central Market of San Lorenzo, making it easy to walk around on your own.
Night 2: Villa San Lucchese, Chianti: Set in the hills of the Chianti wine district, this 15th-century villa has amazing views of the Tuscan landscape below.
Nights 3 & 4: Hotel Tiferno, Città di Castello: Built in 1895, this historic boutique hotel was once a 17th century monastery and is perfectly located in a quaint square in the center of beautiful Città di Castello.
Nights 5 & 6: Hotel San Michele, Cortona: Enjoy modern comforts in an ancient 15th-century palace, located in the historic center of Cortona. You’ll not only find beautifully and uniquely decorated rooms but incredible ancient artwork in the lobby.
What is Included
- All Local Transportation
- Double Occupancy Lodging
- 6 Breakfasts + 2 Lunches (with wine included) + 6 Dinners (two with wine included)
- 10 Tastings at Wine Estates
- Cooking Class, Olive Oil Tasting, Guided City Walks, Pecorino Cheese Tasting, Visit to Chocolate Maker/Coffee Roaster
- Professional Tour Host
Not Included: Travel to and from destination, wine with some meals, personal expenses, and optional gratuities to local staff and your Host. Travel insurance is also not included, though we highly recommend it. Check out our Travel Insurance page for more information.
While the general trip itinerary will remain the same, the actual restaurants, hotels, and activities listed are subject to modifications. Changes that are out of our control are common — restaurants close or lose their amazing chef, a winery changes their visiting hours, a hotel gets remodeled, etc. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance.
Arrival & Departure
We meet in the early afternoon on the first day of the tour at a downtown Florence hotel, allowing you to arrive either that morning or the day before. The tour finishes in Cortona before lunch on the final day of the tour. Cortona is on the mail rail line connecting Florence to Rome, so you can fly out of either city. One nice option is to fly into Florence and out of Rome, so you can visit both cities.Book Now