7 Days Ultimate Wine Holidays in Tuscany, Italy

  • Villa Barberino, Viale Barberino, 19 52022, San Giovanni Valdarno, Cavriglia, Arezzo, Tuscany, Italy

Italy Wine Tours

Experience Tuscany and live like a local for a week. Immerse yourself in the culture and actually interact and share experiences with the locals. You will discover the most stunning wineries not easily found by tourists, eat at enotecas and restaurants where the locals eat, cook with resident local chefs, share secret typical Tuscan recipes with you, and visit cultural sites led by local, native guides. Once you’ve experienced Tuscany, you will never forget La Dolce Vita.


  • Wine tastings and winery tours
  • Hands-on local cuisine cooking class
  • Siena and Florence city tours accompanied by an English speaking guide
  • Daily meals with beverages and wine
  • Transportation during the tours
  • 6 nights accommodation
  • Fully hosted
  • 7 days with instruction
  • English
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Situated where Siena, Florence, and Arezzo intersect, Villa Barberino is your home for the next seven days. Here, you will relax, learn to cook authentic amazing Italian dishes, make new friends, and live like a local.

The villa dates back to the 14th century and served as a political and military stronghold. Today, the villa sits nestled in cypress trees and is home to our host family which has restored it to its former beauty. We welcome you to join us and become part of the family.

Overlooking a beautiful wooded valley and a lake, full and lush is what memories are made of, and memories are exactly what you will make. You can walk the beautiful grounds when you are not cooking or participating in one of the many activities that A Toast to Travel has in store for you. You can enjoy the swimming pool, solarium, tennis courts, Italian gardens, hiking, and panoramic views at the host villa for your unforgettable and relaxing week in the Tuscan countryside where you are surrounded by olive trees, rolling hills, and the vineyards of Tuscany. Walk through the Italian gardens and while enjoying a nice glass of Tuscan wine.

Our host villa has preserved the traditional Italian charm of the property while adding modern conveniences. All of the guest rooms have private bathrooms, air conditioning, LCD TV, free Wi-Fi, hairdryer, telephone, and shower. Remember, when you are a guest, you are part of the family and this will come through in every aspect of your time with A Toast to Travel.

These experiences are fully hosted and all-inclusive once you are with the group and your hosts.

Day 1 - Benvenuti a Tuscany!

You will meet tonight around 6 p.m. for the welcome cocktail (aperitivo) surrounded by the beautiful hills of Tuscany and begin to sample some of the local wines and appetizers which can range from bruschetta with fresh tomatoes and local olive oil, to prosciutto and salami, while you socialize with fellow guests and toast to travel!

After the aperitivo, you will gather around the Tuscan dinner table for a meal specially prepared for you including fresh made pasta, filets of meat, fresh vegetables, and possibly the most delicious Italian desserts you’ve ever tried.

As you toast each other with the local Tuscan wine, A Toast to Travel shares with you all the exciting experiences in store for the week ahead. Pace yourself, pace yourself!

Day 2 - Siena, a UNESCO World Heritage Site

After breakfast and around 10 a.m., you will travel to Siena, a UNESCO World Heritage Site, where you will be guided by a local on a walking tour of Siena visiting its most important sites and learning about its rich history and culture. Siena is not to be missed!

You will sit down for lunch together at a delicious local restaurant (with wine, of course) and then, you’ll have free time on your own to relax, do some shopping, or have a coffee in one of the famous town squares and simply people watch (people watching in Italy can’t be beat!).

The guided tour lasts about two hours and after lunch, you’ll have a few hours on your own to enjoy Siena as the local do.

You will have dinner together tonight and A Toast to Travel has a surprise in store! Try to save some room for dinner tonight as there is a special meal planned and of course, the wine will flow.

Day 3 - From Villa Barberino with love

After breakfast, you will meet as a group for a hands-on cooking lesson with the resident chef to learn how the locals cook. Today, you will learn how to make local favorites, a starter, pasta and an unforgettable sauce which you will enjoy for lunch. You’ll have time this afternoon to enjoy the villa and relax.

Later, you will meet in the host villa’s underground wine cellar for a tour, a conversation about its history (including the wartime escape hatches that led residents safely into the surrounding woods) and of course, to sample the wine.

Dinner tonight is a feast prepared just for you at Villa Barberino.

Day 4 - A toast to Chianti!

After a satisfying breakfast, around 10 a.m., you will head over to another beautiful winery in Chianti, taking beautiful winding roads overlooking the beauty of Tuscany along with its historic castles, wineries, and people. You will visit the winery, sample delicious wines, and enjoy a gourmet lunch together.

After all that hard work, you will head to another stunning winery to taste more wine in beautiful Chianti.

After a fun filled day in Chianti, you will head back to the host villa to enjoy your dinner together. It’s time to relax and enjoy our evening together with a gourmet meal prepared specially for you by the resident chef. It’s a meal not to be missed!

Day 5 - The glass is always half full in Chianti!

After breakfast this morning, get ready to visit one of the most beautiful wineries in the world of Tuscany! You will be heading to one of A Toast to Travel’s favorite wineries where you’ll have the opportunity to learn about the wines, take a tour of the winery, and sample wines from the vineyard during the wine tasting.

Then, you will head to a beautiful town where you will have an authentic Tuscan lunch together (with wine, of course!). After lunch, you will be heading to another one of A Toast to Travel’s favorite wineries in Tuscany for - you guessed it - more wine! You will have a tour and a tasting all before heading back to the host villa for an authentic Tuscan dinner. No evening is complete without a toast - a toast to travel!

Day 6 - Onward to the empire!

After a satisfying breakfast, you will meet as a group around 10 a.m. to be transported to Florence, one of the culturally richest cities in the world. You will start with a walking city tour, then, you will stop for an exclusive sit down lunch and wine pairing at an enoteca in the heart of Florentine old town where you savor the flavors, scents, colors, and moments together of cured meats, Tuscan cheese, and of course, Tuscan wine.

After lunch, you’ll have free time for any exploration you wish to do on your own, shopping or simply enjoying a coffee at any one of the many cafes in famous town squares. You will meet for dinner later in the evening in Florence to enjoy one of the best Bistecca alla Fiorentina in town.

Florence is known for great food and even better wine. This restaurant is one of A Toast to Travel’s personal favorites and at the top of the list. Buon appetito!

Day 7 - It’s not goodbye, just until next time

After breakfast this morning, don’t forget to take your final photos of beautiful Tuscany, the host villa, and all the new friends you’ve made. Take a last stroll in the gardens, visit the olive trees, smell the fresh Tuscan air, smiling into the sun for it’s not farewell but until next time.

Just remember, you may leave Tuscany but Tuscany will never leave you. Once you’ve experienced Tuscany, you will never forget La Dolce Vita. Besides, after having lived like a local for the week, you are now part of the family.

You will enjoy Siena and Florence city tours accompanied by an English speaking guide.

This retreat will take place in Tuscany, Italy.

In total, you will be served six breakfasts, five lunches, and six dinners. Wine is included with all meals. Please contact A Toast to Travel regarding any food allergies and sensitivities and/or any dietary restrictions. A Toast to Travel will endeavor to accommodate but please note that given typical Tuscan recipes and ingredients, this may not always be possible.

  • 6 nights accommodation
  • 6 breakfasts, 5 lunches, and 6 dinners
  • 4 winery tours and tastings fees
  • 2 guided city tours (Siena and Florence with English speaking guide)
  • 1 hands-on cooking class
  • Transportation to and from all destinations listed in the itinerary
  • Gratuities for all tours and activities in standard itinerary
  • Wine is included with all meals
  • A reservation requires a deposit of 100% of the total price.
  • The deposit is fully refundable if the booking is cancelled up to 120 days before the arrival date.

Gold Coast, Chicago, United States

A Toast to Travel is all about bringing together great people who have a love of wine, travel, having fun, and creating lifetime memories.

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7 days / 6 nights

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