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Tuscany Wine Tours

Welcome to Tuscany! You will have a fun filled weekend visiting the ultimate Tuscan wineries in Chianti, tasting, drinking, and toasting to some of the best wine on the planet! You will be eating and drinking your way through Tuscany as you live like a local at the wineries in Chianti and spending a day in Florence. It really is the ultimate Tuscan wine experience!


  • Wine tastings and winery tours
  • City tour in Florence with an English speaking guide
  • Free time to explore and do exciting activities in the villa or its surrounding areas
  • Daily meals with beverages and wine
  • Transportation during the tour
  • 3 nights accommodation

Skill level

  • Beginner
  • Intermediate
  • Advanced


4 days with instruction in English
Spoken languages: English
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You will stay in a beautiful Tuscan villa, Villa Barberino, with private hotel rooms and apartments. The villa is full of tradition and history and surrounded by olive trees, rolling hills, and the vineyards of Tuscany.


Day 1 - The glass is always half full in Tuscany!

Around 10 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.

You will have a gourmet lunch together and after lunch, you’ll have the opportunity to spend some time in a beautiful medieval village to take in the sights, relax, or do some shopping!

Later, you will be heading to another one of the favorite wineries in Tuscany for - you guessed it - more wine! You will have a tour, a tasting and then, all sit together for an authentic Tuscan dinner. No evening is complete without a toast!

Day 2 - Onward to the empire!

After a satisfying breakfast, you will meet 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 as a group 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 3 - 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 a farewell dinner together. It’s time to relax and enjoy the last evening together with a gourmet meal prepared specially for you by the resident chef. It’s a meal not to be missed!

Day 4 - 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, you are now part of the family.

Included excursions

You will enjoy a guided city tour in Florence, accompanied by an English speaking guide.


This retreat will take place in Tuscany, Italy.



  • Hiking
  • Shopping
  • Swimming pool (outdoor)
  • Tennis court
  • Wine tasting


  • Air-conditioned rooms
  • Bar
  • Garden
  • Restaurant
  • Patio


  • Free Wi-Fi
  • Hair dryer
  • Room cleaning


In total, you will be served 3 breakfasts, 3 lunches, and 3 dinners. Beverages and wine are 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.

The following meals are included:

  • Breakfast
  • Lunch
  • Dinner
  • Drinks

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

What's included

  • 3 nights accommodation
  • 3 breakfasts, 3 lunches, and 3 dinners
  • 4 winery tours and tastings fees
  • 1 guided city tour with English speaking guide
  • Transportation to and from all destinations listed in the itinerary
  • Gratuities for all tours and activities in standard itinerary
  • Beverages (and wine) are included with all meals

Cancellation Policy

  • The deposit is fully refundable if the booking is cancelled up to 120 days before the arrival date.
  • The rest of the payment should be paid 120 days before arrival.
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