Wineries and hills in Tuscany Italy

Tuscany 2023 Group Trip

Join us for a food and wine adventure in Tuscany! Shared Adventures Travel is hosting a delicious small-group experience next October, and we have just a few spots left. You do not want to miss out!


– Unique accommodations: two nights in Florence in a beautiful city center hotel, and five nights at a charming wine estate in the Tuscan countryside

– 7 breakfasts, 4 lunches & 7 dinners

– An array of fascinating food and wine-related experiences

– Fully-escorted by Shared Adventures Travel, with expert local drivers/guides

looking out from a stone wall on the classic trees and rolling hills of tuscany


October 14th -21st 2023

We’re limiting it to fewer than 20 people, to ensure a personal feel, so we recommend getting in touch ASAP before it fills up!


Grand Hotel Baglioni in the heart of Florence, we’ll enjoy a 2-night stay at this charming 19th-century hotel. Its rooftop terrace boasts impressive views of the city. And its elegantly furnished rooms show off a true Florentine style.

Buccelletti Casale and Cantina pool, lounge chairs and stone building surrounded by the green hills of Tuscany

Buccelletti Casali and Cantina– Five nights in this gorgeous, family-owned, and female-led villa and wine resort. Located in the stunning Val di Chio, just outside the town of Castiglion Fiorentino. The extensive grounds feature rustic rooms, stunning views, olive groves, vineyards, and a winery


Florence Duomo and the city behind it

Day 1

Arrive in Florence any time today and check in to the Grand Hotel Baglioni. We will all meet up for a welcome dinner at a nearby Florence restaurant.

(dinner included)

Day 2

Today we’ll enjoy a guided walking tour of Florence, including a visit to the Academia to see Michelangelo’s David. We’ll include time in the middle of our tour for lunch at the Mercato Centrale, and we’ll all meet back up again for dinner at another fabulous local restaurant.

(breakfast and dinner included)

Day 3

We’ll pack up and check out today and take a private transfer out into the countryside, to the Buccelletti Casali and Cantina. We’ll check in to our accommodations in Borgo Gaggioleto and gather together for a welcome dinner at the vineyard.

(breakfast and dinner included)

Day 4

Today is all about the olives! We’ll take part in the olive harvest in the morning, followed by a lunch and winetasting, and a guided tour of Castiglion Fiorentino this afternoon. We’ll have dinner together at a local restaurant in town.

(breakfast, lunch and dinner included)

Day 5

Daytrip in Val D’Orcia. We’ll visit the charming town of Pienza, tour (and taste) at the famous farm-to-table Podere il Casale, and do a winetasting along the way. Dinner this evening will be a fun hands-on cooking class back at the Cantina kitchen.

(breakfast, lunch and dinner included)

Day 6

Truffle hunting! We’ll visit a local farm and head out with the dogs to try our luck at finding some truffles, and then enjoy a delicious lunch at the farm. Dinner this evening is a pizza feast back at the Cantina.

(breakfast, lunch and dinner included)

Day 7

For our final day together, we’ll explore Cortona, the town famous as the setting for “Under the Tuscan Sun”. We’ll enjoy a guided tour, lunch at a local restaurant and time to shop and explore a bit on your own, before we head back for a special farewell dinner at the Cantina.

(breakfast, lunch and dinner included)

Day 8

This morning you’ll check out, and we’ve included a transfer to the local Castiglion Fiorentino train station. Depending on your onward travel plans, we can of course arrange a private transfer to the Florence or Rome airport, at added cost. (breakfast included)

How to Book

Total cost for this 7-night/8-day guided experience is 3800 Euros per person. There is no surcharge for solo travelers. Space is extremely limited, and will sell out quickly.

Email for sign-up information!


You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)