Tuscan Escape is an eight-day journey through Tuscany with me and Jill Bruce, built around three things we love: wine, food and culture. We start near Florence and travel through Chianti Classico, Montalcino and Bolgheri, with time in San Gimignano, Siena and Florence along the way.
The idea
I did not want to build a tour. I wanted to plan a week the way I would for friends: slow mornings in the vineyards, long lunches that turn into afternoons, and dinners where the wine finally makes sense because you have met the people who made it.
We open the cellar doors of Chianti Classico, Montalcino and Bolgheri, and we go where the small family-run producers are. We cook together in a Tuscan kitchen, taste olive oil and cheese where they are made, and walk through San Gimignano, Siena and Florence with local guides.
It all started in 2025, with the group in the photo. The group stays small and semi-private, with 12 guests at most. Forget coaches and standard visits.
You travel with two wine professionals, Jill and me, so every glass comes with its story. By the end of the week, Tuscany stops being a destination and becomes a place you know.
Meet Jill
Jill Bruce is an Executive Sommelier who creates curated wine and food experiences, from small-group tastings to guest wine education. Based in Tennessee, she co-leads Tuscany Wine Journeys and is my partner in Tuscan Escape.
We share the same passion from two complementary perspectives: Jill brings the needs and expectations of an American audience, while I bring deep local knowledge of Tuscany and its producers.
We met in the field in 2024. With the third edition sold out this October, the next Tuscan Escape in May 2027 will be our fourth.
Next 2027 edition at a glance
The next Tuscan Escape is already taking shape. Here is when it runs, who travels with you and what the week is built around.
- Dates: May 2nd to 9th, 2027 (8 days, 7 nights)
- With: Claudia Callegari and Jill Bruce
- Where: Tuscany, from Florence to Chianti Classico, Montalcino and Bolgheri
- Focus: wine, food and culture
Places are limited and we will keep a waiting list. Write to me at claudia@callegari.wine to ask for a spot.
The itinerary
Day 1 · Sunday
- Hotel check-in near Florence, according to your travelling schedule
- Dinner at the Castle
Day 2 · Monday
- Chianti Classico winery tour, tasting and lunch
- Gallo Nero discovery
- Visit to a small, family-run Chianti Classico producer
- Dinner at the Castle
Day 3 · Tuesday
- Olive oil tour and tasting
- San Gimignano guided tour
- Cooking class with dinner
Day 4 · Wednesday
- Cheese factory tour and hands-on activity
- Siena guided tour
- Dinner in Montalcino
Day 5 · Thursday
- Tempio del Brunello visit
- Poggio Stenti butcher tour and tasting
- Tour and tasting in a Brunello di Montalcino winery
- Dinner at the hotel
Day 6 · Friday
- Bolgheri sightseeing
- Family lunch with garden products
- Stroll on the Mediterranean coast
- “Blend your own wine” game activity
- Grand tasting recap
Day 7 · Saturday
- Departure to Florence city centre
- Florence guided city walk
- Free time for shopping
- Pizza in Florence
Day 8 · Sunday
- Check out and bye bye Tuscany!
This itinerary is tentative and subject to change. Adjustments may be made based on factors such as weather conditions and availability.
Interested?
Behind the scenes, Tuscan Escape is organized with the support of Storywalking, our Italian tour operator partner, so that every detail is handled professionally. They take care of the bookings and reservations, the drivers who take us from one place to the next, and secure payments, so you can arrive, relax and enjoy the week while Jill and I look after the wine.
Write to me and I will come back to you with all the information. The quickest way to reach me is on WhatsApp at +39 339 4708113. You can also write to claudia@callegari.wine or use the contact form just below.