Tuscany Active Culinary Hiking & Walking Tour
Gourmet Adventure in Italy from Chianti to Val d’Orcia
Tuscany’s greatest pleasures are simple: beautiful walks, exceptional food and good company. Discover all three on a journey through vineyard-clad hills, medieval villages and unforgettable farm-to-table experiences.
We rate our trips based on a range of activity levels from 1-5.
See this trip's Activity Options & Terrain for more details.
From $4,599 - $4,899/person
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Snapshots from the Trip
Trip at a Glance
Highlights
- Stroll through lush vineyards and old-world villages like Radda in Chianti and Pienza
- Cook with locals, learning farm-to-table recipes passed down through generations—buon appetito!
- Hike the cypress-lined white roads of southern Tuscany and sip Chianti Classico in the hills where it was born
- Share in Italy’s culinary traditions, from your first plate of handmade pasta to the last bowl-scraping spoonful of tiramisu
- Retreat to inviting Tuscan estates and boutique hotels that pair authentic local heritage with refined modern style
Sample itinerary. Trip details may vary by departure.
Start Arezzo Airport & Travel Details
- Get a taste of Tuscany’s rolling countryside as you trek from just outside the village of Castellina to our hotel
- Explore the famed wine-growing area around Radda
- Hike from one stunning vista to the next, pausing for lunch at a favorite local agriturismo
- Learn to prepare a homestyle Italian meal in a hands-on cooking class led by an engaging local chef
- Sip Chianti Classico and discover the traditions behind regional recipes
- Relax at our beautiful hotel in the heart of the Chianti Valley.
Nights 1-2
Deluxe Hotel
Beautiful vineyards surround this elegant retreat in the Chianti countryside—fit with a spa and wellness center housed in an ancient wine cellar. (pool, spa)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
- Journey into southern Tuscany’s Crete Senesi, famed for its moonlike landscape
- Walk through the vineyards and woodlands of Montalcino, birthplace of renowned Brunello wines
- Follow the strade bianche (white roads) of UNESCO-listed Val d’Orcia, home to celebrated pecorino cheese
- Savor regional specialties like truffles during memorable meals showcasing local culinary traditions
- Stroll through Renaissance-era Pienza, Pope Pius II’s visionary ideal city
- Enjoy lunch at a friend’s gourmet trattoria, complete with a dessert-making demonstration
- Soak in our hotel’s restorative thermal pools or unwind with a spa treatment
- Say arrivederci to Tuscany with a leisurely hike through the countryside surrounding Bagno Vignoni.
Nights 3-5
Deluxe Hotel
Set in the medieval village of Bagno Vignoni, La Posta is an elegant boutique hotel centered around a tranquil garden courtyard. Thermal waters from the area's natural underground springs feed the hotel's pools and spa, continuing the village's long tradition as a historic spa destination. Stylish rooms, a lively bar and peaceful outdoor spaces create a relaxing place to unwind at the end of the day. (pool, spa)
Hotels may vary on select departures. Click View Dates and choose a departure to see any variations.
End Florence Airport & Travel Details
This trip has an activity level range of 1-3
All breakfasts, 5 lunches, 4 dinners
All accommodations on your Backroads trip
All gratuities at hotels and restaurants
Expertise and services of Backroads Trip Leaders
Lightweight carbon hiking poles
Backroads On Trip App with route maps, elevation profiles, daily snapshots and more
Additional local guides and experts, plus equipment for included activities as detailed in your itinerary
Exclusive activities, tours and cultural experiences, as detailed in your itinerary
All luggage transfers and porterage during your trip
Snacks and beverages between meals
Private cocktail and wine receptions on the first and last nights of your trip
Choice of Backroads t-shirt or hat, plus water bottle and luggage tag
Detailed Travel Planner with destination tips and pre-trip information
