Tuscany Active Culinary Hiking & Walking Tour
6 days
5 nights
Activity Levels 1-3
Deluxe Hotels
Tuscany Active Culinary Hiking & Walking Tour
6 days
5 nights
Activity Levels 1-3
Deluxe Hotels
2026: Aug-Oct 2027: May-Oct
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.
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
Start Arezzo
End Florence
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary
Days 1-2
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
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.
Days 3-6
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
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.
What's Included
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Dates & Prices
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