Italy Adventure 2026

Tuscany  ·  September 19 – October 3, 2026

Master Itinerary — 13 Days

Villa check-in Sat Sept 19 · Check-out Sun Oct 3 · Dinner at villa every evening

Sun 20 Sep
Cortona
14 people  ·  Art & History
La Loggetta 12:15 PM confirmed  ·  TOP Festival afternoon
✅ Lunch Confirmed
Day Guide
Mon 21 Sep
Wine Tour: La Combarbia + Poggio Sorbello
14 people  ·  Food & Wine
Large van confirmed  ·  Lunch at Poggio Sorbello included
⚠️ Monday ✅ Lunch Confirmed
Day Guide
Tue 22 Sep
Panzano — Officina Cecchini
14 people  ·  Food & Wine
Aperitif 12:00 PM · Seated 12:30 PM · €50 pp wine included
✅ Lunch Confirmed 🎂 Birthday Feast
Day Guide
Wed 23 Sep
Florence
8 people  ·  Art & History
Train from Camucia-Cortona · Wave 0 departs today
Day Guide
Thu 24 Sep
Pienza + Montepulciano
9 people  ·  Food & Wine · Art & History
Day Guide
Fri 25 Sep
Castiglione del Lago + Isola Maggiore
9 people  ·  Active & Outdoor
Day Guide
Sat 26 Sep
The Chiantigiana — Greve + Panzano
9 people  ·  Food & Wine
Day Guide
Sun 27 Sep
Orvieto + Civita di Bagnoregio
8 people  ·  Religious & Cultural
Monday closures apply — check card before finalising
⚠️ Monday Rules
Day Guide
Mon 28 Sep
Bagno Vignoni + Montalcino
8 people  ·  Food & Wine
Monday closures — Brunello cellars and enotecas typically open
⚠️ Monday
Day Guide
Tue 29 Sep
Monteriggioni + San Gimignano
6 people  ·  Art & History
Day Guide
Wed 30 Sep
Siena
6 people  ·  Art & History
Day Guide
Thu 1 Oct
Norcia — Truffle Hunt
3 people  ·  Food & Wine · Immersive Experience
Truffle season opens today 🍄 · Hutzul family only
🍄 Truffle Season Opens 🎂 Ron's 50th
Day Guide
Fri 2 Oct
Crete Senesi + Monte Oliveto Maggiore
3 people  ·  Religious & Cultural
Last full day in Tuscany
Day Guide