May 31 – June 7, 2026 – max group size is 8 people
Join Europe Your Own Way for this weeklong escape in the heart of Tuscany.
This trip blends the best of Italian countryside living with unforgettable cultural and culinary experiences. Each day offers a balance of exploration and relaxation — from charming hill towns and organic farms to hands-on cooking and a truffle-hunting adventure. Anchored at a beautiful villa near Montepulciano, the trip features wine tastings, farm-to-table meals, medieval villages, and the timeless rhythm of Tuscan life.
Day-by-Day Itinerary
Sunday, May 31 | Arrival in Tuscany
Arrive at the villa in the later afternoon and settle in. Relax at the villa or enjoy a short visit to nearby Paciano. We’ll begin the trip with a welcome aperitivo and dinner together.
Monday, June 1 | Pienza & Countryside Flavors
Full-day excursion with visits to Pienza and an area cheese producer, where a farm-fresh lunch is included. Enjoy free time to wander Pienza’s Renaissance streets and shops before returning to the villa. Dinner at leisure.
Tuesday, June 2 | Montepulciano & Wine Explorations
Head to Montepulciano area winery to kick off the day with a morning tasting, then enjoy time exploring Montepulciano. Lunch and a wine cellar tour in central Montepulciano, followed by an afternoon visit to another area winery. Return to the villa in the evening.
Wednesday, June 3 | Tuscan Cooking Experience
Spend the day learning Tuscan cooking techniques with a hands-on class. The group lunch will feature the dishes prepared together. Evening at leisure.
Thursday, June 4 | Spello, Assisi & Perugia
Day trip to three Umbrian gems: stroll the flower-lined lanes of Spello, explore historic Assisi, and enjoy lunch and sightseeing in Perugia before returning to the villa. Dinner at leisure.
Friday, June 5 | Montalcino & Olive Oil Farm
Visit an Organic Farm in the Val d’Orcia for an olive oil experience and included lunch. Continue to Montalcino for free time to wander this Brunello wine capital, with an optional winery stop before heading back to the villa.
Saturday, June 6 | Truffle Hunting & Farewell Dinner
Set out for a truffle hunting experience followed by lunch. Return to the villa to relax and prepare for a festive farewell dinner together in the evening.
Sunday, June 7 | Departure
Depart the villa in the morning.
Includes: 7 nights’ accommodation at a beautiful villa with pool about 45 minutes from Montepulciano; city taxes; each bedroom has private bathroom, AC, WIFI; meals included: daily breakfasts, 5 lunches, 2 dinners; arrival and departure transfers to/from Florence airport or central train station; ground transportation by private vehicle (includes gas, tolls, and parking); day trip excursions outlined in itinerary.
Personalized additions either before or after the noted itinerary are possible and gladly accommodated for additional costs.
Price: $4675 pp double occupancy; $5275 pp single occupancy. (Trip subject to modification as necessary due to weather, etc.)
Not included: airfare, tips, meals other than those noted, excursions and activities other than those noted, travel insurance.
If you’re interested, please contact me with any questions or to book your spot. Space is limited.
Hope you can join us!!!