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Under the Tuscan Sun

3 or 4‐Night Stay for 4 in Cortona, Chef Dinner, Wine Tasting


This Experience for 4 Includes:

  • Your choice of a 3-night weekend or 4-night weekday stay for 4 people in Tuscany (Cortona, Italy)
  • Wine Tasting
  • 3-course dinner in your apartment prepared by a private chef
  • Winspire booking & concierge service


With its manicured fields, rustic farms, cypress-lined driveways, and towns clinging to nearly every hill, Tuscany is our romantic image of village Italy. Visitors to Tuscany come for many reasons, some in search of fine art, others to explore the extraordinary countryside. Gourmets and wine buffs descend on Tuscany to enjoy the simple yet wonderful cuisine and wine.. Time seems to slow in this effortlessly idyllic place. And what better way to unwind than by savoring a glass of vino or eating a homemade meal under the Tuscan sun?

Wine Tasting

Enjoy a cool wine tasting in town, learning about, and sampling 4 different wines from one of the most famous regions in the world for quality wine.

Charming Apartment

Enjoy a 3-night weekend (Friday – Sunday) or a 4-night weekday stay (Monday – Thursday) in a charming 2-bedroom, 2-bath apartment for 4 in the center of Cortona. This stone-clad town with olives and vineyards creeping up to its walls offers stunning views over Lake Trasimeno and the plain of the Valdichiana.

Additional Information: Climbing a staircase is required to access apartment. The building does not have an elevator.

Dinner in your apartment

One evening of your stay will include a 3-course dinner will be prepared by a private chef in your apartment. Observe first-hand the preparation of a traditional Italian meal, and of course, enjoy consuming it! Accompanied by great local wine, this will be an unforgettable part of your trip in Tuscany.

NOTE: Cortona is approximately a 1.5-hour drive from Florence and a 2.5-hour drive from Rome. Nearby cities: Perugia 45 km; Siena 70 km; Florence 100 km; Rome 205 km; Pisa 200 km.

Package Redemption

Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.

Booking & Concierge Services

Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.

Additional Information

Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.