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Tuscany Lovers

Romantic Dinner, Jewelry Boutique, 3 or 4‐Night Stay for 2 in Cortona


This Experience for 2 Includes:

  • Your choice of a 3-night weekend or 4-night weekday stay in Tuscany (Cortona, Italy)
  • Welcome bottle of Champagne 
  • Visit an artisanal jewelry boutique
  • Romantic dinner
  • Chocolate and wine tasting
  • Winspire booking & concierge service


Cortona is among the most beautiful and romantic places in Tuscany. The amazing never-ending views are enough in itself to create romantic moments. Add classic architecture, genuine hospitality, and farm-fresh foods and Cortona will capture your heart.

Jewelry Boutique

Visit the very unique Del Brenna Jewelry, an artisanal boutique located in one of the oldest and most distinguished buildings in town. Enjoy the beautiful showroom while sipping a glass of Prosecco. Choose a piece of jewelry to wear that evening with the option of purchasing it or returning it the next day.

Romantic Dinner

Enjoy a 3-course meal at a romantic table in the intimate setting of Ristorante la Loggetta. Housed in the cellars of a building from the 1200’s, the classic Tuscan-style restaurant will amaze you with their wonderful ceilings adorned with wooden beams, terra cotta floors, brick arches and fine frescoes on the walls. Alcohol not included. End your evening at Sottovoce Wine Bar for a sensual pairing between chocolate and wine in one of the most charming spots in town and discover just how spectacular this combination is.

Luxury Apartment

Enjoy a 3-night weekend (Friday – Sunday) or a 4-night weekday stay (Monday – Thursday) in a charming apartment for 2 in the center of the stunning hilltop town of Cortona. Toast your arrival with a welcome bottle of champagne.

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

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.