Tuscany Lovers: Romance, Style & Flavor in Cortona
Romantic Dinner, Jewelry Boutique, Chocolate & Wine Tasting, and 3‐ or 4‐Night Stay for 2
This Experience for 2 Includes:
- 3-night weekend (Fri–Sun) or 4-night weekday (Mon–Thu) stay in Cortona, Tuscany
- Welcome bottle of Champagne on arrival
- Visit to Del Brenna Jewelry, an artisanal boutique with Prosecco and private showroom access
- Romantic 3-course dinner at Ristorante La Loggetta
- Chocolate & wine pairing at Sottovoce Wine Bar
- Winspire booking & concierge service — seamless support from planning to travel
Perched on a sun-drenched Tuscan hilltop, Cortona is the kind of place that feels written for love stories. Winding cobblestone streets lead you past frescoed churches and piazzas where the golden light lingers on terracotta rooftops. From nearly every vantage point, the landscape unfolds like a painting — endless vineyards, silvery olive groves, and rolling hills that stretch toward the horizon. Here, romance is everywhere: in the architecture carved by centuries, in the warmth of the locals who greet you like family, and in every plate of rustic, farm-to-table cuisine that invites you to slow down and savor the moment.
Artisanal Jewelry Experience
Step inside Del Brenna Jewelry, a hidden gem tucked within one of Cortona’s most storied palazzi. With a flute of chilled Prosecco in hand, you’ll be surrounded by the sparkle of hand-crafted pieces that reflect both artistry and heritage. From delicate filigree earrings to bold statement necklaces, each jewel carries the soul of Tuscan craftsmanship. For your evening out, select a piece to wear — transforming the night into a moment of elegance and self-expression. The next morning, return it to the atelier, or choose to keep it forever as a tangible reminder of your time in Cortona.
Romantic Dinner & Chocolate Pairing
As twilight settles over the town, your evening begins at Ristorante La Loggetta, an intimate, candlelit haven housed in the vaulted cellars of a 13th-century palazzo. Beneath wooden beams and terracotta floors, each course tells a story of Tuscany — rich pastas, earthy flavors, and recipes rooted in generations of tradition. After dinner, step out into the moonlit streets of Cortona, where history and romance seem to linger in the air. Hand in hand, make your way to Sottovoce Wine Bar, a cozy hideaway where your night concludes with a decadent pairing of fine wines and artisanal chocolates — a sensual finale to a day steeped in passion, flavor, and timeless Italian charm.
Luxury Apartment Stay
Your home in Cortona is a charming private apartment for two, blending classic Tuscan character with modern comforts. From its central location, you’ll be just steps away from Cortona’s shops, trattorias, and piazzas. Toast your arrival with a chilled bottle of Champagne and let Tuscany’s rhythm welcome you into its timeless embrace.
Additional Information: Climbing a staircase is required to access apartment. The building does not have an elevator.
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
Why This Experience Captivates Donors and Closes Bids
- Romantic appeal — perfect for couples seeking intimacy and indulgence
- Layered inclusions — jewelry, fine dining, wine, and lodging in one unforgettable package
- High perceived value — exclusive boutique access and historic dining settings add rarity
- Turnkey ease — with Winspire’s concierge, every detail is seamlessly handled
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.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply.
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