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.
Ground transportation is the responsibility of the winner unless otherwise stated.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply.
Cortona & Rome with Guided Tours, Fine Dining and 5‐ or 6‐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
- 2-night stay at Hotel Dei Mellini in a Superior Room
- Choice of one guided Rome experience
- Winspire booking & concierge service — seamless support from planning to travel
This journey blends two sides of Italy’s soul — Rome’s monumental history and Tuscany’s intimate romance. Begin among ancient wonders and iconic piazzas, then slow the pace in Cortona, where golden light settles over terracotta rooftops and life unfolds one indulgent moment at a time. It’s a perfectly balanced escape: culture and charm, grandeur and intimacy, discovery and delight.
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.
Your Rome Stay: Hotel Dei Mellini
Set along the Tiber River in an elegant residential neighborhood, Hotel Dei Mellini offers a refined Roman retreat just moments from the Vatican, historic piazzas, and celebrated landmarks. Your Superior Room blends classic style with modern comfort — a peaceful haven after days filled with art, architecture, and unforgettable walks through history.
Choose Your Rome Experience
Highlights of the Vatican & Sistine Chapel (Semi-Private)
Step inside one of the world’s most extraordinary collections of art and history. With expert guidance and intimate group size, explore the Vatican Museums, Raphael Rooms, and stand beneath Michelangelo’s Sistine Chapel — a moment that leaves even seasoned travelers in awe.
Best of the Colosseum with Arena Floor Access
Enter Rome’s most iconic monument through the Gladiators’ Gate and stand on the Arena floor itself — where history once thundered. Continue through the Roman Forum and Palatine Hill, uncovering stories of emperors, power, and ancient daily life.
Evening Walking Tour: Fountains & Squares
As Rome glows under lantern light, stroll through its most beautiful piazzas and fountains — from the Spanish Steps to Trevi and Piazza Navona. Toss a coin, sip an espresso or cappuccino, and experience the city at its most romantic hour.
Christian Rome & the Underground Basilicas
Descend beneath the streets to uncover Rome’s early Christian history. Visit hidden crypts, ancient basilicas, and sacred spaces that reveal a quieter, deeply moving side of the Eternal City.
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
-
- Two iconic regions — Rome’s history paired with Tuscany’s romance
- Choice-driven design — donors select the Rome experience that fits their style
- Layered luxury — guided tours, fine dining, wine, jewelry, and boutique lodging
- Romantic appeal — ideal for couples, anniversaries, and milestone celebrations
- High perceived value — exclusive access and unforgettable settings
- Turnkey ease — Winspire’s concierge handles every detail
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.
Ground transportation is the responsibility of the winner unless otherwise stated.
Blackout Dates
The week of major holidays and major local events. Additional dates may apply.
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