Under the Tuscan Sun: Wine, Cuisine & Charm in Cortona
Italy Escape for 4 with Wine Tasting & Private Chef Dinner
This Experience for 4 Includes:
- Your choice of a 3-night weekend (Fri–Sun) or 4-night weekday (Mon–Thu) stay in Tuscany for 4 guests
- Wine tasting in Cortona featuring 4 local wines from one of the world’s most celebrated regions
- Private chef-prepared 3-course dinner served in your apartment
- Winspire booking & concierge service — seamless support from planning to departure
Imagine strolling cobblestone streets at golden hour, the rooftops of Cortona glowing in the late-day light as church bells echo across the valley. In every direction, vineyards and olive groves roll toward the horizon, while the scent of freshly baked bread and simmering sauces drifts from nearby trattorias. For four lucky guests, this is Tuscany not as a tourist sees it, but as a local feels it — intimate, authentic, and unforgettable.
Stay in the Heart of Cortona
Your private apartment is nestled within Cortona’s medieval walls, offering both modern comfort and old-world charm. Wake up to sunlight spilling across terracotta rooftops, then step outside to discover markets filled with cheeses, olive oils, and handmade goods. With winding alleys, Renaissance churches, and sweeping valley views, Cortona invites you to slow down and savor la dolce vita.
Taste the Wines of Tuscany
Gather around the table for a guided tasting of four wines that define the region. From bold reds to elegant blends, each sip tells a story of the soil, climate, and centuries of winemaking tradition. Your host will guide you through aromas, textures, and pairings — making this not just a tasting, but an education in Tuscany’s liquid art.
An Evening with a Private Chef
One evening, the flavors of Tuscany arrive at your doorstep. A private chef will prepare a 3-course dinner in your apartment, using ingredients sourced from local markets and family farms. As you savor each dish — handmade pasta, slow-simmered sauces, and rustic desserts — the chef shares the history and inspiration behind the recipes. With glasses raised and laughter echoing, it becomes more than a meal; it’s a memory woven into the heart of 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.
Why This Experience Captivates Donors and Closes Bids
- Bucket-list appeal: Tuscany’s timeless beauty, wine, and cuisine are universally enticing
- Layered inclusions: wine tasting, private chef dinner, and accommodations create a full cultural immersion
- Group-friendly: designed for 4 guests, making it perfect for couples or friends traveling together
- Turnkey ease: Winspire concierge handles every detail, ensuring a seamless, stress-free getaway
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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