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Tuscany Wine & Florence Escape for Four

Currency:USD Category:Travel Start Price:4,550.00 USD Estimated At:NA
Tuscany Wine & Florence Escape for Four
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[?]Bidding Ends At 2026 Aug 17 @ 19:06 (UTC-08:00 : PST/AKDT)
Private Dining, Tuscan Vineyards & Renaissance Charm for 4


Booking & Travel Guidelines:
Travelers will have 1 year from the purchase date to book their experience and 2 years to complete travel.

Blackout Dates:
Blackout dates include the weeks of major holidays and significant local events. Additional restrictions may apply. Any packages with different booking or travel requirements have been noted individually above on each package.

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
- 2-night stay in Florence at Hotel Rosso 23 in a Classic Room (2 rooms)
- Florence Walking Tour with Duomo
- Winspire booking & concierge service — seamless support from planning to departure

Imagine strolling cobblestone streets at golden hour, as the rooftops of Cortona glow in soft amber light and church bells echo gently across the valley. Vineyards and olive groves ripple toward the horizon, and the air carries the comforting aroma of freshly baked bread and slow-simmered sauces drifting from nearby trattorias. Time slows here — inviting you to linger, savor, and settle into the rhythm of Tuscany.

Continue your journey to Florence, a city that doesn’t simply preserve history — it lives within it. Renaissance masterpieces rise from sunlit piazzas, cathedral bells ring from soaring domes, and café culture hums from morning espresso to evening aperitivo. Every street feels deliberate, every view worthy of pause. Florence sets the tone for what follows: beauty layered with meaning, culture infused with warmth, and moments that feel both timeless and deeply personal.

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.

Your Florence Stay: Hotel Rosso 23

Tucked into Florence’s historic center, Hotel Rosso offers a warm, classic retreat just steps from the city’s most celebrated landmarks. Intimate and inviting, it places you within effortless walking distance of museums, piazzas, and trattorias, while offering a comfortable haven to unwind after days filled with art and exploration. Wake to the rhythm of the city, linger over morning coffee, and step outside into one of the world’s great cultural capitals.

Florence Walking Tour with Duomo
Step into the heart of the Renaissance as your guided walking tour brings Florence to life through elegant piazzas, cobblestone streets, and timeless masterpieces. Wander past the Ponte Vecchio and lively Piazza della Signoria before arriving at the breathtaking Florence Cathedral — the iconic Duomo whose soaring dome and intricate marble façade have inspired travelers for centuries. As church bells echo through the city and the scent of fresh espresso drifts from nearby cafés, your expert guide shares the stories of artists, visionaries, and Medici rulers who shaped Florence into one of the world’s most beautiful and culturally rich cities.

Why This Experience Captivates Donors and Closes Bids

Instant bucket-list appeal: Tuscany’s rolling hills, world-class wine, and iconic cuisine resonate with nearly every traveler
Rich, layered value: Wine tastings, a private chef dinner, and immersive stays combine to create a complete cultural escape
Perfect for sharing: Designed for four guests — ideal for couples, friends, or milestone celebrations
Effortless luxury: Every detail is handled by Winspire’s expert concierge team, making the experience seamless from start to finish