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, paired with local wine
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.

Package blackout dates: The week of major holidays and major local events. Additional dates may apply.

WINSPIRE 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.

WINSPIRE 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.

Certificates cannot be resold or replaced if lost, stolen, or destroyed. Ground transportation is the responsibility of the winner unless otherwise stated.

Ferrari Fantasy: Speed, Style & Flavors of Modena

Ferrari Test Drive, Museum & Factory Visit, Balsamic Cellar Tour with Lunch, and 3-Night Stay for 2

This Experience for 2 Includes:

Ferrari Test Drive on the official 65 km Ferrari route through the Italian countryside and mountain roads
Guided Ferrari Museum and Factory tour in Maranello (factory tour by shuttle bus)
Half-day balsamic cellar visit with tastings, cheese pairings, Lambrusco wine, and light lunch
3-night stay in a 4-star hotel in Modena's historic Old Town
Winspire booking & concierge service - stress-free planning from start to finish

The engine growls, your hands grip the wheel, and with one press of the pedal, the Ferrari Portofino springs to life - sleek, powerful, unmistakably Italian. You'll fly along 65 kilometers of countryside and mountain roads, the wind rushing past as vineyards and hilltop villages blur in your periphery. With an expert guide in the passenger seat, each curve becomes a thrill, each straightaway an open invitation to feel the raw power that has made Ferrari a legend.

The Ferrari Experience

After your exhilarating test drive, step into Ferrari's world in Maranello. Wander through the Ferrari Museum, where gleaming race cars, championship trophies, and design marvels tell the story of speed and innovation. Then, board a shuttle for a guided factory tour, circling the hallowed grounds where artistry and engineering merge to create the world's most iconic cars.

Balsamic Cellar Visit with Lunch

From horsepower to heritage, Modena also seduces with its flavors. At a traditional aceto balsamico tradizionale cellar, oak barrels line the walls, each filled with vinegar that has been patiently aging for decades. The air is sweet, tangy, alive with history. Learn how generations have perfected this craft, then sit down to a light lunch where every bite sings of the region: sharp cheeses paired with silky balsamic, sparkling Lambrusco wine that dances on the palate, and stories shared over the table. It's an authentic taste of Emilia-Romagna's soul.

Accommodations in Modena

Your home base is a 4-star hotel in Modena's Old Town, surrounded by cobblestone streets, medieval towers, and the soaring Romanesque cathedral. Wake to church bells echoing across the piazza, sip espresso at a sidewalk café, and wander through bustling markets where locals trade fresh pasta, cheeses, and flowers. At night, trattorias beckon with rich ragù, tortellini in brodo, and the warmth of Italian hospitality. This is Modena - historic, vibrant, and unforgettable.

(Please note: drivers must be 21+ with an international driver's license; entry into the factory floor is not permitted.)

Package Blackout Dates: The week of major holidays and major local events. Additional dates may apply.

WINSPIRE 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.

WINSPIRE 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.

Certificates cannot be resold or replaced if lost, stolen, or destroyed. Ground transportation is the responsibility of the winner unless otherwise stated.