7-Day Trip for 2 to Tuscany, Italy

Purchase a ticket for your chance to win a 7-day Trip for two to Tuscany, Italy!

This carefully curated 7-day escape to Tuscany offers you and your travel companion the perfect blend of relaxation, culinary adventure, and authentic Italian charm.

Nestled in the heart of the Valdarno valley, your private villa in Pergine Valdarno serves as the ideal home base for exploring Tuscany's treasures.

This picturesque area offers the tranquility of countryside living while remaining perfectly positioned for day trips to Florence, Siena, and the Chianti wine region. With your own rental car providing complete freedom to explore at your own pace, you'll discover charming trattorias tucked away in hillside towns, visit family-owned wineries where generations of tradition come alive in every bottle, and meander through weekly markets brimming with local cheeses, fresh produce, and artisanal crafts.

Before you leave, you'll receive expert guidance during a comprehensive one-hour planning consultation, where we'll discuss the region's best-kept secrets, recommended restaurants where locals dine, and suggested wineries that welcome visitors for intimate tastings. This is more than a vacation-it's your invitation to live la dolce vita, if only for a week.

Included with your trip:
• Private Villa accommodations - complete with authentic architecture and countryside views
• Economy standard airfare from Winnipeg, MB to Rome for yourself and a travel companion
• Car rental (or equivalent value of private transportation) - providing flexibility to explore hidden gems, vineyards, and hilltop towns on your schedule. *Private transfers available upon request, trip winner pays any cost difference.
• 3 Tours/Excursions (maximum total value of $1,000)
• One hour pre-trip consultation with Continental Travel to help you maximize your Tuscan experience with insider recommendations and itinerary guidance.

This trip is fully customizable! Included excursion options for you to choose from:

• Grocery experience by local producer or farmers' market with simple cooking
• Wine experience (meal + wine pairing)
• Bread & Focaccia making experience
• Ceramic lab or Olive wood carving
• Gelato making workshop
• Cheese Farm and Tasting
• Cooking Italian (pasta or meat/fish or pastries)
• Outdoor cinema with aperitivo
• Special Private Dinners in Secret locations
• Pizza making with Giropizza ("all you can eat")
• Hops Garden & Brewery tour (lunch and transfer incl.)
• Tuscany from above (ultralight aircraft tour)
• Foraging or mushroom hunting experience
• Hike (all levels) with visit to local producer or picnic (seasonal)
• E-bike/Horse/quads tour with guide
• River Trekking to natural pools with picnic
• Stargazing night : hike at dusk on local mountain + picnic (seasonal, all levels)

The raffle winner will have the opportunity to work with Continental Travel to make this trip extraordinary!

In Support of Assiniboine Park Conservancy

Proceeds from this raffle directly support the Park’s continued care and enhancement, including the upkeep of its expansive lawns and greenspaces, the cultivation of world-class garden displays, and the maintenance of scenic pathways and naturalized areas enjoyed by millions each year—free of charge.

Thank you to our Raffle Partners for their support