Wine, Dine & Unwind in Tuscany for 4

Discover the beauty, flavors, and timeless charm of Tuscany with a weeklong escape to Cortona, one of the region’s most picturesque hill towns. Surrounded by rolling countryside, vineyards, olive groves, and the unmistakable landscapes of central Italy, Cortona offers an idyllic setting for experiencing the relaxed pace and celebrated lifestyle of Tuscany. 

Spend seven nights in the heart of this historic walled town, where cobblestone streets lead to inviting cafés, local restaurants, wine bars, artisan shops, and centuries of Italian history. Your stay is complemented by two distinctly Tuscan experiences—a private wine tasting and an interactive cooking experience followed by dinner—giving you and your guests an authentic taste of the region’s renowned food and wine traditions. 

 

Property Description 

Set within the historic walls of Cortona, your charming two-bedroom residence places you and your guests in the heart of one of Tuscany’s most captivating towns. Thoughtfully furnished with traditional Italian character, the residence blends the charm of its historic surroundings with the comforts of home. Accommodating up to four guests, it features two bedrooms, two bathrooms, a comfortable living area, a fully equipped kitchen, Wi-Fi, and air conditioning. 

Step outside and discover Cortona’s beautiful piazzas, local restaurants, cafés, wine bars, and shops just moments from your door. Begin the morning with coffee in town, spend the afternoon exploring the rolling Tuscan countryside, and return to the comfort of your residence after an evening of incredible food and wine. Midweek cleaning with fresh linens and towels, utilities, and final cleaning are also included, allowing you to settle in and enjoy your week in Tuscany. 

 

Private Wine Tasting 

Tuscany’s winemaking heritage is an essential part of the region’s culture, and this private tasting offers the perfect opportunity to experience it firsthand. You and your guests will visit Sottovoce Wine Bar, ideally locatedin Cortona’s main square, for an intimate tasting highlighting the distinctive wines and flavors of Tuscany. 

Guided by knowledgeable local hosts, you’ll sample a curated selection of wines while discovering more about the vineyards, grape varieties, winemaking traditions, and stories that have shaped Tuscany’s celebrated wine culture. Surrounded by the atmosphere of historic Cortona, it’s a relaxed and memorable way to raise a glass to your Tuscan escape. 

 

Cooking Show & Tuscan Dinner 

Discover another side of Tuscany’s culinary traditions with an interactive cooking experience at a local restaurant just steps from your residence. You and your guests will watch traditional dishes come to life while learning about regional ingredients, time-honored recipes, and cooking techniques that have been passed down through generations. 

Following the cooking experience, settle in for a delicious dinner inspired by the flavors and traditions you’ve just explored. Combining local cuisine, authentic surroundings, and the pleasure of sharing a meal together, the evening offers a memorable taste of Tuscan life. 

 

Blackout Dates 

Blackout dates include the weeks of major U.S. holidays and significant local events. Additional blackout dates may apply. 

 

Package Redemption 

Charity Booster experiences must be booked within one year of the purchase date, and travel must be completed within 24 months of the purchase date. 

Charity Booster provides experienced travel professionals to assist with redeeming your experience. Our booking team will coordinate travel details and make reservations for every component of your package. 

We can also assist with additional arrangements such as extra hotel nights, room upgrades, transportation, and accommodation for additional guests. 

 

Additional Information 

• All reservations are subject to availability, blackout dates, and major holidays. 

• Reservations must be made a minimum of 60 days prior to the intended travel date. 

• A valid passport is required for international travel. 

• All reservations are final once confirmed, and cancellations or changes to travel dates are not permitted. Experiences may not be transferred, reassigned, or resold under any circumstances. 

• Purchases made through charity fundraisers are non-refundable. 

• All guests must comply with the rules, policies, and requirements of the property where they stay. 

• Ground transportation is not included and remains the responsibility of the winner unless otherwise specified. 

• Local, destination, and transfer fees are not included and are the responsibility of the winner. 

• In the rare event that circumstances beyond our control, including force majeure, property damage, or a change in ownership, make the represented property unavailable, Charity Booster reserves the right to provide a replacement stay or experience of comparable value and quality.