Winner’s Choice | Tuscany, Telluride or Costa Rica

Three Incredible Escapes. One Unforgettable Choice.

Discover three extraordinary destinations with this Winner’s Choice luxury getaway, offering a trio of distinctive travel experiences across the rolling hills of Tuscany, the Colorado Rockies, and Costa Rica’s Caribbean coast. Whether your ideal escape includes mountain adventure in Telluride, savoring Tuscan food and wine in Cortona, or relaxing on a secluded jungle-lined beach in Costa Rica, the winning bidder selects the destination that best fits their travel style.

Each option offers private accommodations, curated experiences, and immersive surroundings designed for relaxation, connection, and unforgettable moments. From vineyard tastings and alpine adventures to beachfront serenity and wildlife encounters, every experience delivers exceptional comfort in a truly remarkable setting.

Experience Includes (Winner Chooses One)

Tuscan Villa Escape for 10 — Cortona, Italy

Experience the timeless beauty of Tuscany with a seven-night stay for up to ten guests in a charming private villa or elegant apartment in or near the historic hill town of Cortona. Each hand-selected property offers its own unique character, from sweeping countryside views and private terraces to warm interiors ideal for gathering with family and friends.

This gourmet-focused getaway includes a private chef dinner served in your villa, where fresh seasonal ingredients are transformed into a multi-course Tuscan feast. A full case of fine local wines is also included for you to enjoy throughout your stay, whether over leisurely dinners, sunset aperitivos, or evenings under the stars.

Spend your days exploring Cortona’s cobblestone streets, local markets, nearby vineyards, and the iconic landscapes that have made Tuscany one of the world’s most beloved destinations.

Experience Includes

• 7-night stay for up to 10 guests in a private villa or premium apartment in Cortona or the surrounding Tuscan countryside
• Choice from a curated selection of available properties
• Private chef dinner for the group featuring a multi-course Tuscan meal with fresh local ingredients
• One case of fine Tuscan wines to enjoy during your stay
• The perfect home base for exploring Tuscany’s villages, vineyards, and scenic countryside

Telluride Slopeside Retreat for 8 — Colorado Mountain Luxury

Experience the magic of the San Juan Mountains with a five-night stay in a luxurious ski-in/ski-out townhome in Telluride’s prestigious Mountain Village. Located just steps from the lifts and trails, this elegant four-bedroom alpine residence places you in the heart of one of North America’s most breathtaking mountain destinations.

The spacious townhome features soaring ceilings, expansive living areas, a fully equipped gourmet kitchen, and panoramic views of the surrounding peaks. After a day on the slopes or exploring alpine trails, relax together in the comfortable living spaces or enjoy the crisp mountain air from the private outdoor area.

With world-class skiing, hiking, mountain biking, rafting, and vibrant village dining just moments away, this mountain retreat provides the perfect balance of adventure and relaxation.

Experience Includes

• Luxurious 5-night stay for up to 8 guests in a premier 4-bedroom, 4-bath ski-in/ski-out townhome in Telluride Mountain Village
• Prime slopeside location — steps from lifts, trails, and immediate access to world-class skiing, snow sports, and year-round mountain adventures
• Spacious alpine-inspired interiors featuring expansive living areas, soaring ceilings, panoramic mountain views, and a fully equipped gourmet kitchen
• Private outdoor space for relaxation, gatherings, and soaking in the stunning San Juan scenery

Costa Rica Beachfront Escape for 8 — Punta Uva

Nestled along the pristine Caribbean shoreline of Punta Uva, this enchanting beachfront villa blends tropical elegance with the raw beauty of Costa Rica’s jungle coast. Located beside the Gandoca-Manzanillo Wildlife Refuge, the property offers a serene retreat where wildlife, ocean breezes, and lush rainforest create a truly unforgettable setting.

The property features two villas, separated by just a few steps. The larger of the two, has three spacious bedrooms with king-size beds (or a flexible twin/king configuration), and mesmerizing ocean views, while the other has one bedroom, one bathroom, and a beautiful open concept living space, offering stunning vistas and a gentle sea breeze. Spend your days kayaking along the turquoise coastline, relaxing in hammocks beneath swaying palms, or enjoying the incredible biodiversity that surrounds the property.

This experience also includes unique curated moments, from a private chef dinner featuring fresh local ingredients to a guided visit to a nearby bird sanctuary where vibrant green macaws soar overhead.

Experience Includes

• 6-night stay in this beautiful beachfront property for 8
• Prime beachfront location in a cozy modern accommodation (4 king-size beds, two full kitchens and 2.5 bathrooms, including an outdoor shower, with stunning ocean views)
• Includes access to kayaks and beach chairs for coastal exploration.
• Guided visit to the Ara Manzanillo Sanctuary, where you’ll marvel at the vibrant macaws in their natural habitat while supporting vital conservation efforts.
• Private yoga class led by a skilled local instructor, where the jungle ambiance guides your practice. This tailored session is suitable for all levels.
• An exclusive three-course private chef dinner, featuring locally sourced ingredients like fresh seafood and tropical fruits, served with the Caribbean waves as your backdrop.

Details

• Terms, availability, blackout dates, and booking timelines vary by destination.
• Full details will be provided in the winner’s certificate and booking materials.
• Reservations are subject to availability and scheduling policies.
• In the rare event that a package or experience becomes unavailable due to circumstances beyond our control—including force majeure, property damage, change of ownership, or operational changes—Charity Ace reserves the right to substitute a comparable experience of equal or greater value.