Vine, Alpine or Coastline for 6+

Tuscan Wine Country, Telluride Mountain Living, or Costa Rica’s Pacific Coast

Choose your perfect escape between the vineyards and hill towns of Tuscany, the mountains of Telluride, or the Pacific coast of Costa Rica.

Does a week in the Tuscan countryside sound like your kind of getaway? Would you rather wake up steps from the slopes in the Colorado Rockies? Or are ocean views, tropical surroundings, and days along Costa Rica’s Pacific coast calling your name? With this Winner’s Choice package, the destination is up to you.

Choose Italy and spend seven nights with up to six guests in a three-bedroom, three-bathroom private villa in the countryside surrounding Cortona. This historic Tuscan hill town is known for its medieval streets, artisan shops, traditional trattorias, and Etruscan heritage, giving you a classic home base for experiencing this celebrated corner of Tuscany. Your private villa adds plenty of time to simply enjoy being there, with your own pool and two traditional Tuscan dinners prepared by a private chef.

Head to Telluride for five nights of mountain living in a four-bedroom, four-bathroom ski-in/ski-out townhome in Mountain Village. Steps from the lifts and trails, the residence puts skiing and snowboarding within easy reach while giving you plenty of reasons to enjoy the mountains beyond winter. Expansive living areas, panoramic San Juan Mountain views, a fully equipped gourmet kitchen, and private outdoor space make it an inviting home base for up to eight guests.

Or trade mountain peaks for Costa Rica’s Pacific coast with five nights in a private three-bedroom villa in the Guanacaste region. Set within a tropical hillside community, your villa offers a private plunge pool along with access to the beach club, hiking and biking trails, wellness and fitness amenities, and convenient transportation throughout the community. An included group catamaran experience takes you out along the Pacific coast, adding a day on the water to your Costa Rican stay.

Experience Includes (Winner Chooses One)

TUSCAN WINE

• 7-night stay for up to 6 guests in a 3-bedroom, 3-bathroom private villa with a private pool in the countryside surrounding Cortona, Tuscany
• 2 traditional Tuscan dinners prepared in the villa by a private chef
• Case of fine local wine for your stay
• Private pool at your Tuscan villa — a relaxing place to spend slow mornings, sunny afternoons, or time together between exploring Cortona and the surrounding countryside
• Dedicated concierge service to help you arrange additional activities, restaurant reservations, or personalized experiences during your stay

TELLURIDE SKI

• 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
• All-inclusive room taxes & fees — no hidden costs on accommodations
• Pre-arrival concierge service

COSTA RICA SEA

• 5-night stay for up to 6 guests in a private 3-bedroom villa in Costa Rica’s Guanacaste region, based on availability
• Group catamaran experience along the Pacific coast with swimming stops
• Private plunge pool
• Beach club access
• Wellness and fitness benefits including weekly yoga, bounce & sculpt classes, gym access, plus 1 hour per day of tennis and pickleball court use with equipment included
• Outdoor recreation including daily access to hiking and biking trails
• Complimentary transportation within the community
• Dining and wellness discounts including up to 15% off at select restaurants and up to 10% off at the Wellness Center
• Weekly activities and guided tours with exclusive benefits on select experiences
• Daily housekeeping, resort fees, and local service charge included

Details

• Terms, availability, blackout dates, and booking timelines vary by destination.
• The winner must select Tuscany, Telluride, or Costa Rica.
• Full details will be provided in the winner’s certificate and marketing 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.