Idyllically nestled within an ancient mahogany grove on the Platinum Coast of Barbados, overlooking a tranquil 1,000 ft. crescent of white coral sand beach and turquoise waters, Sandy Lane is widely acclaimed as the most iconic luxury resort in the world.

Four lucky couples are invited to relax and unwind in the beautifully appointed, beachfront Bluff House at Sandy Lane. This magnificent six-ensuite bedroom retreat offers an unrivaled blend of elegance and exclusivity, complete with a pool, private beach access, and your very own villa chef, butler, and housekeeper. Hidden behind private gates and nestled within manicured gardens, Bluff House is an unparalleled sanctuary for family and friends to experience an unforgettable stay at Sandy Lane. Spend your days in paradise golfing the iconic Green Monkey, unwinding at the spa, or relaxing next to the turquoise waters of the sparkling Caribbean Sea. Allow your private chef to wine and dine you each evening while you take in the beautiful views from your beachfront terrace.

Rejuvenation begins the moment you step foot onto the marvelous, marbled staircase of The Spa at Sandy Lane. A 47,000-square-foot monument dedicated to exquisite relaxation, the lavishly appointed Spa is a world unto itself.

For more than 60 years, discerning travelers have chosen Sandy Lane as their Caribbean home to experience decadent relaxation, exclusive privacy, and unrivaled leisure. This signature lot is not to be missed.

THIS LOT INCLUDES:

• Seven (7) night stay at the 6-ensuite bedroom Bluff House at Sandy Lane for four (4) couples
• Complimentary spa service for four (4) couples
• Dinner at The Monkey Club for four (4) couples
• Villa staff including a chef, butler, gardener, laundress, and security for the duration of your stay

RESTRICTIONS: Must be booked at least 60 days in advance and subject to availability on mutually agreeable dates. Blackout dates include December 20 - January 10 and all major US holidays. Expires April 30, 2026.

The Cayman Cookout is hosted by Chef Eric Ripert and set along Seven Mile Beach at the luxurious Ritz-Carlton, Grand Cayman. Bringing together some of the world's most talented chefs, wine and spirit experts, and culinary influencers, the Cayman Cookout is possibly the most prestigious celebration of food and wine in the world. Guests at this exclusive, interactive festival enjoy dynamic cooking demonstrations, tastings and dining events, exciting local tours, and unique epicurean experiences, all presented with a sense of barefoot elegance. The schedule of intimate events and celebrations allows for access and interaction with some of the world's most famous chefs set in one of the Caribbean's most exclusive resorts.

Four couples will get to cross the Cayman Cookout off their bucket list, January 14-19, 2026, in a 3,518 square-foot private home at the Ritz-Carlton, Grand Cayman. Spanning two floors, this beautiful residence overlooks the lagoon and has a private pool. Each floor features two bedrooms with the master, junior master, and one other bedroom each housing a King bed. The fourth bedroom offers two Queens. Chef Tim Creehan joins you and your group one evening at your villa to create a multi-course dinner with local flair to kick off your culinary adventure.

One of the signature events of the Cayman Cookout, the Beach Bash, whisks you away by catamaran across the Caribbean to the newly renovated Rum Point. Here you'll indulge in food stations that range from sizzling grilled delights to delectable seafood creations. Artisanal cocktails, crafted with the utmost precision and artistry, ensure a casual beachfront feast that surpasses expectations. - This once-in-a-lifetime experience is one you won't want to miss!

THIS LOT INCLUDES:

• Five (5) night stay in a private 4-bedroom, 4-ensuite bathroom villa at The Ritz-Carlton, Grand Cayman, January 14-19, 2026, for four (4) couples
• Private chef dinner hosted by Tim Creehan for four (4) couples
• Tickets to the Cayman Cookout Barefoot Barbecue for four (4) couples
• Tickets to the Cayman Cookout Beach Bash with catamaran transportation for four (4) couples
• Golf cart access for the duration of your stay
• Full access to Ritz-Carlton, Grand Cayman resort amenities
• On-site private concierge

RESTRICTIONS: This lot is date-specific for January 14-19, 2026, and cannot be rescheduled. Additional Cayman Cookout events and dinner reservations may be added at the winner's expense and coordinated by your personal concierge. Events listed above may be exchanged for events of equal or lesser value. Expires January 19, 2026.

This lot benefits: Emerald Coast Autism Center

Immerse yourself in an astonishing world of reefs, wrecks, and volcanic vents, just minutes offshore in the beautiful waters of Nevis. Known for its colorful sea, three couples are invited to spend a week soaking in the tranquility of your own personal paradise in a private villa within one of the island's most exclusive communities.

One of just 13 properties, your beautifully appointed Indonesian-style villa in Paradise Beach, Nevis boasts four bedrooms with ensuite bathrooms, a private patio with plunge pool, and a thatched cabana for outdoor dining. The two master suites enjoy King beds and views of the ocean with private terraces and outdoor showers. One junior master has a Queen bed, the other a King bed, and both offer stunning garden views that allow you to bring the outside in. The villa's well-equipped gourmet kitchen is the perfect setting for a private chef to pamper your group with a decadent in-home meal made with fresh island ingredients.

Spend your days hiking the tropical mountains, scuba diving in the clear blue waters, taking in the rich cultural diversity of the island, or relaxing by your private plunge pool with a cocktail in hand. The options are endless when you spend your days in paradise.

THIS LOT INCLUDES:

• Seven (7) night stay in a 4-bedroom, 4.5-bathroom villa in Paradise Beach, Nevis West Indies for three (3) couples or eight (8) people
• In-home chef dinner for up to eight (8) people
• Activity credit

RESTRICTIONS: Must be booked at least 60 days in advance and is based on availability. Blackout dates include all major US holidays and spring break. Activity credit to not exceed $1,500. Chef dinner to not exceed $2,500. Expires April 30, 2026.

This lot benefits: Ascension Sacred Heart Emerald Coast

Three couples are invited to spend seven nights on the exclusive island of St. Barthelemy, a destination that offers European sophistication infused with tropical opulence. St. Barths is a peaceful, laid-back island located in the French West Indies, often referred to as the "Gem of the Caribbean." It is a haven for those seeking complete relaxation with a touch of French chic. This arid escape spans just eight square miles and is home to an eclectic mix of iguanas, night-blooming cacti, and fabulous beaches, as well as luxury yachts, designer boutiques, and celebrities.

Situated not far from Flamands, St. Jean, and the island's capital Gustavia, your luxurious three-bedroom Villa The One is chic and contemporary in design and décor. Its hillside location treats guests to a magical view of the sea and the neighboring islands Bonhomme and Frégate. The interior opens to a deck with a wealth of outdoor living space. Its focal point is an elegant, elongated infinity pool with chaise lounges perfectly positioned for sunbathing and a modern take on a gazebo at its end for shade-seekers. A covered poolside dining area makes al fresco meals delightful.

There's always plenty to do among the tropical landscapes and in the crystal-clear waters. Whether you're looking to spend your days with fun in the sun, or relaxing and recharging in an exotic Caribbean setting, St. Barths has the perfect activity for you.

THIS LOT INCLUDES:

• Seven (7) night stay at the private 3-ensuite bedroom Villa The One in St. Barths for three (3) couples
• $1,000 amenities or excursions credit per couple

RESTRICTIONS: This lot is available for booking June - December 15. Must be booked at least 60 days in advance and is subject to availability on mutually agreeable dates. Blackout dates include December 15 - January 15. Villa may be available during the blackout period for an upgrade fee. Due to Villa The One's limited availability, a comparable property may be offered. Amenities or excursions exceeding the $3,000 total credit are available at the winning bidders' expense. Expires December 15, 2026.

One of DCWAF's most sought-after destinations, Rosewood Little Dix Bay, is once again swinging its oceanfront doors open to welcome three couples, August 2-6, 2025, for a once-in-a-lifetime island getaway in a private villa.

A haven of tranquility, Rosewood Little Dix Bay offers an escape from the ordinary. Since 1964, high-profile guests have been captivated by this truly authentic and quintessentially Caribbean Island experience. Laurance House offers three oversized, ensuite bedrooms - two boasting King beds and one with double Queen beds, a full kitchen with stainless-steel appliances, and a spacious terrace leading to a private pool and dining gazebo, all with stunning resort and bay views.

Virgin Gorda is known to celebrate the best of sea and sand. Whether you're unwinding at the spa, island hopping to beach bars, or snorkeling the crystal-clear waters around the world-famous Baths, this quaint island invites any traveler. The third largest of the British Virgin Islands, natural beauty and boating culture anchors its playful personality.

THIS LOT INCLUDES:

• Five (5) night stay in the 3-bedroom Laurance House, August 2-6, 2025, at Little Dix Bay for three (3) couples
• Private chef dinner in the villa for three (3) couples
• Resort and amenities credit
• Roundtrip airport transfers

RESTRICTIONS: This lot is date-specific for August 2-6, 2025, and cannot be rescheduled. Resort credit and chef dinner to not exceed $1,500 each. Expires August 6, 2025.

Rosewood's Le Guanahani St. Barth is a haven of casual luxury, comfort and elegance, cherished for its authentic reflection of the islands. Meaning "welcome" in the native Arawak language of the island, the resort's name is a tribute to the island's culture and history.

Embark on a romantic getaway when you board your privately chartered plane to paradise. Spend five nights within this captivating landscape where vibrantly hued guest cottages are scattered along garden paths that wind through lush bougainvillea, hibiscus, and palms beside the sweeping beaches and reef-protected lagoon. This charming boutique resort offers two pools, the restorative Sense spa, an array of watersports, a fitness center, and a tennis court. The resort's elegant restaurants and bars, including a new beachfront dining venue, offer freshly prepared, refined cuisine presented with unobtrusive service in stunning settings.

THIS LOT INCLUDES:

• Five (5) night stay in Ocean Bay accommodations at Rosewood Le Guanahani St. Barth for two (2) people
• Round trip private air charter to St. Barths from either San Juan, St. Thomas, Antigua, or Anguilla for two (2) people
• Daily breakfast at Beach House St. Barth
• Round-trip airport transfers

RESTRICTIONS: Must be booked in advance and is based on availability on mutually agreeable dates. Blackout dates include May 22 - 27, June 28 - July 5, August 28 - September 2, October 10 - October 14, November 21 - December 1. Expires December 18, 2025.