Valid from Early, Spring & Mid Seasons (May 8 – June 26, 2026) as well as Mid & Fall Seasons (Sept. 14 – Oct. 24, 2026).
Cabot 4 Bedroom Home (Villa, Cliffs Residence or Dunes Cottage based on availability) 3 nights
Each bedroom will have 1 King size bed
1 Round for 4 players on The Cliffs:
No. 12 in Golfweek’s 2025 Top 100 International Courses
2 Rounds for 4 players on The Links:
Ranked No. 45 in Golfweek’s 2025 Top 100 International Courses
1 Round for 4 players on The Nest:
A newer 11‑hole par‑3 short course (par‑33) by Rod Whitman & Dave Axland (opened 2020)
***Airfare not included in prize package
***$4,000 package spending stipend included
2 Garden View Rooms @ The Lodge at Pebble Beach for 3 Nights
up to two golfers per room
The package is valid from August 27, 2025 – August 27, 2026
Golf for 4 players, including carts on:
1 Round: Pebble Beach Golf Links (#1 Golf Digest U.S. Public Courses)
1 Round: Spyglass Hill Golf Course (#13 Golf Digest U.S. Public Courses)
1 Round: The Links at Spanish Bay (#56 Golf Digest U.S. Public Courses)
Package must be selected within 30 days of the Raffle end date
***Spanish Bay will be closed from March of 2026 through April of 2027
should your trip take place during the closure, funds associated with that round
can be applied to dining, retails purchases, the Spa or additional rounds of golf
Black out dates include the week of the AT&T Pro-Am, Pure Insurance, Concours week and other times at the course and resorts discretion.
***Airfare not included in prize package
***$3,000 package spending stipend included
Drift into an island dream with a 5-night stay for up to 6 guests in a luxury oceanfront villa in Virgin Gorda
***$2,000 package spending stipend included
Details
***Airfare not included in prize package
***$3,000 package spending stipend included
Discover the magical region of Piedmont with a breathtaking retreat to a newly renovated Italian villa in the Roero hills.
Reach new heights of relaxation with an in-house spa, Jacuzzi, Finnish sauna, and panoramic-view infinity pool.
Embrace Piedmont’s esteemed Epicurean flair with an in-villa wine tasting, case of local wine, and pre-stocking included.
Your Piedmont experience includes 5 nights for up to 6 guests in a newly renovated contemporary villa in Italy’s Roero hills.
***$3,000 package spending stipend included
Embark on an unforgettable angling adventure with a sportfishing getaway to an ocean-view apartment in Cabo.
Embrace upscale amenities in a gated community, including residents’ clubhouse, infinity swimming pool, and gym.
Go for a Grand Slam with two full days of sportfishing included, as well as breakfast, lunch, and beers.
Your Cabo San Lucas experience includes 7 nights for up to 6 guests in a sleek ocean-view apartment minutes from the beach.
***$3,000 package spending stipend included
Indulge in unparalleled oceanfront luxury with a retreat to a breathtaking designer villa minutes from the beach.
Embrace sun-kissed living with a private infinity pool, daily housekeeping, and living spaces bathed in ocean views.
Indulge in VIP amenities including chef services, private beach and beach club access, and residents’ tennis courts.
Your Zihuatanejo experience includes 5 nights for 10 guests in a luxurious oceanfront villa minutes from the beach.
***$3,000 package spending stipend included
Your St. Martin experience includes 5 nights for up to 6 guests in a stunning ocean-view villa.
Bask in St. Martin’s opulent style with a five-night stay for six in a luxury villa overlooking the ocean above Orient Bay.
Soak up stunning bay vistas from the sparkling waters of your private pool or drive to the sun-kissed beaches minutes away.
Savor rich Caribbean flavors with a four-course gourmet dinner included, prepared in-villa by your private chef.
***$3,000 package spending stipend included
Live the luxury of simplicity with a five-night stay for up to six guests in a stunning modern villa near Playa Tamarindo with daily housekeeping.
Experience seamless open-air living with sliding glass doors leading to a spacious terrace with dramatic central pool.
Enjoy private beach access and membership to Langosta Beach Club, breakfast preparation, and a two-hour private surf lesson included for all guests.
Experience a feeling of total escape with a 5-night stay in a luxury modern villa in Tamarindo.
***$3,000 package spending stipend included
Step into a picture-perfect oasis with a five-night stay for up to eight guests in a luxurious villa overlooking the Pacific in Puerto Vallarta.
Embrace the art of open-air living with a spacious terrace and heated infinity pool offering breathtaking ocean views.
Discover the secluded sands of Hidden Beach with a five-hour sailing tour of the Marietas Islands included for all guests.
Your Puerto Vallarta experience includes 5 nights for up to 8 guests in a luxurious ocean view villa.
***$3,000 package spending stipend included
St. Martins Sands
Enjoy the lively yet laid-back feel of St. Martin, with a five-night stay for six guests in a luxury ocean view villa.
Discover the best of island life with a half-day sailing charter included and optional in-villa massages to add-on.
Relax in your villa’s private pool, tucked amidst the lush tropics of the exclusive Terres Basses community.
Your St. Martin experience includes 5 nights for up to 6 guests in a stylish ocean-view villa in exclusive Terres Basses.
Whitefish, Montana
Follow your wanderlust to Whitefish for a breathtaking alpine retreat in a luxury modern penthouse.
Unwind by the crackling central fireplace or soak up panoramic alpine views from your private hot tub.
Hit the slopes of Whitefish Resort minutes away or discover endless alpine adventures in Glacier National Park.
Your Whitefish experience includes 4 nights for up to 6 guests in a luxury penthouse apartment in Montana.
***$3,000 package spending stipend included
Choose the ultimate flexibility with a $15,000 cash prize — no strings attached.
Use it however you like: travel, save, splurge, or invest in something meaningful.
Winner is responsible for any applicable taxes.
Prize will be awarded via check, subject to identity verification and raffle rules.
Enjoy a $15,000 voucher to Golf Cart World in St. Augustine, where you can build your custom 4-seater golf cart.
Choose from a wide selection of colors and premium features to make it truly your own.
Final selections will be made in collaboration with Golf Cart World ownership to ensure the perfect ride.