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Stay & Play in Hilton Head

America’s Cup Sail, 2‐Night Stay in Hilton Head, South Carolina for 2

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This Experience for 2 Includes:

  • Afternoon sail on an America’s Cup sailboat for two
  • 2-night stay at The Westin Hilton Head Island Resort & Spa
  • Winspire booking & concierge service

With pristine beaches, world-class golf, and charming southern hospitality, Hilton Head, SC invites you to unwind, rejuvenate, and rediscover the true meaning of relaxation. Your serene escape awaits! Let Hilton Head be your oasis of calm.

America’s Cup Sail

A sailboat cruise from Hilton Head is a peaceful way to see gorgeous Lowcountry landscapes without the roar of a motor. Join the captain and crew aboard a 39-foot long (12 meter) sailboat that competed in America’s Cup. Keep an eye out for the Atlantic bottle-nose dolphins while enjoying the sun and sights of Hilton Head Island’s coastal waters. Relax on this 90-minute afternoon sail and work on your tan or join in and help with the sails. Beverages are available for purchase.

The Westin Hilton Head Island Resort & Spa

Enjoy a 2-night stay in a standard guest room at this oceanfront resort. Nestled on a pristine stretch of Hilton Head Island’s Atlantic beachfront, this resort offers three outdoor pools, ‘farm & sea-to-table” dining at its on-site restaurants, and an award-winning luxury spa. Prepare to leave feeling restored and renewed. 

Available September-May. Blackout dates: June, July, August, and major US holidays 

Package Redemption

Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.

Booking & Concierge Services

Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.

Additional Information

Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.

Blackout Dates

June, July, August, and major US holidays