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Stay & Play in Hilton Head

2‐Night Stay for 2 at The Westin Hilton Head (South Carolina) with America's Cup Sail


This Experience for 2 Includes:

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


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 out 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. Located on a pristine stretch of Hilton Head Island’s Atlantic beachfront, with 3 outdoor pools, ‘farm & sea to table” dining at the resort’s on-site restaurants, and an award-winning luxury Spa, you’ll leave feeling restored and renewed.  

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.