Next Level Sailing

On our list of the best activities in San Diego.

The 139-foot America under sail off Shelter Island is a working replica of the yacht that won the Royal Yacht Squadron's Guinea Cup race in 1851, built in Albany, New York in 1995 and brought to San Diego by longtime yacht club member Troy Sears. Guests can raise sail themselves or sit back with a glass of sparkling wine as the boat swings past Point Loma at sunset. Whale-watching cruises run alongside the sunset sails, both departing from the dock on Shelter Island Drive.