Best results for Sailing

Private sail on West Grand Traverse Bay with a licensed captain and mate

Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights

Choose a morning or afternoon private sail for up to 5

Sail a luxury yacht at sunset and see St. Augustine's historic bayfront

Experience a private 3-hour sail on a classic sloop in calm San Juan waters with optional hands-on instruction

Sail Choctawhatchee Bay with a captain, spot wildlife, and try steering the catamaran

Sip cocktails as the sun dips below the horizon on a relaxed evening sail.

Sail beneath the Golden Gate and enjoy panoramic views with a complimentary drink

Sail Oahu's North Shore and discover vibrant reefs on a relaxed, crowd-free snorkel adventure.

Sail Waikiki on a luxury yacht equipped with water sports gear for a relaxing day afloat

Spend half a day sailing Cape Cod Bay with a private crew and optional swim stop.

Explore Kailua's reefs on a 3-hour traditional Hawaiian sailing canoe and hear local stories from expert watermen

Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center

Build confidence on the water with a dedicated instructor and custom coaching for up to three sailors

Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.

Sail Oyster Bay Harbor at golden hour and share unforgettable sunset views with up to 24 fellow passengers.

Sail a handcrafted catamaran under the stars with your own drinks and snacks.

Glide across Lake Erie at dusk on a private sailboat led by an experienced captain.

Sail to Cape Lookout for beach time, catered lunch, and lighthouse views on a stable catamaran

Sail 2.5 hours to watch wild dolphins with expert commentary and refreshments

Enjoy exclusive use of the Kibou for a 1–3 hour cruise with up to 35 guests.

Snorkel Waikīkī reefs on a 2-hour sail with chances to see turtles

Cruise to Cape Lookout for two stops with catered lunch, swimming, and lighthouse views on a 45-foot catamaran

Savor a private 3-hour sunset cruise for up to six on the Roanoke Sound