Best results for Sailing
Showing 73-96 of 302 results
Private Boat ChartersUp to 6
Private Ko Olina Yacht with Crew & Open Bar
Set your own Ko Olina itinerary with snorkeling, sailing, and hosted bar, guided by a certified crew
5.0 • 341 reviews
Key West Day Sail with Snorkel & Kayak Lunch
Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.
4.9 • 5.6K reviews
Hilton Head Sunset Sail on Stars & Stripes
Watch Hilton Head's vibrant sunset while relaxing or helping crew aboard the historic Stars & Stripes
4.8 • 7.6K reviews
Key West Champagne Sunset Sail on Schooner
Sip complimentary champagne as you watch a legendary Key West sunset aboard the elegant Schooner America 2.0.
4.9 • 417 reviews
Waikiki Sunset Catamaran Cruise with Swimming
Enjoy a swim-optional sunset sail along the Waikiki coastline with inside and outside seating
4.8 • 4K reviews
Oahu Island Tour with Polynesian Canoe Sunset Sail
See Oahu’s top sights by van, then sail at sunset on a Polynesian canoe
4.7 • 1.3K reviews
West Oahu Dolphin Sail with Lunch & Snorkeling
See wild dolphins, snorkel with turtles, and enjoy lunch on a 3-hour West Oahu sail
4.6 • 1.4K reviews
Sail to Cape Lookout for Beach Time & Lunch
Sail to Cape Lookout for beach time, catered lunch, and lighthouse views on a stable catamaran
5.0 • 1.1K reviews
Boat RentalsUp to 4
13' Catamaran Rental on Wai Kai Lagoon
Sail the Wai Kai Lagoon with gear included, or add a captain for an easy, fun first-time experience
4.3 • 253 reviews
Waikiki BYOB Afternoon Sail to Diamond Head
Sail Waikiki’s coast on a 1-hour BYOB cruise with Diamond Head views
5.0 • 100 reviews
Friday Night Fireworks Cruise on Kealoha
Watch Waikiki's fireworks from a 55ft catamaran with inside seating and ocean views
4.8 • 4K reviews
NYC Harbor Day Sail on Clipper City Tall Ship
Sail past the Statue of Liberty and skyline aboard NYC's only passenger tall ship
4.5 • 699 reviews
Evening Wine and Jazz Concert Sail on Clipper City
Sail past the NYC skyline with live jazz and two glasses of wine on a summer evening
4.5 • 699 reviews
Hobie Cat Ride Along in Margaritaville Bay
Sail Margaritaville Bay with an experienced Hobie Cat captain—learn to sail or relax on a 30–60 minute ride
4.8 • 4.6K reviews
Sunset and Dolphin Watch Sail on the Island Time Catamaran
Sail calm waters to spot dolphins and catch a Gulf sunset
4.8 • 4.4K reviews
Learn To Sail On A Hobie Catamaran
Sail with an instructor for an easy, first-time-friendly session on calm Soundside waters
Custom San Francisco Bay Cruise
Choose where to explore on a private, captain-led sail for up to 6 guests
Private 2-Hour Day Sail In Port Townsend Bay
Enjoy a private sail with a licensed captain and choose a relaxed or more thrilling ride
5.0 • 28 reviews
Advanced Windsurfing Private Lesson in Kahului
2-hour private advanced windsurf lesson at Kanaha Beach Park
Sandbar, Snorkel & Sunset Sail in Key West
Sail to a Key West sandbar with snorkeling, snacks, and sunset views
Afternoon Cocktail Sail Along Waikiki Coastline
Cruise Waikiki toward Diamond Head with drinks and snacks included
Ko Olina Sunset Sail & Luau Experience
Sail Ko Olina at sunset, then head ashore for a Kaula Luau
2-Hour Sunset Sail in Key West
Sail a restored 1925 schooner at sunset with drinks and charcuterie
Sail San Francisco Bay & Alcatraz Night Tour
Combine an afternoon bay sail with an Alcatraz Island night visit