Best results for Sailing
Showing 169-192 of 225 results
Handcrafted Catamaran Sail with Captain & BYOB
Sail a handcrafted catamaran under the stars with your own drinks and snacks.
4.9 • 597 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
Nights of Lights Twinkle Cruise
See St. Augustine's holiday lights aboard a 75-minute yacht cruise with dessert and a festive drink included
4.9 • 697 reviews
Polynesian Adventure Cruise on Muskegon Lake
Sail Muskegon Lake with Polynesian dancers and sunset views
4.6 • 367 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
Sunset Sail on Presque Isle Bay and Lake Erie
Relax on a 2-hour sail with captain, crew, and complimentary drinks as Lake Erie glows at sunset
5.0 • 146 reviews
Learn To Sail On A Hobie Catamaran
Sail with an instructor for an easy, first-time-friendly session on calm Soundside waters
4.9 • 66 reviews
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
Sunset Whale Watch Sail from Ma‘alaea Harbor
Sail at sunset with appetizers and beverages while spotting humpback whales
4.7 • 2.5K reviews
Key West Sunset Sail with Wine & Craft Beer
Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline
4.9 • 5.6K reviews
Private Yacht ChartersUp to 35
Private Yacht Charter in Kailua-Kona
Enjoy exclusive use of the Kibou for a 1–3 hour cruise with up to 35 guests.
4.9 • 1.1K reviews
Private Boat ChartersUp to 6
Private Lake Erie Sunset Sail in Sandusky
Glide across Lake Erie at dusk on a private sailboat led by an experienced captain.
5.0 • 34 reviews
Private Boat ChartersUp to 6
Private Sailboat Charter on the Maine Coast
Experience Acadia’s wildlife and scenery with an expert captain and a trip tailored to you
5.0 • 391 reviews
Private Boat ChartersUp to 37
Cape Lookout Private Cruise on 45ft Catamaran
Cruise to Cape Lookout for two stops with catered lunch, swimming, and lighthouse views on a 45-foot catamaran
5.0 • 1.1K reviews
Hilton Head Kayak Rentals
Hourly rentals for all experience levels on scenic Lowcountry waterways
4.7 • 228 reviews
Adult Sunset Whale Watch Sail
Enjoy premium appetizers and whale facts while spotting humpbacks at sunset
4.7 • 2.5K reviews
Dolphin Sightseeing Sail Aboard the Footloose Catamaran
Fun Dolphin Sightseeing & Complimentary Beverage
4.9 • 2.7K reviews
Na Pali Coast Deluxe Morning Power Catamaran Tour
Glide along the Na Pali Coast on a fast catamaran with calmer morning seas and chances to spot dolphins
3-Hour Head Boat Bay Fishing Trip
Fish calm, sheltered bay waters with crew support and more time with lines in than riding
4.8 • 248 reviews
Private 3-Hour Fishing Or Party Cruise
Rent the whole boat for your group and cruise the bay day or night
4.8 • 248 reviews
Historic Boston Harbor Sail with Landmark Views
Sail an 80-foot classic schooner and admire Boston Harbor landmarks
4.7 • 1.5K reviews
2-Hour Sunset Sail in Provincetown Harbor
Enjoy a relaxing two-hour cruise as daylight fades over the water
5.0 • 35 reviews
Salem Harbor Sunset Sail on 1812 Schooner
Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.
5.0 • 535 reviews