Best results for Sailing
Showing 241-264 of 302 results
Private Boat ChartersUp to 12
Private Dolphin Sightseeing Sail on Daydreams
Enjoy sailing and dolphin sightseeing in paradise
4.9 • 2.7K reviews
Private Boat ChartersUp to 6
Half-Day Private Sail & Swim in Cape Cod Bay
Spend half a day sailing Cape Cod Bay with a private crew and optional swim stop.
4.9 • 35 reviews
Sail Kailua's Reefs & Hear Hawaiian Stories
Explore Kailua's reefs on a 3-hour traditional Hawaiian sailing canoe and hear local stories from expert watermen
4.7 • 53 reviews
Boat RentalsUp to 3
19' Sailboat Rental in Nantucket for 2 Hours
Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center
5.0 • 2 reviews
Whale Watching Cruise in Maui with Lunch
Experience an unforgettable whale watching journey aboard the Ocean Spirit, Maui’s premier eco-friendly sailing catamaran.
4.6 • 293 reviews
Learn to Sail with Personal Coach in Nantucket
Build confidence on the water with a dedicated instructor and custom coaching for up to three sailors
5.0 • 2 reviews
Guided Hobie Cat Sail with Captain Included
Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.
4.7 • 404 reviews
Intimate 24-Guest Sunset Sail on Oyster Bay
Sail Oyster Bay Harbor at golden hour and share unforgettable sunset views with up to 24 fellow passengers.
4.5 • 62 reviews
Handcrafted Catamaran Sail with Captain & BYOB
Sail a handcrafted catamaran under the stars with your own drinks and snacks.
4.9 • 597 reviews
Polynesian Adventure Cruise on Muskegon Lake
Sail Muskegon Lake with Polynesian dancers and sunset views
4.6 • 367 reviews
Ocean Spirit Adult Sunset Sail
Sail into the sunset on an adults-only catamaran cruise with pupus and island-style music
4.7 • 2.5K reviews
Learn to Sail in New York Harbor
Sail a Catalina 34 and build practical skills in 2.5 hours
2-Hour Private Dolphin Catamaran Sail In Cocoa Beach
Sail the Indian River Lagoon on a private catamaran and watch for dolphins
Sail Boston Harbor on the Cutter Bloodhound
Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival
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
Sail a Private FIFA World Cup Charter in NYC
Charter a private NYC sail for FIFA World Cup match day
Private Boat ChartersUp to 10
Private Nights of Lights Cruise in St Augustine
See St. Augustine's holiday lights aboard a 75-minute yacht cruise with dessert and a festive drink included
4.9 • 697 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
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