Best results for Sailing
Discover Sailing or Practice Sessions
Hands-on sailing with an instructor on Narragansett Bay
Sunset and Dolphin Watch Sailing Cruise on Island Time II Catamaran
Sail calm waters to spot dolphins and enjoy a Gulf sunset with dancing and games
Private Sailing and Wood Island Lighthouse Tour
Sail Saco Bay and explore historic Wood Island Lighthouse with a private guide.
Private 1.5Hr Kids Sailing Lesson in Nantucket
Learn essential sailing skills in a personalized 1.5-hour session for kids aged 5–12
Montauk Sunset Sailing with Cocktails
Sip cocktails as the sun dips below the horizon on a relaxed evening sail.
Traverse City Private Sailing Tour with Captain
Private sail on West Grand Traverse Bay with a licensed captain and mate
Haleiwa Snorkeling & Sailing Tour, North Shore
Sail Oahu's North Shore and discover vibrant reefs on a relaxed, crowd-free snorkel adventure.

St Augustine Private Sailing for Up to 5 Guests
Choose a morning or afternoon private sail for up to 5
Private Sunset Sailing in St. Augustine
Sail a luxury yacht at sunset and see St. Augustine's historic bayfront

Private Day Sailing Tour From Orcas Island
Experience a private 3-hour sail on a classic sloop in calm San Juan waters with optional hands-on instruction
Private 2-Hour Sailing Lesson
Customize your sailing skills on calm river waters with an experienced instructor
Private 2 Hour Sailing Cruise on West Bay
Relax on a private sail across Grand Traverse West Bay, ideal for families and friends
Private Catamaran Sailing Tour from Manteo
Enjoy scenic Roanoke and Albemarle Sounds on a comfortable 40' catamaran
Waikiki Day Trip Aboard Luxury Sailing Yacht
Sail Waikiki on a luxury yacht equipped with water sports gear for a relaxing day afloat
Seattle Evening Colors Sunset Sail
Sail Puget Sound at sunset with skyline views aboard Seattle’s largest public sailing vessel
Private Dolphin Sightseeing Sail on Daydreams
Enjoy sailing and dolphin sightseeing in paradise
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.
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
Nantucket Sailboat Rental: 2-Hour Rhodes 19
Enjoy a two-hour self-guided sail aboard a stable Rhodes 19 from Jetties Sailing Center
Whale Watching Cruise in Maui with Lunch
Experience an unforgettable whale watching journey aboard the Ocean Spirit, Maui’s premier eco-friendly sailing catamaran.
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
Guided Hobie Cat Sail with Captain Included
Glide across Grapevine Lake on a guided 1-hour Hobie Cat sail with captain included.
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.
Handcrafted Catamaran Sail with Captain & BYOB
Sail a handcrafted catamaran under the stars with your own drinks and snacks.
