Best results for Sailing

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

Sail for 3 hours with up to 6 guests and a welcome cocktail or mocktail

Practice coastal navigation theory in a four-day ASA course

Train to skipper a 30–50 ft sailboat on a 4-day ASA 106 course

Sail Grand Traverse Bay and enjoy Moomers ice cream on a 2-hour fall cruise

Cruise NYC Harbor at sunset on the historic yacht Ventura

Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

Private 3.5-hour catamaran sail with snorkeling, sunset, and summer fireworks

90-minute sail with open bar and Friday night fireworks views

Sip fine wines and craft beers on an intimate schooner sail as the sun sets off Key West’s coastline

Sail a private catamaran whale watch from Ma‘alaea Harbor with hydrophone listening

Sail at sunset with whale watching and pupu appetizers from Maʻalaea Harbor

Paddle Skull Creek marshes and learn about Lowcountry tides and wildlife

Private sailboat whale watch from Ma‘alaea Harbor (Jan–Apr), with hydrophone listening

Private 2-hour whale watching sail from Honolulu with optional snorkeling

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

Enjoy premium appetizers and whale facts while spotting humpbacks at sunset

Sail from Mā'alaea Harbor and watch for humpback whales

Fun Dolphin Sightseeing & Complimentary Beverage

Glide along the Na Pali Coast on a fast catamaran with calmer morning seas and chances to spot dolphins

4-week comfort neck dry suit rental with shipping or Port Gamble pickup

Private 3.5-hour Waikiki cruise with snorkeling gear and fresh poké for up to 6 guests

Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.