Sailing

Sail Lake Michigan with a licensed captain, snacks, and refreshments

Sail historic harbor waters with maritime insights and optional hands-on sailing

2-hour Maui sunset sail with live music, menu, and open bar

Sail at sunset aboard a 49-passenger windjammer

Celebrate on a shared catamaran with an onboard bar, social energy, and harbor views

Sail Waikīkī at sunset with drinks and light bites included

Sail Key West’s waters aboard a 105-foot schooner with Christmas brunch and drinks

Sail Casco Bay at sunset with live music and a BYOB vibe

Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail

Sail West Grand Traverse Bay at sunset with a champagne toast

Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay

2-hour rosé fireworks sail from Broad Creek Marina

Help hoist the sails aboard New Jersey's Official Tall Ship

Build sailing skills with a private youth lesson for up to 3 sailors

Sail New York Harbor aboard a historic tall ship with close Statue of Liberty views

Cruise Oyster Bay Harbor as the sun sets

Cruise Lake Tahoe on a 55-foot catamaran with lakewide views

Sail into sunset aboard a catamaran with live local music

Sail Provincetown at sunset on the historic Schooner Hindu

Sail the historic Cutter Bloodhound during the Sail Boston 2026 Festival

A private evening sail with spacious decks and sunset views

Private catamaran sailing with island stops, paddling, and wildlife viewing

Set sail on a shaded 27-foot sailboat with drinks and Gulf Coast wildlife views

Sail Pensacola Bay with an optional swim stop on a 27-foot sailboat