Sailing

Relax on a spacious, stable sailboat with room to spread out

Tailor a private sail with time to anchor and swim

Build Practical Sailing Skills With Private, Hands-On Instruction

Honor your loved one with a private sailing memorial shaped around your family's wishes

Learn sailing basics with classroom and dockside instruction

Sail past Diamond Head, then anchor off Waikiki for a swim

Trade the city streets for coastal views under sail

Make the boat your own with a captain-tailored cruise

Sail a classic yacht your way, with hands-on options or time to unwind

Sail, swim and snorkel along Waikiki on your own catamaran

Make the boat your own for a customizable sailing adventure

Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

Find a quiet spot for two on a spacious sunset sail

An evening sail with sunset views, sails, and the chance to spot wildlife

Take the Helm and Learn Hands-On Sailing Skills

Unwind on the bay or take a turn at the helm

Learn sailing basics in a small group of 2–4 people

Sunset catamaran sail with live music, appetizers, and included drinks

Take in San Diego’s city views under sail

Enjoy the whole boat and a captain-tailored cruise

Take the helm or relax on a private sail aboard Galene

Sail past Shell Island and watch for dolphins on a private sunset charter

Take to the coast aboard a renewably powered catamaran

Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks