Aloha Sailing Key West

Aloha Sailing Key West is a two-person operation working out of Stock Island Marina Village on Shrimp Road, a working waterfront a few minutes from Old Town and a world away from the cruise ship docks. Captain Eddie Kertis is a licensed USCG captain and a Royal Yachting Association Yachtmaster, and he and Joanne run the charters themselves, which is why no two trips look alike.

There is no fixed itinerary. Tell them what you are after and the day gets built around it. A quiet anchorage in the Florida Keys National Marine Sanctuary where you can swim off the back of the boat. An uninhabited island with nobody’s footprints on it. An afternoon of snorkeling, or an afternoon of doing nothing at all with the sails up and the engine off.

The long trip is the one worth clearing your calendar for: three days and two nights out to the Dry Tortugas, seventy miles west of Key West, where Fort Jefferson sits on an island in the middle of open water with a moat around it and almost nobody else there. You sail out, you paddleboard, you snorkel, you sleep aboard, and you come back having seen a part of Florida that most visitors only read about.

They also take on captain and vessel delivery work throughout the Keys, so if you own the boat and need somebody qualified to move it, this is the number to call.