When and If
Marrying old-world elegance with racing performance, this classic yacht is steeped in history and brimming with top-of-the-line detail.
You don’t have to be a history buff to fall in love with When and If, but it certainly helps. With her classic elegance and immaculate details, the classic yacht turns heads wherever she sails...
“When the war is over, and If I return, Bea and I are going to sail her around the world.”
Sadly, with Patton’s untimely death in 1945, it was not meant to be. From the first time Captain Seth spotted When and If sailing off the coast of Maine...
From November to May, When and If graces the waters of Key West... until then she will be shared with our guests.
Malabar X
A true classic, this 1930 wooden schooner yacht was built to win the Newport Bermuda races of her time - which she did, smashing records in 1930 and 1932. With her spacious cockpit and convenient low deck housing, Malabar X is perfect for a classic schooner sail in the Keys.
To sail on Malabar X is to step back in time; on the beautiful sprung teak deck beneath a cloud of white canvas, surrounded by gleaming varnish and antique bronze hardware, the viewer is transported to the glory days of sail.
Widely considered to be the magnum opus of designer John Alden's private schooner portfolio, Malabar X boasts three private cabins sleeping 6 people, as well as a spacious salon, galley and navigation station. Click below to book your a la carte sail, or get in touch for enquiries about custom charters.
High Tide
With a large, comfortable cockpit, High Tide is perfect for group fun in the sun– family snorkeling trips to the National Wildlife Preserve, bachelorette parties, lilypad lounging, and visits to the mangrove island bird sanctuary.
If the thought of getting chummy with the captain, learning the ropes, and taking a turn at the wheel floats your boat, High Tide is your gal. A super-fast, nimble sloop with a 12-person capacity, High Tide is one of only two medium-sized sailboats in the Key West able to venture into the backcountry. She is also well-suited for romantic sunset sails and celebrating special occasions such as proposals or anniversaries.
Like so many things we love, High Tide is a child of the ‘80s. A Key West, original, she was built locally by the legendary Admiral Finbar for day sailing and snorkeling trips. In 1980, this 33-foot Glander– the first charter sailboat in Key West– lifted anchor and has been bringing the joy of sailing to guests ever since. Captain Seth first sailed on High Tide over 20 years ago. He considers her a trusty, old friend and hopes you will, too.
Make Your Next Event Unforgettable
Whether you're planning something intimate or pulling out all the stops, we’ve hosted custom private charters for all kinds of celebrations. From laid-back gatherings to milestone moments — we’ve got the boat, the vibe, and the crew to make it happen.
