Bloody Mary Day Sail

Bloody Mary Sail

The absolute best way to begin your day here in Key West is on the open water, with a warm tropical breeze filling the sails of a traditional wooden sailing schooner. Our Bloody Mary Sail gives you just that opportunity.

The deck on the Appledore II is spacious. At 18’wide and 65 ft on deck no more than 49 passengers, there is plenty of seating and room to spread out. Commissioned as the second boat by the Smith family in a series of Appledores built for global exploration, she has all the amenities of a passenger windjammer.

With Key West’s Historic Seaport receding in the background, take a deep breath of fresh sea air and feel completely relaxed and invigorated at the same time. Take a turn at the wheel and see what it feels like to be a captain of a schooner. And if you always wanted to hoist sails on a tall ship, this is your chance.

Sip cocktails and soak in your tropical surroundings. There is no better way to start your day in paradise! While enjoying your sail remember there is plenty to see on the water’s surface or circling in the blue sky above you. Perhaps an osprey will plummet down to the water to catch its lunch or a pelican will make a splash landing near the schooner. A pod of dolphins may surface or you might spot a turtle floating by.

Complimentary champagne and mimosas are served as well as poinsettia cocktails, premium beers, full cocktail bar, soft drinks and water to complete this upscale morning sail. So relax in your tranquil surroundings. Spread out and soak up the rays of our tropical sun.


Wide decks with room to walk around

Generous seating

Up to 49 passengers

A spacious head (bathroom)


Grab your hat, sunglasses, camera and love of adventure. We will do the rest!

Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age.


Welcome back!  We are pleased to announce our official re-opening on June 5th with reduced capacities and additional safety protocols to ensure a safe and enjoyable experience for both passengers and crew.  Advanced reservations (book Online or Call) are required. No walk ups are permitted per the City of Key West at this time.