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Bloody Mary Sail

Bloody Mary Sail - Book Online & Save 14%

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 gorgeous traditional sailing schooner. Sebago’s Bloody Mary Sail gives you just that opportunity.

Accommodations on the Appledore II are spacious. At 18’wide and 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 modern 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.

You will be sailing on Sebago's Appledore II, a two-masted 86' windjammer featuring:

Wide decks with room to walk around

Generous seating

Only 49 passengers for an intimate sail

A spacious head (bathroom)

What To Bring

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.


$34.95Regularly $39.95

Smiling Girl
AGES 4-11:


Baby Boy

No Charge


2 Hours


11:00 AM

Boarding Starts 1/2 Hour Before. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.

Tour Includes:

  • Sail Past Local Key West Landmarks
  • Take Part in Hoisting the Sails and a Turn at the Wheel
  • Complimentary Bloody Mary’s, Champagne, Mimosas, Poinsettias, Premium Beers, Full cocktail bar, Soft Drinks and Filtered Water

In accordance with the best practices and guidelines established by the CDC and City of Key West, Effective Friday, March 20th, Sebago Watersports will suspend our regularly scheduled excursions until April 3rd. Future reservations are still being accepted.  We will evaluate on a weekly basis and post regular updates on our website and social media channels. Our office also remains open and available to assist you over the phone.  Please call 305-902-5136 for additional assistance. Sebago Watersports has been a leading provider of watersports activities in Key West for over 30 years and during this time has faced, and overcome, many challenges. We, with you, will overcome this as well.