Set out on a captivating day sail aboard the historic schooner Bloody Mary in the heart of Key West. Sip on unlimited Bloody Marys and cocktails as you glide past vibrant pastel homes and iconic landmarks like the Southernmost Point Buoy. With a knowledgeable guide sharing insights into the vessel’s maritime history, this serene voyage offers an unforgettable blend of scenic beauty and cultural richness. Discover why this $49 per person experience has become a must-do activity for visitors to the Florida Keys.
Key Points

- Offers a scenic day sail on the historic schooner Bloody Mary with unparalleled views of Key West’s natural beauty and architectural landmarks.
- Includes an open bar with premium cocktails, such as Bloody Marys, mimosas, and Poinsettia cocktails, for guests to enjoy while sailing.
- Provides insights into the evolution of schooner design and Key West’s rich maritime history through expert-led commentary.
- Accommodates up to 49 passengers and costs $49 per person, with free cancellations up to 24 hours before the experience.
- Requires a valid government-issued ID for guests to consume alcohol during the sail.
Explore the Historic Schooner Bloody Mary
The historic schooner Bloody Mary provides an unparalleled sailing experience in the waters off Key West.
This classic tall ship, built in 1989, offers a glimpse into maritime history. Passengers can marvel at the majestic sails and the skilled crew as they navigate the boat through the picturesque harbor.
The Bloody Mary’s sturdy construction and stable design ensure a comfortable and smooth ride, making it the perfect platform to sip Bloody Marys and enjoy the tropical scenery.
The Bloody Mary’s sturdy construction and stable design provide a comfortable ride to sip Bloody Marys and admire the tropical scenery.
This unique day sail is a must-do activity for anyone visiting the Florida Keys.
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Indulge in Unlimited Bloody Marys and Cocktails

As passengers board the historic schooner Bloody Mary, they’re greeted with an array of tantalizing cocktails and refreshments.
The open bar offers:
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Bloody Marys made with premium vodka
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Mimosas crafted with fresh-squeezed orange juice
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Poinsettia cocktails featuring sparkling wine
Throughout the day, guests can sip on these libations as they sail the vibrant waters of Key West.
The in-person guide, who also serves as the driver, ensures a seamless and enjoyable experience for all aboard the Bloody Mary.
Embrace the Scenic Views of Key West From the Water

Sailing aboard the historic schooner Bloody Mary, guests revel in the stunning vistas that Key West has to offer.
From the water, they’ll marvel at the vibrant pastel-hued homes, swaying palm trees, and historic landmarks that dot the coastline. The sail takes them past the iconic Key West Harbor, where fishing boats and yachts dot the sparkling turquoise waters.
As they glide along, passengers can snap photos of the picturesque Old Town and the towering Southernmost Point Buoy, the southernmost point of the continental United States.
This serene voyage provides an unparalleled perspective of Key West’s breathtaking natural beauty.
Discover the Rich Maritime History of the Schooner
Although the schooner Bloody Mary sets sail on the tranquil waters of Key West, its rich maritime history adds depth and intrigue to the experience.
Guests can learn about:
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The evolution of the schooner design, known for its speed and maneuverability
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The pivotal role schooners played in Key West’s history as a center of trade and commerce
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The skilled captains and crews who navigated these iconic vessels through treacherous waters
This blend of history and modern-day enjoyment creates a truly immersive tour that celebrates Key West’s enduring nautical heritage.
Enjoy the Relaxing Ambiance of the Day Sail
Guests aboard the Bloody Mary can sit back, relax, and soak in the serene atmosphere of the day sail. Sip on a refreshing Bloody Mary or mimosa as the schooner glides across the calm waters of Key West.
Breathe in the salty sea air and admire the stunning views of the island’s historic landmarks. The onboard guide provides entertaining commentary, sharing insights into the boat’s rich history and the surrounding marine environment.
With a full open bar and non-alcoholic options, the day sail offers a perfect blend of relaxation and exploration, allowing guests to unwind and enjoy the Florida Keys’ enchanting coastal setting.
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Key West Attractions to Explore Before or After the Tour
Key West, the vibrant island city, offers an array of captivating attractions that visitors can explore before or after their Schooner Bloody Mary Day Sail.
From the iconic Hemingway Home and Museum to the lively Duval Street, there’s no shortage of unique experiences. Guests can also venture to the Southernmost Point, a popular photo spot, or enjoy the creative energy of the Key West Shipwreck Museum.
With its diverse mix of history, culture, and entertainment, Key West provides the perfect complement to the relaxing day sail, allowing visitors to make the most of their time in this Florida Keys destination.
Essential Information and Booking Details
To book the Schooner Bloody Mary Day Sail in Key West, guests can conveniently reserve their spot online or by phone.
The tour costs $49 per person and accommodates up to 49 travelers. The meeting point is at 200 William St, and check-in is at the far end near the Western Union sign.
Participants must present a valid government-issued ID to consume alcohol. Cancellations are free up to 24 hours before the experience.
Participants must present a valid government-issued ID to consume alcohol. Cancellations are free up to 24 hours before the experience.
The tour includes an open bar with Bloody Marys, mimosas, and other premium beverages, as well as non-alcoholic options. An in-person guide will serve as the driver.
The Sum Up
Embark on the Schooner Bloody Mary Day Sail for an unforgettable experience in Key West. Cruise past iconic landmarks, indulge in unlimited cocktails, and learn about the schooner’s rich maritime history. This serene voyage blends scenic beauty and cultural heritage, making it a must-do activity during your time in this vibrant Florida destination.
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