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Bloody Mary Sail: Key West’s Iconic Morning Adventure - Miami

Bloody Mary Sail: Key West’s Iconic Morning Adventure

Key Westeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for most fitness levels; minimal physical exertion required with opportunities to steer if desired.

Overview

Kickstart your day in Key West aboard the beautiful Appledore II with complimentary cocktails and stunning wildlife sightings. Ready your sea legs for an unforgettable morning sail!

Key West, Florida

Bloody Mary Sail

The Right Way to Start Your Day in Key West

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Adventure Photos

Bloody Mary Sail photo 1

About This Adventure

Start your day in Key West aboard the stunning Appledore II, a traditional sailing schooner. Enjoy spacious seating, breathtaking views, and the chance to steer the ship. Sip on complimentary cocktails, including signature drinks, while watching dolphins and pelicans in their natural habitat. Experience paradise like never before!

The best way to begin your day in Key West#


Book Online and Save!

  • Adults (Ages 12+): Regularly $49.95 | Online discounts available!
  • Child (Ages 4-11): $29.95
  • Young Child (Ages 3 & under): No Charge

Tour Details

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.

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.

New this season - Now we're also featuring cocktails in our all-inclusive price. Sails up with a Schooner Appledore signature Bloody Mary or Dark & Stormy. Request your own favorite cocktail from our treasure chest of top-shelf brands.

Complimentary champagne and mimosas are served as well as poinsettia cocktails, premium beers, 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.

Adventure Tips

Arrive Early to Secure Seating

Arriving 15 minutes early helps you choose your preferred spot to enjoy the views and breeze.

Bring Sunscreen and a Hat

Even in the morning, Florida sun can be strong—protect your skin to stay comfortable throughout the trip.

Motion Sickness Precaution

If you’re prone to seasickness, consider medication or ginger candy before boarding to enjoy the sail fully.

Dress in Layers

Early mornings can be cooler; lightweight layers help you adjust as the temperature rises.

Local Insights

Wildlife

  • Bottlenose dolphins swimming alongside the schooner
  • Brown pelicans gliding gracefully over the water

History

Key West’s maritime history is rich, with schooners like the Appledore II evoking the island’s legacy of trade and exploration dating back centuries.

Conservation

Appledore - Key West supports marine life protection efforts by practicing eco-friendly sailing and educating guests on minimizing environmental impact.

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Adventure Hotspots in Miami

Frequently Asked Questions

Recommended Gear

Sunglasses

Essential

Protect your eyes from glare reflecting off the water during bright mornings.

summer specific

Light Waterproof Jacket

Stay dry if caught in an unexpected rain shower or sea spray.

fall specific

Reusable Water Bottle

Essential

Stay hydrated throughout your sail while minimizing plastic waste.

Non-Slip Shoes

Essential

Ensure stable footing on wet or slippery deck surfaces.