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Classic Tall Ship Sailing with Appledore in Key West - Miami

Classic Tall Ship Sailing with Appledore in Key West

Key Westeasy

Difficulty

easy

Duration

3–4 hours

Fitness Level

Basic mobility needed to move around decks and participate in raising sails; suitable for beginners and families.

Overview

Step aboard the Appledore II in Key West for a tall ship sailing experience that combines historic rigging, vibrant marine life, and refreshing cocktails. Discover coastal landmarks and marine wildlife as you sail in style.

Key West, Florida

Windjammer Classic Day Sail

Experience Sailing on a Majestic 2-Masted Schooner | Available November - May

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Adventure Photos

Windjammer Classic Day Sail photo 1

About This Adventure

Set sail on the stunning Appledore II, a 2-masted schooner, and immerse yourself in a unique blend of adventure and luxury. Experience the thrill of raising the sails, enjoy complimentary cocktails, and witness the beauty of Key West's coastline and marine life. This unforgettable journey captures the essence of sailing history.

Key West Tall Ship Sailing#


Rates:

  • Adults (Ages 12+): Starting at $49.95
  • Child (Ages 4-11): $29.95
  • Young Child (Ages 3 & under): No Charge

Tour Details

Experience sailing on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger windjammer. At only 49 passengers, her decks are spacious and comfortable.

The Appledore II is the second in a series of historic schooners commissioned by the Smith family to travel the world. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship.

Appledore II is no pampered ship, she sails year-round. Summers are spent sailing around Camden, Maine and winters are here in tropical Key West. Twice a year Appledore II sails the 2,000 mile ocean voyage between her two homeports. Some of the crew on your tour have made this exciting journey – ask them about their adventures.

Sails flying in the wind, you leave behind the Historic Seaport and head out to the Atlantic. Soon there is wind in your hair and the warm, tropical salt air kisses your face. Take in the view as the schooner navigates her way past Key West’s Harbor, Mallory Square, the Navy Mole, Sunset Key and historic Fort Zachary Taylor.

Quench your thirst with complimentary homemade sangria, boutique wine, frosty cold premium beers, soft drinks and water.

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.

While there is abundant marine life under the water, there is also plenty to see on the water's surface or circling in the blue sky above you. A pod of dolphins may surface or you might spot a turtle floating by. Perhaps an osprey will plummet down to the water to catch its lunch or a pelican will make a splash landing near the vessel.

With the Historic Seaport drawing closer, your schooner sail cruise is nearing its end. Life is good in paradise.

Adventure Tips

Wear Non-Slip Shoes

Decks can get wet—choose shoes with good grip to stay steady while moving around the schooner.

Bring Sun Protection

Wide-brim hats and sunscreen are crucial for midday sails on open water under Florida’s strong sun.

Arrive Early

Give yourself time to check in and get oriented before departure at Key West’s Historic Seaport.

Motion Sensitivity

If prone to seasickness, consider taking preventive medication—waves on the Atlantic side can be choppy.

Local Insights

Wildlife

  • Bottlenose dolphins
  • Green sea turtles

History

The Appledore II inherits the design legacy of the Smith family's series of schooners known for circumnavigating and bridging northern and tropical waters for over a century.

Conservation

Appledore emphasizes sustainable tourism practices by limiting passenger counts and encouraging respect for local marine wildlife and habitats.

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Adventure Hotspots in Miami

Frequently Asked Questions

Recommended Gear

Non-slip deck shoes

Essential

Protects your footing on wet, moving decks.

Sunglasses with UV protection

Essential

Reduces glare and protects eyes from intense sun.

summer specific

Light windbreaker or layered jacket

Essential

Keeps you comfortable during cooler mornings and breezy sails.

spring specific

Water bottle

Essential

Stay hydrated during the sunny day on the water.