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Compare boat and sailing experiences by itinerary, duration and departure arrangements. Read the individual inclusions to distinguish sightseeing trips from experiences with meals or activities.
Explore experience ↗◷ 2 hr
Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by Genera
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Explore experience ↗◷ 4 hr
Experience the Florida Keys like a true Conch! Our 4-hour Backcountry Sandbar Excursion takes you to a stunning location chosen by your
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Explore experience ↗◷ 2 hr
*Visit Stockislandboatcharters.com for alternate availabilities and pricing.* Embark on a tour around the island of Key West on our 20
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Explore experience ↗◷ 1 hr
This location was carefully selected to offer convenience to all guests arriving on cruise ships or those looking to parasail downtown.
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Explore experience ↗◷ 3 hr
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose our popular 3-hour Day Sail
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Explore experience ↗◷ 3 hr
Aboard our spacious 42-foot sailing catamaran, you'll experience the pure joy of sailing as the lightweight boat glides across the wate
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Explore experience ↗◷ 4 hr
Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the San
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Explore experience ↗◷ 2 hr
Witness a breathtaking Florida Keys sunset aboard Island Girls Excursions. Departing from Sparky’s Landing in Marathon, this relaxing c
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Explore experience ↗◷ 4 hr
Escape the crowds and discover hidden sandbars on a private eco tour through Key West’s backcountry waters. Swim, snorkel, or simply re
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Explore experience ↗◷ 2 hr
Embark on a lively 1.5-hour Tiki Fun Cruise through the stunning Florida Keys. Glide over crystal-clear waters on an authentic tiki bar
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Explore experience ↗◷ 2 hr
Cruise into a stunning Florida Keys sunset aboard a comfortable 53’ catamaran. Your crew will guide you through the waters surrounding
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Explore experience ↗◷ 4 hr
Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the
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View datesPlan a Key West sunset cruise from the Historic Seaport with practical advice on vessel styles, seasonal timing, advertised prices, boarding logistics, mobility questions, and booking details.
Choose between a Key West catamaran and schooner by comparing atmosphere, activities, trip length, passenger capacity, departure dock, accessibility, and price.
A Key West schooner sunset sail is a relaxed evening on the water, but the right trip depends on vessel type, guest count, inclusions, weather, and boarding logistics. Use this guide to choose between a shared sail and p
