5 Key West Sailing Excursions

Key West Sailing Excursions & Sailing Cruise Shore Excursions in Key West - Enjoy our selected list of Sailing Excursions in Key West while in Key West cruise port by Shore Excursioneer, the leading independent Cruise Shore Excursion Expert Worldwide!
Key West Parasailing Shore Excursion
Key West Parasailing Shore Excursion
  • Convenient meeting spot close to your Key West cruise terminal!
  • Round-trip parasail boat adventure!
  • Options for single, tandem, and triple parasail rides are available!
  • Accommodates up to 12 passengers per departure!
  • Friendly and professional guides, all Coast Guard-inspected and certified!
Enjoy tropical music and the fresh breeze of Key West as you cruise out to its crystal clear waters. Get ready to enjoy a nice boat ride and jump to the parasail harness to slowly raise in the air, flying you high above Key West as you gain an amazing view of the beautiful turquois waters of Florida.
Full refund for cancellations 24+ hours in advance.
Activity Level: Low
Minimum Age: 5 Years Old
Excursion ID:  S2704
Duration: 1 hours
Languages: EN
From USD $6999 Reg Price: USD $89.99
Key West Island Ting Adventure Sail, Kayak, and Dolphin Watching Excursion
  • Top-rated Key West excursion!
  • Comfortable catamaran ride (shaded lounge area, sundeck, stairway, restrooms, and freshwater showers)!
  • English-speaking catamaran crew and captain!
  • Dolphin Watching at the Dolphin Playground protected area!
  • Kayak tour through the mangrove channels!
  • Professional kayak guides!
  • Complimentary breakfast, full buffet lunch, and snacks!
  • Soft drinks and beverages are included (alcoholic drinks and beer are served after water activities)!
This top-selling combo excursion includes sailing, kayaking in the mangroves, and dolphin watching! Plus breakfast and lunch along with drinks. Get to see some of the best Key West has to offer and enjoy your day.
Cancel any time for a full refund
Activity Level: Moderate
Minimum Age: All Ages
Excursion ID:  S3135
Duration: 6 hours
Languages: EN
From USD $13499 Reg Price: USD $154.99
Key West Sunset Catamaran Sip and Sail Excursion
Key West Sunset Catamaran Sip and Sail Excursion
  • Professional catamaran shore excursion guides!
  • Convenient meeting location close to your Key West cruise ship terminal!
  • Complimentary drinks and snacks!
  • Full toilets on board!
  • Brand new state-of-the-art 65-foot catamaran!
Watch the famous Key West sunset aboard a luxury catamaran. Enjoy hearty appetizers, snacks, and a full open bar, champagne, wine, ice-cold beer, soft drinks, and more on this unique shore excursion! 
Full refund for cancellations 24+ hours in advance.
Activity Level: Low
Minimum Age: All Ages
Excursion ID:  S6233
Duration: 2 hours
Languages: EN
From USD $7999 Reg Price: USD $94.99
Key West Marine Sanctuary Sandbar Catamaran and Kayak Excursion
Key West Marine Sanctuary Sandbar Catamaran and Kayak Excursion
  • Convenient meeting location close to your Key West cruise ship terminal!
  • Catamaran ride to sandbar!
  • All necessary kayaking gear!
  • English-speaking shore excursion guides!
  • Guided kayak excursion, paddle boards, and all snorkeling equipment!
  • Complimentary cold drinks and snacks!
  • Relax on a private secluded sandbar!
Explore the beautiful Florida Marine Sanctuary and enjoy a secluded sandbar on this one-of-a-kind catamaran and kayak shore excursion from your Key West cruise ship terminal. Kayak through the backcountry for fun and excitement as you explore the local marine wildlife and mangrove mazes on this Key West Catamaran Excursion!
Full refund for cancellations 24+ hours in advance.
Activity Level: Moderate
Minimum Age: All Ages
Excursion ID:  S6231
Duration: 5 hours
Languages: EN
From USD $12499 Reg Price: USD $143.00
Key West Dolphin Watching and Snorkel Excursion Combo
Key West Dolphin Watching and Snorkel Excursion Combo
  • The best dolphin-seeking crew in Key West!
  • Unlimited draft beer and soft drinks after snorkeling!
  • Round trip power catamaran ride from the meeting point!
  • Professional, friendly captain and crew!
  • The Snorkel set includes varied-sized fins, a sanitized snorkel, a silicone mask, and a vest!
  • Clean, modern bathrooms!
  • State-of-the-art sound system!
A great combo excursion while in Key West - watch the dolphins play and then snorkel at one of the best sites of the Florida Keys. Relax and enjoy your day on the beautiful luxury 54-foot state-of-the-art catamaran!
Full refund for cancellations 24+ hours in advance.
Activity Level: Low
Minimum Age: All Ages
Excursion ID:  S6216
Duration: 3 hours
Languages: EN
From USD $6499 Reg Price: USD $79.00