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Top Key West Day Cruises

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Small-Group Key West Sunset Sail with Wine

clock 2 hours
  • Sail off into the sunset with an array of international and homegrown wines, brews and hors d'oeuvres. Whether you're looking for a romantic evening or just some time to relax with friends, this cruise will be perfect. Please make sure to arrive 30 minutes before you set sail to check...Read more

Key West Sunset Sail Aboard Schooner

clock 2 hours
  • Relish in a magnificent two-hour sunset voyage on board a breathtaking modern schooner! Witness the majestic sights of Key West from Schooner America 2.0, the most exquisite schooner around, as you sail past Mallory Square, Sunset Pier, and Sand Key Light Tower and more. While indulging in complimentary libations, savor individually prepared...Read more

Key West Sunset Cruise with Live Island Music

clock 2 hours
  • Set sail on the salty sea and listen to some of Key West's greatest musical acts, all while taking in a breathtaking sunset. Join us for an unforgettable evening with food, drinks and live music as we watch the sun dip below the horizon. So take someone by the hand and let the music carry you away on this amazing Key West Sunset...Read more

Key West Glass-Bottom Boat Tour with Sunset Option

clock 2 hours

  • View the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat journey from Key West! Enjoy a relaxing cruise while looking down to see an abundance of marine life below, such as tropical fish, hard and soft corals, sponges, snails, jellyfish, anemones, crabs, lobsters, rays, sea turtles, nurse...Read more

Sunset Sail in Key West with Beverages Included

clock 1 hour 30 minutes
  • Key West is renowned for its incredible sunsets and Floridays is well-known for our extraordinary, serene champagne sunset cruise. Our dedication to providing exemplary service and meticulous attention to detail on the voyage at dusk is legendary. Being out in the ocean for a Key West sundown experience is like being INSIDE the...Read more

Key West Day Sail Aboard Schooner

clock 1 hour 30 minutes
  • Set sail on the most spectacular and graceful schooner in Key West, Schooner America 2.0! An exact replica of the 1851 Schooner America, which won the inaugural America's Cup Race, you'll be awed by her beauty while gliding along smooth Caribbean waters with a drink in hand. Look out to see attractions such as Fort Zachary Taylor, Mallory...Read more

Glass Bottom Boat Island Eco Adventure

clock 3 hours 30 minutes
  • Max 6 people can embark on a journey of exploration in the Looking Glass, our 28' glass bottom boat. This vessel allows you to craft your own adventure, be it snorkelling at the reef, investigating an offshore island, searching for dolphin and other sea creatures or simply taking pleasure in lounging on a sandbar with your feet partly...Read more

Private Key West Sunset Sail

clock 2 hours
  • Please note: price is for up to 6 guests. The perfect Key West sunset sail - peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks with ice provided for any adult beverages you choose to...Read more
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