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Fun in Key West Sailing Adventures

Key West hosts amazing sailing year round. Weather you'd prefer a day sail or a sailing adventure to snorkel & kayak we have have a great day waiting for you. brush stroke
Check out our Top Picks Below

  • Choose your Sailing Adventure:

    Click Below for more Info or to Book Now

    4 Hour Private Charter Snorkel Sail: Fun above and below the waterline!

    2 Hour Schooner Day Sail: Sail away on the gorgeous 1939 wooden schooner yacht built for General George S. Patton.

     

    Sail, Snorkel, & Kayak Excursion: Set sail for an epic adventure that will satisfy every member of the family! Kayak through mangrove-shaded channels, snorkel through crystal-clear water, or relax on deck in the sweet Florida breeze.

     

     

  • What's cool about it?

    • Private Sailing Trips or Budget Friendly options available
    • Learn more about sailing: raise the sails and even man-the-helm for a bit
    • All equipment & instruction included
  • What to Bring?

    • Sun Protective clothing: hat, shirt, reef-safe sunscreen
    • BYOB and enjoy a perfect day on the water
    • Camera
    • Bathing Suit & Towel

Book a Private or Budget Friendly Option Today

OurKeyWest has been on the Island since 1974. Our Portfolio of Premium Guest Activities presents the highest quality experiences in Key West. The best activities have limited availability, so make sure to book your fun well in advance. You can book with confidence knowing OurKeyWest is local and available to assist you every day from 8am-8pm, or by visiting our Welcome Lounge in Old Town Key West.

Call for More Info
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Lexi Roberts, OKW Concierge specialist
Your Local Concierge,
Lexi Roberts

The staff at Our Key West is exceptional and know the meaning of excellent customer service.

-Del Arnold

These Folks are Super Cool!

-Annie

Their shop is dope.

-Francesca, from Pittsburgh

Let's Connect!

Party Invites • Fishing Videos • Stories from Havana • Original Music • New Works of Art • Join our Happy Hour
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Key West Insight

Cuban Artist

Cuban Art & Artists of Havana

The People of Cuba have little in the way of material possessions, but their creativity, warmth and ability to find joy in daily life serves as an inspiration for those of us fortunate enough to spend time on this historic and magical island. Music, dancing, and art are primary passions of the Cuban people.  Throughout […]

Read More

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About Us

Local since 1974, we facilitate authentic and compelling guest experiences emphasizing the natural world, art, music, food, history, and local characters. We provide premium concierge services, and serve as market-maker for a select pre-screened portfolio of the island’s best guest activity providers. We have a commitment to quality and manage a full-service local concierge call center providing personal guest support from 8am to 8pm every day.

Learn More
Activities
  • Havana Day Trip
  • Fishing Charters
  • Golf Cart Rental
  • Boat Rental
  • Paddle the Mangroves
  • All Day Water Adventure
  • Dolphin Watch & Snorkel
  • Old Town Bike Ride
  • Bike Rentals
  • Bike Rentals
  • Personal Chef & Catering
  • Sky Dive
  • Key West Private Custom Boat Charter
  • Schooner Sunset Sail
  • Dry Tortugas- Ferry
  • Jet Ski Tour
  • Schooner Sunset Sail
  • Take an Art Stroll

Contact Info

Our Key West logo

613 Simonton St
Key West, Florida 33040

(305) 290-2049

PROUD MEMBER OF

Key West Business Guild Key West Attractions Association

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