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The Best Key West Tours & Activities For Relaxation

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Key West Tours

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Sometimes, you just want to sit back and let the scenery go by. Whether you prefer a boat ride out to the Dry Tortugas followed by a day on the beach, a catamaran cruise to the reef for a quick snorkel before sunset happy hour, or a sampling of fine wines on the deck of a classic sailing craft, count on Cool Key West to bring on the serious Relaxation.

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  • Key West Deep Sea Fishing Charter
    Likely to Sell Out
    Likely to Sell Out
    4.9 (263)

    Key West Deep Sea Fishing Charter

    Cool Key West takes you on a Key West Deep Sea Fishing Charter for high adventure and big fish on the deep blue waters that

     4, 6 or 8 hours (approx.)  Free Cancellation
    $1,000
    $900
    $1,000
    $900
  • Key West Split Fishing Charter
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.8 (493)

    Key West Split Fishing Charter

    Cool Key West presents the Key West Split Fishing Charter: the most cost-effective and convenient way to get offshore and enjoy some Key West sportfishing.

     4 or 6 hours (approx.)  Free Cancellation
    $350
    $200
    $350
    $200
  • Key West Sail, Snorkel, Kayak with Sunset Option
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,482)

    Key West Sail, Snorkel, Kayak with Sunset Option

    Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge.

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $99
    $90
    $99
    $90
  • Key West Backcountry Safari
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (2,482)

    Key West Backcountry Safari

    Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness.

     4.5 or 6.5 hours (approx.)  Free Cancellation  Instant Confirmation
    $120
    $99
    $120
    $99
  • Sunset Sip & Sail
    Likely to Sell Out
    Likely to Sell Out
    4.7 (324)

    Sunset Sip & Sail

    Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •

     2 hours  Free Cancellation
    from
    $72
    from
    $72
  • Key West Snorkeling Adventure
    4.8 (1,396)

    Key West Snorkeling Adventure

    Envision yourself swimming freely among the vibrant fish of the Florida Keys during a Key West snorkeling tour. This tranquil catamaran cruise provides easy snorkeling

     3 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $49.95
    Best Rate
    $49.95
  • Key West Dolphin Watch Sunset Snorkel Cruise
    Likely to Sell Out
    Likely to Sell Out
    4.7 (308)

    Key West Dolphin Watch Sunset Snorkel Cruise

    The Cool Key West Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world

     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    from
    $69.95
  • Key West Sunset Snorkel Sail
    Likely to Sell Out
    Likely to Sell Out
    4.8 (147)

    Key West Sunset Snorkel Sail

    Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and

     3 hours  Free Cancellation  Instant Confirmation
    from
    $69.95
    from
    $69.95
  • Key West Party Boat Fishing Charter
    4.7 (146)

    Key West Party Boat Fishing Charter

    Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West

     6 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $69.69
    Best Rate
    $69.69
  • Key West Snorkeling
    4.7 (541)

    Key West Snorkeling

    Rise and Reef Key West Snorkel Trip on The 65 foot custom built Sandie Cat. Your 3 hour snorkel trip will start with a Light

     3 hours  Free Cancellation  Instant Confirmation
    from
    $35
    from
    $35
  • Key West Private Deep Sea Fishing Charter (up to 41 passengers)
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    Likely to Sell Out
    4.9 (18)

    Key West Private Deep Sea Fishing Charter (up to 41 passengers)

    Cool Key West brings you the ultimate Private Deep Sea Fishing Charter experience with a classic 63-foot sportfishing boat that can show 41 day-trip guests

     4-12 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $1,700
    Best Rate
    $1,700
  • Key West Dolphin Watch & Snorkel Tour with FREE shuttle to location
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
    4.9 (24)

    Key West Dolphin Watch & Snorkel Tour with FREE shuttle to location

    Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins.

     3 hours 30 minutes (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    Best Rate
    $99
    Best Rate
    $99
  • Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak
    4.9 (216)

    Key West Schooner Appledore Backcountry Eco-Tour: Sail, Snorkel & Kayak

    Set sail from Historic Seaport on the Key West Schooner Backcountry Eco-Tour adventure!

     5 hours (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $109.95
    Best Rate
    $109.95
  • Key West Original Watersports Adventure
    4.8 (325)

    Key West Original Watersports Adventure

    Get ready for the thrill of a lifetime with our Do It All Watersports Combo, the ultimate way to experience the best of Key West!

     6 hours  Free Cancellation  Instant Confirmation
    from
    $179.95
    from
    $179.95
  • Key West Safari Snorkel Adventure
    4.7 (198)

    Key West Safari Snorkel Adventure

    Explore Key West in a fun and unique way! Avoid the crowds on this exciting snorkel safari adventure and captain your own speedboat through 28

     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $197.12
    from
    $197.12
  • Key West Snuba® (No Dive Certification Required)
    5.0 (474)

    Key West Snuba® (No Dive Certification Required)

    If you want to go beyond snorkeling and experience the world's underwater beauty in the safest and easiest way possible, try Snuba®!

     3 hours 30 minutes  Instant Confirmation
    from
    $160
    from
    $160
  • Key West Full-Day Catamaran Eco Tour
    Special Offer
    Special Offer
    4.9 (558)

    Key West Full-Day Catamaran Eco Tour

    Beautiful Key West is surrounded by sparkling blue waters of the Gulf of Mexico, making kayaking and dolphin watching the perfect way to spend a

     6 hours (approx.)  Instant Confirmation
    $124.95
    $119.95
    $124.95
    $119.95
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