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Explore Greetwell

Explore extraordinary experiences in 500+ destinations

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Tours & Sightseeing

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On the Water

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Rentals & Charters

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  • Yacht Charters

Questions? We're here to help.Real people, 7 days a week.

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  • How to Budget for Yacht Charter Costs
  • Best 1234

    things to do in Sugarloaf Key, FL

    Showing 481-504 of 1,234 results
    Key West Snorkeling Vest Rental

    Key West Snorkeling Vest Rental

    Stay comfortably afloat while snorkeling with a vest sized for juniors and adults

    5.0 • 28 reviews
    $11/ vest
    Clear Kayak Eco-Tour in Big Pine Key

    Clear Kayak Eco-Tour in Big Pine Key

    Paddle clear kayaks through mangrove tunnels and look for Florida Keys wildlife

    4.9 • 54 reviews
    $147
    Sunset Glow Kayak Tour Through Key West Mangroves

    Sunset Glow Kayak Tour Through Key West Mangroves

    Glide into the night with LEDs lighting the water beneath your kayak

    4.9 • 54 reviews
    $147/ kayak
    Private Fishing Charter in Key West on a 43' Boat

    Private Fishing Charter in Key West on a 43' Boat

    Fish Key West waters from a private 43-foot sport-fishing boat

    4.9 • 53 reviews
    $1,060& up
    Private 3-Hour Sailing Lesson in Key West

    Private 3-Hour Sailing Lesson in Key West

    Choose your boat and learn to sail with a private instructor in Key West

    4.9 • 51 reviews
    $143& up
    Private Sailing Lesson in Key West for All Levels

    Private Sailing Lesson in Key West for All Levels

    Learn at your own pace with private instruction on the water

    4.9 • 51 reviews
    $95& up
    2-Hour Beginner Sailing Lesson in Key West

    2-Hour Beginner Sailing Lesson in Key West

    Learn sailing fundamentals aboard Hobie Wave catamarans

    4.9 • 51 reviews
    $48/ person
    Private Dolphin Watch & Snorkel Sail in Key West

    Private Dolphin Watch & Snorkel Sail in Key West

    Sail Key West and snorkel the backcountry on your own private boat

    4.8 • 376 reviews
    $959
    Private Key West Sailing Charter with Giant Lily Pad Float

    Private Key West Sailing Charter with Giant Lily Pad Float

    Private sail to a shallow-water anchorage with time to lounge on a Lilypad float

    4.8 • 376 reviews
    $789
    Sail a Private Key West Harbor Sunset Charter

    Sail a Private Key West Harbor Sunset Charter

    Private 2-hour Key West sunset sail with captain and mate

    4.8 • 376 reviews
    $732
    Private 1939 Patton Schooner Day Sail in Key West

    Private 1939 Patton Schooner Day Sail in Key West

    Sail a 1939 wooden schooner and take a turn at the helm

    4.8 • 376 reviews
    $1,345
    Key West Sunset Snorkel Cruise

    Key West Sunset Snorkel Cruise

    Sail, snorkel and watch the Key West sunset from your private boat

    4.8 • 376 reviews
    $1,129
    Sail Key West Harbor on a 90-Minute Private Charter

    Sail Key West Harbor on a 90-Minute Private Charter

    Private Key West harbor sail with time at the helm

    4.8 • 376 reviews
    $448
    Key West Sunset Proposal Sail

    Key West Sunset Proposal Sail

    Set the scene for your proposal aboard a private sunset sail

    4.8 • 376 reviews
    $936/ boat
    Sunset Sail Charter in Key West

    Sunset Sail Charter in Key West

    Sail Key West aboard a 1939 wooden schooner with captain and crew

    4.8 • 376 reviews
    $2,474
    Stargazing Sail Charter in Key West

    Stargazing Sail Charter in Key West

    A private evening sail with quiet stargazing beyond Key West's lights

    4.8 • 376 reviews
    $675
    Historic Schooner Sail in Key West

    Historic Schooner Sail in Key West

    Sail Key West aboard a 1939 wooden schooner built for General George S. Patton

    4.8 • 376 reviews
    $85/ person
    Key West Sunset Schooner Cruise

    Key West Sunset Schooner Cruise

    Sail Key West’s Atlantic coast at sunset aboard a historic schooner

    4.8 • 376 reviews
    $124/ person
    Private Snorkel, Boca Grande & Sunset Charter in Key West

    Private Snorkel, Boca Grande & Sunset Charter in Key West

    Private 4-hour snorkel and Boca Grande cruise with sunset finish

    5.0 • 26 reviews
    $1,108
    Explore a Key West Island & Dolphin Watching Charter

    Explore a Key West Island & Dolphin Watching Charter

    Private 4-hour island and sandbar charter from Key West for up to 6

    5.0 • 26 reviews
    $757
    Key West 4-Hour Lunch Cruise & Sandbar Stop

    Key West 4-Hour Lunch Cruise & Sandbar Stop

    Cruise Key West, grab dockside lunch, and cool off at a nearby sandbar

    5.0 • 26 reviews
    $874
    Snorkel & Sunset Cruise in Key West

    Snorkel & Sunset Cruise in Key West

    Private 3–4 hour snorkel charter with two stops and a sunset finish

    5.0 • 26 reviews
    $757
    Private Key West Boat Charter with Tiki Bar & Sandbar Stop

    Private Key West Boat Charter with Tiki Bar & Sandbar Stop

    Private Key West cruise with a Tiki Bar stop and sandbar swim

    5.0 • 26 reviews
    $875
    Dolphin Watching & Swimming Boat Tour in Key West

    Dolphin Watching & Swimming Boat Tour in Key West

    Swim and sightsee on a 2-hour Key West charter

    5.0 • 26 reviews
    $583
    1…202122…52
    Fishing Charters226Boat Tours178Boat Rentals108Yacht Charters100Snorkeling99
    More
    • Sailing83
    • Scuba Diving74
    • Car Rentals52
    • Sunrise and Sunset Tours45
    • Bike Rentals34
    • Private Fishing Charters25
    • Dolphin Watching24
    • Kayaking Tours18
    • Jet Skiing17
    • Scooter Rentals12
    • Ghost and Haunted9
    • Scavenger Hunts8
    • Dinner Cruises7
    • Scenic Flights7
    • Bar and Pub Crawl6
    • Parasailing6
    • Private Boat Charters6
    • Helicopter Tours5
    • Historical Tours5
    • Paddleboarding5