Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Sugarloaf Key FL

    Best 859 things to do in Sugarloaf Key, FL

    Showing 217-240 of 859 results
    Sunrise & Sunset Catamaran Charter in Key West
    Yacht Charters

    Sunrise & Sunset Catamaran Charter in Key West

    Enjoy a private catamaran outing in a clothing-optional setting at your comfort level

    Enjoy a private catamaran outing in a clothing-optional setting at your comfort level
    5.0 • 4 reviews
    $1,007
    4-Hour Sailing Catamaran Charter in Key West
    Sailing

    4-Hour Sailing Catamaran Charter in Key West

    Private catamaran sailing with a full bathroom and kitchen

    Private catamaran sailing with a full bathroom and kitchen
    5.0 • 4 reviews
    $1,219
    Key West Sandbar Boat Charter
    Boat Tours

    Key West Sandbar Boat Charter

    Private charter with local captains and flexible sandbar stops

    Private charter with local captains and flexible sandbar stops
    $689& up
    Fishing Charter on a 39' Yellowfin in Key West
    Fishing Charters

    Fishing Charter on a 39' Yellowfin in Key West

    Reef, offshore, and island adventures aboard a private Yellowfin charter

    Reef, offshore, and island adventures aboard a private Yellowfin charter
    4.5 • 1.7K reviews
    $1,006& up
    Naturist Sailing Catamaran Charter in Key West
    Sailing

    Naturist Sailing Catamaran Charter in Key West

    Sail privately in a clothing-optional setting shaped around your comfort

    Sail privately in a clothing-optional setting shaped around your comfort
    5.0 • 4 reviews
    $1,590
    Naturist Catamaran Charter in Key West
    Sailing

    Naturist Catamaran Charter in Key West

    Spend a private day on a clothing-optional sailing catamaran

    Spend a private day on a clothing-optional sailing catamaran
    5.0 • 4 reviews
    $1,855
    Private 8-Hour Yacht Charter in Key West
    Yacht Charters

    Private 8-Hour Yacht Charter in Key West

    Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops

    Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops
    4.9 • 56 reviews
    $6,867
    Private Sunset Catamaran Charter in Key West
    Yacht Charters

    Private Sunset Catamaran Charter in Key West

    Sail, snorkel, and toast the sunset on your own Key West yacht

    Sail, snorkel, and toast the sunset on your own Key West yacht
    4.9 • 56 reviews
    $2,088& up
    Customize a 4-Hour Private Yacht Charter
    Yacht Charters

    Customize a 4-Hour Private Yacht Charter

    Charter a private yacht for 4 hours with snorkeling or sailing options

    Charter a private yacht for 4 hours with snorkeling or sailing options
    4.9 • 56 reviews
    $4,029
    Half-Day Key West Snorkel & Sandbar Charter
    Snorkeling

    Half-Day Key West Snorkel & Sandbar Charter

    See reefs below the surface and relax at a Key West sandbar

    See reefs below the surface and relax at a Key West sandbar
    5.0 • 59 reviews
    $793
    Key West Full-Day Snorkel & Sandbar Charter
    Snorkeling

    Key West Full-Day Snorkel & Sandbar Charter

    Design your own reef and sandbar escape aboard a glass-bottom boat

    Design your own reef and sandbar escape aboard a glass-bottom boat
    5.0 • 59 reviews
    $1,362
    Key West 6-Hour Private Yacht Charter
    Yacht Charters

    Key West 6-Hour Private Yacht Charter

    Choose your yacht for private snorkeling, swimming, and Key West Harbor cruising

    Choose your yacht for private snorkeling, swimming, and Key West Harbor cruising
    4.9 • 56 reviews
    $5,732
    Key West Reef Snorkeling Charter
    Snorkeling

    Key West Reef Snorkeling Charter

    Snorkel coral reefs and relax at a Key West sandbar

    Snorkel coral reefs and relax at a Key West sandbar
    5.0 • 59 reviews
    $169/ person
    Key West Naturist Boat Charter
    Boat Tours

    Key West Naturist Boat Charter

    Private fast-boat access to shallow waters, sandbars, and a clothing-optional escape

    Private fast-boat access to shallow waters, sandbars, and a clothing-optional escape
    $1,375
    Naturist Sailing Charter in Key West
    Sailing

    Naturist Sailing Charter in Key West

    Private clothing-optional sailing with a licensed captain and crew

    Private clothing-optional sailing with a licensed captain and crew
    $2,011
    Naturist Sailing Charter in Key West
    Sailing

    Naturist Sailing Charter in Key West

    Private sailing with a captain, crew, paddle gear, and refreshments

    Private sailing with a captain, crew, paddle gear, and refreshments
    $2,647
    Sunset Cruise in Key West
    Sunrise and Sunset Tours

    Sunset Cruise in Key West

    Take in Key West’s sunset with glass-bottom views of marine life

    Take in Key West’s sunset with glass-bottom views of marine life
    5.0 • 59 reviews
    $482
    Key West 2-Hour Guided Jet Ski Tour
    Jet Skiing

    Key West 2-Hour Guided Jet Ski Tour

    Circle Key West by jet ski with guided stops and free-ride time

    Circle Key West by jet ski with guided stops and free-ride time
    5.0 • 59 reviews
    $237/ jet ski
    90-Minute Key West Jet Ski Tour
    Jet Skiing

    90-Minute Key West Jet Ski Tour

    Circle Key West by Yamaha WaveRunner with landmark and sandbar stops

    Circle Key West by Yamaha WaveRunner with landmark and sandbar stops
    5.0 • 59 reviews
    $215/ jet ski
    Custom Charter in Key West
    Yacht Charters

    Custom Charter in Key West

    Build a private Key West day around sandbars, snorkeling, dolphins, and more

    Build a private Key West day around sandbars, snorkeling, dolphins, and more
    5.0 • 74 reviews
    $1,479& up
    Key West Wildlife Refuge Eco Charter
    Ecotours

    Key West Wildlife Refuge Eco Charter

    Explore protected Lower Keys waters with a captain-led conservation focus

    Explore protected Lower Keys waters with a captain-led conservation focus
    5.0 • 74 reviews
    $1,055
    Key West Private Sunset Cruise
    Boat Tours

    Key West Private Sunset Cruise

    A private evening on the water for toasts, music and horizon views

    A private evening on the water for toasts, music and horizon views
    5.0 • 74 reviews
    $1,055
    Key West 4-Hour Private Sandbar Charter
    Yacht Charters

    Key West 4-Hour Private Sandbar Charter

    Trade crowded boat routes for secluded Lower Keys sandbars

    Trade crowded boat routes for secluded Lower Keys sandbars
    5.0 • 74 reviews
    $1,267
    4-Hour Key West Reef Snorkel Charter
    Snorkeling

    4-Hour Key West Reef Snorkel Charter

    Private reef time aboard a 30-foot Jeanneau yacht

    Private reef time aboard a 30-foot Jeanneau yacht
    5.0 • 74 reviews
    $1,267
    1…91011…36