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 409-432 of 859 results
    Key West Sunset Cruise
    Sunrise and Sunset Tours

    Key West Sunset Cruise

    Cruise Key West waters at sunset with your private group (up to 6)

    Cruise Key West waters at sunset with your private group (up to 6)
    $397
    4-Hour Private Sandbar Charter in Key West
    Boat Tours

    4-Hour Private Sandbar Charter in Key West

    Private 4-hour sandbar charter for up to 6 in Key West

    Private 4-hour sandbar charter for up to 6 in Key West
    $908
    Swim & Relax on a 6-Hour Key West Sandbar Charter
    Boat Tours

    Swim & Relax on a 6-Hour Key West Sandbar Charter

    Private 6-hour sandbar charter for up to 6 people

    Private 6-hour sandbar charter for up to 6 people
    $1,135
    Explore Key West on a 23' Fishing Boat Rental
    Boat RentalsUp to 6

    Explore Key West on a 23' Fishing Boat Rental

    Rent a 23' center console and fish Key West your way

    Rent a 23' center console and fish Key West your way
    4.1 • 134 reviews
    $568/ boat
    21' Backcountry Boat Rental in Key West
    Boat Rentals2 to 8

    21' Backcountry Boat Rental in Key West

    Self-guided shallow-water fishing, snorkeling, and sandbar exploring

    Self-guided shallow-water fishing, snorkeling, and sandbar exploring
    4.1 • 134 reviews
    $568/ boat
    Key West Sandbar Boat Rental
    Boat Rentals2 to 8

    Key West Sandbar Boat Rental

    Explore Key West waters with onboard navigation and sandbar-ready comforts

    Explore Key West waters with onboard navigation and sandbar-ready comforts
    4.1 • 134 reviews
    $568/ boat
    Key West 23' Fishing Boat Rental
    Boat Rentals2 to 8

    Key West 23' Fishing Boat Rental

    Set your own course for fishing, snorkeling, and sandbars

    Set your own course for fishing, snorkeling, and sandbars
    4.1 • 134 reviews
    $568/ boat
    Houseboat Charter in Key West
    Boat RentalsUp to 6

    Houseboat Charter in Key West

    Charter a custom houseboat and relax on a remote Key West mooring

    Charter a custom houseboat and relax on a remote Key West mooring
    4.8 • 89 reviews
    $1,166& up
    Key West Sunset Charter
    Boat Tours

    Key West Sunset Charter

    Tailor a private sunset outing with water activities and island exploration

    Tailor a private sunset outing with water activities and island exploration
    4.8 • 89 reviews
    $318& up
    3.5-Hour Key West Eco Charter
    Boat Tours

    3.5-Hour Key West Eco Charter

    Design a private Key West day of paddling, snorkeling, fishing, and island exploration

    Design a private Key West day of paddling, snorkeling, fishing, and island exploration
    4.8 • 89 reviews
    $530& up
    Key West Eco Charter
    Yacht Charters

    Key West Eco Charter

    Explore reefs, wildlife habitats, and private islands on a flexible Key West charter

    Explore reefs, wildlife habitats, and private islands on a flexible Key West charter
    4.8 • 89 reviews
    $742& up
    Explore Dry Tortugas From Key West on a 10-Hour Charter
    National Parks

    Explore Dry Tortugas From Key West on a 10-Hour Charter

    Cruise by private boat from Key West to Dry Tortugas and tour Fort Jefferson

    Cruise by private boat from Key West to Dry Tortugas and tour Fort Jefferson
    5.0 • 101 reviews
    $3,074
    Customize Your Key West Private Boat Charter
    Boat Tours

    Customize Your Key West Private Boat Charter

    Build your own private Key West day on the water for up to 6 guests

    Build your own private Key West day on the water for up to 6 guests
    5.0 • 101 reviews
    $1,007& up
    Key West 4-Hour Fishing Charter
    Fishing Charters

    Key West 4-Hour Fishing Charter

    Fish Key West your way with a charter tailored to your preferred style

    Fish Key West your way with a charter tailored to your preferred style
    5.0 • 101 reviews
    $954& up
    Key West Private Sandbar Cruise
    Boat Tours

    Key West Private Sandbar Cruise

    Cruise to a Key West sandbar for swimming, walking, and time in the sun

    Cruise to a Key West sandbar for swimming, walking, and time in the sun
    5.0 • 101 reviews
    $1,007& up
    10-Hour Dry Tortugas Snorkeling Cruise
    Snorkeling

    10-Hour Dry Tortugas Snorkeling Cruise

    Snorkel the Dry Tortugas and explore Fort Jefferson on Garden Key

    Snorkel the Dry Tortugas and explore Fort Jefferson on Garden Key
    5.0 • 101 reviews
    $795/ person
    Lobster Mini Season Charter in Key West
    Fishing Charters

    Lobster Mini Season Charter in Key West

    Catch lobsters during Key West's July Mini Season

    Catch lobsters during Key West's July Mini Season
    5.0 • 101 reviews
    $1,060& up
    Waterfront Bar Crawl Charter in Key West
    Bar and Pub Crawl

    Waterfront Bar Crawl Charter in Key West

    Set your own pace between Key West's waterfront bar stops by boat

    Set your own pace between Key West's waterfront bar stops by boat
    5.0 • 34 reviews
    $689& up
    Cruise to Local Sandbars & Islands on a Private Charter
    Yacht Charters

    Cruise to Local Sandbars & Islands on a Private Charter

    Private sandbar and island-hopping charter with 4, 6, or 8-hour options

    Private sandbar and island-hopping charter with 4, 6, or 8-hour options
    5.0 • 34 reviews
    $848& up
    Island-Hopping Private Charter
    Yacht Charters

    Island-Hopping Private Charter

    Choose a 4, 6, or 8-hour private charter to island hop local waters

    Choose a 4, 6, or 8-hour private charter to island hop local waters
    5.0 • 34 reviews
    $1,007& up
    Private Sandbar Charter in Key West
    Yacht Charters

    Private Sandbar Charter in Key West

    Swim, relax, and island-hop at local sandbars

    Swim, relax, and island-hop at local sandbars
    5.0 • 34 reviews
    $901& up
    Island-Hopping Charter in Key West
    Boat Tours

    Island-Hopping Charter in Key West

    Explore backcountry islands, shipwrecks, and sandbars on a private charter

    Explore backcountry islands, shipwrecks, and sandbars on a private charter
    5.0 • 34 reviews
    $1,007& up
    Key West Reef & Sandbar Private Charter
    Boat Tours

    Key West Reef & Sandbar Private Charter

    Swim, relax and explore local waters at your own pace

    Swim, relax and explore local waters at your own pace
    5.0 • 34 reviews
    $1,431
    Key West 2-Hour Sunset Charter
    Sunrise and Sunset Tours

    Key West 2-Hour Sunset Charter

    Cruise the historic seaport as the sun sets over Key West

    Cruise the historic seaport as the sun sets over Key West
    5.0 • 34 reviews
    $583
    1…171819…36