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. /Water Activities

    Best results for Water Activities in Sugarloaf Key, FL

    Showing 409-432 of 654 results
    Sail a Private Key West Harbor Sunset Charter
    Sailing

    Sail a Private Key West Harbor Sunset Charter

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

    Private 2-hour Key West sunset sail with captain and mate
    4.8 • 376 reviews
    $732
    Key West Sunset Snorkel Cruise
    Snorkeling

    Key West Sunset Snorkel Cruise

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

    Sail, snorkel and watch the Key West sunset from your private boat
    4.8 • 376 reviews
    $1,129
    Charter a Private Yacht in Key West
    Yacht Charters

    Charter a Private Yacht in Key West

    Bareboat yacht charter for groups over 6, with snorkel and float gear included

    Bareboat yacht charter for groups over 6, with snorkel and float gear included
    4.9 • 34 reviews
    $1,362& up
    Luxury Private Yacht Charter in Key West
    Yacht Charters

    Luxury Private Yacht Charter in Key West

    Charter a private motor yacht in Key West with flexible 1.5–8 hour options

    Charter a private motor yacht in Key West with flexible 1.5–8 hour options
    4.9 • 34 reviews
    $1,519& up
    Sail Key West Harbor on a 90-Minute Private Charter
    Sailing

    Sail Key West Harbor on a 90-Minute Private Charter

    Private Key West harbor sail with time at the helm

    Private Key West harbor sail with time at the helm
    4.8 • 376 reviews
    $448
    Private Fishing Charter in Key West
    Fishing Charters

    Private Fishing Charter in Key West

    Target offshore species aboard a comfortable sportfishing boat

    Target offshore species aboard a comfortable sportfishing boat
    4.1 • 53 reviews
    $1,272
    1.5-Hour Key West Parasailing Adventure
    Parasailing

    1.5-Hour Key West Parasailing Adventure

    See Key West and the Florida Keys from above the water

    See Key West and the Florida Keys from above the water
    5.0 • 31 reviews
    $64/ person
    4-Hour Private Fishing Charter in Key West
    Private Fishing Charters

    4-Hour Private Fishing Charter in Key West

    Fish Key West on a fully equipped 24 ft bay boat—ideal for first-time anglers

    Fish Key West on a fully equipped 24 ft bay boat—ideal for first-time anglers
    5.0 • 83 reviews
    $793
    6-Hour Private Fishing Charter In Key West
    Private Fishing Charters

    6-Hour Private Fishing Charter In Key West

    Fish longer on a 6-hour private charter to reach less-pressured spots

    Fish longer on a 6-hour private charter to reach less-pressured spots
    5.0 • 83 reviews
    $1,019
    8-Hour Fishing Charter in Key West
    Fishing Charters

    8-Hour Fishing Charter in Key West

    Fish Key West waters on an 8-hour charter for up to 4 anglers

    Fish Key West waters on an 8-hour charter for up to 4 anglers
    5.0 • 83 reviews
    $1,359
    Private Sailing Charter in Key West
    Sailing

    Private Sailing Charter in Key West

    Charter the 54-foot Schooner Valora for a private sail in Key West

    Charter the 54-foot Schooner Valora for a private sail in Key West
    4.9 • 3K reviews
    $1,340
    Sail a Key West Champagne Sunset Cruise
    Sailing

    Sail a Key West Champagne Sunset Cruise

    Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

    Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included
    4.9 • 3K reviews
    $134/ person
    Sailing, Kayaking & Snorkeling Tour of Key West Backcountry
    Snorkeling

    Sailing, Kayaking & Snorkeling Tour of Key West Backcountry

    Explore mangrove islands by schooner, kayak and snorkel

    Explore mangrove islands by schooner, kayak and snorkel
    4.9 • 3K reviews
    $146/ person
    Private Sunset Sail in Key West
    Sailing

    Private Sunset Sail in Key West

    Settle into a classic schooner for an intimate Key West sunset

    Settle into a classic schooner for an intimate Key West sunset
    4.9 • 3K reviews
    $134
    Key West Seafood Boil Snorkel Sail
    Snorkeling

    Key West Seafood Boil Snorkel Sail

    Two reef snorkel stops with a seafood boil and open bar

    Two reef snorkel stops with a seafood boil and open bar
    4.7 • 8.1K reviews
    $89/ person
    3.5-Hour Key West Sandbar Cruise
    Boat Tours

    3.5-Hour Key West Sandbar Cruise

    Spend the day at a Key West sandbar aboard the 53-foot tiki boat Lazy Lady

    Spend the day at a Key West sandbar aboard the 53-foot tiki boat Lazy Lady
    4.7 • 8.1K reviews
    $139/ person
    Afternoon Snorkeling Cruise at Florida Keys Reef
    Snorkeling

    Afternoon Snorkeling Cruise at Florida Keys Reef

    Sail to a coral reef with snorkeling gear, instruction, and complimentary drinks

    Sail to a coral reef with snorkeling gear, instruction, and complimentary drinks
    4.7 • 8.1K reviews
    $51/ person
    Mimosa Snorkel Sail in Key West
    Snorkeling

    Mimosa Snorkel Sail in Key West

    Sail to the Florida Keys Reef for guided snorkeling, lunch, and drinks

    Sail to the Florida Keys Reef for guided snorkeling, lunch, and drinks
    4.7 • 8.1K reviews
    $51/ person
    Glass Bottom Boat Reef Eco Tour in Key West
    Boat Tours

    Glass Bottom Boat Reef Eco Tour in Key West

    See Key West’s reef through glass viewing panels on an air-conditioned catamaran

    See Key West’s reef through glass viewing panels on an air-conditioned catamaran
    4.9 • 12.7K reviews
    $70/ person
    Jet Ski, Parasail & Waterpark Adventure in Key West
    Jet Skiing

    Jet Ski, Parasail & Waterpark Adventure in Key West

    Parasail, ride a Jet Ski, and play on Key West’s ocean waterpark in 3.5 or 6–6.5 hours

    Parasail, ride a Jet Ski, and play on Key West’s ocean waterpark in 3.5 or 6–6.5 hours
    4.9 • 12.7K reviews
    $146/ person
    90-Minute Guided Jet Ski Tour in Key West
    Jet Skiing

    90-Minute Guided Jet Ski Tour in Key West

    Ride your own jet ski on a 28-mile guided loop around Key West

    Ride your own jet ski on a 28-mile guided loop around Key West
    4.9 • 12.7K reviews
    $197/ jet-ski
    Key West 28-Mile Guided Jet Ski Tour
    Jet Skiing

    Key West 28-Mile Guided Jet Ski Tour

    Ride Key West waters with a guide and views of island landmarks

    Ride Key West waters with a guide and views of island landmarks
    4.9 • 12.7K reviews
    $165/ Jet Ski
    Snorkel Key West Reef With Margaritas
    Snorkeling

    Snorkel Key West Reef With Margaritas

    Snorkel Key West’s coral reef, then relax with complimentary margaritas

    Snorkel Key West’s coral reef, then relax with complimentary margaritas
    4.9 • 12.7K reviews
    $63/ person
    Sail a Live Music Sunset Cruise in Key West
    Sailing

    Sail a Live Music Sunset Cruise in Key West

    Sunset catamaran sail with live music, appetizers, and included drinks

    Sunset catamaran sail with live music, appetizers, and included drinks
    4.9 • 12.7K reviews
    $101/ person
    1…171819…28

    Travel guides for Water Activities

    13 Stunning Beaches in Florida With Clear Water You Need to Visit
    Best of Florida • 2026

    13 Stunning Beaches in Florida With Clear Water You Need to Visit

    Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.