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    1. Local experiences
    2. /All experiences
    3. /Water Activities

    Best results for Water Activities in Summerland Key, FL

    Showing 169-192 of 611 results
    4-Hour Boat Charter in Key West
    Yacht Charters

    4-Hour Boat Charter in Key West

    Shallow-draft sandbar hopping with dolphin and turtle watching

    Shallow-draft sandbar hopping with dolphin and turtle watching
    $1,219
    Private Sailing Catamaran Charter in Key West
    Sailing

    Private Sailing Catamaran Charter in Key West

    Spend the day sailing Key West waters aboard a private catamaran

    Spend the day sailing Key West waters aboard a private catamaran
    $2,567
    8-Hour Private Sailing Catamaran Charter in Key West
    Sailing

    8-Hour Private Sailing Catamaran Charter in Key West

    Private sailing, ocean scenery, and a setting built around your comfort

    Private sailing, ocean scenery, and a setting built around your comfort
    5.0 • 1 reviews
    $1,855
    Sandbar Charter in Key West
    Yacht Charters

    Sandbar Charter in Key West

    Cruise shallow waters with sandbar stops and onboard comforts

    Cruise shallow waters with sandbar stops and onboard comforts
    5.0 • 1 reviews
    $1,219
    4-Hour Charter in Key West
    Boat Tours

    4-Hour Charter in Key West

    Choose a sandbar or reef outing, weather permitting

    Choose a sandbar or reef outing, weather permitting
    5.0 • 1 reviews
    $371/ person
    Key West Sunrise or Sunset Catamaran Charter
    Sailing

    Key West Sunrise or Sunset Catamaran Charter

    Private catamaran sailing for sunrise or sunset ocean views

    Private catamaran sailing for sunrise or sunset ocean views
    5.0 • 1 reviews
    $1,007
    4-Hour Sailing Catamaran Charter in Key West
    Sailing

    4-Hour Sailing Catamaran Charter in Key West

    Private sailing with an onboard bathroom and kitchen

    Private sailing with an onboard bathroom and kitchen
    5.0 • 1 reviews
    $1,219
    6-Hour Private Sailing Charter in Key West
    Sailing

    6-Hour Private Sailing Charter in Key West

    Private catamaran sailing with ocean serenity

    Private catamaran sailing with ocean serenity
    5.0 • 1 reviews
    $1,590
    4-Hour Sandbar or Reef Charter in Key West
    Boat Tours

    4-Hour Sandbar or Reef Charter in Key West

    Bring your own drinks for a shared ocean charter to a weather-dependent sandbar or reef

    Bring your own drinks for a shared ocean charter to a weather-dependent sandbar or reef
    5.0 • 1 reviews
    $371/ person
    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 • 1 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 • 1 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
    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 • 54 reviews
    $6,867
    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 • 54 reviews
    $4,029
    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
    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 • 69 reviews
    $1,479& up
    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 • 69 reviews
    $1,055
    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 • 69 reviews
    $1,267
    Marquesas Keys Private Charter
    Yacht Charters

    Marquesas Keys Private Charter

    Cruise 30 miles offshore to snorkel, explore sandbars, and shape your own day

    Cruise 30 miles offshore to snorkel, explore sandbars, and shape your own day
    5.0 • 69 reviews
    $2,761& up
    Key West Patch Reef Fishing Charter
    Fishing Charters

    Key West Patch Reef Fishing Charter

    Private light-tackle fishing aboard a 30-foot Jeanneau with a licensed captain

    Private light-tackle fishing aboard a 30-foot Jeanneau with a licensed captain
    5.0 • 69 reviews
    $1,479& up
    Historic Harbor Cruise in Key West
    Boat Tours

    Historic Harbor Cruise in Key West

    Cruise Key West’s waterfront with local history narrated by a licensed captain

    Cruise Key West’s waterfront with local history narrated by a licensed captain
    5.0 • 69 reviews
    $1,055
    Dry Tortugas Full-Day Charter
    Yacht Charters

    Dry Tortugas Full-Day Charter

    Explore the islands and glide through clear waters on a full-day charter

    Explore the islands and glide through clear waters on a full-day charter
    $3,286
    Daytime Sandbar Cruise in Key West
    Boat Tours

    Daytime Sandbar Cruise in Key West

    Cruise Key West waters with snorkeling gear and a flexible island itinerary

    Cruise Key West waters with snorkeling gear and a flexible island itinerary
    $1,362
    3-Hour Key West Sandbar Charter
    Boat Tours

    3-Hour Key West Sandbar Charter

    Cruise to shallow sandbars and glide through mangroves in the Florida Keys

    Cruise to shallow sandbars and glide through mangroves in the Florida Keys
    $56/ person
    1…789…26

    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.