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

    Best results for Water Activities in Cudjoe Key, FL

    Showing 193-216 of 618 results
    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
    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 • 1 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 • 1 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 • 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
    Private Charter or Rental in San Jose
    Boat Rentals

    Private Charter or Rental in San Jose

    Customize a private outing for up to 9 people

    Customize a private outing for up to 9 people
    $850& up
    3-Hour Charter in San Jose
    Yacht Charters

    3-Hour Charter in San Jose

    Shape a private boat outing around your group's interests

    Shape a private boat outing around your group's interests
    $737
    24' Sea Fox Boat Rental in Key West
    Boat RentalsUp to 8

    24' Sea Fox Boat Rental in Key West

    Self-guided Key West boating with flexible docking options

    Self-guided Key West boating with flexible docking options
    4.7 • 21 reviews
    $460/ boat
    24' Boat Rental in Key West
    Boat RentalsUp to 8

    24' Boat Rental in Key West

    Flexible Key West boat days with onboard GPS and radio

    Flexible Key West boat days with onboard GPS and radio
    4.7 • 21 reviews
    $460/ boat
    20' Boat Rental in Key West
    Boat RentalsUp to 5

    20' Boat Rental in Key West

    Chart your own Key West day aboard a 20-foot Sea Fox Viper

    Chart your own Key West day aboard a 20-foot Sea Fox Viper
    4.7 • 21 reviews
    $397/ boat
    22' Sea Fox Boat Rental in Key West
    Boat Rentals

    22' Sea Fox Boat Rental in Key West

    Take the helm for flexible Key West boating, from a half day to a week

    Take the helm for flexible Key West boating, from a half day to a week
    4.7 • 21 reviews
    $426/ boat
    Key West 13-Person Pontoon Rental
    Boat RentalsUp to 13

    Key West 13-Person Pontoon Rental

    Cruise Key West waters with onboard GPS, shade, and a cooler

    Cruise Key West waters with onboard GPS, shade, and a cooler
    4.7 • 21 reviews
    $460/ boat
    6-Hour Key West Sandbar Private Charter
    Boat Tours

    6-Hour Key West Sandbar Private Charter

    Explore Key West backcountry sandbars on a private charter for up to 6

    Explore Key West backcountry sandbars on a private charter for up to 6
    5.0 • 76 reviews
    $875
    1…8910…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.