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

    Best results for Water Activities in Cudjoe Key, FL

    Showing 169-192 of 618 results
    Key West Sandbar Private Charter
    Yacht Charters

    Key West Sandbar Private Charter

    Ride a 60-knot Freeman for sandbars and wildlife watching

    Ride a 60-knot Freeman for sandbars and wildlife watching
    $2,329
    Sandbar Charter in Key West
    Yacht Charters

    Sandbar Charter in Key West

    Reach sandbars quickly on a private Freeman charter

    Reach sandbars quickly on a private Freeman charter
    $2,965
    Key West Sandbar Charter
    Yacht Charters

    Key West Sandbar Charter

    Cruise Key West waters at speeds up to 60 knots

    Cruise Key West waters at speeds up to 60 knots
    $3,601
    4-Hour Charter in Key West
    Yacht Charters

    4-Hour Charter in Key West

    Explore Key West waters aboard a fast, shallow-draft private boat

    Explore Key West waters aboard a fast, shallow-draft private boat
    $1,693
    8-Hour Dry Tortugas Charter
    Yacht Charters

    8-Hour Dry Tortugas Charter

    Cruise to the Dry Tortugas on a fast, shallow-draft private boat

    Cruise to the Dry Tortugas on a fast, shallow-draft private boat
    $3,392
    Dry Tortugas 10-Hour Private Charter From Key West
    Yacht Charters

    Dry Tortugas 10-Hour Private Charter From Key West

    Reach Dry Tortugas fast aboard a private boat with an onboard bathroom

    Reach Dry Tortugas fast aboard a private boat with an onboard bathroom
    $4,028
    Key West 8-Hour Private Fishing Charter
    Fishing Charters

    Key West 8-Hour Private Fishing Charter

    A shallow-draft private boat for fishing, sandbar stops and wildlife viewing

    A shallow-draft private boat for fishing, sandbar stops and wildlife viewing
    $3,180
    Key West 42' Sailing Catamaran Charter
    Sailing

    Key West 42' Sailing Catamaran Charter

    Sail the ocean in privacy with a full bathroom and kitchen onboard

    Sail the ocean in privacy with a full bathroom and kitchen onboard
    $2,138
    Sandbar Charter in Key West
    Boat Tours

    Sandbar Charter in Key West

    Private shallow-draft boating for sandbars, swings and wildlife watching

    Private shallow-draft boating for sandbars, swings and wildlife watching
    $1,219
    4-Hour Shared Charter in Key West
    Boat Tours

    4-Hour Shared Charter in Key West

    Head to the sandbar or reef on a shared Key West charter

    Head to the sandbar or reef on a shared Key West charter
    $398/ person
    42' Sailing Catamaran Charter in Key West
    Sailing

    42' Sailing Catamaran Charter in Key West

    Private sailing with a full bathroom and kitchen

    Private sailing with a full bathroom and kitchen
    $1,709
    42' Sailing Catamaran Charter in Key West
    Sailing

    42' Sailing Catamaran Charter in Key West

    Sail Key West waters privately with an onboard kitchen and full bathroom

    Sail Key West waters privately with an onboard kitchen and full bathroom
    $1,817
    Sunrise & Sunset Catamaran Charter in Key West
    Sailing

    Sunrise & Sunset Catamaran Charter in Key West

    Sail Key West waters on a private catamaran timed for sunrise or sunset

    Sail Key West waters on a private catamaran timed for sunrise or sunset
    $1,375
    42' Sailing Catamaran Charter in Key West
    Sailing

    42' Sailing Catamaran Charter in Key West

    Sail the ocean on a private catamaran with a full bathroom and kitchen

    Sail the ocean on a private catamaran with a full bathroom and kitchen
    $1,693
    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
    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.