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  • What Is a Mailboat? Working Postal Routes You Can Ride in 2026
  • Best results for

    Yacht Charters in Key West, FL

    Showing 25-48 of 99 results
    Custom Snorkel & Reef Fishing Charter in Key West

    Custom Snorkel & Reef Fishing Charter in Key West

    Build your ideal day with snorkeling, fishing and time on the water

    5.0 • 41 reviews
    $1,267& up
    Private Full-Day Captained Boat Charter in Key West

    Private Full-Day Captained Boat Charter in Key West

    Private captained day on the water with lunch, floats, and refreshments

    5.0 • 189 reviews
    $1,304
    Key West 4-Hour Sandbar Charter

    Key West 4-Hour Sandbar Charter

    Explore Key West’s turquoise waters and white-sand sandbars with food and drinks included

    5.0 • 39 reviews
    $279/ person
    Cruise to Local Sandbars & Islands on a Private Charter

    Cruise to Local Sandbars & Islands on a Private Charter

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

    5.0 • 35 reviews
    $848& up
    Marquesas Keys Private Charter

    Marquesas Keys Private Charter

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

    5.0 • 79 reviews
    $2,761& up
    Private Full-Day Custom Boat Charter in Key West

    Private Full-Day Custom Boat Charter in Key West

    Customize your Key West private charter with a captain and your choice of 3 activities

    4.8 • 25.1K reviews
    $1,078
    Full-Day Private Yacht Charter & Reef Snorkeling in Key West

    Full-Day Private Yacht Charter & Reef Snorkeling in Key West

    Charter a private sailing catamaran or power yacht for 8 hours of snorkeling and island stops

    4.9 • 56 reviews
    $6,867
    4-Hour Private Boat Charter in Key West Backcountry

    4-Hour Private Boat Charter in Key West Backcountry

    Customize a 4-hour private tri-toon cruise with a licensed captain in Key West’s backcountry

    4.8 • 996 reviews
    $523
    Full-Day Private Sandbar & Snorkel Charter in Big Pine Key

    Full-Day Private Sandbar & Snorkel Charter in Big Pine Key

    Design a Lower Keys charter with sandbars, reefs, snorkeling, or bar stops

    5.0 • 26 reviews
    $900
    Key West Sandbar Private Charter

    Key West Sandbar Private Charter

    Swim, paddle, and relax at a secluded Key West island or sandbar

    5.0 • 26 reviews
    $758
    Private Sandbar, Snorkel & Dolphin Charter in Key West

    Private Sandbar, Snorkel & Dolphin Charter in Key West

    Choose sandbar time, snorkeling, or dolphin watching on a 4-hour private charter

    5.0 • 25 reviews
    $1,484
    Private Sandbar Boat Charter in Key West

    Private Sandbar Boat Charter in Key West

    Relax and explore local sandbars aboard a 37-foot Edgewater

    5.0 • 21 reviews
    $2,452
    Key West Boat Wedding Charter

    Key West Boat Wedding Charter

    Exchange vows on the waters of Key West

    5.0 • 41 reviews
    $737& up
    Private Captained Boat Charter in Key West

    Private Captained Boat Charter in Key West

    Cruise Key West waters aboard a private captained Boston Whaler

    5.0 • 189 reviews
    $900
    6-Hour Key West Sandbar Charter

    6-Hour Key West Sandbar Charter

    Enjoy a Key West sandbar day with food and drinks included

    5.0 • 39 reviews
    $391/ person
    Island-Hopping Private Charter

    Island-Hopping Private Charter

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

    5.0 • 35 reviews
    $1,007& up
    Private Bachelor & Bachelorette Sandbar Charter in Key West

    Private Bachelor & Bachelorette Sandbar Charter in Key West

    Build a private Key West celebration around your group's ideal day on the water

    5.0 • 79 reviews
    $1,479& up
    Private Luxury Motor Yacht Charter in Key West

    Private Luxury Motor Yacht Charter in Key West

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

    4.9 • 34 reviews
    $1,362& up
    Private Sunset Yacht Cruise & Snorkel in Key West

    Private Sunset Yacht Cruise & Snorkel in Key West

    Sail, snorkel, and toast the sunset on your own Key West yacht

    4.9 • 56 reviews
    $2,088& up
    Private Full-Day Key West Backcountry Boat Charter

    Private Full-Day Key West Backcountry Boat Charter

    Customize your Key West backcountry day on a captained tri-toon with a swim deck

    4.8 • 996 reviews
    $1,161
    Customize a Private Boat Charter in Key West

    Customize a Private Boat Charter in Key West

    Private Key West luxury activity boat charter for up to 13

    4.8 • 94 reviews
    $907& up
    Key West Sunset Sandbar Private Charter

    Key West Sunset Sandbar Private Charter

    Set out for sandbar time, island sightseeing, and sunset views on a private Key West boat trip

    5.0 • 26 reviews
    $1,750
    Key West Sunset Private Charter

    Key West Sunset Private Charter

    Harbor cruising and sunset views aboard a private boat

    5.0 • 25 reviews
    $1,007
    Key West Private Sunset Cruise

    Key West Private Sunset Cruise

    Celebrate with champagne, hors d'oeuvres, and sunset views on a private charter

    5.0 • 21 reviews
    $3,923
    12345
    Key West Things To Do
    Yacht ChartersFishing Charters199Boat Tours170Snorkeling87Sailing82
    More
    • Boat Rentals68
    • Scuba Diving58
    • Car Rentals48
    • Sunrise and Sunset Tours39
    • Bike Rentals34
    • Private Fishing Charters25
    • Dolphin Watching24
    • Kayaking Tours15
    • Jet Skiing14
    Scooter Rentals
    13
  • Ghost and Haunted9
  • Scavenger Hunts8
  • Scenic Flights7
  • Bar and Pub Crawl6
  • Dinner Cruises6
  • Parasailing6
  • Private Boat Charters6
  • Helicopter Tours5
  • Historical Tours5
  • Bike Tours4