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Explore Greetwell

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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 73-96 of 99 results
    Sandbar Charter in Key West

    Sandbar Charter in Key West

    Cruise shallow waters with sandbar stops and onboard comforts

    5.0 • 4 reviews
    $1,219
    Dry Tortugas Private Cruise From Key West

    Dry Tortugas Private Cruise From Key West

    Explore Fort Jefferson and vibrant reefs by private yacht

    $2,120
    Cruise the Key West Sandbar on an 8-Hour Charter

    Cruise the Key West Sandbar on an 8-Hour Charter

    Private 8-hour sandbar charter for up to 6, with stops at Marvin Key and Snipes Key

    $1,362
    Private Leopard 51 Power Catamaran Charter in Key West

    Private Leopard 51 Power Catamaran Charter in Key West

    Spread out on the water with open-air lounges and 360° views

    $2,554
    Key West 3-Hour Boat Charter

    Key West 3-Hour Boat Charter

    Speed across Key West waters for sandbars, swings and wildlife watching

    $1,375
    Dry Tortugas Full-Day Charter

    Dry Tortugas Full-Day Charter

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

    $3,286
    Sail a Private Catamaran Charter in Key West

    Sail a Private Catamaran Charter in Key West

    Charter a Lagoon 450 F catamaran for up to 12 guests

    $2,838& up
    Full-Day Key West Sandbar Charter

    Full-Day Key West Sandbar Charter

    A private white-sand escape for your group

    $954
    Private 60' Schooner Wedding at Sea in Key West

    Private 60' Schooner Wedding at Sea in Key West

    Exchange vows at sea with a licensed captain officiating

    $1,703
    Sunrise & Sunset Catamaran Charter in Key West

    Sunrise & Sunset Catamaran Charter in Key West

    Enjoy a private catamaran outing in a clothing-optional setting at your comfort level

    5.0 • 4 reviews
    $1,007
    Private Leopard 51 Power Catamaran Charter in Key West

    Private Leopard 51 Power Catamaran Charter in Key West

    Make room for downtime with private cabins and open-air lounging

    $3,008
    Private Sandbar Hopping Boat Charter in Key West

    Private Sandbar Hopping Boat Charter in Key West

    Ride a 60-knot Freeman for sandbars and wildlife watching

    $2,329
    64' Power Catamaran Charter in Key West

    64' Power Catamaran Charter in Key West

    Stretch out across teak decks, lounges, and a spacious salon on the water

    $6,810
    Private Full-Day Power Catamaran Charter in Key West

    Private Full-Day Power Catamaran Charter in Key West

    Spread out across indoor lounges, an aft deck and a panoramic flybridge

    $3,320
    Sandbar Charter in Key West

    Sandbar Charter in Key West

    Reach sandbars quickly on a private Freeman charter

    $2,965
    8-Hour Key West Yacht Charter

    8-Hour Key West Yacht Charter

    Cruise aboard a sleek Sea Ray with a bright, high-end cabin

    $2,838
    Private 37' Boat Charter & Sandbar Hopping in Key West

    Private 37' Boat Charter & Sandbar Hopping in Key West

    Cruise Key West waters at speeds up to 60 knots

    $3,601
    Private 37' Boat Charter & Sandbar Hopping in Key West

    Private 37' Boat Charter & Sandbar Hopping in Key West

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

    $1,693
    Sunset Cruise in Key West

    Sunset Cruise in Key West

    Sail into the evening aboard a sleek Sea Ray 420 Sundancer

    $1,135
    Private Sandbar Hopping Fast Boat Charter in Key West

    Private Sandbar Hopping Fast Boat Charter in Key West

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

    $3,392
    Private Sandbar Hopping Boat Charter in Key West

    Private Sandbar Hopping Boat Charter in Key West

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

    $4,028
    4-Hour Boat Charter in Key West

    4-Hour Boat Charter in Key West

    Shallow-draft sandbar hopping with dolphin and turtle watching

    $1,219
    8-Hour Key West Sandbar Charter

    8-Hour Key West Sandbar Charter

    Build a flexible day of sandbars, mangroves, and island stops

    5.0 • 76 reviews
    $1,272
    Key West Sunset Charter

    Key West Sunset Charter

    Cruise the Historic Seaport as the sun sets

    5.0 • 35 reviews
    $448
    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