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

    Fishing Charters in Sugarloaf Key, FL

    Showing 97-120 of 226 results
    Private 3/4-Day Light Tackle Fishing Charter in Key West

    Private 3/4-Day Light Tackle Fishing Charter in Key West

    Cast for a variety of species with fishing gear and licenses included

    5.0 • 6 reviews
    $1,007
    Key West 42' Fishing Charter

    Key West 42' Fishing Charter

    Fish Key West waters from a spacious, performance-built SeaHunter

    4.7 • 50 reviews
    $1,192& up
    Private 3/4-Day Fly Fishing Charter Near Key West

    Private 3/4-Day Fly Fishing Charter Near Key West

    Fish with Sage and Loomis rods, with tackle and licenses included

    5.0 • 4 reviews
    $954
    Key West Private Boat Navigation Charter

    Key West Private Boat Navigation Charter

    Learn Key West waterways from a local captain aboard your own boat

    5.0 • 19 reviews
    $530& up
    Key West Offshore Fishing Charter

    Key West Offshore Fishing Charter

    Light-Tackle Reef and Wreck Fishing for Families and Beginners

    5.0 • 6 reviews
    $678& up
    Private Light Tackle Fishing Charter in Key West

    Private Light Tackle Fishing Charter in Key West

    Chase offshore species with light tackle and a crew that keeps you hands-on

    4.8 • 1K reviews
    $1,360& up
    Offshore Tuna Fishing Charter in Key West

    Offshore Tuna Fishing Charter in Key West

    Chase seasonal offshore species with live bait and light tackle

    5.0 • 18 reviews
    $1,022& up
    Fort Jefferson Full-Day Fishing Charter

    Fort Jefferson Full-Day Fishing Charter

    Fish Dry Tortugas grounds aboard a private, fully equipped charter boat

    5.0 • 25 reviews
    $3,816
    Private Swordfish Fishing Charter on Stock Island

    Private Swordfish Fishing Charter on Stock Island

    Target swordfish offshore with specialized electric reels

    4.7 • 10 reviews
    $2,544
    10-Hour Dry Tortugas National Park Fishing Charter

    10-Hour Dry Tortugas National Park Fishing Charter

    Fish and explore Dry Tortugas National Park on a 10-hour family-friendly charter

    4.7 • 3 reviews
    $3,180
    Key West Night Fishing Charter

    Key West Night Fishing Charter

    Target tarpon or sharks when nocturnal activity picks up

    5.0 • 30 reviews
    $530/ boat
    Big Pine Key Lobster & Fishing Charter

    Big Pine Key Lobster & Fishing Charter

    Fish for snapper and grouper, catch lobster, then unwind at a Keys sandbar

    5.0 • 25 reviews
    $1,166
    Private Full-Day Inshore Fishing Charter in Key West

    Private Full-Day Inshore Fishing Charter in Key West

    Fish light tackle inshore, with the option to head offshore when weather permits

    5.0 • 6 reviews
    $1,219
    Key West Shrimp Boat Fishing Charter

    Key West Shrimp Boat Fishing Charter

    Fish the offshore shrimp-boat grounds at first light

    4.7 • 50 reviews
    $1,703
    Private Half-Day Key West Fly & Spin Flats Fishing Charter

    Private Half-Day Key West Fly & Spin Flats Fishing Charter

    Fish the Florida Keys flats with a captain who brings 30+ years of guiding experience

    5.0 • 4 reviews
    $848
    Key West Inshore Fishing Charter

    Key West Inshore Fishing Charter

    Cast light tackle in Key West's calm backcountry waters

    5.0 • 1 reviews
    $1,060& up
    Key West 36' Fishing Charter

    Key West 36' Fishing Charter

    Fish Key West's shallow backcountry channels aboard a 36-foot boat

    5.0 • 1 reviews
    $1,060& up
    Private Key West Offshore Fishing Charter on 47' Hatteras

    Private Key West Offshore Fishing Charter on 47' Hatteras

    Fish offshore with three generations of Key West experience

    4.8 • 1K reviews
    $1,415/ boat
    Shared Deep Sea Fishing Charter in Key West

    Shared Deep Sea Fishing Charter in Key West

    Fish offshore with expert crew support, gear, and space to relax

    5.0 • 1 reviews
    $249/ person
    Air-Conditioned Yacht Fishing Charter in Key West

    Air-Conditioned Yacht Fishing Charter in Key West

    Troll for Mahi or Wahoo with yacht comforts close at hand

    5.0 • 1 reviews
    $1,131& up
    Private Reef & Wreck Fishing Charter on Stock Island

    Private Reef & Wreck Fishing Charter on Stock Island

    Get hands-on with light tackle in the Florida Keys

    4.7 • 10 reviews
    $1,484
    Key West 8-Hour Fishing Charter

    Key West 8-Hour Fishing Charter

    Fish Key West backcountry and Marquesas Keys for tarpon, permit, and more

    4.7 • 3 reviews
    $1,272
    Private Flats Fishing Charter in Key West, Fly or Spin

    Private Flats Fishing Charter in Key West, Fly or Spin

    Explore shallow flats on a guided fishing outing tailored to you

    $530& up
    Inshore Snapper & Grouper Fishing in Big Pine Key

    Inshore Snapper & Grouper Fishing in Big Pine Key

    Cast light tackle around reefs, coral heads, and shallow wrecks

    5.0 • 25 reviews
    $847
    1…456…10
    Sugarloaf Key Things To Do
    Fishing ChartersBoat Tours178Boat Rentals108Yacht Charters100Snorkeling99
    More
    • Sailing83
    • Scuba Diving74
    • Car Rentals52
    • Sunrise and Sunset Tours45
    • Bike Rentals34
    • Private Fishing Charters25
    • Dolphin Watching24
    Kayaking Tours18
  • Jet Skiing17
  • Scooter Rentals12
  • Ghost and Haunted9
  • Scavenger Hunts8
  • Dinner Cruises7
  • Scenic Flights7
  • Bar and Pub Crawl6
  • Parasailing6
  • Private Boat Charters6
  • Helicopter Tours5
  • Historical Tours5
  • Paddleboarding5