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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 121-144 of 226 results
    Private Half-Day Light Tackle Fishing Charter in Key West

    Private Half-Day Light Tackle Fishing Charter in Key West

    Target a range of Key West fish with light tackle and weather-dependent offshore options

    5.0 • 6 reviews
    $795
    42' Offshore Sportfishing Charter in Key West

    42' Offshore Sportfishing Charter in Key West

    Fish with room to spread out and a cool cabin for breaks

    4.7 • 50 reviews
    $2,100/ boat
    Full-Day Private Fly Fishing Charter Near Key West

    Full-Day Private Fly Fishing Charter Near Key West

    Enjoy your choice of fly fishing, spin fishing, or both

    5.0 • 4 reviews
    $1,060
    Reef & Wreck Fishing Charter in Key West

    Reef & Wreck Fishing Charter in Key West

    Target Grouper and Snapper on reef and wreck fishing grounds

    5.0 • 1 reviews
    $1,060& up
    Offshore & Reef Fishing Charter in Sugarloaf Key

    Offshore & Reef Fishing Charter in Sugarloaf Key

    Fish the Florida Keys local-style with Captain Larry

    $1,023
    Private 45' Deep-Sea Fishing Charter in Key West

    Private 45' Deep-Sea Fishing Charter in Key West

    Fish offshore with an experienced crew aboard a tournament-winning Hatteras

    4.8 • 1K reviews
    $1,305& up
    Private Reef & Wreck Fishing Charter in Key West

    Private Reef & Wreck Fishing Charter in Key West

    Fish reefs and historic wrecks with a local crew and room to relax

    $1,240& up
    Half-Day Offshore Fishing Charter in Key West

    Half-Day Offshore Fishing Charter in Key West

    Fish the Florida Keys with native experts

    $954
    Private Reef & Wreck Fishing Charter on Stock Island

    Private Reef & Wreck Fishing Charter on Stock Island

    Explore Lower Keys fishing grounds with an experienced local captain

    4.7 • 10 reviews
    $1,696
    6-Hour Key West Fishing Charter

    6-Hour Key West Fishing Charter

    Fish near Key West with a relaxed charter for families and first-time anglers

    4.7 • 3 reviews
    $1,802
    Private Pulley Ridge Deep Sea Fishing Charter from Key West

    Private Pulley Ridge Deep Sea Fishing Charter from Key West

    Fish deep-water grounds beyond the reach of typical charter trips

    4.3 • 6 reviews
    $5,300
    Lobstering & Inshore Fishing Charter in Big Pine Key

    Lobstering & Inshore Fishing Charter in Big Pine Key

    Catch mangrove snapper and lobster with all catching gear included

    5.0 • 25 reviews
    $1,007
    Private Full-Day Marquesas Inshore Fishing from Key West

    Private Full-Day Marquesas Inshore Fishing from Key West

    Pair inshore fishing with patch-reef snorkeling when weather permits

    5.0 • 6 reviews
    $1,431
    Fishing Charter Aboard a 34' Yellowfin in Marathon

    Fishing Charter Aboard a 34' Yellowfin in Marathon

    Private fishing and island adventures with a captain

    4.4 • 2.8K reviews
    $1,007& up
    Private Fishing Charter in Key West

    Private Fishing Charter in Key West

    Target offshore species aboard a comfortable sportfishing boat

    4.1 • 54 reviews
    $1,272
    Offshore Fishing Charter in Key West

    Offshore Fishing Charter in Key West

    Chase mahi, tuna, and wahoo in deep Atlantic waters

    5.0 • 1 reviews
    $1,590& up
    Private Marquesas Keys Fishing Charter from Key West

    Private Marquesas Keys Fishing Charter from Key West

    Fish beyond the usual grounds in waters rich with Spanish shipwreck history

    4.8 • 1K reviews
    $1,960& up
    Reef & Wreck Fishing Trip in Marathon, FL

    Reef & Wreck Fishing Trip in Marathon, FL

    Try reef fishing with no specialized skills needed

    4.1 • 669 reviews
    $85/ person
    Private Offshore Deep Sea Fishing Charter in Key West

    Private Offshore Deep Sea Fishing Charter in Key West

    Chase big-game fish with an experienced crew and onboard comforts

    $1,773& up
    Half-Day Spearfishing Trip in Key West

    Half-Day Spearfishing Trip in Key West

    Spearfish Florida Keys waters with island experts

    $954
    Private Full-Day Offshore Fishing Charter in Stock Island

    Private Full-Day Offshore Fishing Charter in Stock Island

    Fish the Florida Keys with specialized tackle for reef, wreck, and deep-water fishing

    4.7 • 10 reviews
    $1,908
    Key West 4-Hour Fishing Charter

    Key West 4-Hour Fishing Charter

    Stay close to Key West for a family-friendly fishing outing

    4.7 • 3 reviews
    $1,272
    Private Full-Day Swordfishing Charter in Key West

    Private Full-Day Swordfishing Charter in Key West

    Take your shot at a big swordfish offshore

    4.3 • 6 reviews
    $3,710
    Full-Day Free Dive Lobster Hunting in Big Pine Key

    Full-Day Free Dive Lobster Hunting in Big Pine Key

    Free-dive coral reefs for lobster with all gear supplied

    5.0 • 25 reviews
    $1,007
    1…567…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