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

    Best results for Water Activities in Summerland Key, FL

    Showing 145-168 of 611 results
    Key West Inshore Fishing Charter
    Fishing Charters

    Key West Inshore Fishing Charter

    Fish Key West’s shallow waters with light tackle and local expertise

    Fish Key West’s shallow waters with light tackle and local expertise
    5.0 • 19 reviews
    $1,022& up
    Sandbar Fishing Charter in Key West
    Fishing Charters

    Sandbar Fishing Charter in Key West

    Fish and relax at Florida Keys sandbars with light tackle and live bait

    Fish and relax at Florida Keys sandbars with light tackle and live bait
    5.0 • 19 reviews
    $851& up
    Offshore Tuna Fishing Charter in Key West
    Fishing Charters

    Offshore Tuna Fishing Charter in Key West

    Chase seasonal offshore species with live bait and light tackle

    Chase seasonal offshore species with live bait and light tackle
    5.0 • 19 reviews
    $1,022& up
    Fishing Charter on a 39' Yellowfin in Key West
    Fishing Charters

    Fishing Charter on a 39' Yellowfin in Key West

    Reef, offshore, and island adventures aboard a private Yellowfin charter

    Reef, offshore, and island adventures aboard a private Yellowfin charter
    4.5 • 1.7K reviews
    $1,006& up
    Key West Sunset Sail
    Sailing

    Key West Sunset Sail

    Sail past Key West landmarks and relax on a private catamaran cruise at sunset

    Sail past Key West landmarks and relax on a private catamaran cruise at sunset
    5.0 • 23 reviews
    $907
    Key West 3-Hour Boat Charter
    Yacht Charters

    Key West 3-Hour Boat Charter

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

    Speed across Key West waters for sandbars, swings and wildlife watching
    $1,375
    Key West Naturist Charter
    Yacht Charters

    Key West Naturist Charter

    Private sandbar charter with dolphin and turtle watching

    Private sandbar charter with dolphin and turtle watching
    5.0 • 1 reviews
    $1,219
    Cruise Key West Sandbar Or Reef Shared Charter
    Boat Tours

    Cruise Key West Sandbar Or Reef Shared Charter

    4-hour Key West shared charter to the sandbar or reef with snacks and water

    4-hour Key West shared charter to the sandbar or reef with snacks and water
    $398/ person
    Key West Private Half-Day Sail
    Sailing

    Key West Private Half-Day Sail

    Sail Key West waters your way with snorkeling, kayaking, fishing, and time to unwind

    Sail Key West waters your way with snorkeling, kayaking, fishing, and time to unwind
    5.0 • 23 reviews
    $1,134& up
    Key West Full-Day Private Sailing Charter
    Sailing

    Key West Full-Day Private Sailing Charter

    Sail beyond Key West for snorkeling, kayaking, fishing and lunch

    Sail beyond Key West for snorkeling, kayaking, fishing and lunch
    5.0 • 23 reviews
    $1,815& up
    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
    1…678…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.