Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /All experiences
    3. /Big Pine Key Florida

    Best results for Big Pine Key Florida

    Showing 409-432 of 1,006 results
    Customize Your Key West Private Boat Charter
    Boat Tours

    Customize Your Key West Private Boat Charter

    Build your own private Key West day on the water for up to 6 guests

    Build your own private Key West day on the water for up to 6 guests
    5.0 • 101 reviews
    $1,007& up
    Key West 4-Hour Fishing Charter
    Fishing Charters

    Key West 4-Hour Fishing Charter

    Fish Key West your way with a charter tailored to your preferred style

    Fish Key West your way with a charter tailored to your preferred style
    5.0 • 101 reviews
    $954& up
    Key West Private Sandbar Cruise
    Boat Tours

    Key West Private Sandbar Cruise

    Cruise to a Key West sandbar for swimming, walking, and time in the sun

    Cruise to a Key West sandbar for swimming, walking, and time in the sun
    5.0 • 101 reviews
    $1,007& up
    Lobster Mini Season Charter in Key West
    Fishing Charters

    Lobster Mini Season Charter in Key West

    Catch lobsters during Key West's July Mini Season

    Catch lobsters during Key West's July Mini Season
    5.0 • 101 reviews
    $1,060& up
    Key West Mangrove Paddleboard Eco Tour
    Stand Up Paddle Boarding

    Key West Mangrove Paddleboard Eco Tour

    Relaxed paddling and a lesson through Key West's mangrove creeks

    Relaxed paddling and a lesson through Key West's mangrove creeks
    4.9 • 8K reviews
    $79/ person
    Key West Sunset Cruise
    Sunrise and Sunset Tours

    Key West Sunset Cruise

    Look for dolphins as the sun sets over Key West waters

    Look for dolphins as the sun sets over Key West waters
    5.0 • 39 reviews
    $223/ person
    Key West 4-Hour Sandbar Charter
    Yacht Charters

    Key West 4-Hour Sandbar Charter

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

    Explore Key West’s turquoise waters and white-sand sandbars with food and drinks included
    5.0 • 39 reviews
    $279/ person
    6-Hour Key West Sandbar Charter
    Yacht Charters

    6-Hour Key West Sandbar Charter

    Enjoy a Key West sandbar day with food and drinks included

    Enjoy a Key West sandbar day with food and drinks included
    5.0 • 39 reviews
    $391/ person
    Key West Sunset Dolphin Watch Cruise
    Dolphin Watching

    Key West Sunset Dolphin Watch Cruise

    Spot dolphins as Key West skies turn toward sunset

    Spot dolphins as Key West skies turn toward sunset
    5.0 • 39 reviews
    $335/ person
    Key West Manatee Mangrove Cruise
    Boat Tours

    Key West Manatee Mangrove Cruise

    Slowly cruise Key West mangroves while looking for manatees and other wildlife

    Slowly cruise Key West mangroves while looking for manatees and other wildlife
    5.0 • 39 reviews
    $335/ person
    Key West Sunset Charter
    Sunrise and Sunset Tours

    Key West Sunset Charter

    Watch the Key West sunset and look for dolphins from the water

    Watch the Key West sunset and look for dolphins from the water
    5.0 • 39 reviews
    $335/ person
    Key West Guided Reef & Wreck Dive Charter
    Scuba Diving

    Key West Guided Reef & Wreck Dive Charter

    Explore Key West coral reefs and shipwrecks with dive guides

    Explore Key West coral reefs and shipwrecks with dive guides
    5.0 • 39 reviews
    $783/ person
    Key West 4-Hour Sandbar Charter
    Yacht Charters

    Key West 4-Hour Sandbar Charter

    Enjoy turquoise waters, white sand beaches, and food and drinks on a Key West sandbar outing

    Enjoy turquoise waters, white sand beaches, and food and drinks on a Key West sandbar outing
    5.0 • 39 reviews
    $447/ person
    Key West 6-Hour Sandbar Charter
    Yacht Charters

    Key West 6-Hour Sandbar Charter

    Cruise to Key West's sandbar for Caribbean water and white-sand beaches

    Cruise to Key West's sandbar for Caribbean water and white-sand beaches
    5.0 • 39 reviews
    $559/ person
    Key West Sunset Dolphin Cruise
    Dolphin Watching

    Key West Sunset Dolphin Cruise

    Pair sunset views with a chance to spot dolphins on the water

    Pair sunset views with a chance to spot dolphins on the water
    5.0 • 39 reviews
    $223/ person
    Key West Mangrove Manatee Cruise
    Boat Tours

    Key West Mangrove Manatee Cruise

    Slow mangrove cruise with chances to spot manatees and wildlife

    Slow mangrove cruise with chances to spot manatees and wildlife
    5.0 • 39 reviews
    $223/ person
    Key West 4-Hour Guided Dive Charter
    Scuba Diving

    Key West 4-Hour Guided Dive Charter

    Explore Key West coral reefs and shipwrecks with expert guides

    Explore Key West coral reefs and shipwrecks with expert guides
    5.0 • 39 reviews
    $559/ person
    28-Mile Guided Jet Ski Tour of Key West
    Jet Skiing

    28-Mile Guided Jet Ski Tour of Key West

    Circle Key West by jet ski with guided landmark stops and swim time

    Circle Key West by jet ski with guided landmark stops and swim time
    5.0 • 59 reviews
    $237/ jet ski
    Freestyle Jet Ski Ride in Key West
    Jet Skiing

    Freestyle Jet Ski Ride in Key West

    Open the throttle in Key West’s open-water freeride zones

    Open the throttle in Key West’s open-water freeride zones
    5.0 • 59 reviews
    $182/ jet ski
    2-Hour Kayak Rental in Key West
    Kayaking Tours

    2-Hour Kayak Rental in Key West

    Paddle mangrove creeks and calm coastal waters at your own pace

    Paddle mangrove creeks and calm coastal waters at your own pace
    4.9 • 8K reviews
    $45/ person
    Kayak Through Mangroves & Spot Marine Life
    Kayaking Tours

    Kayak Through Mangroves & Spot Marine Life

    Paddle serene mangrove waterways with an expert guide and spot vibrant marine life.

    Paddle serene mangrove waterways with an expert guide and spot vibrant marine life.
    4.8 • 996 reviews
    $70/ person
    Key West Guided Night Kayak Tour
    Kayaking Tours

    Key West Guided Night Kayak Tour

    Light up the sea floor on a guided kayak paddle beneath the stars

    Light up the sea floor on a guided kayak paddle beneath the stars
    4.8 • 996 reviews
    $93/ kayak
    Key West Mangrove Maze Kayak Rental
    Kayaking Tours

    Key West Mangrove Maze Kayak Rental

    Paddle at your own pace through serene mangroves and discover Key West’s vibrant marine life.

    Paddle at your own pace through serene mangroves and discover Key West’s vibrant marine life.
    4.8 • 996 reviews
    $46& up
    4-Hour Private Boat Charter in Key West Backcountry
    Yacht Charters

    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

    Customize a 4-hour private tri-toon cruise with a licensed captain in Key West’s backcountry
    4.8 • 996 reviews
    $523
    1…171819…42