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
    • 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 337-360 of 739 results
    30-Minute Private Sunset Helicopter Flight In Key West
    Helicopter Tours

    30-Minute Private Sunset Helicopter Flight In Key West

    Private sunset helicopter flight over Key West with a champagne toast

    Private sunset helicopter flight over Key West with a champagne toast
    4.9 • 273 reviews
    $592
    10-Minute Private Helicopter Tour in Key West
    Helicopter Tours

    10-Minute Private Helicopter Tour in Key West

    See Key West landmarks from above on a 10-minute private helicopter flight

    See Key West landmarks from above on a 10-minute private helicopter flight
    4.9 • 273 reviews
    $215
    Key West Guided Helicopter Discovery Flight
    Flying Lessons

    Key West Guided Helicopter Discovery Flight

    Take the controls with a Certified Flight Instructor over the Keys

    Take the controls with a Certified Flight Instructor over the Keys
    4.9 • 273 reviews
    $1,059/ person
    Key West Beach Proposal Flight
    Scenic Flights

    Key West Beach Proposal Flight

    Turn a Key West flight into a beachside proposal

    Turn a Key West flight into a beachside proposal
    4.9 • 273 reviews
    $683
    Key West Backcountry Private Flight
    Scenic Flights

    Key West Backcountry Private Flight

    Explore historic landmarks and backcountry waters on a private scenic flight

    Explore historic landmarks and backcountry waters on a private scenic flight
    4.9 • 273 reviews
    Contact for pricing
    Lobstering & Spearfishing Charter
    Private Fishing Charters

    Lobstering & Spearfishing Charter

    Catch lobster by hand with 3–8 hour charter options for up to 6 people

    Catch lobster by hand with 3–8 hour charter options for up to 6 people
    5.0 • 6 reviews
    $507& up
    Key West Fishing & Snorkeling Charter
    Fishing Charters

    Key West Fishing & Snorkeling Charter

    Pair reef exploration with fishing, lobstering, and sandbar time

    Pair reef exploration with fishing, lobstering, and sandbar time
    5.0 • 6 reviews
    $507& up
    Marquesas Keys Charter From Key West
    Yacht Charters

    Marquesas Keys Charter From Key West

    Explore remote islands, patch corals, and shipwrecks by charter

    Explore remote islands, patch corals, and shipwrecks by charter
    5.0 • 6 reviews
    $1,129& up
    Key West Sandbar & Snorkel Charter
    Snorkeling

    Key West Sandbar & Snorkel Charter

    Explore Florida Keys sandbars and mangrove mazes by boat

    Explore Florida Keys sandbars and mangrove mazes by boat
    5.0 • 6 reviews
    $337& up
    Key West Offshore Fishing Charter
    Fishing Charters

    Key West Offshore Fishing Charter

    Light-Tackle Reef and Wreck Fishing for Families and Beginners

    Light-Tackle Reef and Wreck Fishing for Families and Beginners
    5.0 • 6 reviews
    $678& up
    4-Hour Private Fishing Charter in Key West
    Private Fishing Charters

    4-Hour Private Fishing Charter in Key West

    Fish or relax on a private 4-hour charter with a local captain

    Fish or relax on a private 4-hour charter with a local captain
    5.0 • 2 reviews
    $954
    6-Hour Private Fishing Charter in Key West
    Private Fishing Charters

    6-Hour Private Fishing Charter in Key West

    Private 6-hour fishing charter for up to 4 anglers

    Private 6-hour fishing charter for up to 4 anglers
    5.0 • 2 reviews
    $1,113
    8-Hour Private Fishing Charter in Key West
    Private Fishing Charters

    8-Hour Private Fishing Charter in Key West

    Spend 8 hours on the water with a private captain and gear for up to 4 anglers

    Spend 8 hours on the water with a private captain and gear for up to 4 anglers
    5.0 • 2 reviews
    $1,272
    E-Foiling Lesson in Marathon, Florida
    Paddleboarding

    E-Foiling Lesson in Marathon, Florida

    Learn to e-foil in 1–2 hours with up to 3 riders

    Learn to e-foil in 1–2 hours with up to 3 riders
    4.7 • 233 reviews
    $397& up
    Kiteboarding Lesson at Keys Cable Park
    Kiteboarding

    Kiteboarding Lesson at Keys Cable Park

    Learn kiteboarding fundamentals with cable towing in 1.5 hours

    Learn kiteboarding fundamentals with cable towing in 1.5 hours
    4.7 • 233 reviews
    $226
    Private Beginner Cable Wakeboarding at Keys Cable Park
    Water Skiing

    Private Beginner Cable Wakeboarding at Keys Cable Park

    Learn to ride with a private 2-point cable session at Keys Cable Park

    Learn to ride with a private 2-point cable session at Keys Cable Park
    4.7 • 233 reviews
    $187& up
    Private Wakeboard Session at Keys Cable Park
    Water Skiing

    Private Wakeboard Session at Keys Cable Park

    Book a private cable-riding session for groups of 12+ at Keys Cable Park

    Book a private cable-riding session for groups of 12+ at Keys Cable Park
    4.7 • 233 reviews
    $1,130& up
    Intro Foilboarding Lesson at Keys Cable Park
    Surfing Lessons

    Intro Foilboarding Lesson at Keys Cable Park

    Try foilboarding with a 1-hour lesson built for experienced board riders

    Try foilboarding with a 1-hour lesson built for experienced board riders
    4.7 • 233 reviews
    $226
    2-Hour Sandbar Sailing Charter
    Sailing

    2-Hour Sandbar Sailing Charter

    Sail a captained Hobie Cat to a local sandbar with complimentary beverages

    Sail a captained Hobie Cat to a local sandbar with complimentary beverages
    4.7 • 233 reviews
    $283
    Floating Aqua Park Session in Grassy Key
    Theme and Water Parks

    Floating Aqua Park Session in Grassy Key

    Jump, climb, and slide across a floating obstacle course

    Jump, climb, and slide across a floating obstacle course
    4.7 • 233 reviews
    $40/ person
    Key West GPS History E-Bike Rental
    Bike Rentals

    Key West GPS History E-Bike Rental

    Ride historic Key West with optional GPS narration

    Ride historic Key West with optional GPS narration
    $56/ bike
    Reef Snorkeling Charter in Key West
    Snorkeling

    Reef Snorkeling Charter in Key West

    Snorkel Florida Keys reefs with gear, food, and drinks included

    Snorkel Florida Keys reefs with gear, food, and drinks included
    5.0 • 39 reviews
    $503/ person
    4-Hour Key West Snorkeling Cruise
    Snorkeling

    4-Hour Key West Snorkeling Cruise

    Snorkel Florida Keys Reefs With Gear, Food and Drinks Included

    Snorkel Florida Keys Reefs With Gear, Food and Drinks Included
    5.0 • 39 reviews
    $335/ person
    Sandbar Charter in the Florida Keys
    Boat Tours

    Sandbar Charter in the Florida Keys

    Cruise to Florida Keys sandbars with water, ice, and cooler space included

    Cruise to Florida Keys sandbars with water, ice, and cooler space included
    4.9 • 110 reviews
    $681& up
    1…141516…31