Free Concierge Service
    Text or call (650) 414-7338
    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

    Concierge Support

    • Help Center
    [email protected](650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Free Concierge Service
    Text or call (650) 414-7338
    Ask AIAI
    Ask AIAI

    Best results for Water Activities in Summerland Key FL

    Showing 193-216 of 251 results
    Private Sailing Charter in Key West
    Sailing

    Private Sailing Charter in Key West

    Charter the 54-foot Schooner Valora for a private sail in Key West

    Charter the 54-foot Schooner Valora for a private sail in Key West
    $1,340
    Sail a Key West Champagne Sunset Cruise
    Sailing

    Sail a Key West Champagne Sunset Cruise

    Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

    Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included
    $125/ person
    Two-Stop Snorkel Cruise in Key West
    Snorkeling

    Two-Stop Snorkel Cruise in Key West

    Snorkel two Key West reef stops with an all-you-can-eat seafood boil and open bar

    Snorkel two Key West reef stops with an all-you-can-eat seafood boil and open bar
    4.7 • 8K reviews
    $81/ person
    Sandbar Safari Cruise in Key West
    Boat Tours

    Sandbar Safari Cruise in Key West

    Ride the 53-foot tiki boat to a Key West sandbar

    Ride the 53-foot tiki boat to a Key West sandbar
    4.7 • 8K reviews
    $127/ person
    Afternoon Snorkel Cruise in Key West
    Snorkeling

    Afternoon Snorkel Cruise in Key West

    Snorkel the Florida Keys Reef on a sailing cruise with gear, instruction, and drinks included

    Snorkel the Florida Keys Reef on a sailing cruise with gear, instruction, and drinks included
    4.7 • 8K reviews
    $46/ person
    Mimosa Morning Snorkel Sail in Key West
    Snorkeling

    Mimosa Morning Snorkel Sail in Key West

    Sail to the Florida Keys Reef for an easy morning snorkel

    Sail to the Florida Keys Reef for an easy morning snorkel
    4.7 • 8K reviews
    $46/ person
    Watch Dolphins on a Key West Sunset Sail
    Sailing

    Watch Dolphins on a Key West Sunset Sail

    Sail a luxury catamaran at sunset with tapas, drinks, and dolphin watching

    Sail a luxury catamaran at sunset with tapas, drinks, and dolphin watching
    4.7 • 8K reviews
    $81/ person
    Champagne Sunset Catamaran Cruise in Key West
    Sailing

    Champagne Sunset Catamaran Cruise in Key West

    Sail Key West at sunset with complimentary champagne and drinks

    Sail Key West at sunset with complimentary champagne and drinks
    4.7 • 8K reviews
    $58/ person
    Cruise to a Key West Sandbar With Lunch
    Boat Tours

    Cruise to a Key West Sandbar With Lunch

    Sail to a Key West sandbar with island-style lunch and drinks

    Sail to a Key West sandbar with island-style lunch and drinks
    4.7 • 8K reviews
    $185/ person
    Culinary Snorkel & Dolphin Watch Sail In Key West
    Snorkeling

    Culinary Snorkel & Dolphin Watch Sail In Key West

    Snorkel the Key West reef with an onboard seafood boil and open bar

    Snorkel the Key West reef with an onboard seafood boil and open bar
    4.7 • 8K reviews
    $81/ person
    Guided Backcountry Fishing Charter in Key West
    Fishing Charters

    Guided Backcountry Fishing Charter in Key West

    Backcountry flats fishing for up to 4 anglers on the ShadowCaster

    Backcountry flats fishing for up to 4 anglers on the ShadowCaster
    $742
    6-Hour Offshore Fishing Charter in Key West
    Fishing Charters

    6-Hour Offshore Fishing Charter in Key West

    Fish lesser-fished offshore waters for mutton snapper and grouper on a 6-hour charter

    Fish lesser-fished offshore waters for mutton snapper and grouper on a 6-hour charter
    $1,272
    4-Hour Reef & Wreck Fishing Charter
    Fishing Charters

    4-Hour Reef & Wreck Fishing Charter

    Fish reef, wreck, and inshore waters with gear and license included

    Fish reef, wreck, and inshore waters with gear and license included
    $954& up
    12-Hour Dry Tortugas Fishing Charter From Key West
    Fishing Charters

    12-Hour Dry Tortugas Fishing Charter From Key West

    Fish and explore Fort Jefferson on a 12-hour Dry Tortugas charter

    Fish and explore Fort Jefferson on a 12-hour Dry Tortugas charter
    $2,968
    4-Hour Reef & Wreck Fishing Charter in Key West
    Fishing Charters

    4-Hour Reef & Wreck Fishing Charter in Key West

    Fish Key West reefs and wrecks on a 4-hour morning charter

    Fish Key West reefs and wrecks on a 4-hour morning charter
    $954
    10-Hour Swordfishing Charter In Key West
    Fishing Charters

    10-Hour Swordfishing Charter In Key West

    Fish the continental shelf for Broadbill Swordfish from Key West

    Fish the continental shelf for Broadbill Swordfish from Key West
    $2,120
    2-Tank Vandenberg Wreck Dive in Key West
    Scuba Diving

    2-Tank Vandenberg Wreck Dive in Key West

    Explore the USNS Vandenberg on a 2-tank morning wreck dive

    Explore the USNS Vandenberg on a 2-tank morning wreck dive
    $249/ person
    Scuba Refresher Course & 2-Tank Reef Dive in Key West
    Scuba Diving

    Scuba Refresher Course & 2-Tank Reef Dive in Key West

    Refresh your scuba skills with a pool session and a guided 2-tank reef dive

    Refresh your scuba skills with a pool session and a guided 2-tank reef dive
    $121/ person
    Afternoon 2-Tank Reef Dive In Key West
    Scuba Diving

    Afternoon 2-Tank Reef Dive In Key West

    Dive Key West’s barrier reef on a 2-tank afternoon trip

    Dive Key West’s barrier reef on a 2-tank afternoon trip
    $6/ person
    Sunset & Night Dive in Key West
    Scuba Diving

    Sunset & Night Dive in Key West

    Boat night dive for certified divers on Wednesday and Saturday nights

    Boat night dive for certified divers on Wednesday and Saturday nights
    $187/ person
    4-Hour Key West Sandbar & Snorkel Boat Charter
    Boat Tours

    4-Hour Key West Sandbar & Snorkel Boat Charter

    Customize your Downtime on a tritoon charter for just 6 guests

    Customize your Downtime on a tritoon charter for just 6 guests
    $158/ person
    Private Guided Sandbar Trip in Key West
    Private Boat ChartersUp to 10

    Private Guided Sandbar Trip in Key West

    Swim and snorkel at Key West sandbars with a licensed captain and included gear

    Swim and snorkel at Key West sandbars with a licensed captain and included gear
    5.0 • 3 reviews
    $597& up
    4-Hour Private Bar Crawl Boat Tour in Key West
    Private Boat ToursUp to 6

    4-Hour Private Bar Crawl Boat Tour in Key West

    Explore Key West bars and waters on a private 4-hour charter with a USCG-licensed captain

    Explore Key West bars and waters on a private 4-hour charter with a USCG-licensed captain
    5.0 • 3 reviews
    $563
    Private 3-Hour Sailing Lesson in Key West
    Sailing

    Private 3-Hour Sailing Lesson in Key West

    Choose your boat and learn to sail with a private instructor in Key West

    Choose your boat and learn to sail with a private instructor in Key West
    $143& up
    1…7891011