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
    Best results for

    Kayaking Tours in Summerland Key, FL

    Showing 1-19 of 19 results
    Key West Guided Night Kayak Tour

    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
    Marathon LED Kayak Night Tour

    Marathon LED Kayak Night Tour

    Paddle calm, shallow waters with glass-bottom views of illuminated marine life

    Paddle calm, shallow waters with glass-bottom views of illuminated marine life
    4.4 • 509 reviews
    $63/ person
    Clear Kayak Mangrove Tour in Sugarloaf Key Near Key West

    Clear Kayak Mangrove Tour in Sugarloaf Key Near Key West

    Paddle clear waters and mangrove tunnels with an eco-guide

    Paddle clear waters and mangrove tunnels with an eco-guide
    5.0 • 1.3K reviews
    $81/ person
    Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

    Key West 3.5-Hour Sandbar Kayak & Paddleboard Tour

    Cruise to a Key West sandbar with kayaking, paddleboards, lunch, and drinks

    Cruise to a Key West sandbar with kayaking, paddleboards, lunch, and drinks
    4.9 • 12.7K reviews
    $110/ person
    2-Hour Kayak Rental in Key West

    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
    Guided Clear Kayak Eco-Tour in Marathon

    Guided Clear Kayak Eco-Tour in Marathon

    Paddle Marathon’s mangroves and seagrass flats in a clear tandem kayak with a guide

    Paddle Marathon’s mangroves and seagrass flats in a clear tandem kayak with a guide
    4.9 • 391 reviews
    $116/ person
    Private Mangrove Eco Paddle Tour Near Key West

    Private Mangrove Eco Paddle Tour Near Key West

    Set your own pace through Key West’s mangrove waterways

    Set your own pace through Key West’s mangrove waterways
    4.9 • 140 reviews
    $461
    Key West Kayak Tour with Sandbar & Lunch

    Key West Kayak Tour with Sandbar & Lunch

    Paddle mangrove tunnels then relax on a secluded sandbar with lunch and unlimited drinks

    Paddle mangrove tunnels then relax on a secluded sandbar with lunch and unlimited drinks
    4.8 • 24.1K reviews
    $148/ person
    Kayak Rental in Marathon

    Kayak Rental in Marathon

    Paddle the calm waters of the Florida Keys at your own pace

    Paddle the calm waters of the Florida Keys at your own pace
    4.7 • 86 reviews
    $35/ kayak
    Single Kayak Rental in Marathon

    Single Kayak Rental in Marathon

    Paddle calm coastal waters and look for local wildlife

    Paddle calm coastal waters and look for local wildlife
    4.5 • 95 reviews
    $37/ kayak
    Clear Kayak Eco-Tour in Big Pine Key

    Clear Kayak Eco-Tour in Big Pine Key

    Paddle clear kayaks through mangrove tunnels and look for Florida Keys wildlife

    Paddle clear kayaks through mangrove tunnels and look for Florida Keys wildlife
    $147
    Key West Guided Mangrove Kayak or SUP Tour

    Key West Guided Mangrove Kayak or SUP Tour

    Paddle Key West’s mangrove waterways with a naturalist guide

    Paddle Key West’s mangrove waterways with a naturalist guide
    4.9 • 140 reviews
    $88& up
    Kayak Through Mangroves & Spot Marine Life

    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 Backcountry Mangrove Kayak Tour & Sandbar

    Key West Backcountry Mangrove Kayak Tour & Sandbar

    Explore Key West’s remote backcountry with guided paddling and sandbar time

    Explore Key West’s remote backcountry with guided paddling and sandbar time
    4.8 • 24.1K reviews
    $148/ person
    Key West Mangrove Maze Kayak Rental

    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
    Sunset Glow Kayak Tour Through Key West Mangroves

    Sunset Glow Kayak Tour Through Key West Mangroves

    Glide into the night with LEDs lighting the water beneath your kayak

    Glide into the night with LEDs lighting the water beneath your kayak
    $147/ kayak
    Key West Sandbar Cruise at Sunset

    Key West Sandbar Cruise at Sunset

    Guided mangrove kayaking, paddleboarding and dolphin watching in Key West

    Guided mangrove kayaking, paddleboarding and dolphin watching in Key West
    4.8 • 24.1K reviews
    $148/ person
    Full-Day Kayak & Snorkel Rental in Marathon

    Full-Day Kayak & Snorkel Rental in Marathon

    Paddle shallow bay waters with snorkel gear and park access

    Paddle shallow bay waters with snorkel gear and park access
    4.7 • 1.2K reviews
    $66/ kayak
    Lower Keys Guided Mangrove Paddle & Key Deer Tour

    Lower Keys Guided Mangrove Paddle & Key Deer Tour

    Paddle mangrove tunnels, enjoy a picnic, and look for Key Deer

    Paddle mangrove tunnels, enjoy a picnic, and look for Key Deer
    $192/ person
    Summerland Key Things To Do
    Kayaking Tours18Fishing Charters200Boat Tours111Snorkeling96Yacht Charters91
    More
    • Boat Rentals90
    • Sailing71
    • Scuba Diving68
    • Sunrise and Sunset Tours44
    • Car Rentals43
    • Private Fishing Charters27
    • Bike Rentals25
    Dolphin Watching22
  1. Jet Skiing17
  2. Scenic Flights9
  3. Scavenger Hunts8
  4. Dinner Cruises7
  5. Ghost and Haunted7
  6. Scooter Rentals7
  7. Bar and Pub Crawl6
  8. Paddleboarding6
  9. Parasailing6
  10. Private Boat Charters6
  11. Helicopter Tours5
  12. Historical Tours5