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. /Water Activities
    4. /Sailing

    Best results for Sailing in Key Biscayne, FL

    Showing 1-11 of 11 results
    Hobie Wave Sailing Rental in Key Biscayne
    Key Biscayne

    Hobie Wave Sailing Rental in Key Biscayne

    Sail Biscayne Bay on a stable Hobie Wave catamaran

    Sail Biscayne Bay on a stable Hobie Wave catamaran
    4.2 • 217 reviews
    $113/ boat
    Key Biscayne 1-Hour Hobie Getaway Sailboat Rental
    Key Biscayne

    Key Biscayne 1-Hour Hobie Getaway Sailboat Rental

    Cruise and swim aboard a stable Hobie Getaway catamaran

    Cruise and swim aboard a stable Hobie Getaway catamaran
    4.2 • 217 reviews
    $170/ boat
    1-Hour Windsurfing Lesson in Key Biscayne
    Key Biscayne

    1-Hour Windsurfing Lesson in Key Biscayne

    Build windsurfing fundamentals in calm, shallow water

    Build windsurfing fundamentals in calm, shallow water
    4.2 • 217 reviews
    $85
    Biscayne Bay Wildlife Sailing Tour
    Sailing

    Biscayne Bay Wildlife Sailing Tour

    Sail, swim and snorkel among Biscayne Bay’s sandbars and mangroves

    Sail, swim and snorkel among Biscayne Bay’s sandbars and mangroves
    $158/ person
    Biscayne Bay Eco Sailing Tour
    Sailing

    Biscayne Bay Eco Sailing Tour

    Sail Biscayne Bay’s sandbars and mangroves while looking for local wildlife

    Sail Biscayne Bay’s sandbars and mangroves while looking for local wildlife
    $159/ person
    8-Hour Private Sailing Charter From Treasure Island
    Sailing

    8-Hour Private Sailing Charter From Treasure Island

    Sail for 8 hours and choose Egmont Key, Anna Maria, or Shell Key

    Sail for 8 hours and choose Egmont Key, Anna Maria, or Shell Key
    $2,221
    4-Hour Private Sailing Charter to Shell Key
    Sailing

    4-Hour Private Sailing Charter to Shell Key

    Sail to Shell Key for swimming, snorkeling, and shelling

    Sail to Shell Key for swimming, snorkeling, and shelling
    $1,653
    Cruise Treasure Island On A 2-Hour Sunset Sail
    Sailing

    Cruise Treasure Island On A 2-Hour Sunset Sail

    Private 2-hour sunset sail with bay views and dolphin spotting

    Private 2-hour sunset sail with bay views and dolphin spotting
    $1,112
    Miami Beach Yacht Party Cruise
    Yacht Charters

    Miami Beach Yacht Party Cruise

    Sail Biscayne Bay with music, snacks, drinks, and water toys

    Sail Biscayne Bay with music, snacks, drinks, and water toys
    4.0 • 166 reviews
    $149/ person
    Miami 40' Sailing Catamaran Charter
    Sailing

    Miami 40' Sailing Catamaran Charter

    Sail aboard a 40-foot catamaran with giant nets and an interior cabin

    Sail aboard a 40-foot catamaran with giant nets and an interior cabin
    4.0 • 166 reviews
    $456/ hour
    Fort Lauderdale 3.5-Hour Sail & Splash Cruise
    Sailing

    Fort Lauderdale 3.5-Hour Sail & Splash Cruise

    Catamaran cruise with water toys, music, and a swim stop

    Catamaran cruise with water toys, music, and a swim stop
    4.9 • 529 reviews
    $112/ person