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. /Sailing

    Best results for Sailing

    Showing 385-408 of 497 results
    Private Sailing Charter in Maalaea Bay
    Maalaea, HI

    Private Sailing Charter in Maalaea Bay

    Celebrate on a private catamaran with onboard appetizers and drinks

    Celebrate on a private catamaran with onboard appetizers and drinks
    5.0 • 163 reviews
    $2,729& up
    Maui Sunset Sailing Cruise
    Wailuku, HI

    Maui Sunset Sailing Cruise

    Island music, appetizers, and Pacific views at sunset

    Island music, appetizers, and Pacific views at sunset
    4.7 • 2.7K reviews
    $149/ person
    Sunset Sailing Charter in Destin
    Destin, FL

    Sunset Sailing Charter in Destin

    Private 45-foot yacht sailing with a beach stop, waterfront lunch, and Gulf sunset

    Private 45-foot yacht sailing with a beach stop, waterfront lunch, and Gulf sunset
    4.9 • 6.2K reviews
    $2,280
    Hobie Cat Sailboat Rental Pensacola Beach
    Pensacola Beach, FL

    Hobie Cat Sailboat Rental Pensacola Beach

    Take the helm of a Hobie sailboat on Pensacola Beach

    Take the helm of a Hobie sailboat on Pensacola Beach
    4.7 • 622 reviews
    $87/ boat
    Downtown San Diego Sailing Charter
    San Diego, CA

    Downtown San Diego Sailing Charter

    Sail a comfortable cruiser with responsive handling and a spacious onboard layout

    Sail a comfortable cruiser with responsive handling and a spacious onboard layout
    4.4 • 246 reviews
    $1,200/ boat
    Sailing Charter in San Diego Aboard Dufour 37
    San Diego, CA

    Sailing Charter in San Diego Aboard Dufour 37

    Cruise San Diego’s coast aboard a sleek, comfortable Dufour 37

    Cruise San Diego’s coast aboard a sleek, comfortable Dufour 37
    4.4 • 246 reviews
    $875/ boat
    Catalina 320 Sailboat Charter in San Diego
    San Diego, CA

    Catalina 320 Sailboat Charter in San Diego

    Enjoy cabin comforts and a spacious cockpit on a private sailboat charter

    Enjoy cabin comforts and a spacious cockpit on a private sailboat charter
    4.4 • 246 reviews
    $575/ boat
    Coronado Catalina 320 Sailboat Charter
    San Diego, CA

    Coronado Catalina 320 Sailboat Charter

    Sail Coronado waters aboard a well-equipped Catalina with cabin comfort

    Sail Coronado waters aboard a well-equipped Catalina with cabin comfort
    4.4 • 246 reviews
    $575/ boat
    Coronado 40' Catamaran Charter
    San Diego, CA

    Coronado 40' Catamaran Charter

    Set sail on a 40-foot catamaran built for sailing comfort

    Set sail on a 40-foot catamaran built for sailing comfort
    4.4 • 246 reviews
    $1,750/ boat
    3- or 6-Hour Sailing Charter in San Diego
    San Diego, CA

    3- or 6-Hour Sailing Charter in San Diego

    Small-group sailing with room to relax below deck

    Small-group sailing with room to relax below deck
    4.4 • 246 reviews
    $725/ boat
    San Diego 3-Hour Sailboat Charter
    San Diego, CA

    San Diego 3-Hour Sailboat Charter

    Sail a 41-foot Jeanneau with spacious comfort and easy deck access

    Sail a 41-foot Jeanneau with spacious comfort and easy deck access
    4.4 • 246 reviews
    $1,050/ boat
    San Diego 3- or 6-Hour Sailing Charter
    San Diego, CA

    San Diego 3- or 6-Hour Sailing Charter

    A spacious catamaran for a day on the water with your group

    A spacious catamaran for a day on the water with your group
    4.4 • 246 reviews
    $1,400/ boat
    San Diego Limo Boat Charter
    San Diego, CA

    San Diego Limo Boat Charter

    A small-group limo boat sailing outing

    A small-group limo boat sailing outing
    4.4 • 246 reviews
    $1,750/ boat
    San Diego Limo Boat Charter
    San Diego, CA

    San Diego Limo Boat Charter

    Small-group sailing aboard a limo boat

    Small-group sailing aboard a limo boat
    4.4 • 246 reviews
    $2,014/ boat
    San Diego Sunset Sailing Charter
    San Diego, CA

    San Diego Sunset Sailing Charter

    Sail into sunset views of San Diego’s skyline

    Sail into sunset views of San Diego’s skyline
    4.4 • 246 reviews
    $800
    4-Hour Catamaran Flotilla in Coronado
    San Diego, CA

    4-Hour Catamaran Flotilla in Coronado

    Anchor, swim, and celebrate aboard a two-catamaran Coronado flotilla

    Anchor, swim, and celebrate aboard a two-catamaran Coronado flotilla
    4.4 • 246 reviews
    $3,200
    San Diego 26' Sailboat Rental
    San Diego, CA

    San Diego 26' Sailboat Rental

    Take the tiller on a sleek sailboat with pets welcome

    Take the tiller on a sleek sailboat with pets welcome
    4.4 • 246 reviews
    $125/ boat
    San Diego Limo Boat Charter
    San Diego, CA

    San Diego Limo Boat Charter

    Set sail on a small-group limo boat experience

    Set sail on a small-group limo boat experience
    4.4 • 246 reviews
    $1,500/ boat
    4-Hour San Diego Bay Sailing Charter
    San Diego, CA

    4-Hour San Diego Bay Sailing Charter

    Sail San Diego Bay with Coronado Bridge views

    Sail San Diego Bay with Coronado Bridge views
    4.4 • 246 reviews
    $1,200/ boat
    4-Hour Sailing Charter on San Diego Bay
    San Diego, CA

    4-Hour Sailing Charter on San Diego Bay

    Sail San Diego Bay with Coronado Bridge and skyline views

    Sail San Diego Bay with Coronado Bridge and skyline views
    4.4 • 246 reviews
    $2,000
    Private Sailing Lesson in Natick
    Natick, MA

    Private Sailing Lesson in Natick

    Build sailing skills with a private instructor-led session

    Build sailing skills with a private instructor-led session
    4.6 • 42 reviews
    $174/ person
    Key West 1.5-Hour Classic Day Sailing Cruise
    Key West, FL

    Key West 1.5-Hour Classic Day Sailing Cruise

    Sail Key West on Schooner America 2.0 with complimentary soft drinks

    Sail Key West on Schooner America 2.0 with complimentary soft drinks
    4.9 • 593 reviews
    Contact for pricing
    Salem Harbor Sunset Sail on 1812 Schooner
    Salem, MA

    Salem Harbor Sunset Sail on 1812 Schooner

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.
    5.0 • 535 reviews
    $49/ person
    Private Sailing Lesson in Nantucket
    Nantucket, MA

    Private Sailing Lesson in Nantucket

    Learn to sail with a private instructor at Jetties Beach

    Learn to sail with a private instructor at Jetties Beach
    5.0 • 2 reviews
    $265
    1…161718…21