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 Sailing

    Showing 145-168 of 403 results
    Afternoon Cocktail Sail Along Waikiki Coastline
    Sailing

    Afternoon Cocktail Sail Along Waikiki Coastline

    Cruise Waikiki toward Diamond Head with drinks and snacks included

    Cruise Waikiki toward Diamond Head with drinks and snacks included
    4.8 • 652 reviews
    $86/ person
    Ko Olina Sunset Sail & Luau Experience
    Sailing

    Ko Olina Sunset Sail & Luau Experience

    Sail Ko Olina at sunset, then head ashore for a Kaula Luau

    Sail Ko Olina at sunset, then head ashore for a Kaula Luau
    4.8 • 652 reviews
    $342/ person
    Sail San Francisco Bay & Alcatraz Night Tour
    Sailing

    Sail San Francisco Bay & Alcatraz Night Tour

    Combine an afternoon bay sail with an Alcatraz Island night visit

    Combine an afternoon bay sail with an Alcatraz Island night visit
    4.7 • 620 reviews
    $139/ person
    Golden Hour Cocktail Sail in New York City
    Sailing

    Golden Hour Cocktail Sail in New York City

    Sail past the Statue of Liberty with a welcome cocktail at golden hour

    Sail past the Statue of Liberty with a welcome cocktail at golden hour
    4.5 • 699 reviews
    $104
    Cruise West Grand Traverse Bay at Noon in Traverse City
    Sailing

    Cruise West Grand Traverse Bay at Noon in Traverse City

    Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay

    Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay
    4.8 • 1.2K reviews
    $58/ person
    2-Hour Maui Sunset Catamaran Cruise From Lahaina
    Sailing

    2-Hour Maui Sunset Catamaran Cruise From Lahaina

    Sail Lahaina’s sunset with appetizers and an open bar

    Sail Lahaina’s sunset with appetizers and an open bar
    4.8 • 4K reviews
    $114/ person
    Sail a 270' Catalina Charter in San Diego Bay
    Sailing

    Sail a 270' Catalina Charter in San Diego Bay

    Charter a Catalina 270 sailboat on San Diego Bay with 3- or 6-hour options

    Charter a Catalina 270 sailboat on San Diego Bay with 3- or 6-hour options
    $395& up
    Sail a Catalina 270 Charter in San Diego
    Sailing

    Sail a Catalina 270 Charter in San Diego

    Charter an 8-person Catalina 270 sailboat with 3- or 6-hour options

    Charter an 8-person Catalina 270 sailboat with 3- or 6-hour options
    $395/ boat
    Sail at Sunset in San Diego
    Sailing

    Sail at Sunset in San Diego

    Sail into sunset views of San Diego’s skyline with a USCG-licensed captain

    Sail into sunset views of San Diego’s skyline with a USCG-licensed captain
    $250/ boat
    2-Hour Learn-to-Sail Lesson in Coronado
    Sailing

    2-Hour Learn-to-Sail Lesson in Coronado

    Learn to sail a Capri 22 with an experienced skipper

    Learn to sail a Capri 22 with an experienced skipper
    $195/ 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
    Learn Coastal Navigation Online in St. Augustine
    Sailing

    Learn Coastal Navigation Online in St. Augustine

    Build coastal navigation skills with a self-paced ASA 105 online course

    Build coastal navigation skills with a self-paced ASA 105 online course
    5.0 • 736 reviews
    $795/ person
    Sail a 5-Hour Power Island Cruise From Traverse City
    Sailing

    Sail a 5-Hour Power Island Cruise From Traverse City

    Private 5-hour sail to Power Island with time to anchor and swim

    Private 5-hour sail to Power Island with time to anchor and swim
    4.9 • 8 reviews
    $794
    2-Hour Happy Hour Sail in Traverse City
    Sailing

    2-Hour Happy Hour Sail in Traverse City

    Sail Grand Traverse Bay with included regional drinks

    Sail Grand Traverse Bay with included regional drinks
    4.9 • 328 reviews
    $146/ person
    Enjoy a 2-Hour Erie Sunset Sail & Couples Massage
    Sailing

    Enjoy a 2-Hour Erie Sunset Sail & Couples Massage

    Book a 1-hour couples massage plus a 2-hour Lake Erie sail for two

    Book a 1-hour couples massage plus a 2-hour Lake Erie sail for two
    5.0 • 146 reviews
    $779
    Snorkel & Sail Full-Day Charter in Maalaea Bay
    Yacht Charters

    Snorkel & Sail Full-Day Charter in Maalaea Bay

    Sail Maalaea Bay and snorkel from a private 42' monohull

    Sail Maalaea Bay and snorkel from a private 42' monohull
    5.0 • 153 reviews
    $5,731
    San Diego Whale Watching Tour on 138ft Yacht
    Whale Watching

    San Diego Whale Watching Tour on 138ft Yacht

    Sail on a stable 138-foot yacht to spot migrating whales off San Diego

    Sail on a stable 138-foot yacht to spot migrating whales off San Diego
    4.8 • 433 reviews
    $91/ person
    Sail a Private Sunset Charter in Ko Olina
    Yacht Charters

    Sail a Private Sunset Charter in Ko Olina

    Book a private Ko Olina yacht charter with snorkeling gear and a flexible agenda

    Book a private Ko Olina yacht charter with snorkeling gear and a flexible agenda
    5.0 • 354 reviews
    $2,165& up
    Full-Day Snorkel & Sail Catamaran Charter In Maui
    Yacht Charters

    Full-Day Snorkel & Sail Catamaran Charter In Maui

    Sail Maalaea Bay on a private catamaran with guided snorkeling and lunch

    Sail Maalaea Bay on a private catamaran with guided snorkeling and lunch
    5.0 • 153 reviews
    $9,552
    Sail From Historic Charleston to Kiawah Island, South Carolina
    Yacht Charters

    Sail From Historic Charleston to Kiawah Island, South Carolina

    Sail offshore with licensed captains to Charleston's barrier islands on a full-day adventure

    Sail offshore with licensed captains to Charleston's barrier islands on a full-day adventure
    4.9 • 247 reviews
    $1,712& up
    Kona Luxury Dolphin Snorkel Sail with Lunch
    Snorkeling

    Kona Luxury Dolphin Snorkel Sail with Lunch

    Sail Kona’s coast on a luxury catamaran, snorkel top reefs, spot dolphins, and enjoy lunch

    Sail Kona’s coast on a luxury catamaran, snorkel top reefs, spot dolphins, and enjoy lunch
    4.8 • 498 reviews
    $455/ 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
    Sunset Dinner Cruise in St. Augustine
    Dinner Cruises

    Sunset Dinner Cruise in St. Augustine

    Private sunset sail with a chef-prepared four-course dinner

    Private sunset sail with a chef-prepared four-course dinner
    5.0 • 736 reviews
    $1,862& up
    Sail a Private Bachelorette Catamaran in St. Augustine
    Yacht Charters

    Sail a Private Bachelorette Catamaran in St. Augustine

    Celebrate on a private catamaran with a licensed captain and crew

    Celebrate on a private catamaran with a licensed captain and crew
    5.0 • 736 reviews
    $2,813& up
    1…678…17