We're here to help
    Book online 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
    concierge@greetwell.com(650) 414-7338

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    We're here to help
    Book online or call (650) 414-7338
    Ask AIAI
    Ask AIAI

    Best results for Sailing

    Showing 1-24 of 302 results
    Private Sunset Sailing Charter in St Augustine
    Private Yacht ChartersUp to 6

    Private Sunset Sailing Charter in St Augustine

    Experience a luxury sunset sail with stunning views of St Augustine’s historic landmarks.

    Experience a luxury sunset sail with stunning views of St Augustine’s historic landmarks.
    4.9 • 697 reviews
    $669& up
    Key West Day Sail on 105ft Schooner America 2.0
    Sailing

    Key West Day Sail on 105ft Schooner America 2.0

    Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.

    Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.
    4.9 • 417 reviews
    $64/ person
    Lahaina Sunset Sailing with Dinner & Open Bar
    Sailing

    Lahaina Sunset Sailing with Dinner & Open Bar

    Enjoy a 2-hour sunset sail with catered dinner and a complimentary premium bar

    Enjoy a 2-hour sunset sail with catered dinner and a complimentary premium bar
    4.8 • 360 reviews
    $168/ person
    Rockwall Catamaran Sailing: 1.5-Hour Sunset Cruise
    Sailing

    Rockwall Catamaran Sailing: 1.5-Hour Sunset Cruise

    Relax on the hand-built Seawolf catamaran during a 1.5-hour sunset sail while enjoying your own drinks and snacks

    Relax on the hand-built Seawolf catamaran during a 1.5-hour sunset sail while enjoying your own drinks and snacks
    4.9 • 597 reviews
    $51/ person
    Saco Sailing Tour at Sunset, Small Groups
    Sailing

    Saco Sailing Tour at Sunset, Small Groups

    Sail the Maine coast at golden hour with small groups and room to spread out

    Sail the Maine coast at golden hour with small groups and room to spread out
    5.0 • 376 reviews
    $138/ person
    Hilton Head Sailing on Historic America's Cup Yacht
    Sailing

    Hilton Head Sailing on Historic America's Cup Yacht

    Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht

    Join the crew or relax on a 1.5-hour Hilton Head coastal sail aboard a historic America’s Cup yacht
    4.8 • 7.6K reviews
    $53/ person
    Waikiki Sunset Catamaran Sail from Honolulu
    Sailing

    Waikiki Sunset Catamaran Sail from Honolulu

    Watch the sky blaze over Waikiki on a relaxing two-hour catamaran sail

    Watch the sky blaze over Waikiki on a relaxing two-hour catamaran sail
    4.8 • 2.1K reviews
    $144/ person
    2-Hour Catamaran Sail Past Diamond Head & Waikiki
    Sailing

    2-Hour Catamaran Sail Past Diamond Head & Waikiki

    Soak in Honolulu and Diamond Head views on a 2-hour catamaran sail

    Soak in Honolulu and Diamond Head views on a 2-hour catamaran sail
    4.8 • 2.1K reviews
    $144/ person
    Sailing & Brunch Cruise in St. Augustine
    Sailing

    Sailing & Brunch Cruise in St. Augustine

    Savor mimosas and a boxed brunch while sailing St. Augustine with a captain and crew

    Savor mimosas and a boxed brunch while sailing St. Augustine with a captain and crew
    4.9 • 697 reviews
    $224/ person
    St. Augustine Sailing with Wine & Mimosas
    Sailing

    St. Augustine Sailing with Wine & Mimosas

    Savor mimosas or seasonal wines while sailing St. Augustine’s scenic waterways with a captain

    Savor mimosas or seasonal wines while sailing St. Augustine’s scenic waterways with a captain
    4.9 • 697 reviews
    $201/ person
    Private Crewed Sail Through St. Augustine Bay
    Private Boat ChartersUp to 6

    Private Crewed Sail Through St. Augustine Bay

    See St Augustine landmarks on a private crewed sail

    See St Augustine landmarks on a private crewed sail
    4.9 • 697 reviews
    $894
    St Augustine Sunset Sailing Charter
    Sailing

    St Augustine Sunset Sailing Charter

    Sail at sunset past St Augustine landmarks with a small group and professional crew

    Sail at sunset past St Augustine landmarks with a small group and professional crew
    4.9 • 697 reviews
    $201/ person
    Sail Historic Waters & Spot Wild Dolphins
    Sailing

    Sail Historic Waters & Spot Wild Dolphins

    Spot dolphins and coastal wildlife as you sail historic St. Augustine

    Spot dolphins and coastal wildlife as you sail historic St. Augustine
    4.9 • 697 reviews
    $201/ person
    Three-Hour Sailing Tour of Bodega Bay
    Sailing

    Three-Hour Sailing Tour of Bodega Bay

    Sail Bodega Bay for three hours and watch for sea lions, whales, and birds

    Sail Bodega Bay for three hours and watch for sea lions, whales, and birds
    4.7 • 26 reviews
    $403
    2-Hour Sailing Adventure on Choctawhatchee Bay
    Sailing

    2-Hour Sailing Adventure on Choctawhatchee Bay

    Sail Choctawhatchee Bay with a captain, spot wildlife, and try steering the catamaran

    Sail Choctawhatchee Bay with a captain, spot wildlife, and try steering the catamaran
    5.0 • 58 reviews
    $371
    Jolly Mon 2-Hour Sailing Adventure
    Sailing

    Jolly Mon 2-Hour Sailing Adventure

    Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages

    Sail Pensacola Beach with up to 6 guests and enjoy complimentary beverages
    5.0 • 1.8K reviews
    $120& up
    3-Hour Jolly Mon Sailing Adventure with Optional Swim Stop
    Sailing

    3-Hour Jolly Mon Sailing Adventure with Optional Swim Stop

    Sail scenic waters near Pensacola with an optional swim and a chance to spot dolphins

    Sail scenic waters near Pensacola with an optional swim and a chance to spot dolphins
    5.0 • 1.8K reviews
    $176/ person
    4-Hour Jolly Mon Sailing Adventure
    Sailing

    4-Hour Jolly Mon Sailing Adventure

    Sail Pensacola Bay with a licensed captain, with time to swim or snorkel and spot wildlife.

    Sail Pensacola Bay with a licensed captain, with time to swim or snorkel and spot wildlife.
    5.0 • 1.8K reviews
    $523
    Daytime Catamaran Sailing Cruise
    Sailing

    Daytime Catamaran Sailing Cruise

    Relax on a 35-minute Monterey Bay sail with included drink and snacks

    Relax on a 35-minute Monterey Bay sail with included drink and snacks
    $63/ person
    Afternoon Sailing and Snorkeling at Kealakekua Bay
    Sailing

    Afternoon Sailing and Snorkeling at Kealakekua Bay

    Sail a 50-ft catamaran to snorkel Kealakekua Bay's reefs, with drinks included and chances to see dolphins

    Sail a 50-ft catamaran to snorkel Kealakekua Bay's reefs, with drinks included and chances to see dolphins
    4.8 • 2.6K reviews
    $143/ person
    Morning Sailing and Snorkeling Tour in Kealakekua Bay
    Sailing

    Morning Sailing and Snorkeling Tour in Kealakekua Bay

    Sail a 50-foot catamaran and snorkel pristine reefs at Kealakekua Bay

    Sail a 50-foot catamaran and snorkel pristine reefs at Kealakekua Bay
    4.8 • 2.6K reviews
    $189/ person
    Private Sailing Charter on New York Harbor
    Private Boat ChartersUp to 6

    Private Sailing Charter on New York Harbor

    Charter a private sail with skyline and Statue of Liberty views

    Charter a private sail with skyline and Statue of Liberty views
    5.0 • 253 reviews
    $557
    New York Harbor Group Sail
    Sailing

    New York Harbor Group Sail

    Enjoy a 2.5-hour sail with skyline views of the Statue of Liberty and Brooklyn Bridge

    Enjoy a 2.5-hour sail with skyline views of the Statue of Liberty and Brooklyn Bridge
    5.0 • 253 reviews
    $116/ person
    New Product Title
    Sailing

    New Product Title

    Sail Wrightsville Beach with coffee, mimosas, and pastries aboard Bella

    Sail Wrightsville Beach with coffee, mimosas, and pastries aboard Bella
    $159& up
    12345…13