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

    Concierge Support

    • 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 337-360 of 510 results
    Sail Charleston Harbor on a 90-Minute Dolphin Sail
    Sailing

    Sail Charleston Harbor on a 90-Minute Dolphin Sail

    Cruise Charleston Harbor on the 84-foot Schooner Pride and spot local wildlife

    Cruise Charleston Harbor on the 84-foot Schooner Pride and spot local wildlife
    4.7 • 4.9K reviews
    $50/ person
    Sunset Catamaran Adventure
    Sailing

    Sunset Catamaran Adventure

    Sail at sunset on a catamaran with time to spot marine life and relax on the water

    Sail at sunset on a catamaran with time to spot marine life and relax on the water
    4.5 • 27 reviews
    $493
    Wednesday Night Sunset Cruise With Live Music
    Sailing

    Wednesday Night Sunset Cruise With Live Music

    Sail Casco Bay at sunset with live music and a BYOB vibe

    Sail Casco Bay at sunset with live music and a BYOB vibe
    4.9 • 135 reviews
    $48/ person
    Day Sail From Mackinac Island
    Sailing

    Day Sail From Mackinac Island

    Sail the Straits on a catamaran with time to relax, swim, and try stand-up paddleboarding

    Sail the Straits on a catamaran with time to relax, swim, and try stand-up paddleboarding
    $101/ person
    Sail Lake Tahoe on a Live Music Sunset Cruise
    Sailing

    Sail Lake Tahoe on a Live Music Sunset Cruise

    Cruise Lake Tahoe at sunset with live local music

    Cruise Lake Tahoe at sunset with live local music
    4.4 • 136 reviews
    $171/ person
    Watch Friday Night Fireworks on a Waikiki Sail
    Sailing

    Watch Friday Night Fireworks on a Waikiki Sail

    Friday fireworks sail with front-row views from the water

    Friday fireworks sail with front-row views from the water
    4.9 • 145 reviews
    $117/ person
    Sunset Swim & Sail Cruise in Waikiki
    Sailing

    Sunset Swim & Sail Cruise in Waikiki

    Sail Waikīkī’s Gold Coast at sunset with optional swim time

    Sail Waikīkī’s Gold Coast at sunset with optional swim time
    4.9 • 145 reviews
    $74/ person
    Sail Boothbay Harbor on a 1.5-Hour Guided Cruise
    Sailing

    Sail Boothbay Harbor on a 1.5-Hour Guided Cruise

    Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip

    Sail Boothbay Harbor aboard the Friendship Sloop Bay Lady on a 1.5-hour trip
    4.7 • 175 reviews
    $45/ person
    3-Hour Private Sail in Kennebunkport
    Sailing

    3-Hour Private Sail in Kennebunkport

    Charter your own sailboat for up to 6 on the Saco River and Saco Bay

    Charter your own sailboat for up to 6 on the Saco River and Saco Bay
    5.0 • 382 reviews
    $941& up
    Boat Handling Lesson on a 26' Twin Outboard Striper
    Sailing

    Boat Handling Lesson on a 26' Twin Outboard Striper

    Learn boat handling and docking in a 3–6 hour lesson for 1–2 people

    Learn boat handling and docking in a 3–6 hour lesson for 1–2 people
    $543& up
    Private Boat Handling Lesson in Belvedere Tiburon
    Sailing

    Private Boat Handling Lesson in Belvedere Tiburon

    Learn boat handling on your own boat with an instructor who comes to you

    Learn boat handling on your own boat with an instructor who comes to you
    $576& up
    2-Hour Private Sunset Catamaran Sail In Cocoa Beach
    Sailing

    2-Hour Private Sunset Catamaran Sail In Cocoa Beach

    Sail into the Cocoa Beach sunset on a private 2-hour catamaran cruise

    Sail into the Cocoa Beach sunset on a private 2-hour catamaran cruise
    4.4 • 125 reviews
    $339
    2-Hour Sunset Catamaran Sail in Cocoa Beach
    Sailing

    2-Hour Sunset Catamaran Sail in Cocoa Beach

    Sail a Cocoa Beach sunset cruise with chances to spot dolphins and manatees

    Sail a Cocoa Beach sunset cruise with chances to spot dolphins and manatees
    4.4 • 125 reviews
    $56/ person
    3-Hour Private Catamaran Cruise in Cocoa Beach
    Sailing

    3-Hour Private Catamaran Cruise in Cocoa Beach

    Private 3-hour catamaran sail with a spoil island swim stop

    Private 3-hour catamaran sail with a spoil island swim stop
    4.4 • 125 reviews
    $452
    Sail, Snorkel & Kayak Key West Sunset Cruise
    Sailing

    Sail, Snorkel & Kayak Key West Sunset Cruise

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

    Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset
    4.9 • 5.7K reviews
    $149/ person
    Morning Schooner Cruise in Bar Harbor
    Sailing

    Morning Schooner Cruise in Bar Harbor

    Sail Frenchman Bay for sea views of Acadia National Park

    Sail Frenchman Bay for sea views of Acadia National Park
    4.4 • 461 reviews
    $48/ person
    Sail Ko Olina on a 1.5-Hour Sunset Catamaran Cruise
    Sailing

    Sail Ko Olina on a 1.5-Hour Sunset Catamaran Cruise

    Sail Ko Olina at sunset with live Hawaiian music and an open bar

    Sail Ko Olina at sunset with live Hawaiian music and an open bar
    $160/ person
    Sail Provincetown on the Schooner Hindu
    Sailing

    Sail Provincetown on the Schooner Hindu

    Sail Cape Cod Bay on the historic Schooner Hindu

    Sail Cape Cod Bay on the historic Schooner Hindu
    $64/ person
    2-Hour Sunset Sail in Provincetown
    Sailing

    2-Hour Sunset Sail in Provincetown

    Sail Provincetown at sunset on the historic Schooner Hindu

    Sail Provincetown at sunset on the historic Schooner Hindu
    $94/ person
    2-Hour Provincetown Wine Tasting Sail
    Sailing

    2-Hour Provincetown Wine Tasting Sail

    Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown

    Taste Truro Vineyards pours on a 2-hour schooner sail in Provincetown
    $116/ person
    Private Afternoon Sail in Waikiki
    Sailing

    Private Afternoon Sail in Waikiki

    Private Waikiki afternoon catamaran sail with Diamond Head views and beach boarding

    Private Waikiki afternoon catamaran sail with Diamond Head views and beach boarding
    4.9 • 807 reviews
    $2,250
    Private Sunset Catamaran Sail In Cocoa Beach
    Sailing

    Private Sunset Catamaran Sail In Cocoa Beach

    Sail a private catamaran at sunset with room to lounge

    Sail a private catamaran at sunset with room to lounge
    4.4 • 125 reviews
    $339
    Champagne Sunset Cruise in Traverse City
    Sailing

    Champagne Sunset Cruise in Traverse City

    Sail West Grand Traverse Bay at sunset with a champagne toast

    Sail West Grand Traverse Bay at sunset with a champagne toast
    4.8 • 298 reviews
    $94/ person
    Cruise West Grand Traverse Bay on a Kids Sailboat
    Sailing

    Cruise West Grand Traverse Bay on a Kids Sailboat

    Sail the Nauti-Cat on a 1.5-hour kids cruise in Traverse City

    Sail the Nauti-Cat on a 1.5-hour kids cruise in Traverse City
    4.8 • 298 reviews
    $39/ person
    1…141516…22