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 241-264 of 403 results
    Swim, Snorkel & Dolphin Sail in Panama City Beach
    Sailing

    Swim, Snorkel & Dolphin Sail in Panama City Beach

    Sail to Shell Island Beach for snorkeling, swimming, and dolphin sightseeing

    Sail to Shell Island Beach for snorkeling, swimming, and dolphin sightseeing
    4.9 • 2.8K reviews
    $132/ person
    2-Hour Sunset Dolphin Sail in Panama City Beach
    Sailing

    2-Hour Sunset Dolphin Sail in Panama City Beach

    Sail at sunset and look for dolphins aboard Daydreams

    Sail at sunset and look for dolphins aboard Daydreams
    4.9 • 2.8K reviews
    $114/ person
    San Diego Bay Afternoon Sail Aboard A Classic Yacht
    Sailing

    San Diego Bay Afternoon Sail Aboard A Classic Yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht

    Sip craft beer and wine as you sail San Diego Bay on an intimate six-passenger classic yacht
    5.0 • 94 reviews
    $125/ person
    San Diego Bay Sunset Sail on a Classic Yacht
    Sailing

    San Diego Bay Sunset Sail on a Classic Yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht

    Savor a San Diego Bay sunset with drinks on an intimate six-passenger sail aboard a classic yacht
    5.0 • 94 reviews
    $125/ person
    Sail a Live Music Sunset Cruise in Key West
    Sailing

    Sail a Live Music Sunset Cruise in Key West

    Sunset catamaran sail with live music, appetizers, and included drinks

    Sunset catamaran sail with live music, appetizers, and included drinks
    4.5 • 3.9K reviews
    $101/ person
    3.5-Hour Jolly Mon Sail and Snorkel Adventure
    Sailing

    3.5-Hour Jolly Mon Sail and Snorkel Adventure

    Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain

    Sail Pensacola waters and snorkel shallow sites with gear, instruction, and a licensed captain
    5.0 • 1.9K reviews
    $501
    Enjoy a Live Music Sunset Sail in Saint Augustine
    Sailing

    Enjoy a Live Music Sunset Sail in Saint Augustine

    Sail Saint Augustine at sunset with live music and complimentary drinks

    Sail Saint Augustine at sunset with live music and complimentary drinks
    4.8 • 221 reviews
    $81/ person
    Sunset Catamaran Cruise in Lihue
    Sailing

    Sunset Catamaran Cruise in Lihue

    Cruise Kalapaki at sunset with music, narration, and a full-service bar

    Cruise Kalapaki at sunset with music, narration, and a full-service bar
    $121/ person
    Chrissy Lobster Sloop Cruises
    Sailing

    Chrissy Lobster Sloop Cruises

    Small, intimate cruises available for private charter

    Small, intimate cruises available for private charter
    4.2 • 2.5K reviews
    $530
    Cruise the Saco River & Saco Bay on a 2-Hour Sail
    Sailing

    Cruise the Saco River & Saco Bay on a 2-Hour Sail

    Sail Maine’s coast in a small group of 6 or fewer

    Sail Maine’s coast in a small group of 6 or fewer
    5.0 • 376 reviews
    $127/ person
    Sail on a Private 2-Hour Charter in Maine
    Sailing

    Sail on a Private 2-Hour Charter in Maine

    Reserve a private sail for up to 6 on the Saco River and Saco Bay

    Reserve a private sail for up to 6 on the Saco River and Saco Bay
    5.0 • 376 reviews
    $694& up
    2-Hour Boston Harbor Sunset Sail Near Castle Island
    Sailing

    2-Hour Boston Harbor Sunset Sail Near Castle Island

    Sail Boston Harbor at sunset on an 80-foot schooner

    Sail Boston Harbor at sunset on an 80-foot schooner
    4.7 • 1.5K reviews
    $75/ person
    Sail a Private Catamaran Cruise in Manteo
    Sailing

    Sail a Private Catamaran Cruise in Manteo

    Private 2.5–3 hour catamaran sail from Manteo for up to 6

    Private 2.5–3 hour catamaran sail from Manteo for up to 6
    4.9 • 523 reviews
    $543
    Sail Wrightsville Beach on a 2-Hour Afternoon Cruise
    Sailing

    Sail Wrightsville Beach on a 2-Hour Afternoon Cruise

    Sail across Masonboro Inlet on a 2-hour afternoon cruise

    Sail across Masonboro Inlet on a 2-hour afternoon cruise
    5.0 • 279 reviews
    $106/ person
    Sunset Sail Cruise on the Philadelphia Waterfront
    Sailing

    Sunset Sail Cruise on the Philadelphia Waterfront

    Sail the Delaware River at sunset with a USCG-licensed captain

    Sail the Delaware River at sunset with a USCG-licensed captain
    $113/ person
    2-Hour Daytime Charleston Harbor Shared Sail
    Sailing

    2-Hour Daytime Charleston Harbor Shared Sail

    Sail Charleston Harbor by day on a shared catamaran with shade, restrooms, and an onboard bar

    Sail Charleston Harbor by day on a shared catamaran with shade, restrooms, and an onboard bar
    5.0 • 689 reviews
    $54/ person
    Sunset Sail Cruise in Charleston Harbor
    Sailing

    Sunset Sail Cruise in Charleston Harbor

    Sail into sunset views with music and an onboard bar

    Sail into sunset views with music and an onboard bar
    5.0 • 689 reviews
    $54/ person
    2-Hour Charleston Harbor Party Sail
    Sailing

    2-Hour Charleston Harbor Party Sail

    Shared 2-hour Charleston Harbor party sail with an onboard bar (21+ only)

    Shared 2-hour Charleston Harbor party sail with an onboard bar (21+ only)
    5.0 • 689 reviews
    $54/ person
    Sail Lake Tahoe on a 2-Hour Catamaran Cruise
    Sailing

    Sail Lake Tahoe on a 2-Hour Catamaran Cruise

    Cruise Lake Tahoe on a 55-foot catamaran with lakewide views

    Cruise Lake Tahoe on a 55-foot catamaran with lakewide views
    $170/ person
    Sail York River on a 1.5-Hour Yorktown Cruise
    Sailing

    Sail York River on a 1.5-Hour Yorktown Cruise

    Cruise the York River on a 1.5-hour tall-ship day sail

    Cruise the York River on a 1.5-hour tall-ship day sail
    4.7 • 1.9K reviews
    $61/ person
    Sail a 2-Hour Sunset Cruise in Seattle
    Sailing

    Sail a 2-Hour Sunset Cruise in Seattle

    Sail Seattle’s harbor at sunset with skyline views and an onboard bar

    Sail Seattle’s harbor at sunset with skyline views and an onboard bar
    4.8 • 352 reviews
    $76/ person
    Waikoloa Signature Sunset Sail
    Sailing

    Waikoloa Signature Sunset Sail

    Unwind on a 1.5-hour coastal sunset sail with a full bar and light bites

    Unwind on a 1.5-hour coastal sunset sail with a full bar and light bites
    4.8 • 498 reviews
    $160/ person
    Sail a 2-Hour Champagne Sunset Cruise in St. Thomas
    Sailing

    Sail a 2-Hour Champagne Sunset Cruise in St. Thomas

    Sail St. Thomas at sunset with an open bar and appetizers

    Sail St. Thomas at sunset with an open bar and appetizers
    4.8 • 4.7K reviews
    $117/ person
    Kona Signature Sunset Sail
    Sailing

    Kona Signature Sunset Sail

    Sail the Kona Coast at sunset with light bites and drinks included

    Sail the Kona Coast at sunset with light bites and drinks included
    4.8 • 498 reviews
    $115/ person
    1…101112…17