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 193-216 of 403 results
    2-Hour Waikiki Sail & Snorkel Catamaran Cruise
    Snorkeling

    2-Hour Waikiki Sail & Snorkel Catamaran Cruise

    Sail and snorkel off Diamond Head on a 40-foot catamaran

    Sail and snorkel off Diamond Head on a 40-foot catamaran
    4.7 • 307 reviews
    $95/ person
    Guided 1.5-Hour Skull Creek Kayaking Tour
    Kayaking Tours

    Guided 1.5-Hour Skull Creek Kayaking Tour

    Paddle Skull Creek marshes on a 1.5-hour guided kayak tour

    Paddle Skull Creek marshes on a 1.5-hour guided kayak tour
    4.7 • 237 reviews
    $42/ kayak
    West Maui 4-Hour Snorkel Sail
    Snorkeling

    West Maui 4-Hour Snorkel Sail

    Sail and snorkel West Maui with breakfast, lunch, and an open bar

    Sail and snorkel West Maui with breakfast, lunch, and an open bar
    4.9 • 2.3K reviews
    $177/ person
    Cruise the Southern California Coast on a 3-Hour Charter
    Yacht Charters

    Cruise the Southern California Coast on a 3-Hour Charter

    Charter a 42-foot Lagoon catamaran with staterooms, paddle boards, and lounge space

    Charter a 42-foot Lagoon catamaran with staterooms, paddle boards, and lounge space
    $1,352
    Sail Monterey Bay on a 30' Hunter Sailboat Rental
    Boat Rentals

    Sail Monterey Bay on a 30' Hunter Sailboat Rental

    Rent the 30' Hunter Willow and sail Monterey Bay your way

    Rent the 30' Hunter Willow and sail Monterey Bay your way
    4.9 • 228 reviews
    $360/ boat
    Kealakekua Bay Snorkel and Sail
    Snorkeling

    Kealakekua Bay Snorkel and Sail

    Sail the Kona Coast and snorkel Kealakekua Bay with gear, breakfast, and lunch included

    Sail the Kona Coast and snorkel Kealakekua Bay with gear, breakfast, and lunch included
    4.9 • 671 reviews
    $206/ person
    Sail a Private Statue of Liberty Tour in New York
    Yacht Charters

    Sail a Private Statue of Liberty Tour in New York

    Private sail for close-up views of the Statue of Liberty and New York Harbor

    Private sail for close-up views of the Statue of Liberty and New York Harbor
    4.9 • 79 reviews
    $783& up
    3-Hour Private Fishing Charter in Ocean City
    Private Fishing ChartersUp to 32

    3-Hour Private Fishing Charter in Ocean City

    Rent the whole boat for your group and cruise the bay day or night

    Rent the whole boat for your group and cruise the bay day or night
    4.8 • 248 reviews
    $962
    Coral Gardens Coastal Snorkel And Sail
    Snorkeling

    Coral Gardens Coastal Snorkel And Sail

    Sail Maui’s coastline, snorkel Coral Gardens, and enjoy lunch onboard

    Sail Maui’s coastline, snorkel Coral Gardens, and enjoy lunch onboard
    4.8 • 4K reviews
    $137/ person
    2-Hour Private Wingsurfing Lesson in Maui
    Surfing Lessons

    2-Hour Private Wingsurfing Lesson in Maui

    Learn wingsurfing basics with a 2-hour private lesson near Kanaha Beach Park

    Learn wingsurfing basics with a 2-hour private lesson near Kanaha Beach Park
    4.2 • 5 reviews
    $400/ person
    2.5-Hour Snorkel Sail Cruise From Ko Olina
    Snorkeling

    2.5-Hour Snorkel Sail Cruise From Ko Olina

    Snorkel and sail West Oʻahu with an open bar from Ko Olina Marina

    Snorkel and sail West Oʻahu with an open bar from Ko Olina Marina
    4.8 • 652 reviews
    $172/ person
    Afternoon Snorkel & Sail Tour in Haleiwa
    Snorkeling

    Afternoon Snorkel & Sail Tour in Haleiwa

    Sail the North Shore and snorkel near Waimea Bay in a small group

    Sail the North Shore and snorkel near Waimea Bay in a small group
    4.7 • 383 reviews
    $161/ person
    4-Week Dry Suit Rental in Port Gamble, WA
    Equipment Rental

    4-Week Dry Suit Rental in Port Gamble, WA

    4-week comfort neck dry suit rental with shipping or Port Gamble pickup

    4-week comfort neck dry suit rental with shipping or Port Gamble pickup
    4.7 • 208 reviews
    $346/ suit
    2-Hour Key West Sunset Catamaran Sail With Live Music
    Sunrise and Sunset Tours

    2-Hour Key West Sunset Catamaran Sail With Live Music

    Sunset catamaran sail with live music, full bar, and appetizers

    Sunset catamaran sail with live music, full bar, and appetizers
    4.7 • 8K reviews
    $69/ person
    Sail Waikiki on a Sunset Tasting Cruise
    Dinner Cruises

    Sail Waikiki on a Sunset Tasting Cruise

    2-hour Waikiki sunset sail with tasting menu and hosted bar options

    2-hour Waikiki sunset sail with tasting menu and hosted bar options
    5.0 • 354 reviews
    $267/ person
    2-Hour Waikiki Turtle Canyon Snorkel Sail
    Snorkeling

    2-Hour Waikiki Turtle Canyon Snorkel Sail

    Sail Waikīkī and snorkel Turtle Canyon with gear, snacks, and drinks included

    Sail Waikīkī and snorkel Turtle Canyon with gear, snacks, and drinks included
    4.8 • 652 reviews
    $115/ person
    Sail a Private Catamaran Cruise in Manteo
    Sailing

    Sail a Private Catamaran Cruise in Manteo

    Private 3-hour catamaran sail on Roanoke Sound for up to 6

    Private 3-hour catamaran sail on Roanoke Sound for up to 6
    5.0 • 40 reviews
    $546
    Sail Boston Harbor on a Classic Schooner Day Cruise
    Sailing

    Sail Boston Harbor on a Classic Schooner Day Cruise

    Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail

    Cruise Boston Harbor on a 1.5- or 2-hour schooner day sail
    4.7 • 1.5K reviews
    $61/ person
    1.5-Hour San Francisco Bay Catamaran Sail
    Sailing

    1.5-Hour San Francisco Bay Catamaran Sail

    Sail past Alcatraz and under the Golden Gate on a 1.5-hour catamaran cruise

    Sail past Alcatraz and under the Golden Gate on a 1.5-hour catamaran cruise
    4.9 • 1K reviews
    $69/ person
    Sail San Francisco Bay at Sunset From Pier 39
    Sailing

    Sail San Francisco Bay at Sunset From Pier 39

    Cruise the Bay at sunset with 1 beer or wine included

    Cruise the Bay at sunset with 1 beer or wine included
    4.9 • 1K reviews
    $85/ person
    Sunset Sail & Tasting in Ko Olina
    Sailing

    Sunset Sail & Tasting in Ko Olina

    Sail into the Ko Olina sunset with a pupu tasting menu

    Sail into the Ko Olina sunset with a pupu tasting menu
    5.0 • 354 reviews
    $250/ person
    2-Hour Sunset Sail in Provincetown Harbor
    Sailing

    2-Hour Sunset Sail in Provincetown Harbor

    Enjoy a relaxing two-hour cruise as daylight fades over the water

    Enjoy a relaxing two-hour cruise as daylight fades over the water
    5.0 • 35 reviews
    $74/ person
    Private 3-Hour Midday Sail in San Diego
    Sailing

    Private 3-Hour Midday Sail in San Diego

    Sail San Diego on a private 3-hour daytime charter

    Sail San Diego on a private 3-hour daytime charter
    5.0 • 811 reviews
    $631& up
    Fort Lauderdale Sunset Catamaran Cruise
    Sailing

    Fort Lauderdale Sunset Catamaran Cruise

    Watch fiery skies and enjoy a complimentary champagne toast on a relaxed evening sail.

    Watch fiery skies and enjoy a complimentary champagne toast on a relaxed evening sail.
    4.9 • 498 reviews
    $112/ person
    1…8910…17