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 193-216 of 302 results
    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
    5.0 • 58 reviews
    $482
    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
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    Sail a 4-Hour Private Sunset Cruise in Kennebunkport
    Sailing

    Sail a 4-Hour Private Sunset Cruise in Kennebunkport

    Extend your private sunset sail to 4 hours, with space for up to 6 guests

    Extend your private sunset sail to 4 hours, with space for up to 6 guests
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    Cruise Pensacola Beach for Blue Angels Practice
    Sailing

    Cruise Pensacola Beach for Blue Angels Practice

    Sail to see the Blue Angels practice from the water (up to 6 guests)

    Sail to see the Blue Angels practice from the water (up to 6 guests)
    Contact for pricing
    Waikiki 1-Hour Friday Night Fireworks Cruise
    Sailing

    Waikiki 1-Hour Friday Night Fireworks Cruise

    Sail out for close-up views of Honolulu’s Friday night fireworks

    Sail out for close-up views of Honolulu’s Friday night fireworks
    Contact for pricing
    Sail the Delaware River on a 3-Hour History Tour
    Sailing

    Sail the Delaware River on a 3-Hour History Tour

    Sail the Delaware River and hear Philadelphia waterfront history from your guide

    Sail the Delaware River and hear Philadelphia waterfront history from your guide
    Contact for pricing
    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
    Contact for pricing
    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
    Contact for pricing
    Provincetown Sailing Tour on Historic Bay
    Sailing

    Provincetown Sailing Tour on Historic Bay

    Treat yourself to a memorable afternoon sail

    Treat yourself to a memorable afternoon sail
    5.0 • 35 reviews
    $64/ person
    Lake Erie Sailing Charter with Island Hopping
    Sailing

    Lake Erie Sailing Charter with Island Hopping

    Spend eight relaxing hours sailing Lake Erie with a private captain and flexible island-hopping itinerary.

    Spend eight relaxing hours sailing Lake Erie with a private captain and flexible island-hopping itinerary.
    5.0 • 34 reviews
    $1,537
    5-Hour Lake Erie Sailing Adventure in Sandusky
    Sailing

    5-Hour Lake Erie Sailing Adventure in Sandusky

    Experience a five-hour Lake Erie sailing adventure with up to six guests

    Experience a five-hour Lake Erie sailing adventure with up to six guests
    5.0 • 34 reviews
    $949
    Traverse City Sailing with Food & Open Bar
    Sailing

    Traverse City Sailing with Food & Open Bar

    Experience a relaxing afternoon sail with regional food and open bar

    Experience a relaxing afternoon sail with regional food and open bar
    4.9 • 328 reviews
    $212/ person
    Ko Olina Sunset Catamaran Sail in Oahu
    Sailing

    Ko Olina Sunset Catamaran Sail in Oahu

    Watch the Hawaiian sunset from a spacious 53-foot catamaran with complimentary cocktails and light appetizers.

    Watch the Hawaiian sunset from a spacious 53-foot catamaran with complimentary cocktails and light appetizers.
    4.9 • 2.9K reviews
    $138/ person
    St. Augustine Nights of Lights Sailing Tour
    Sailing

    St. Augustine Nights of Lights Sailing Tour

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights

    Sail a 35-foot yacht and admire St. Augustine's dazzling Nights of Lights
    4.9 • 697 reviews
    $145/ person
    Grand Traverse Bay Windjammer Sailing Cruise
    Sailing

    Grand Traverse Bay Windjammer Sailing Cruise

    Sail from West Bay Beach for lively afternoon winds and scenic peninsula views

    Sail from West Bay Beach for lively afternoon winds and scenic peninsula views
    4.8 • 1.2K reviews
    $65/ passenger
    1…8910…13