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Explore Greetwell

Curated local experiences in 500+ destinations

What's trending

  • St. Augustine Nights of Lights
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Questions? We're here to help.Real people, 7 days a week.

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  • 15 Best Stuff to Do in Atlanta, GA in 2026
  • Best results for

    Sailing in Waterford, CT

    Showing 1-17 of 17 results
    3-Hour Private Sunset Sailing Cruise in San Diego

    3-Hour Private Sunset Sailing Cruise in San Diego

    Sail the San Diego coast at sunset with complimentary drinks and snacks

    4.9 • 877 reviews
    $631
    Private Classic Wooden Yacht Sail in Watch Hill

    Private Classic Wooden Yacht Sail in Watch Hill

    See Watch Hill from the water aboard a classic wooden yacht

    5.0 • 69 reviews
    $530
    Private 39' Sailboat Charter Near Mystic

    Private 39' Sailboat Charter Near Mystic

    Sail straight into Fishers Island Sound, with room to relax or take the wheel

    5.0 • 49 reviews
    $462/ boat
    Bring Your Own Picnic Sailing Cruise in Old Saybrook

    Bring Your Own Picnic Sailing Cruise in Old Saybrook

    Enjoy your own picnic on the water with a choice of cruising routes

    5.0 • 45 reviews
    $371& up
    Shelter Island Sailing Cruise on a Classic Wooden Yacht

    Shelter Island Sailing Cruise on a Classic Wooden Yacht

    Raise the sails or unwind aboard a historic yacht

    $918
    Private Tailored Sailing Lesson in Sag Harbor

    Private Tailored Sailing Lesson in Sag Harbor

    Focus your time on the sailing skills you want to develop

    $1,166& up
    Private Bachelorette Sailing Charter in San Diego

    Private Bachelorette Sailing Charter in San Diego

    Book a 3-hour private bachelorette sail in San Diego, with daytime or sunset departures

    4.9 • 877 reviews
    $583& up
    Classic Wooden Yacht Sailing Charter on Shelter Island

    Classic Wooden Yacht Sailing Charter on Shelter Island

    Help raise the sails or settle in for a relaxed family outing

    $918
    Private Sailing Charter in Sag Harbor

    Private Sailing Charter in Sag Harbor

    Unwind on deck with paddle boards and pool toys on hand

    $742& up
    Private Sunset Sailing Charter in San Diego

    Private Sunset Sailing Charter in San Diego

    Sail San Diego at sunset on a private 3-hour cruise

    4.9 • 877 reviews
    $631& up
    Private Half-Day Wooden Yacht Sail on Shelter Island

    Private Half-Day Wooden Yacht Sail on Shelter Island

    Sail at your own pace, with room to explore or simply unwind

    $1,262
    Private Classic Sailing Cruise in Sag Harbor

    Private Classic Sailing Cruise in Sag Harbor

    Relax on a private sail with onboard comforts

    $954& up
    Private Romantic Sail for Proposals in San Diego

    Private Romantic Sail for Proposals in San Diego

    Sail privately in San Diego Bay with drinks and snacks included

    4.9 • 877 reviews
    $631& up
    Sunset Sail on a 40' Sailboat in San Diego

    Sunset Sail on a 40' Sailboat in San Diego

    3-hour sunset sail on a 40-foot boat with drinks and snacks included

    4.9 • 877 reviews
    $126/ person
    Shelter Island Sunset Sail on a Classic Wooden Yacht

    Shelter Island Sunset Sail on a Classic Wooden Yacht

    Pair a romantic evening on the water with hands-on sailing

    $975
    Moonrise Sail on a Classic Wooden Yacht in Shelter Island

    Moonrise Sail on a Classic Wooden Yacht in Shelter Island

    Lend a hand with the sails or simply relax as evening unfolds

    $975
    Private Gaff-Rigged Sunset Sail in Watch Hill

    Private Gaff-Rigged Sunset Sail in Watch Hill

    Sail into the evening with sparkling wine and the sound of water against a wooden hull

    5.0 • 69 reviews
    $636
    Waterford Things To Do
    SailingFishing Charters24Boat Tours12Boat Rentals8Bike Rentals6
    More
    • Bike Tours5
    • Escape Games5
    • Surfing Lessons5
    • Motorcycle Tours4
    • Bar and Pub Crawl3
    • Ghost and Haunted3
    • Stand Up Paddle Boarding3