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  • 13 Stunning Beaches in Florida With Clear Water You Need to Visit
  • Best results for

    Water Activities in Shelter Island, NY

    Showing 1-24 of 76 results
    Blackfish Fishing Trip in Waterford

    Blackfish Fishing Trip in Waterford

    Drift over reef structure in search of blackfish

    4.7 • 465 reviews
    $110/ person
    Private Stand Up Paddleboard Lesson in East Hampton

    Private Stand Up Paddleboard Lesson in East Hampton

    Build your paddling confidence with one-on-one attention

    5.0 • 74 reviews
    $187/ person
    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 • 898 reviews
    $631
    Morning Blackfish Fishing Charter in Waterford, CT

    Morning Blackfish Fishing Charter in Waterford, CT

    Target blackfish with fishing gear and catch preparation included

    5.0 • 66 reviews
    $1,124
    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
    Private Fishing Charter in Niantic, CT

    Private Fishing Charter in Niantic, CT

    Head out fishing on a charter just for your group

    4.8 • 76 reviews
    $1,145
    Sunset Cruise from Captain Scott's Lobster Dock in New London

    Sunset Cruise from Captain Scott's Lobster Dock in New London

    Spend sunset on the water

    5.0 • 18 reviews
    $90/ person
    Private Half-Day Fishing Charter in Clinton, CT

    Private Half-Day Fishing Charter in Clinton, CT

    Enjoy a private fishing outing for new and experienced anglers

    4.8 • 34 reviews
    $737
    Full-Day Kayak Rental at Meschutt Beach, Hampton Bays

    Full-Day Kayak Rental at Meschutt Beach, Hampton Bays

    Take to the water solo or share a tandem kayak

    4.8 • 8 reviews
    $126/ kayak
    Blackfish Fishing Trip in Greenport, NY

    Blackfish Fishing Trip in Greenport, NY

    Set out for blackfish with plenty of room to fish

    $159/ person
    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
    Waterford 5-Hour Private Fishing Charter

    Waterford 5-Hour Private Fishing Charter

    Cast off aboard a 42-foot boat for private fishing

    4.7 • 465 reviews
    $942
    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 • 898 reviews
    $583& up
    Private Full-Day Fishing Charter in Old Saybrook, CT

    Private Full-Day Fishing Charter in Old Saybrook, CT

    Pair a day of fishing with a river or coastal lunch stop

    1.0 • 1 reviews
    $1,685
    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 • 898 reviews
    $631& up
    Open Boat Fishing Trip in Niantic, CT

    Open Boat Fishing Trip in Niantic, CT

    Cast a line in good company

    4.8 • 76 reviews
    $106/ person
    Blackfish Fishing Charter in Waterford

    Blackfish Fishing Charter in Waterford

    Fish for blackfish with bait, tackle, and catch cleaning included

    4.7 • 465 reviews
    $1,177
    Single & Tandem Kayak Rental at Meschutt Beach, Hampton Bays
    Up to 2

    Single & Tandem Kayak Rental at Meschutt Beach, Hampton Bays

    Get on the water with kayak options for every skill level

    4.8 • 8 reviews
    $46/ kayak
    Weekday Full-Day Bottom Fishing Trip in Greenport

    Weekday Full-Day Bottom Fishing Trip in Greenport

    Target seasonal fish with bait, tackle, and fish cleaning included

    $106/ person
    Single & Tandem Kayak Rental in Hampton Bays

    Single & Tandem Kayak Rental in Hampton Bays

    Find your fit with kayak options for new and experienced paddlers

    4.8 • 8 reviews
    $80/ kayak
    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 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

    $1,435
    1234
    Shelter Island Things To Do
    Fishing Charters24Boat Tours18Sailing15Boat Rentals9Bike Rentals6
    More
    • Bike Tours5
    • Bar and Pub Crawl3
    • Stand Up Paddle Boarding3

    Travel guides for Water Activities

    13 Stunning Beaches in Florida With Clear Water You Need to Visit
    Best of Florida • 2026

    13 Stunning Beaches in Florida With Clear Water You Need to Visit

    Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide
    Best of Florida • 2026

    Do You Need a License to Rent a Boat in Florida? Your Complete Guide

    Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.