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Best results for

Water Activities in Old Saybrook, CT

Showing 1-24 of 37 results
Thimble Islands 45-Minute Narrated Cruise

Thimble Islands 45-Minute Narrated Cruise

Explore island history and local legends from the water

4.7 • 162 reviews
$19/ 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 • 877 reviews
$631
42' Fishing Charter in Waterford

42' Fishing Charter in Waterford

Cast off on a private fishing trip aboard the Sunbeam VI

4.7 • 465 reviews
$1,166& up
2-Hour Hampton Bays Cruise

2-Hour Hampton Bays Cruise

A customizable private boat outing with sandbar stops and coastal wildlife viewing

$791& up
Westerly Fall Harbor Seal Nature Cruise

Westerly Fall Harbor Seal Nature Cruise

See fall foliage and watch for harbor seals along Rhode Island’s coast

$27/ person
Private Striped Bass Fishing Charter in New London, CT

Private Striped Bass Fishing Charter in New London, CT

Enjoy a private fishing trip with a lifelong angler and room to relax on board

$859& up
Blackfish Fishing Trip in Greenport, NY

Blackfish Fishing Trip in Greenport, NY

Set out for blackfish with plenty of room to fish

$159/ person
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

$1,685
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
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
Stony Creek Sunset Cruise Charter

Stony Creek Sunset Cruise Charter

Private sunset cruise with space for your food, drinks, and playlist

4.7 • 162 reviews
$583
Morning Cruise in Hampton Bays

Morning Cruise in Hampton Bays

Cruise waterfront coves and pause for an island swim

$791& up
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

$90/ person
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
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
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
Full-Day Private Fishing Charter in Old Saybrook, CT

Full-Day Private Fishing Charter in Old Saybrook, CT

Settle into a full day on the water

$1,292
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
Blackfish Fishing Trip in Waterford

Blackfish Fishing Trip in Waterford

Drift over reef structure in search of blackfish

4.7 • 465 reviews
$110/ person
Gardiners Bay Bottom Fishing Trip from Greenport

Gardiners Bay Bottom Fishing Trip from Greenport

Cast a line with bait, tackle, and fish cleaning included

$133/ person
Half-Day Private Fishing Charter in Old Saybrook

Half-Day Private Fishing Charter in Old Saybrook

Learn fishing techniques from an experienced crew

$955
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
Thimble Islands Live-Narrated Cruise

Thimble Islands Live-Narrated Cruise

See the Thimble Islands from open decks with live narration

4.8 • 95 reviews
$21/ person
Drive Your Own Boat on a 3-Hour Mystic River Tour

Drive Your Own Boat on a 3-Hour Mystic River Tour

Captain your own boat on a guided 3-hour Mystic River ride

4.8 • 197 reviews
$238/ person
12
Old Saybrook Things To Do
Fishing Charters18Boat Tours11Bike Rentals6Bike Tours5Sailing5
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  • Bar and Pub Crawl3
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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.