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Best results for

Water Activities in Winthrop, MA

Showing 97-107 of 107 results

Hourly Stand-Up Paddleboard Rental in Beverly

Hourly Stand-Up Paddleboard Rental in Beverly

Paddle Beverly Harbor and Salem Sound at your own pace

5.0 • 48 reviews

$27/ paddleboard

Gloucester Schooner Festival Private Sailing Charter

Gloucester Schooner Festival Private Sailing Charter

Sail in company with visiting schooners during Gloucester Schooner Festival Weekend

5.0 • 107 reviews

$477

Beverly Hourly Kayak Rental

Beverly Hourly Kayak Rental

Explore Beverly Harbor and Salem Sound at your own pace

5.0 • 48 reviews

$27/ kayak

Private Kayak & SUP Lessons in Salem

Private Kayak & SUP Lessons in Salem

Build confidence on the water with personalized paddling instruction

5.0 • 48 reviews

$80/ person

Charles River Canoe Rental

Charles River Canoe Rental

Paddle calm Charles River waters through Nahanton Park

4.7 • 134 reviews

$39/ canoe

2-Hour Boston Harbor Tall Ships Cruise

2-Hour Boston Harbor Tall Ships Cruise

Cruise Boston Harbor for views of the tall ships on a classic schooner

4.6 • 438 reviews

$77/ person

Boston Harbor Sunset Tall Ships Sail

Boston Harbor Sunset Tall Ships Sail

Sail Boston Harbor at sunset for views of the tall ships and skyline lights

4.6 • 438 reviews

$90/ person

Stand-Up Paddleboard Rental on Lake Massapoag

Stand-Up Paddleboard Rental on Lake Massapoag

Paddle Lake Massapoag at your own pace

$26/ paddleboard

Private SUP & Kayak Lesson in Beverly

Private SUP & Kayak Lesson in Beverly

Build paddling skills with private instruction tailored to your experience

5.0 • 48 reviews

$80/ person

Lake Massapoag Single Kayak Rental

Lake Massapoag Single Kayak Rental

Paddle Lake Massapoag at your own pace in a single kayak

$26/ kayak

Canoe Rental on Lake Massapoag

Canoe Rental on Lake Massapoag

Paddle Lake Massapoag at your own pace in a canoe

$37/ canoe

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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.

Winthrop Things To Do

Historical Tours55 Sailing35 Boat Tours23 Ghost and Haunted19 Food Tours14

More

Yacht Charters12
Bike Rentals10
Kayaking Tours10
Dessert Tours9
Fishing Charters9
Architectural Tours8
Scooter Rentals8

Movie Location Tours

7

Heritage Walks6

Stand Up Paddle Boarding6

Cooking Classes5

Themed Experiences5

Bar and Pub Crawl4

Off-Road Adventures4

Photography Tours4

Culinary Tours3