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Best results for

Water Activities in Brewster, MA

Showing 73-94 of 94 results
Striped Bass & Bluefish Fishing & Whale Watching Charter

Striped Bass & Bluefish Fishing & Whale Watching Charter

Private charter to fish for striped bass and bluefish and look for whales

4.9 • 179 reviews
$1,214
4-Hour Private Boat Charter in Provincetown

4-Hour Private Boat Charter in Provincetown

Choose your beach and use the boat as your home base for swimming and relaxing

4.9 • 179 reviews
$843
Shark Tour in Harwich

Shark Tour in Harwich

Scan the water for sharks with a naturalist guide and aerial spotting support

4.8 • 134 reviews
$335/ person
Sunset Sail in Provincetown

Sunset Sail in Provincetown

Watch Provincetown’s shoreline glow from a classic Victorian yacht

$94/ person
2-Hour Cape Cod Bay Fishing Charter

2-Hour Cape Cod Bay Fishing Charter

Try fishing in Cape Cod Bay on a 2-hour kids-friendly private charter

$477
Harwich Sunset Cruise

Harwich Sunset Cruise

Share a sunset motorboat ride through the harbor

4.8 • 134 reviews
$85/ person
8-Hour Kayak & Paddleboard Rental in Mashpee

8-Hour Kayak & Paddleboard Rental in Mashpee

Set out on a self-guided paddle through Popponesset Bay

5.0 • 208 reviews
$96/ equipment
Sandwich Kayaking & Glassblowing Experience

Sandwich Kayaking & Glassblowing Experience

Paddle Scorton Creek and create your own blown-glass piece

5.0 • 208 reviews
$283/ person
Harwich 4-Hour Private Inshore Fishing Charter

Harwich 4-Hour Private Inshore Fishing Charter

Cast a line on a private inshore trip with a captain and gear included

4.8 • 134 reviews
$1,100& up
Paddleboard Scorton Creek Guided Tour

Paddleboard Scorton Creek Guided Tour

Stand-up paddleboard tour up Scorton Creek with an ACA Certified guide

5.0 • 208 reviews
$110/ person
Private Sailing Charter in Provincetown

Private Sailing Charter in Provincetown

Charter a private sail in Provincetown for up to 34 guests

$2,542& up
2-Hour Kids Sea Creature Cruise in Provincetown

2-Hour Kids Sea Creature Cruise in Provincetown

Cruise for seals, fish, and lobster traps with the kids

4.9 • 179 reviews
$604
Provincetown Seal & Lighthouse Cruise

Provincetown Seal & Lighthouse Cruise

See seals and three historic lighthouses from Provincetown Harbor

4.9 • 179 reviews
$551
Fish Cape Cod Bay on a 6-Hour Charter

Fish Cape Cod Bay on a 6-Hour Charter

Join a 6-hour Cape Cod Bay fishing charter with a licensed captain

$981
14' Catamaran Rental on Pleasant Bay

14' Catamaran Rental on Pleasant Bay

Take the helm of a forgiving catamaran for easy bay sailing

4.8 • 134 reviews
$143/ boat
Sail Boston Harbor on the Historic Schooner Hindu

Sail Boston Harbor on the Historic Schooner Hindu

Sail Boston during Sail Boston 2026 on the restored Schooner Hindu

$73/ person
2-Hour Stand-Up Paddleboard Tour on Popponesset River

2-Hour Stand-Up Paddleboard Tour on Popponesset River

Beginner stand-up paddleboard tour with ACA-certified guidance

5.0 • 208 reviews
$110/ person
90-Minute Private Schooner Charter in Provincetown

90-Minute Private Schooner Charter in Provincetown

Private classic schooner sail with lighthouse and cove views

$3,149& up
Full Moon Kayak Tour On Popponesset Bay

Full Moon Kayak Tour On Popponesset Bay

Paddle Popponesset Bay at sunset and into the full moonlight

5.0 • 208 reviews
$182/ kayak
Self-Guided Kayak & Paddleboard Rental in Falmouth

Self-Guided Kayak & Paddleboard Rental in Falmouth

Paddle a Cape Cod inlet at your own pace

5.0 • 208 reviews
$85/ equipment
1-Hour Kayak & Paddleboard Rental in Falmouth

1-Hour Kayak & Paddleboard Rental in Falmouth

Paddle a Cape Cod inlet at your own pace

5.0 • 208 reviews
$57/ equipment
Beginner Kayak Lesson in Sandwich

Beginner Kayak Lesson in Sandwich

Build foundational paddling skills with an ACA-certified guide

5.0 • 208 reviews
$110/ person
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Brewster Things To Do
Bike Rentals36Boat Tours18Kayaking Tours12Paddleboarding12Sailing12
More
  • Private Fishing Charters8
  • Fishing Charters7
  • Stand Up Paddle Boarding7
  • Whale Watching6
  • Sunrise and Sunset Tours5
  • Yacht Charters5
  • Boat Rentals4

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.

Scenic Flights3