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

    Water Activities in Chesapeake Beach, MD

    Showing 121-144 of 153 results
    Canoe Rental on Little Blackwater River

    Canoe Rental on Little Blackwater River

    Paddle a brackish waterway beside Blackwater Refuge

    4.9 • 556 reviews
    $56/ canoe
    Private Potomac River Charter

    Private Potomac River Charter

    Host a river celebration with 360-degree views, a dance floor and party-ready amenities

    4.4 • 27 reviews
    $3,502& up
    2-Hour Beer Tasting Cruise in St. Michaels

    2-Hour Beer Tasting Cruise in St. Michaels

    Savor rotating craft beer tastings aboard the historic Lady Patty

    5.0 • 1.4K reviews
    $159/ person
    1-8 Hour Paddleboard Rental on Little Blackwater River

    1-8 Hour Paddleboard Rental on Little Blackwater River

    Paddle the Little Blackwater River and watch for wildlife along its banks

    4.9 • 556 reviews
    $34/ paddleboard
    Annapolis Stand-Up Paddleboard Rental

    Annapolis Stand-Up Paddleboard Rental

    Flexible paddleboard rentals for your time on the water

    4.9 • 173 reviews
    $29/ paddleboard
    8-Hour Chesapeake Bay Cruise to Oxford

    8-Hour Chesapeake Bay Cruise to Oxford

    See Chesapeake landmarks and explore historic Oxford by boat

    4.7 • 199 reviews
    $1,229/ boat
    Washington, DC Sunset Wellness Yacht Cruise

    Washington, DC Sunset Wellness Yacht Cruise

    Make your wellness gathering feel at home on a 45-foot yacht

    $2,675
    Historic Ketch Sailing Lesson in St. Michaels

    Historic Ketch Sailing Lesson in St. Michaels

    Take the Helm and Learn Hands-On Sailing Skills

    5.0 • 1.4K reviews
    $1,792
    Chesapeake Bay Lighthouse Boat Tour from Edgewater, MD

    Chesapeake Bay Lighthouse Boat Tour from Edgewater, MD

    See three historic lighthouses from the water

    4.7 • 199 reviews
    $819/ boat
    Private Historic Harbor Cruise in St. Michaels

    Private Historic Harbor Cruise in St. Michaels

    Take in maritime history and waterfront scenery from your own private boat

    $145
    Private Miles River Boat Cruise in St. Michaels

    Private Miles River Boat Cruise in St. Michaels

    Help shape your route through the waterways of Chesapeake Country

    $319
    Anacostia River Single Kayak Rental

    Anacostia River Single Kayak Rental

    Paddle solo on the Anacostia River near Nationals Park

    4.4 • 22 reviews
    $27/ kayak
    Snakehead Fishing Kayak Rental in Cambridge, MD

    Snakehead Fishing Kayak Rental in Cambridge, MD

    Reach shallow fishing spots beyond the reach of deeper-draft boats

    4.9 • 556 reviews
    $39/ kayak
    Washington Anacostia River Kayak Cleanup

    Washington Anacostia River Kayak Cleanup

    Paddle the Anacostia River while helping remove floating trash

    4.4 • 22 reviews
    $11/ person
    Washington DC Private 38' Yacht Charter

    Washington DC Private 38' Yacht Charter

    Unwind on a private yacht with below-deck seating and onboard comforts

    4.4 • 27 reviews
    $1,294& up
    Sailboat Wedding & Elopement Cruise in St. Michaels

    Sailboat Wedding & Elopement Cruise in St. Michaels

    Exchange vows aboard a historic sailboat with a ceremony shaped around you

    5.0 • 1.4K reviews
    $2,274
    Kayak & Paddleboard Rental in Chesapeake Beach, MD

    Kayak & Paddleboard Rental in Chesapeake Beach, MD

    Choose your way to paddle, with rentals starting on the hour

    4.2 • 3K reviews
    $22/ rental
    Kayak & Paddleboard Rental in Chesapeake Beach, MD

    Kayak & Paddleboard Rental in Chesapeake Beach, MD

    Take to the water with rentals starting on the hour

    4.2 • 3K reviews
    $67/ rental
    Stand Up Paddleboard Rental at The Wharf

    Stand Up Paddleboard Rental at The Wharf

    Paddle the calm Washington Channel from The Wharf with board, paddle, and PFD included

    $27/ board
    Cruise Annapolis on a Private Tiki Boat

    Cruise Annapolis on a Private Tiki Boat

    Bring your own drinks and cruise Annapolis on a private tiki boat for 8–16

    $78/ person
    Private Washington, DC Monuments Boat Tour

    Private Washington, DC Monuments Boat Tour

    Customize a private DC-area boat tour from National Harbor (2-hour minimum)

    $1,110& up
    Single Kayak Rental at National Harbor

    Single Kayak Rental at National Harbor

    Paddle National Harbor in a beginner-friendly sit-on-top kayak

    $27/ kayak
    Private Sunset Cruise on the Miles River in St. Michaels

    Private Sunset Cruise on the Miles River in St. Michaels

    Share a sunset with the people who matter most

    $435
    Private Chesapeake Bay Yacht Charter near Annapolis

    Private Chesapeake Bay Yacht Charter near Annapolis

    Cruise Chesapeake Bay with your own drinks, music, and flexible stops

    $2,520& up
    1234567
    Chesapeake Beach Things To Do
    Boat Tours36Museum Tours30Historical Tours26Boat Rentals25Kayaking Tours22
    More
    • Sailing20
    • Yacht Charters19
    • Bus Van and Limo Tours15
    • Bike Rentals8
    • Bike Tours8
    • Fishing Charters8
    • Food Tours8

    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.

    Sporting Events8
  • City Tours7
  • Historical Sites and Monuments7
  • Day Trips6
  • Photography Tours6
  • Private Transfers6
  • Stand Up Paddle Boarding6
  • Wine Tours6
  • Canoeing5
  • Audio Tours4
  • Paddleboarding4
  • Wine Tasting4
  • Ghost and Haunted3