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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 97-120 of 153 results
    Self-Guided Kayak Tour on Transquaking River

    Self-Guided Kayak Tour on Transquaking River

    Paddle a winding one-way river route with a shuttle back to your vehicle

    4.9 • 556 reviews
    $138/ kayak
    Private Potomac River Fishing Charter in Washington, D.C.

    Private Potomac River Fishing Charter in Washington, D.C.

    Fish private “secret” Potomac River spots on a Grady White (up to 6 guests)

    5.0 • 15 reviews
    $795& up
    Private Cruise in Solomons

    Private Cruise in Solomons

    Set out on a private cruise reserved exclusively for your group

    4.9 • 188 reviews
    $318
    Tandem Sit-On-Top Kayak Rental in Annapolis

    Tandem Sit-On-Top Kayak Rental in Annapolis

    A flexible tandem kayak rental for paddling together

    4.9 • 173 reviews
    $41/ kayak
    Youth Advanced Sailing Camp With Flying Scot

    Youth Advanced Sailing Camp With Flying Scot

    Build advanced sailing skills in a 5-day Flying Scot course for ages 8–15

    4.6 • 114 reviews
    $318/ person
    Private Chesapeake Bay Sunset Cruise from Annapolis

    Private Chesapeake Bay Sunset Cruise from Annapolis

    Pair your sunset cruise with handcrafted charcuterie and wine

    5.0 • 14 reviews
    $1,007
    Sunset Champagne Cruise in St. Michaels

    Sunset Champagne Cruise in St. Michaels

    Sail a historic ketch at sunset with champagne and Chesapeake Bay views

    5.0 • 1.4K reviews
    $159/ person
    Double Kayak Rental in Deale

    Double Kayak Rental in Deale

    Paddle Deale’s quiet creeks and bays at your own pace

    4.6 • 36 reviews
    $42/ kayak
    8-Hour Guided Boat Tour to Rock Hall

    8-Hour Guided Boat Tour to Rock Hall

    Cruise Chesapeake Bay to Rock Hall with time to explore ashore

    4.7 • 199 reviews
    $1,229/ boat
    20' Pontoon Boat Rental in Solomons on the Patuxent River
    Up to 8

    20' Pontoon Boat Rental in Solomons on the Patuxent River

    Cruise with family and friends on a stable pontoon built for sightseeing and tubing

    4.6 • 52 reviews
    $353/ boat
    Tiki Cruise in Washington, DC

    Tiki Cruise in Washington, DC

    Cruise the Potomac with a welcome drink, onboard bar, and waterfront views

    4.8 • 387 reviews
    $72/ person
    Double Kayak Rental in Washington, DC

    Double Kayak Rental in Washington, DC

    Rent a double kayak on the Anacostia River from James Creek Marina

    4.5 • 227 reviews
    $40& up
    Little Blackwater River Kayak Rental

    Little Blackwater River Kayak Rental

    Paddle a brackish river beside Blackwater Refuge

    4.9 • 556 reviews
    $34/ kayak
    Private Potomac River Fishing Charter

    Private Potomac River Fishing Charter

    Catch-and-release fishing with Washington, DC views

    5.0 • 15 reviews
    $689& up
    6-Hour Solomons Fishing Charter

    6-Hour Solomons Fishing Charter

    Fish for seasonal gamefish on a shared charter with gear and filleting included

    4.9 • 188 reviews
    $159/ person
    Canoe Rental in Annapolis

    Canoe Rental in Annapolis

    Paddle from Eastport or take a canoe to your favorite launch spot

    4.9 • 173 reviews
    $41/ canoe
    Alexandria 10-Hour Sailing Course

    Alexandria 10-Hour Sailing Course

    Build practical sailing skills with hands-on Flying Scot instruction

    4.6 • 114 reviews
    $583/ person
    Private 45' Luxury Yacht Charter in Washington DC

    Private 45' Luxury Yacht Charter in Washington DC

    Relax on the water while an included captain and crew handle the cruising

    $1,284& up
    Full-Day Private Sailing Charter in St. Michaels

    Full-Day Private Sailing Charter in St. Michaels

    Private catamaran sailing with harbor views and Miles River breezes

    5.0 • 1.4K reviews
    $3,453
    Kayak Rental in Deale

    Kayak Rental in Deale

    Explore Deale's creeks, estuaries, and bay by kayak

    4.6 • 36 reviews
    $32/ kayak
    St. Michaels 8-Hour Guided Boat Trip

    St. Michaels 8-Hour Guided Boat Trip

    Cruise the Chesapeake Bay to explore historic St. Michaels by boat

    4.7 • 199 reviews
    $1,229/ boat
    20' Pontoon Boat Rental in Solomons
    Up to 8

    20' Pontoon Boat Rental in Solomons

    Cruise the Patuxent River at your own pace by pontoon

    4.6 • 52 reviews
    $353/ boat
    Private 1950s Deadrise Boat Charter in St. Michaels

    Private 1950s Deadrise Boat Charter in St. Michaels

    Explore Chesapeake Country on a private cruise shaped around your interests

    $464/ boat
    Tandem Kayak Rental on the Anacostia River

    Tandem Kayak Rental on the Anacostia River

    Paddle the Anacostia River from Ballpark Boathouse

    4.4 • 22 reviews
    $38/ kayak
    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