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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 73-96 of 153 results
    Kayak & Wine Tasting Tour on the Chicamacomico River

    Kayak & Wine Tasting Tour on the Chicamacomico River

    Paddle the Chicamacomico River, then tour the winery and taste wine

    4.9 • 556 reviews
    $122/ person
    Private Potomac River Sightseeing Cruise in Washington, D.C.

    Private Potomac River Sightseeing Cruise in Washington, D.C.

    Cruise the Potomac in a private cabin boat for up to 6 guests

    5.0 • 15 reviews
    $1,325& up
    Private Full-Day Fishing Charter in Solomons

    Private Full-Day Fishing Charter in Solomons

    Private fishing charter with gear, cooler, and fish filleting included

    4.9 • 188 reviews
    $2,035
    Annapolis Sit-On-Top Kayak Rental

    Annapolis Sit-On-Top Kayak Rental

    Launch from Eastport or paddle at your favorite spot

    4.9 • 173 reviews
    $29/ kayak
    Private Harbor Cruise in Solomons Island, MD

    Private Harbor Cruise in Solomons Island, MD

    Bring your group together for a laid-back escape on the water

    4.9 • 153 reviews
    $1,325
    Private 36' Hinckley Yacht Charter in Annapolis

    Private 36' Hinckley Yacht Charter in Annapolis

    Leave the cruising to your captain and relax on the water

    5.0 • 14 reviews
    $1,007
    Full-Day Private Sailing Charter in St. Michaels

    Full-Day Private Sailing Charter in St. Michaels

    Private Chesapeake Bay sailing aboard a 1935 ketch

    5.0 • 1.4K reviews
    $3,868
    2-Hour Private Chesapeake Bay Boat Charter

    2-Hour Private Chesapeake Bay Boat Charter

    Celebrate your occasion aboard a private party boat on Chesapeake Bay

    5.0 • 37 reviews
    $1,674& up
    4-Hour Guided Cruise to Annapolis

    4-Hour Guided Cruise to Annapolis

    A relaxed captain-led ride through Chesapeake Bay tributaries to Annapolis

    4.7 • 199 reviews
    $819& up
    Private Fliteboard eFoil Lesson in Annapolis

    Private Fliteboard eFoil Lesson in Annapolis

    Build your confidence above the water with step-by-step coaching

    4.7 • 134 reviews
    $318& up
    2-Hour Navy Yard Sightseeing Cruise

    2-Hour Navy Yard Sightseeing Cruise

    Sail the Anacostia and Potomac with an onboard bar and landmark views

    4.8 • 387 reviews
    $66/ person
    Captained Potomac River Pontoon Rental in Washington, DC
    Up to 10

    Captained Potomac River Pontoon Rental in Washington, DC

    Share time on the water with friends or family

    5.0 • 6 reviews
    $1,396/ boat
    2-Hour Guided Kayak Tour on Little Blackwater River

    2-Hour Guided Kayak Tour on Little Blackwater River

    Paddle brackish waterways with a guide and look for local wildlife

    4.9 • 556 reviews
    $85/ kayak
    Private Sunset Cruise on the Potomac in Washington, D.C.

    Private Sunset Cruise on the Potomac in Washington, D.C.

    Cruise the Potomac at sunset on a private boat for up to 6

    5.0 • 15 reviews
    $1,325
    Full-Day Private Fishing Charter in Solomons

    Full-Day Private Fishing Charter in Solomons

    Private fishing time to follow seasonal bites farther from shore

    4.9 • 188 reviews
    $2,131
    Annapolis Tandem Sit-Inside Kayak Rental

    Annapolis Tandem Sit-Inside Kayak Rental

    Paddle together at your favorite Annapolis-area spots

    4.9 • 173 reviews
    $41/ kayak
    Stand-Up Paddleboard Rental in Alexandria VA

    Stand-Up Paddleboard Rental in Alexandria VA

    Glide across the water on a stable stand-up paddleboard for a flexible 1- or 2-hour session

    4.6 • 114 reviews
    $30& up
    Private Morning Hinckley Yacht Charter in Annapolis

    Private Morning Hinckley Yacht Charter in Annapolis

    Leave the cruising to your captain and enjoy a relaxed morning on the bay

    5.0 • 14 reviews
    $1,007
    Private Half-Day Sail on a 1935 Ketch in St. Michaels

    Private Half-Day Sail on a 1935 Ketch in St. Michaels

    Sail the Miles River aboard a historic 1935 ketch

    5.0 • 1.4K reviews
    $3,453
    Fall Foliage Cruise in Kent Narrows

    Fall Foliage Cruise in Kent Narrows

    Cruise Chesapeake Bay waterways with fall views and complimentary warm apple cider

    5.0 • 37 reviews
    $45/ person
    Guided 4-Hour Boat Cruise to Galesville

    Guided 4-Hour Boat Cruise to Galesville

    Cruise Chesapeake Bay coves and historic waterfronts en route to Galesville

    4.7 • 199 reviews
    $819& up
    24' Center Console Boat Rental in Solomons
    Up to 8

    24' Center Console Boat Rental in Solomons

    Cruise the Patuxent River for fishing, swimming and water sports

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

    Private Tiki Cruise in Washington, DC

    Celebrate on a private floating bar cruise past Washington, DC landmarks

    4.8 • 387 reviews
    $60/ person
    Self-Drive Potomac River Pontoon Rental in Washington, DC
    Up to 10

    Self-Drive Potomac River Pontoon Rental in Washington, DC

    Share a Bentley pontoon outing with friends or family

    5.0 • 6 reviews
    $2,617/ boat
    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