Sailboats in Chesapeake Bay, Maryland
Sailboats in Chesapeake Bay, Maryland (Tim Tadder/courtesy, Maryland Office of Tourism)

Chesapeake Bay Active and Adventure Travel Tips

  • Learn to sail out of scenic Annapolis Harbor with the Annapolis Sailing School, or the Chesapeake Sailing School. Courses include kids' classes, two-day introductory programs, or weeklong live-aboard certification courses.
  • Explore the bay by kayak to get close to wildlife and experience the bay's diverse ecosystem. Check with the Chesapeake Paddlers Association for information on outfitters, recommended trips, and rentals.
  • Bike the quiet Maryland back roads around Deale, passing marshland, soy fields, local tributaries, and local crab joints for a taste of the bay's famous seafood.
  • On the wild beaches of Assateague Island National Seashore, you can camp, fish in the surf for your dinner, and explore the dunes and forest trails. (But beware of vicious horseflies and mosquitoes in high summer.)
  • Go where the watermen gather for a pitcher of beer and a table covered with crabs at a local institution such as Cantler's Riverside Inn in Annapolis.


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Hotels


Inn at Perry Cabin - Hotel

308 Watkins Lane
St Michaels21663

Distance: 16.6 mi.
(from destination center)

Hotel Class: 5 class stars

expert favorite hotel
Editor Rated & Recommended
5_0

Annapolis Marriott Waterfront - Hotel

80 Compromise Street
Annapolis21401

Distance: 5.6 mi.
(from destination center)

Hotel Class: 4 class stars

Expert Rated & Recommended
4_0
4_0

Chesapeake Beach Resort and Spa - Hotel

4165 Mears Avenue
Chesapeake Beach20732

Distance: 22.6 mi.
(from destination center)

Hotel Class: 2 class stars
Expert Rated & Recommended
4_0
3_0

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Attractions


Hog Rock-Blue Ridge Summit Loop

Catoctin Mountain Park
66602 Foxville Road
Thurmont, Maryland 21788-1598

Distance: 73.3 mi. (from destination center)

Description: This is a five-mile loop from the park's main visitor's center that takes in the panoramic views... Read More
Editor Rated & Recommended
5_0

Old Rag



Distance: 110.8 mi. (from destination center)

Description:

This very popular hike along an inclined saddleback ridge is well worth doing (especially very... Read More

Editor Rated & Recommended
5_0

Annapolis Sailing School

7001 Bembe Beach Road
Annapolis, Maryland 21403

Distance: 5.2 mi. (from destination center)

Description:

Very early in the history of Annapolis Sailing School, they realized that the best way to learn... Read More

Editor Rated & Recommended
4_0

Airports

Major Airports near Chesapeake Bay

Distance (mi.)
Baltimore/Washington International Airport 19.2map
Washington Ronald Reagan National Airport 36.2map
Washington Dulles International Airport 57.3map

Other Smaller Airports near Chesapeake Bay

Distance (mi.)
Salisbury-Ocean City Wicomico Regional Airport 65.6map
Harrisburg International Airport 83.3map
Hagerstown Wash. County Regional Airport 86.3map
More Airports

Chesapeake Bay Active and Adventure Advice

  • Top Ten American Family Adventures
    Adventure need not stop now that kids are in tow. With a slight change in activities and destination, your adventurous side can continue on as always, except now you'll sport a car-seat and an extra suitcase. Gorp Top Ten
  • The Wild Shore Takes Flight
    Serious birdwatchers know that Virginia’s Eastern Shore is the place to be each fall, as millions of songbirds, raptors, shorebirds, and waterfowl fly south for the winter along the Mid-Atlantic flyway. Newbies can get acquainted with it all during the Eastern Shore of Virginia Birding & Wildlife Festival, held each September. Gorp Travel

Chesapeake Bay Active and Adventure Travel Guides


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