Exploring the Chesapeake Bay by Boat

As one of the most prominent geological features of the Mid-Atlantic region, the Chesapeake Bay is also the largest estuary in the United States. The total shoreline, including tidal tributaries, is 11,684 miles, circumnavigating a surface area of 4,480 square miles. It is also a remarkably beautiful place to visit.

Our proximity to The Bay presents opportunities for day trips or weekend getaways throughout the year. Still, summer is definitely the perfect time to get out and explore life in and on the water. Here are some of our favorite counties and towns on or near the Bay where boats are a way of life.

Photo courtesy of Talbot County

Talbot County, Maryland

Talbot County, including the towns of Easton, Oxford, Saint Michaels, and Tilghman Island, boasts a variety of waterways from the Bay to rivers and creeks. Whether you keep a boat in a local marina or rent for a short time, there are many ways to explore the area by water. Sailing, fishing, kayaking, and power boating are all popular. You can even ride on the Oxford-Bellevue Ferry, America’s oldest privately owned ferry.

Boat-related events also draw visitors to the area. Check out the following coming up this fall:

Learn to sail at the Tred Avon Yacht Club with Junior and Adult Sailing programs, and check out their racing calendar for events all year.
Charity Boat Auction at Chesapeake Bay Maritime Museum, Saint Michaels, September 2, 2023 | 8AM-12PM
The 40th Mid-Atlantic Small Craft Festival at Chesapeake Bay Maritime Museum, Saint Michaels, October 6-8, 2023 | 10AM-5PM
Tilghman Island Day – Saturday, October 21, 2023

Photo courtesy of Watermark Tours Charters Cruises

Annapolis, Maryland

Annapolis, the capital of Maryland, is a quaint town located on the Severn River and the Chesapeake Bay. It’s a great place to catch a cruise on the water with Watermark. Check out their full list of public cruises or book a private yacht charter for a special occasion.

Annapolis Harbor & U.S. Naval Academy Cruise

Annapolis City Dock

Step aboard the classic Harbor Queen for a narrated cruise of the Annapolis Harbor and the banks of the U.S. Naval Academy. Hear the history of the Naval Academy, Annapolis’ role as a historic seaport, and the region’s waterways, and catch a glimpse of the Chesapeake Bay Bridge.

$22 Adult & $8 Child | Tickets

Chesapeake Bay Bridge Cruise

Annapolis City Dock

This 90-minute cruise will take you through Annapolis’ historic harbor and by the U.S. Naval Academy. Then you will cruise under the twin spans of the Bay Bridges and marvel at this feat of engineering that connects the eastern and western shores of Maryland.

$32 Adult & $15 Child | Tickets

Bay Lighthouse Cruise

Annapolis City Dock

Pass under the twin spans of the Bay Bridge and past three Chesapeake lighthouses: Sandy Point Shoal, Baltimore Harbor, and Thomas Point on this award-winning 3- to 3½-hour cruise.

$59 Adult & $28 Child | Tickets

Photo courtesy of Northumberland County

The Northern Neck, Virginia

Steeped in history and known for excellent fish, crabs, and oysters, the Northern Neck is nestled between the Potomac and Rappahannock Rivers with the two easternmost counties, Northumberland and Lancaster, directly bordering the Chesapeake Bay. Marinas for recreational and commercial boating abound making it a great location to book a cruise, paddle quietly through nature, or cast some lines.

Northern Neck Water Trails

Scenic Views Map

Bring your own boat, or rent a canoe or kayak at one of the state parks to explore smaller marshes and creeks. Designed for biking and paddling, the Virginia Department of Conservation & Recreation has created a Story Map that follows the scenic views along water trails in the Northern Neck Heritage Area. Pack

Tangier Island Cruises

468 Buzzards Point Road, Reedville, VA

Cruise across the Chesapeake Bay to Tangier, VA. Spend the day eating the freshest seafood and exploring the hidden gems of a Virginia Historic Landmark. Tangier Island Cruises also offer evening and sunset cruises.

Tickets

Take a look at our website for all of our listings available throughout Washington, D.C., Maryland, and Virginia.