Chesapeake Bay Cruises
Colonial capitals and crab towns on America’s largest estuary.
Get Free US Coastal Cruise QuotesChesapeake Bay cruises are America’s history lesson by water. The largest estuary in the United States wraps around Maryland and Virginia, and its shores hold the Naval Academy, colonial capitals, Revolutionary War battlefields and the crab-shack towns that still work the water.
The Typical Chesapeake Itinerary
The overnight Chesapeake cruise is a small-ship round trip from Baltimore. American Cruise Lines lists eight-night versions that call at St. Michaels, where the ship docks at the Chesapeake Bay Maritime Museum in the old shipbuilding village, and Annapolis, Maryland’s capital and home of the U.S. Naval Academy. Some itineraries continue down the bay to Virginia for Yorktown, Williamsburg and Jamestown; a Potomac River version adds Mount Vernon and Washington, D.C. Port lists vary by sailing, so check the one you are booking.
- Baltimore: Inner Harbor, Fort McHenry and Fells Point before or after you sail.
- Annapolis: brick lanes, the State House and the Naval Academy.
- St. Michaels: skipjacks, oyster history and an easy, walkable town.
- Virginia’s Historic Triangle: Jamestown, Williamsburg and Yorktown on longer sailings.
When to Go
Chesapeake Bay cruises are spring and fall trips. Lines schedule them that way because the bay is at its most comfortable for walking tours then: spring brings blossoms and mild days, while late September and October bring dry air and early color. Midsummer on the bay is hot and muggy, and the overnight small ships are generally elsewhere — usually in New England.
Who It Suits
This is a gentle cruise. Distances are short, the water is sheltered, and ports are close together, so seasickness is rarely an issue. It suits history readers, first-time small-ship cruisers and travelers who would rather not fly far: much of the East Coast can drive to Baltimore. It is less suited to anyone after beaches or nightlife.
Make a longer trip of it with a few days in Washington or Philadelphia. Best of the USA has local guides for both, and our cruise advisors at Mister Cruise can arrange the hotel nights as well.
Chesapeake Bay Questions
Where do Chesapeake Bay cruises start?
Most overnight Chesapeake Bay cruises are round trips from Baltimore. American Cruise Lines lists eight-night Baltimore round trips, and some versions add Virginia’s colonial sites or the Potomac River.
What is the best time for a Chesapeake Bay cruise?
Spring and fall, which is when the overnight small-ship sailings are scheduled. Summer is hot and humid on the bay, and winter is quiet.
Are there day cruises on the Chesapeake?
Yes. Harbor tours and sightseeing boats operate from Baltimore, Annapolis and other towns in season. They are a good taste of the bay but are not overnight cruises.
Getting to Baltimore and Making a Week of It
Baltimore is an easy embarkation city. BWI airport is a short drive from the harbor, Amtrak and MARC trains reach Penn Station, and much of the Northeast and Mid-Atlantic can drive in. Arrive the day before and walk the Inner Harbor, or take the water taxi to Fort McHenry, where the flag flew over the bombardment that inspired the national anthem. After the cruise, Annapolis and the Eastern Shore are worth a slower look by car.
Plan a Chesapeake Bay Cruise
Spring or fall, Maryland only or on to Virginia — our cruise advisors at Mister Cruise will find the Chesapeake sailing that fits.
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