Waterside parking at Annapolis City Dock

Randall and Dock Street
Annapolis, MD 21401

Captain Smith must have had a blast when he pulled up to Annapolis City Dock and sat down at one of the many outdoor cafes. His 17th century sailing vessel certainly would have stood out among the yachts and speed boats with which it shared the docks. Thus, my official Captain John Smith Chesapeake Bay National Historic Trail activity for Maryland was to spend the afternoon just as Captain Smith did all those years ago, viewing the sail boats, taking a cruise on the Chesapeake Bay, and having lunch in one of the many restaurants that line this Annapolis, Maryland, tourist area.

Hundreds of boats are moored in the Annapolis harbor

All joking aside, Smith certainly would have passed through the area that would go on to become Annapolis. Along with the Annapolis City Dock, the Annapolis Maritime Museum is also an official stop on the Smith Trail. In fact, just taking a boat trip on the harbor or into the bay would qualify as an official Smith Trail activity.

Sailing and boating in the harbor

I did not see the entire city, but I can say that I would definitely add Annapolis to the list of cities I would like to live in, provided I was rich enough to hang out at the City Dock area on a regular basis. It is certainly a cool place to visit, similar to San Francisco’s Fisherman’s Wharf. Along with having lunch, I took a cruise to the mouth of the Chesapeake Bay. Several cruise companies are located on the docks and offer cruises of various lengths. Just walk up and buy a ticket. In addition to the restaurants and tours, there are also plenty of shops to visit, giving tourists and locals alike ample opportunity to fill the day.

Many day cruise ships leave from the docks

Dock area serves as a people watching park

Arrive by yacht or paddle board

Boats of various sizes use the docks

Arrive by kayak

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