Travel Spotlight on Annapolis and Its 14 Best Attractions

Hopper's travel guide to Annapolis features photos and info on its 14 best attractions, seafood restaurants and historic inns, and has tips from locals.

Hopper Editors - Oct. 26, 2017

A rich history and a vibrant contemporary sailing culture are two excellent reasons to visit Annapolis, the capital of Maryland. The town’s harbour is perhaps the best launching point into Chesapeake Bay, and where the two meet is an essential stop-off for those sailing the eastern seaboard. This means all manner of amazing boats pass through Annapolis, and landlubbers can sit back and watch them parade down the narrow strip of
waterway known as Ego Alley.

The history of the town’s relationship with the sea is explored at a couple of evocative maritime museums. Its broader settler history is preserved at a handful of colonial houses, and at the superb Banneker-Douglass Museum, which charts its African-American heritage. The town is surprisingly accessible to tourists, with a pretty and easily walkable downtown area. And after all this exploration, visitors can relax at several sublime seafood restaurants and waterfront bars.

See where U.S. Navy Officers are taught and trained at the United States Naval Academy

The heart of Maryland’s maritime life today is the US Naval Academy, the training ground for the country’s future force of Naval officers. It’s a grand and stately campus, with the largest single dormitory in the world, a giant pool with a 30-foot-tall ‘abandon ship’ platform, various sports facilities and an ornate chapel. Below the chapel is a crypt containing the grave of one of the Fathers of the United States Navy and hero of the American Revolution John Paul Jones. Visitors can view the Academy by taking a graduate-led tour.

Try out the trade that Annapolis was built on, sailing

There is a great deal of passion for sailing in Annapolis, and many locals refer to it as the sailing capital of the United States – the only state capital to have a large sailing community. For most of its history, of course, the town’s economy orbited pretty much entirely around its port. These days the place to sail is Chesapeake Bay, the largest estuary in North America. There are many ways to get out onto it – bring your own boat, compete in a race, rent a paddle boat, or take a tour aboard a schooner, cruise ship or kayak.

Discover Annapolis’ deep maritime heritage at the Annapolis Maritime Museum

Appropriately housed in the site of the the area’s only remaining oyster packing plant, this engaging little museum explores Annapolis’s maritime heritage. It looks through the many key roles that sailing and the sea have played in the town, whether in the seafood industry or in the lives of people who crossed expanses of open ocean. Visitors can also take a 1.5 mile boat trip out to the striking Thomas Point Shoal Lighthouse, where it overlooks Chesapeake Bay.

Enjoy inventive seafood dishes at the Boatyard Bar & Grill

This superb seafood grill is the kind of place seafood-lovers travel across the US to experience. It serves breakfast, lunch and dinner and integrates as much seafood as they can to create new and delicious dishes suited to each of the meals. A popular breakfast invention, for example, is "Eggs Annapolis": a twist on eggs benedict with a grilled tomato, spiced asparagus, and the Boatyard’s delectable lump crab meat.

Sleep in 18th-century luxury at the Historic Inns of Annapolis

Photo via their official FB page.

Modern luxuries mix with a carefully designed 18th-century style at the Historic Inns of Annapolis, a set of three historic buildings in the center of town. The history of each building is woven into the design of each hotel, sometimes in subtle decorative touches and sometimes in less subtle ways (a restaurant is called "the Treaty of Paris"). If you can tolerate a little kitsch, though, the Historic Inns are supremely characterful places to stay.

Get the Hopper app to find the best deals.
You could save up to 40% on your next flight!