Whether you crave water sports, museums, galleries, or a stroll through a quiet garden, Annapolis offers something to suit every taste.

One of the best ways to experience Annapolis is on the water. Rent a small private boat and discover hidden coves and creeks along the bay. Paddle through the water on a kayak or canoe, catch your own dinner on a sportfishing cruise, or unwind with a sunset sail. If you’re traveling with children, be sure to come aboard for the Pirate Cruise, where the kids get to dress up in pirate garb and fire water cannons.

Severn Inn, seen from the Naval Academy bridge


The past lives on in present day Annapolis, and there is much to see and discover. A great starting point is History Quest, where you can learn about all the ways to experience centuries of history and purchase tickets to walk with a colonial guide or take a trolley tour. Another must-see is the Annapolis Maritime Museum, which preserves 400 years of maritime history. For a glimpse of daily life in early Annapolis, visit the Benson-Hammond House, one of the area’s last surviving farmhouses. To follow in the footsteps of early African Americans, take the self-guided African American Heritage Walking Tour, which departs at the Historic Annapolis Foundation  the Museum Store, a shop offering many nautical and historically- themed books, jewelry, and souvenirs, of which quite a few are locally crafted. The tour includes the Kunte Kinte Alex Haley Memorial.

The Naval Academy offers guided tours and a free film from their visitors center inside Gate 1 near the City Dock.  Walking tours and trolley tours of the historic district  are available from the city's visitors center at 26 West Street and from HistoryQuest at 99 Main Street.  Narrated boat tours of the harbor depart from Susan Campbell Park at the dock.

 Speaking of tours, don't miss the Maryland State House, which is the oldest state house in America continuously used for legistation. George Washington gave his famous speech here when he resigned from the Continental Army. Open most days from 9:00 am - 5:00 pm, the State House no longer provides scheduled tours due to budget cuts, but you can still schedule an excellent curatorial tour of the State House in advance.  

Annapolis is also home to a vibrant arts and entertainment scene. Stop by the Annapolis Pottery to watch potters at work, catch a performance at the Bay Theatre Company, or explore one of the many art galleries downtown.  Maryland Hall for the Creative Arts is home to artisan and dance studios, the symphony orchestra, the ballet, the opera and chorale, and hosts concerts by world-class performers.

During the summer, don't forget to attend St. John's College croquet match, between the Johnnies (St. John's students) and Mids (Naval Academy midshipmen). Popular as social event, the match is a perfect time to gather with friends and enjoy the beautiful location and the entertaining costumes of fellow attendees.

 St. John's College campus

If you have time for a day trip, visit Historic London Town and Gardens, a 23-acre park in Edgewater, Maryland, that includes woodland gardens, a medicinal garden, and an early 18th seaport being reconstructed on the original foundations uncovered by cutting edge archaeology. For fishing enthusiasts, a getaway to Deale or Rose Haven, Maryland provides access to several marinas along the western shore of the Chesapeake Bay.

 

Interested in the shopping and dining in downtown Annapolis? Then park by St. John's College on King George Street -- free nine-hour parking! - and enjoy the walk to downtown past tiny private gardens and old historic homes. Once you reach downtown, grab some coffe from City Dock Coffee, a local institution. Then, run across the street to Then, head up Main Street and pop into Hats in the Belfry,which is full of both traditional and quirky hats for men and women. Don't miss Irish Traditions, a charming store that sells both Irish wares like Irish perfume, pottery, and clothing, as well as Irish-American, green doo-dads. If you are fortunate enough to come on a day when the manager is working, you will get a chance to hear a genuine Irish accent (County Wicklow, that is).

After leaving Irish Traditions with your stash of charming gifts from the land of Eire, walk right across the street to Francis Street, which will take you to State Circle. Just off State Circle is Maryland Avenue, a favorite street among locals. Stop by Evergreen Antiques, a tiny shop that sells carefully selected antiques, not junk, at reasonable prices. Among the wares are antique silver, retro jewelry, charming prints, and vintage furniture. Maryland Avenue also hosts street fairs throughout the year, including a Fall Festival and an Irish Festival.

Farther down the street is the Annapolis Bookstore, a book worms dream, and the quintessential small-town book shop. They recently opened a coffee and pastry shop, so you can munch while you read. The shop's offerings have included used and nearly new Agatha Christie novels, a like-new copy of Mufaro's Beautiful Daughters (a gorgeously illustrated Cinderella-style story set in Africa,), and some engraved "This book belongs to..." bookplates, not to mention an old-style inkwell, gold-colored ink... just about everything that can draw book lovers in like magnets. 

 By the way, Maryland Avenue, State Circle, and Main Street - and just about everywhere downtown - are decked out with live evergreen garlands and colorful wreaths, often of colonial inspiration, during the Christmas season. Each shop does it a little differently, some choosing thin, naturalistic pine garlands, while others hang thick branches heavy with ornaments and lights. Either way, a beautiful display that puts you in a Dickensian spirit right away. 

Christmas Decorations in Downtown Annapolis 

For lunch, stop by Galway Bay Irish Pub on Maryland Avenue. The restaurant serves authentic Irish food in a setting that will transport you back to the little pubs from The Quiet Man. The pub even has gluten-free options: Molly Malone's mussels are delicious, if you can order them without getting tongue-tied. Each year, Maryland Avenue blocks off the road to host a charming Irish Festival, which includes street vendors and performers. It drives Maryland Avenue residents nuts, but what a show!

Later, head back to Main Street to spend a few hours at Clay Bakers to paint your own pottery. The pieces are already made, so you just have to slap on the paint. They take care of the kiln firing, and the pieces are ready in about a week. If you are on a mission to paint a whole collection of eclectic dinnerware, Clay Baker's large selection makes it easily doable. Then, meet friends at 49 West for some great tea and coffee afterwards, serenaded by local jazz bands. The bar's street address is, incredibly, 49 West Street.

Later, enjoy a dinner cooked with locally-produced ingredients at Level on West Street, a tapas/small plates lounge with a delicious, ever-changing menu (including gluten-free!). Level inhabits a former townhouse, with brick walls, hip artwork and various cozy rooms. For your appetizer, you'll find artisan cheeses to savor, accompanied by sweet and savory garnishes. Entree favorites include the cauliflower soup (seasonal) and the radish risotta. 

 Drinks at Level: A Small Plates Lounge   

For a beverage, try the blueberry gimlet (foreground). The drink tastes like a quenching ade, perfect for summer, and doesn't taste a bit like alcohol. Which can be a problem. 

After dinner, grab some more coffee and enjoy a beautiful nighttime stroll along the docks. Sit on the benches, or dangle your feet over the water and watch the boats drifting past. Or head back to Galway Bay for dessert and wine (like the Montgras Cabernet Sauvignon or the Shiraz), a great way to end the evening.