Annapolis Maryland Day Trip or Weekend Getaway by the Bay

Updated on April 6, 2024 by Julie McCool

Annapolis Maryland is full of interesting history, delicious food, quaint neighborhoods, and of course, plenty of ways to get out on the water. Just an hour from Northern Virginia, and even closer to Washington DC, Annapolis is ideal for a weekend getaway for romance, time with friends, and family fun.

Often overshadowed by bigger and busier Baltimore, Annapolis is a more relaxing and easy day trip from Northern Virginia, but stay for a night or two if you can. Just don't try to make the drive during rush hour.

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An Annapolis Maryland day trip or weekend getaway delivers history, dining, shopping, and fun on the water, just a short drive from Washington DC.

We've made several trips to Annapolis—with and without kids—from quick visits, to day trips, to weekend getaways, and we always discover something new to love about this small city by the Chesapeake Bay. This is a popular warm-weather destination, but it's also lovely in quieter months. In December Annapolis becomes a beautiful Christmas town, perfect for holiday shopping and fun.

Fun Things to Do in Annapolis Maryland

Annapolis has a nice, compact downtown and the Visitor Center on West Street is a great place to begin your visit. There is limited parking out back and a pay lot next door. Stop in to pick up maps and info, and to learn about any special events in town.

Annapolis Visitor Center
Annapolis Visitor Center

Take a Tour

For a great overview of the city, consider taking a Discover Annapolis Trolley Tour, which begins at the Visitor Center. You'll visit hidden side streets and bridges while learning about the town's history and architecture. You'll also stop at the Severn River Overlook for lovely views of the river, the U.S. Naval Academy, and the World War II Memorial.

Severn Memorial view Annapolis
Severn River Overlook view

Explore History and Architecture

Annapolis has a storied colonial and maritime history and is a lot of fun to explore on foot. From the State House on top of the hill, down to the waterfront, you can meander on quaint streets and alleyways. As you explore, check out the many historic houses in a variety of architectural styles.

Interesting architecture Annapolis
Interesting architecture Annapolis
Pinkney St cobblestones Annapolis
Pinkney St cobblestones Annapolis

At the Maryland State House, take a self-guided tour to see the restored Old Senate Chamber, where George Washington resigned his commission as Commander in Chief in 1783. The beautiful rotunda, the new Senate and House Chambers, and exhibits and paintings tell the story of the first and only state house to serve as the nation's capital.

Annapolis Maryland State House
Annapolis Maryland State House
Maryland State House chambers
Maryland State House chambers
George Washington Maryland State House
George Washington Maryland State House, Annapolis

The Thurgood Marshall Memorial, near the State House, includes a statue of Marshall as a young lawyer. Additional figures and text document his struggle for equal rights under the law.

Thurgood Marshall Memorial Annapolis
Thurgood Marshall Memorial Annapolis

At City Dock, the Kunta Kinte-Alex Haley Memorial, depicts the acclaimed author of Roots reading to three children of different ethnicities. You can also explore African-American heritage and history in Maryland at The Banneker-Douglas Museum on Franklin Street.

Alex Haley statue Annapolis Maryland
Alex Haley statue Annapolis Maryland

Historic Annapolis preserves and protects historic properties throughout the city, and visitors can tour several of them. Fans of history and nature will enjoy the William Paca House and Gardens, former home of a Governor and signer of the Declaration of Independence.

William Paca House and Gardens
William Paca House and Gardens, Annapolis

Visit the United States Naval Academy

Years ago, we strolled the grounds of the Naval Academy on our own. Now, you can explore the grounds on guided tours ($10.50 adults with senior and child discounts). If you're short on time, stop in the Visitor Center to check out the displays, watch a film about attending the Academy, and visit the gift shop.

USNA Visitors Center
USNA Visitors Center

Enjoy the Water

City Dock is the place to hang out and take in the Annapolis boating life. You can watch the yachts cruising up and down, and docked along, Ego Alley, or get out on the water on a tour boat.

Morning on Ego Alley Annapolis
Morning on Ego Alley Annapolis

One fun option is a narrated, 40-minute cruise on the Harbor Queen, which heads out to the harbor along the banks of the US Naval Academy. You'll have a glimpse of the Chesapeake Bay Bridge before heading back to the dock. Longer cruises are available to explore scenic lighthouses, pass under the Bay Bridge, or even let you join in a pirate adventure.

Naval Academy from Harbor Queen Annapolis
Naval Academy from the Harbor Queen tour boat

The Annapolis Water Taxi winds between the yachts to destinations throughout the harbor including Spa Creek, Back Creek, and Eastport.

Harbor taxi view Annapolis
Harbor taxi view Annapolis
Yacht line-up Annapolis
Yacht line-up from the water taxi Annapolis

Places to Eat and Drink in Annapolis Maryland

Annapolis is full of great restaurants and drinking spots, with historic settings, water views, and delicious food to tempt you back.

Irish Flavors at Galway Bay

There are some lovely Irish Pubs in town, and we highly recommend a stop at Galway Bay for Irish standards, delicious seafood, and a taste of their imported Irish Egg Nog. The egg nog is custom bottled in Galway Ireland and is only available in limited supply.

Back room at Galway Bay Annapolis
Backroom at Galway Bay Annapolis

The cozy, brick interior creates a comfortable setting for enjoying the seafood and Irish specials like Murphy’s Pot Roast served over Irish champ or the Salmon Galway Bay. We tried the Crab and Oysters Chesapeake, a satisfying and filling combination of crabcake and fried oysters with chips.

Waterfront Dining at Carrol's Creek Cafe

If you'd like a water view with your meal, take the water taxi or walk across the Spa Creek Bridge for dinner indoors or on the deck at Carrol's Creek Cafe. If you're a seafood fan you really should try the Sea Scallops rolled in shredded phyllo—so delicious! The generously portioned Herb Encrusted Rockfish with lump crab and tomato risotto is a perfect accompaniment to the sun slowly setting over the harbor.

Carrols Creek appetizers Annapolis
Carrols Creek appetizers Annapolis
Sunset view Carolls Creek Annapolis
Sunset view from Carrols Creek Annapolis

Historic Annapolis Dining at Federal House

Back on historic Market Place, Federal House serves up comforting American pub fare in a tavern built-in 1813. Ask for a table in the large bar area. Or enjoy a booth or table in the main dining room, with a view of the busy street scene. In warmer weather, it is fun to sit at a patio table and watch the Navy Midshipmen in their Summer Whites mingling with tourists along the harbor. The patio is also dog-friendly, and the restaurant even offers a menu of doggie treats.

Federal House bar area seating
Federal House in Annapolis Maryland

Someone recommended the cream of crab soup, and they were so right. The soup is creamy and rich, but not overly thickened, and full of chunks of crab. For our main course, we had the crab cake sandwich and the fish and chips. Both meals were very good—tasty and filling but not too heavy. We generally prefer thin sweet potato chips but the waffle-cut Federal House serves arre tasty too.

Breakfast All Day at Iron Rooster

Just two doors down from Federal House, Iron Rooster has been a popular spot for scratch-made comfort food, including an all-day breakfast menu, since it opened. The vibe is friendly and relaxed, and the staff is unfailingly cheerful. We sat near the window upstairs, but there is more seating downstairs and out front.

Start your visit with a refreshing cocktail, like the vodka-based Hen House and the Sriracharita we enjoyed with a side of bacon. Let’s face it, everything goes well with a side of bacon. If we had been a little hungrier we would have added a side of warm monkey bread too. Next time.

For dinner, we shared a plate of fried chicken and waffles—so delicious and so filling. But not so filling that we did not have room to share a maple bourbon pecan torte for dessert. It is as tasty as it looks.

Drinks and bacon at Iron Rooster
Drinks and bacon at Iron Rooster

Relax and Sip at Great Falls Winery

If you have a car and want a break from town, Great Frogs Winery is less than a 10-minute drive away (or a 3-mile hike if you're feeling ambitious). We were surprised to find a winery in Annapolis Maryland, but it is a fun place to relax and sip.

Great Frogs Winery vineyard
Great Frogs Winery
Great Frogs Winery dessert wines
Great Frogs Winery dessert wines

We were treated to a tasting of 5 wines, 3 dessert wines, and a fabulous cheese platter in the rustic tobacco barn, which serves as a tasting room and store. The dessert wines, particularly the port, were our favorite but everything tasted delicious.

Great Frogs has a nice relaxed vibe, with picnic tables and corn hole games out back to entertain the kids. Bring your own food or order a cheese platter (48 hours in advance). Limited indoor space means you'll need a reservation to enjoy a tasting.

Where to Stay During Your Annapolis Maryland Getaway

We recommend Graduate Annapolis for an overnight or weekend getaway in Annapolis Maryland. Their West Street location is excellent—a close walk to the State House and City Dock, but away from the crowds. Our floor was decorated with a nautical, stained-glass window, and our room was luxuriously comfortable, clean, and quiet.

Check rates and availability at Graduate Annapolis now!

On previous visits, we've stayed in local B&Bs, and there are many country inns and historic lodgings—like Reynold's Tavern and Gibson's Lodgings—to choose from as well.

Whether you are visiting for the day or the weekend, Annapolis Maryland makes a wonderful getaway from Washington DC and Northern Virginia. Easy to reach, easy to explore, and easy to love, we'll be heading back again soon.

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Some of our experiences were hosted by Visit Annapolis (website). All text, photos, and opinions are our own.

An Annapolis Maryland day trip or weekend getaway delivers history, dining, shopping, and fun on the water, just a short drive from Washington DC.
Visit Annapolis Maryland