Annapolis Maryland waterfront

Annapolis Maryland Day Trip or Weekend Getaway by the Bay

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.

Annapolis Maryland Getaway by the Bay

Annapolis Maryland Getaway by the Bay

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.

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, and check out historic houses in a variety of architectural styles.

Interesting architecture Annapolis

Interesting architecture Annapolis

Narrow alley Annapolis

Narrow alley 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 capitol.

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 with additional figures and text documenting 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 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

Dine 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.

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.

Back room at Galway Bay Annapolis

Back room at Galway Bay Annapolis

In front of the Loews Annapolis hotel on West Street, BAROAK serves over 70 varieties of local craft beer and international brews in a sleek taproom with plenty of outdoor seating. They also make delicious omelets, perfect if you plan to overnight at the Loews Annapolis.

BAROAK at Loews Hotel

BAROAK Taproom at Loews Annapolis Hotel

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

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

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 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.

Visit our sister site, McCool Travel, for a few more fun Annapolis places to eat.

Where to Stay During Your Annapolis Maryland Getaway

We recommend Loews Annapolis Hotel 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.

Loews Annapolis Hotel room

Lovely room at Loews Annapolis Hotel

Downstairs, the lobby offers comfy couches and giant board games indoors, and a row of white rockers outside.

Loews Annapolis Hotel lobby

Loews Annapolis Hotel lobby

Check rates and availability at Loews Annapolis hotel 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.

Follow Fun in Fairfax VA on FacebookTwitterPinterest, and Instagram for more great things to do, places to visit, and special events in the greater Washington DC region.

We were hosted by Visit Annapolis during our most recent visit. All text, photos, and opinions are our own.

Annapolis Maryland US Travel. Day trip or weekend getaway with things to do, restaurants, and places to visit in Annapolis Maryland.  

This article was originally published in 2015 and updated in February 2018.

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10 Responses to “Annapolis Maryland Day Trip or Weekend Getaway by the Bay”

  1. Jessica The Dining Traveler September 15, 2015 at 7:49 am #

    Great recap of the trip. Annapolis is one of my favorite day trips from DC!

  2. McCool Travel September 15, 2015 at 8:04 am #

    So much to do in Annapolis. So different than Washington, DC but so close.


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