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How To Spend An Incredible Weekend In Beautiful Annapolis


Source: Travel Awaits, Jill Dutton

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Annapolis, the capital city of Maryland, is located on the Severn River where it meets the Chesapeake Bay, making it a perfect place to get out on the water from spring through October. The boats come off the water at the end of October, but a fall visit will bring crisp weather and the invigoration of sailing with the wind in your face.

If you love a city with distinct seasons, Annapolis has activities to enjoy, no matter the season. Whenever you choose to visit, here’s how to spend an incredible weekend in beautiful Annapolis.

Things To Do In Annapolis

Known as America’s Sailing Capital, Annapolis is a place to spend time on the water — or just watch the waves lap against the shore — but there’s also plenty of history, unique dining, shopping, and nature in this walkable city.

Take A Cruise Aboard The Wilma Lee

The Annapolis Maritime Museum, a not-for-profit educational facility where you can learn about the maritime heritage of Annapolis, now offers a cruise aboard the Wilma Lee. The Wilma Lee is a skipjack listed on the National Register of Historic Places by the National Park Service. Constructed in 1940, she dredged the Chesapeake Bay for 60 years. She has been under restoration since 2018 and is now ready for guided cruises. Excursions include Heritage Tours, Sunset Cruises, Wednesday Night Race Watch Parties, and private charters. The Wilma Lee will be used as an interactive tool to teach about maritime history, oyster dredging, and Chesapeake Bay’s ecology.

Before or after your cruise, take in all the exhibits, tour the Thomas Point Shoal Lighthouse, and visit the museum’s art gallery.

Spend A Day At The Beach

Enjoy a day on the 786-acre Sandy Point State Park on the northwestern shore of the Chesapeake Bay. Take in the views while relaxing on the mile-long public beach and swimming. Or try your hand at crabbing or fishing. If you have your boat with you, there are even 22 public boat ramps for easy access to the Chesapeake Bay. Or use the craft launch ramp for your kayak, canoe, or stand-up paddleboard.

Cruise The Annapolis Harbor Aboard The Harbor Queen

Watermark, in its 47th year of offering cruises, has a variety from which to choose: a Fall Foliage Bay Lighthouse Cruise, a City Lights Cruise, and a Day on the Bay to St. Michaels are just a few of the options.

The Annapolis Harbor and USNA Cruise aboard the Harbor Queen takes you on a narrated cruise of the Annapolis Harbor and the banks of the U.S. Naval Academy. New this year is the option for tableside service, so you can dine during the 40-minute cruise while hearing about the history of the Naval Academy, the region’s waterways, and Annapolis’s role as a historic seaport.

Take A Guided Tour Of The William Paca Garden

Learn about history and horticulture at this 2-acre 18th-century pleasure garden located behind the home of William Paca, a signer of the Declaration of Independence. Enjoy an educational tour or stroll on your own. There’s also a tour of Paca’s two-story home on which you can learn about life in high society in the 1700s. The guided garden tour is currently limited to six people.

Explore The Walkable Town

With a downtown historic district that’s less than a square mile in size, it’s easy to park your car and get around on foot. Walk past the homes of several signers of the Declaration of Independence, such as the William Paca House and Garden, the Chase-Lloyd House, and the Charles Carroll House.

It’s an easy walk to the Banneker-Douglass Museum, Maryland’s official repository for African-American heritage. You’ll find exhibits that celebrate African-American history and culture.

Located in the heart of downtown Annapolis, the Annapolis City Dock is home to shops and art galleries.

After so much walking, don’t miss the chance to sit down for a bit with a cup of coffee and friendly service at Bitty and Beau’s. People with intellectual and developmental disabilities run the shop. Visitors enjoy stopping for a cup of coffee and a unique customer service experience. While you’re there, purchase one of their #notbroken T-shirts or a hat to support the inclusion and acceptance of people with disabilities.

Keep Walking On A Guided Tour

Whether you want to learn about the Golden Age of Annapolis and its architecture or take a walking tour of 18th-century architecture, there are several guided tours to choose from, including Scandalous Annapolis and Colonial Annapolis.
While this one is by boat, the Spirits and Spirits tour is a ghost tour of the Annapolis Historic District where you’ll learn about the haunted waterways and other ghost stories.

Visit A City Within A City

Although Eastport is technically part of Annapolis, you’ll find it has its own unique personality. After a tongue-in-cheek secession from Annapolis in 1998, the area now calls itself the Maritime Republic of Eastport. Take a water taxi or simply walk from downtown Annapolis to Eastport. While there, be sure to sample some of the bars and restaurants, and then spend time shopping at unique shops such as Annapolis Maritime Antiques and Quirk n Bach Pottery.

Best Restaurants In Annapolis

Fresh seafood is always on the menu in Annapolis, but you can also enjoy a range of tastes from steaks to ethnic cuisine at a variety of restaurants.


While still in the reopening stages, Flamant is open on the weekends. In the meantime, it’s worth it just to taste the divine creations by utilizing their Flamant at Home menu. This specially curated menu changes each week based on seasonality and the chef’s imagination — one specialty is the Surf and Turf with grilled prawns, beef tenderloin, green peppercorn sauce, leeks-potato mash with black truffles, and French green beans.

Reynolds Tavern

Many restaurants feel the need to get creative with dining options these days, and Reynolds Tavern is no exception. They’re in the process of introducing outside dining in a bubble this fall. Whether you dine indoors or in the new bubble, consider starting with an order of the baked Brie. This decadent appetizer is wrapped in a puff pastry and served with a Kahlua cream sauce laced with brown sugar, raisins, and pecans.

Since you are in Maryland, you may want to taste some of the famous crab. For an entree, try the Chesapeake crab cakes — two broiled crab cakes served with red bliss mashed potatoes, succotash, and a red pepper remoulade.

Farmers Markets

Choose from several farmers markets in Anne Arundel County to sample local produce, cheese, jams, and other market fare. It’s a great way to get outdoors while enjoying the local bounty.

Recovery Zones

Annapolis has created several Recovery Zones to provide residents and visitors the chance to dine and shop outdoors. In these areas, the streets are closed to vehicular traffic at designated times, allowing restaurants additional seating opportunities and shopowners additional retail space.

Best Hotels In Annapolis

Enjoy a newly renovated waterfront hotel with easy access to all water activities at Annapolis Waterfront Hotel. The location is ideal, not only because it’s located on the water, but also because it’s near the U.S. Naval Academy and the heart of downtown Annapolis.

In the arts district, stay at the ever-so-artsy Graduate. You’ll find nautical motifs befitting the location interspersed with art that celebrates Annapolis history and campus lore. The maritime vibe carries into the Camp Severn Shore, where they serve coastal foods alongside classic cocktails. Whether you choose a room or a suite, the practical and fun decor enhances the stay. Go big with a stay in the Presidential Suite — their crowning, collegiate jewel. In addition to a living room that includes a sleeper sofa, dining table, wet bar, half bath, and two seating areas, there’s a separate master bedroom with a king-size bed that overlooks downtown Annapolis.

If a bed and breakfast is more your style, Flag House Inn and the Inn at Horn Point are two popular options.

Flag House Inn consists of two townhouses built in 1879. Although they’ve kept the traditional decor of the historic homes, they also offer modern amenities and innovative meal options — with an emphasis on fresh, local, and filling — in the dining room.

Located in the eclectic Eastport neighborhood, the Inn at Horn Point is just a short walk to the City Dock area. The breakfast ingredients are sourced from local farmers markets, specialty food stores, and even their own herb garden, and the three-course breakfast features a fresh fruit course, an intermezzo, and a savory or sweet main entree. One sweet favorite is the creme brulee French toast served with thick-sliced bourbon Applewood-smoked bacon.

Pro Tip: Before you visit, take a virtual tour of Annapolis to learn more.

While you’re in Maryland, don’t forget to explore Baltimore. It’s less than 40 miles north of Annapolis and is full of hidden gems!

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