Maryland’s capital city is a must-visit for those looking to experience history, culture, and entertainment. Its convenient location, endless activities, and excursions provide something for everyone. Whether it’s a solo trip or family vacation, Annapolis does not disappoint.

Here’s how to make the most of your visit to one of America’s most charming cities:

Book a stay at Annapolis Waterfront Hotel

Located in downtown Annapolis is the Annapolis Waterfront Hotel. This one-of-a-kind property is ideally in the Annapolis Harbor. The guest rooms are newly renovated featuring luxury amenities and modern decor. One King or Two Queen rooms and suites are available with numerous rooms offering breathtaking views of the water and the surrounding area. Valet parking is available for all guests and warm hospitality awaits when you check-in. 

This Marriott International’s Autograph Collection hotel is steps away from eateries, shops, and other area attractions including the United States Naval Academy.  Pusser’s Caribbean Grille is on-site serving breakfast, lunch, and dinner with dockside seating available. 

The hotel’s welcoming staff goes above and beyond to ensure your stay is exceptional no matter how short or long.  

Take a Stroll Through Downtown Annapolis and the Waterfront 

Annapolis is a true historic, waterfront town. Starting on Main Street, a visit to locally owned businesses, restaurants, and bars, is a must. The 300-year-old buildings are a reminder of the past, while its lively atmosphere shows why Annapolis is ranked as one of America’s most walkable towns. More lodging, music venues, and incredible views await at every turn, including the Maryland State House. 

Discover Annapolis’s Rich African American History and Culture 

Annapolis and Anne Arundel County is dedicated to preserving Maryland’s rich history, heritage, and culture of the people of the African Diaspora. 2024 marks the 60th anniversary of the signing of the Civil Rights Act. The Maryland Commission on African American History and Culture along with the museum have declared this year as “Maryland’s Year of Civil Rights. 

Located on the site of the former Mount Moriah African Methodist Episcopal Church; the Banneker- Douglass Museum is the state’s official repository of African American material culture. While the original building still stands, a recent four-story addition to the museum serves as an excellent source of information and interactive displays. Thomas James’ REVISIT/REIMAGINE is the museum’s newest exhibit showcasing Maryland’s African American leaders, history, and overall experience. 

The city recently celebrated Juneteenth with a lively parade and Juneteenth Festival held at the Bates Athletic Complex. Citizens, local leaders, visitors, and vendors gathered for a full day of music, entertainment, and pride. 

Enjoy Diverse Dining Options 

Annapolis has a large number of restaurants and eateries to satisfy every craving you may have. From fast-casual to fine dining, there’s no need to leave the area. For breakfast lovers, be sure to visit Chick & Ruth’s. This Annapolis institution serves breakfast all day and has been around for over 50 years. No Maryland city visit is complete without crabs! There are many well-known crab houses in and around downtown. For unparalleled views, live music, and a bright and lively atmosphere, The Choptank is the place to go. Local seafood is the highlight and dishes like the crab dip and scallops are a hit.

Explore the Bay by Boat

Perhaps the best way to experience Annapolis and the Bay Area is from the water. Get your feet wet and truly enjoy the Chesapeake. There are several sailing, fishing charters, and boat rentals available. Often called the Sailing Capital of the U.S., getting out on the water is a must. Whether it’s for a few hours or even overnight, what’s better than time spent onboard a boat? Gather your crew and enjoy the green way of riding a boat with Annapolis Electric Boat Rentals. The boats are noiseless, safe, and reliable. A few options for routes are provided as you explore Annapolis’s waterways admiring the remarkable homes and boats. 

Discover Entertainment and Nightlife

The fun in Annapolis doesn’t end when the sun goes down. Many would argue that it’s just beginning. The city’s restaurants, bars, and nightlife venues come alive for whatever itinerary you can imagine. From small bites, to live music, ghost tours, and even speakeasies, your days end when you decide to. 

No matter what you’re looking to experience, you are sure to find it in Annapolis. If you haven’t already, pack your bags and let the adventure begin!