Nearby Attractions

Entertainment

Live theater, immersive experiences, and family fun in the heart of Annapolis.

1804 West Street, Suite 200, Annapolis, MD 21401

Classic Theatre of Maryland

Experience the magic of live theater at the Classic Theatre of Maryland, Annapolis’s only year-round professional theatre company. Enjoy bold and entertaining interpretations of classical works, modern plays, and musicals in an intimate setting that brings you closer to the action.

723 Second St, Annapolis, MD 21403

Annapolis Maritime Museum & Park

Immerse yourself in the rich maritime history of the Chesapeake Bay at the Annapolis Maritime Museum & Park. Explore engaging exhibits on the bay’s ecology and the local oyster economy, and even set sail on a historic skipjack for an unforgettable on-the-water experience.

25 Silopanna Rd, Annapolis, MD 21403

Chesapeake Children's Museum

The Chesapeake Children’s Museum provides a hands-on learning environment where children can explore the ecology, technology, and diverse cultures of the Chesapeake Bay region. Through interactive exhibits and imaginative play, young visitors are encouraged to discover and learn at their own pace, making it an ideal destination for a fun and educational family outing.

40 West St, Annapolis, MD 21401

Mission Escape Rooms

Challenge your wits and teamwork at Mission Escape Rooms, where you’ll be locked in a themed room with only 50 minutes to solve puzzles, uncover clues, and escape. With a variety of immersive scenarios — from a mysterious Chesapeake Bay crabber’s boat to a fairy-tale crime scene — it’s an unforgettable adventure for friends and family.

On The Water

Set sail, cruise the bay, and soak in the waterfront charm of America’s Sailing Capital.

1 Dock St, Annapolis, MD 21401

City Dock Waterfront (Ego Alley)

Ego Alley is a must-see for any visitor to Annapolis — a narrow waterway where a parade of impressive yachts and powerboats creates a unique spectacle. Stroll along the waterfront, enjoy the lively atmosphere, and admire the stunning vessels that give this famous channel its name.

80 Compromise St, Annapolis, MD 21401

Schooner Woodwind Sunset Cruise

Experience the magic of an Annapolis sunset from the deck of a classic 74-foot wooden schooner. On the Schooner Woodwind Sunset Cruise, you’ll sail into the Chesapeake Bay, enjoying breathtaking views as the sun dips below the horizon. Help hoist the sails or simply relax and take in the stunning scenery for a truly unforgettable evening on the water.

1 Dock St, Annapolis, MD 21401

Watermark Cruises & Walking Tours

Experience the heart of Annapolis’s maritime culture with Watermark, a family-owned company with over 50 years of experience. Whether you choose a scenic cruise on the Chesapeake Bay aboard a classic yacht or a historic walking tour led by a guide in period attire, you’ll be immersed in the rich history and charm of this waterfront city.

311 Third St, Annapolis, MD 21403

Pirate Adventures on the Chesapeake

Embark on a swashbuckling adventure aboard a pirate ship with Pirate Adventures on the Chesapeake, a unique and interactive experience for the whole family. Children can dress up as pirates, have their faces painted, and even fire water cannons in a thrilling search for sunken treasure. This unforgettable journey on the Annapolis Harbor creates lasting memories for kids and adults alike.

Historic Sites

Walk through centuries of American history in one of the nation’s oldest and most storied cities.

121 Blake Rd, Naval Academy, MD 21402

US Naval Academy

Explore one of Annapolis’ most iconic landmarks with a visit to the U.S. Naval Academy. Located just a short distance from Reynolds Tavern, the Academy offers visitors a chance to experience the city’s naval heritage, impressive architecture, and storied campus. Guests are encouraged to check tour availability and visitor access details before planning their visit.

199 Duke of Gloucester St, Annapolis, MD 21401

St. Anne's Episcopal Church

Step into history at St. Anne’s Episcopal Church, a cornerstone of Annapolis since 1692. This beautiful Romanesque Revival church — the third on this site — invites you to explore its rich heritage, admire its stunning architecture, and experience a sense of peace in the heart of the city’s historic Church Circle.

84 Franklin St, Annapolis, MD 21401

Banneker-Douglass-Tubman Museum

100 State Cir, Annapolis, MD 21401

Maryland State House

Step into history at the Maryland State House, the oldest state capitol in continuous legislative use and the only one to have ever served as the nation’s capital. It was here that George Washington resigned his commission as commander-in-chief and the Treaty of Paris was ratified, officially ending the Revolutionary War.

99 Main St, Annapolis, MD 21401

Museum of Historic Annapolis

Immerse yourself in over 400 years of American history at the Museum of Historic Annapolis. Through inspiring films, three floors of vibrant exhibits, and a remarkable collection of artifacts, you’ll discover the stories of the revolutionaries, visionaries, and champions who shaped Annapolis and the nation.

186 Prince George St, Annapolis, MD 21401

The William Paca House and Garden

Step into Annapolis’ colonial past at the William Paca House and Garden, a beautifully preserved historic home and restored garden setting. Just a pleasant walk from Reynolds Tavern, this landmark offers a memorable glimpse into 18th-century life, architecture, and landscape design in the heart of the historic district.

107 Duke of Gloucester St, Annapolis, MD 21401

The Charles Carroll House

Add the Charles Carroll House to your historic Annapolis itinerary for a deeper look at the people and places that shaped early Maryland history. This notable house museum offers visitors a meaningful connection to the city’s colonial heritage and pairs well with a day spent exploring Annapolis’ historic streets, waterfront, and landmarks.

Outdoor Activities

Trails, parks, and open spaces — explore the natural beauty surrounding Annapolis.

600 Quiet Waters Park Rd, Annapolis, MD 21403

Quiet Waters Park

Nestled between the South River and Harness Creek, Quiet Waters Park offers a serene 340-acre escape with miles of paved trails for walking and biking, beautiful water views, and art galleries. It’s an ideal spot for a peaceful afternoon surrounded by nature, offering a perfect blend of recreation and relaxation for visitors of all ages.

Start at City Dock, 1 Dock St, Annapolis, MD 21401

App-Guided Walking Tour of Historic Annapolis

Discover Annapolis on this app-led, 60 to 90 minute walking route through historic Annapolis. Start at historic City Dock, then visit the Maryland State House and the Naval Academy’s John Barry Gate. Explore the historic homes of influential African American figures, stop by St. Anne’s Church, and finish at the Banneker-Douglass-Tubman Museum. Learn more and download this National Park Service app here.

51 W Earleigh Heights Rd, Severna Park, MD 21146

Baltimore & Annapolis Trail

Escape the city and immerse yourself in nature on the Baltimore & Annapolis Trail. This 13.3-mile paved trail, following the path of a former railroad, offers a scenic journey through woodlands and parks, perfect for a leisurely walk, run, or bike ride. Discover the area’s history and enjoy the beautiful Maryland landscape on this popular and accessible trail.