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Exploring the Best Places to Visit in Annapolis, Maryland

city dock annapolis

Table of Contents

Day 1: Arrival and Settling In

We arrived in Annapolis on a warm Sunday afternoon, eager to start our week-long family adventure. As we drove into the city, the charm of Annapolis became immediately apparent. The historic homes, cobblestone streets, and vibrant waterfront set the perfect stage for our family vacation. We had heard so much about the unique places to visit in Annapolis and couldn’t wait to experience them firsthand.

After checking into our cozy Airbnb near the city center, we decided to spend the rest of the day settling in and getting a feel for the neighborhood. Our rental home was a charming colonial-style house with a lovely garden, and the kids were thrilled to have their own rooms. Once we unpacked and rested a bit, we took a leisurely stroll around the neighborhood. The local shops and cafes exuded a welcoming vibe, and we couldn’t resist grabbing some ice cream at a local parlor.

enjoy icecream at one of the places to visit in annapolis

Day 2: Discovering the U.S. Naval Academy

Our first full day in Annapolis began with a visit to one of the most iconic places to visit in Annapolis: the U.S. Naval Academy. My husband, a history buff, was particularly excited about this stop. We joined a guided tour, which proved to be an excellent way to learn about the Academy’s rich history and its significance. The tour took us through several key areas, including Bancroft Hall, the largest dormitory in the United States, and the beautiful Naval Academy Chapel. The highlight for the kids was the museum, where they were fascinated by the detailed ship models and naval artifacts. Seeing the midshipmen in their uniforms and hearing about their rigorous training gave us a deep appreciation for their commitment and service.

After the tour, we had lunch at the Alley Restaurant on the Academy grounds. The kids enjoyed their burgers while my husband and I savored some delicious crab cakes. With our stomachs full, we spent the afternoon exploring downtown Annapolis. We wandered through historic Annapolis, visiting quaint shops and enjoying the picturesque views of the harbor.

Day 3: Sailing the Chesapeake Bay

Annapolis is known as America’s Sailing Capital, so a sailing adventure was a must on our list of places to visit in Annapolis. We booked a sailing tour on the Chesapeake Bay, and it turned out to be one of the most memorable experiences of our trip. The day was perfect, with clear skies and a gentle breeze. Captain John, our guide, was not only knowledgeable but also entertaining. He shared fascinating stories about the history of Annapolis and the Chesapeake Bay. The kids were thrilled when he let them take turns steering the sailboat. The views from the water were breathtaking, with the Annapolis skyline on one side and the expanse of the bay on the other. We anchored for a while near a secluded cove and had a picnic on the boat. It was a serene moment, just our family, the gentle rocking of the boat, and the beauty of the bay. As we sailed back, the sunset painted the sky with hues of orange and pink, leaving us in awe of nature’s splendor.

Day 4: Exploring the Maryland State House and City Dock

Our fourth day in Annapolis started with a visit to another historical gem: the Maryland State House. As the oldest state capitol still in continuous legislative use, it’s a must-see among the places to visit in Annapolis. The architecture of the State House is impressive, and the kids were fascinated by the fact that George Washington once walked these halls. We took a self-guided tour, which allowed us to explore at our own pace. The exhibits provided a great overview of Maryland’s history and its role in the founding of the United States. The kids enjoyed the interactive displays and learning about the state’s legislative process.

After the State House, we headed to City Dock, the heart of Annapolis’s waterfront. This bustling area was filled with boats, street performers, and local vendors. We had lunch at one of the waterfront restaurants, Pusser’s Caribban Grille, indulging in fresh seafood while watching the boats go by. The atmosphere was lively, and the kids loved the energy of the place.

In the afternoon, we took a water taxi to the Annapolis Maritime Museum. The museum offered a hands-on experience, which was perfect for the kids. They learned about the Chesapeake Bay’s ecosystem and the history of oystering in the area. The highlight was the chance to climb aboard a historic skipjack, giving us a glimpse into the life of a Chesapeake Bay waterman.

Day 5: A Day in Eastport

We dedicated our fifth day to exploring Eastport, a charming neighborhood just across the Spa Creek from downtown Annapolis. Eastport has its own unique vibe and is one of the lesser-known but equally delightful places to visit in Annapolis. We started our day with breakfast at Eastport Kitchen, known for its delicious pastries and coffee. Our first stop was the Annapolis Maritime Museum’s Eastport campus, where we participated in a family-friendly workshop about marine life. The kids had a blast learning about the creatures of the Chesapeake Bay and even got to touch some of the marine animals.

Next, we visited the Eastport Yacht Club. Although we’re not members, we were able to join a community sailing event. The kids enjoyed trying their hand at sailing smaller boats, and my husband and I relished the opportunity to relax and soak in the beautiful surroundings.

For lunch, we went to a local spot, Boatyard Bar & Grill known for its fresh catches. The crab dip and fish tacos were a hit with everyone. Afterward, we spent some time walking along the Eastport Bridge, enjoying the stunning views of the harbor and downtown Annapolis.

Boatyard Bar & Grill
Boatyard Bar & Grill

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Day 6: Quiet Waters Park and Art Galleries

We decided to spend our day in Annapolis enjoying the natural beauty and local art scene. Quiet Waters Park was our first destination, offering a peaceful retreat from the city’s hustle and bustle. This expansive park is one of the best places to visit in Annapolis for nature lovers. We started with a leisurely hike along the park’s trails, which meander through forests and along the South River. The kids enjoyed spotting wildlife, and we all appreciated the tranquility of the surroundings. We found a lovely picnic spot by a pond and enjoyed a homemade lunch amidst the natural beauty. In the afternoon, we rented kayaks and paddled along the South River. It was a fun and active way to experience the park from a different perspective. The kids had a blast navigating the waterways, and we all enjoyed the serene atmosphere.

After our outdoor adventure, we headed back into the city to explore some local art galleries. Annapolis has a vibrant arts scene, and we visited several galleries showcasing works by local artists. The kids were particularly drawn to a gallery that featured whimsical sculptures and colorful paintings. We ended the day with dinner at a local bistro, reflecting on the week’s adventures.

Day 7: Saying Goodbye

Our final day in Annapolis was bittersweet. We decided to spend the morning revisiting some of our favorite spots and doing a bit of last-minute shopping. The kids wanted to get souvenirs for their friends, and my husband and I wanted to bring back some local delicacies. We started with a leisurely breakfast at our favorite cafe and then walked around the downtown area, visiting shops we hadn’t had a chance to explore earlier. We bought some handmade jewelry, nautical-themed gifts, and, of course, a few boxes of famous Annapolis fudge.

For lunch, we returned to City Dock, wanting to enjoy the waterfront one last time. We chose a different restaurant and indulged in more fresh seafood, savoring every bite. The kids fed the ducks by the dock while my husband and I reminisced about the week’s highlights. In the afternoon, we visited the William Paca House and Garden, a beautiful 18th-century Georgian mansion. The guided tour offered fascinating insights into colonial life, and the meticulously restored gardens were a delight to explore. It was a peaceful and fitting end to our trip, allowing us to appreciate the history and beauty of Annapolis one last time.

As we drove out of Annapolis, we felt a mix of sadness and gratitude. Our week in this charming city had been filled with discovery, adventure, and precious family moments. From the historic landmarks to the scenic waterfront, Annapolis had offered us an unforgettable experience. We left with our hearts full, promising ourselves that we would return to explore even more of the wonderful places to visit in Annapolis.


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Annapolis, Maryland, is a charming historic city that can captivate you in it’s waterfronts, vibrant culture, and rich history. Whether you’re visiting