Things To Do
United States Naval Academy
No visit to Annapolis is complete without experiencing the United States Naval Academy. Established in 1845, the Academy’s campus—known as ‘the Yard’—is filled with history, stunning Beaux-Arts architecture, and sweeping views of the Chesapeake Bay. Visitors can explore highlights like the Naval Academy Chapel, Bancroft Hall, and the beautiful waterfront grounds. Guests are welcome to walk onto campus daily from 9:00 a.m. to 5:00 p.m. with a government-issued ID.
Saint Mary’s Parish
St. Mary’s Catholic Church is one of Annapolis’s most beautiful landmarks. Overlooking the waters of Spa Creek, this historic church is known for its stunning Gothic architecture, soaring spires, and vibrant stained-glass windows. A true gem in the heart of the city, St. Mary’s offers a peaceful retreat just steps from the charm of downtown Annapolis. With its rich history and timeless beauty, it’s not only a destination worth experiencing during your visit—it’s also especially meaningful to us, as Sami’s parents were married here.
Ego Alley
In the heart of downtown Annapolis, you’ll find Ego Alley—a lively stretch of water where boats cruise in to show off and visitors gather along the docks to watch the scene. Lined with waterfront restaurants, shops, and outdoor patios, it’s the perfect place for a stroll, an ice cream cone, or simply taking in the charm of Annapolis by the Bay. Day or night, Ego Alley is always buzzing with energy and gives guests a true taste of the city’s coastal character.
Shops & Restaurants
Downtown Annapolis is full of charm, with cobblestone streets lined with shops, galleries, and some of the best local dining around. A true Annapolis staple is Chick & Ruth’s Delly—famous for its hearty breakfasts, mile-high sandwiches, and old-school diner feel. For those looking for a lively spot with Maryland seafood, O’Brien’s Oyster Bar & Seafood Tavern is a longtime favorite, while McGarvey’s Saloon & Oyster Bar is known for its fresh oysters and bustling waterfront atmosphere. Beyond these classics, you’ll find plenty of boutiques, ice cream shops, and waterfront restaurants to explore, making downtown the perfect place to spend an afternoon or evening.
Movement
If you’re looking to fit in a little movement during your stay, Annapolis has plenty of options. Stroll or jog along the scenic waterfront paths, take a yoga class at one of the local studios, or explore the Naval Academy grounds on foot for a beautiful walking route. For those who prefer the gym, several fitness centers are located right downtown. Whether it’s a morning run by the Bay or a quick workout before the festivities, Annapolis makes it easy to stay active while enjoying the city. For a unique experience, try stand-up paddleboarding or kayaking with Capital SUP. Located in Eastport, they offer rentals and classes on Back Creek, providing a scenic way to stay active.
Rise Up Coffee
For a perfect coffee stop in Annapolis, don’t miss Rise Up Coffee. Born on Maryland’s Eastern Shore, this local favorite is known for its small-batch, organic coffee and laid-back vibe. Whether you’re grabbing a latte before exploring downtown or settling in with a pastry and cold brew, Rise Up is the kind of place that feels both local and welcoming. It also happens to be one of Sami and Mikey’s favorite spots—so it’s a must-visit during your stay!