Annapolis, MD is one of my favorite travel destinations in the world. A cute historic city with a friendly community and fun downtown to explore day or night, there’s so much to see and do. It’s the perfect east coast location for a weekend getaway, and if I lived closer, I’d visit much more often. Whether you’re a foodie, Navy fan, or just want to see all the city has to offer, this is my go-to itinerary for a quick, 3-day visit.

3 days in annapolis itinerary and travel guide

day one

Breakfast (or brunch): Chick and Ruth’s Delly. There’s a huge menu with something for everyone, even if you only want a small pastry. Service is quick, and it’s a local favorite.
Tour the Naval Academy, and aim to be at T-Court, right outside of Bancroft Hall, just before noon so you can witness noon meal formation. The thousands of midshipmen enter T-Court and then stand at perfect attention; it’s really incredible to witness and occurs at 12:05. This occurs every weekday, except for Wednesday. Other Naval Academy spots you’ll want to see: the chapel, the Crypt of John Paul Jones, and the cemetery, where John McCain and Bill Belichick’s parents are buried. Book a tour to get the most of the campus.
Snack: Chick and Ruth’s held us over through lunch, so we headed to Bitty and Beau’s for a coffee and small snack. Much more than just a coffee shop, this cafe is run by people with disabilities so it’s a truly beautiful and heartwarming experience. For me, traveling is also about immersing myself in the local community, and the friendly baristas at Bitty and Beau’s are so engaging and fun to talk to. And yes, the coffee, chai, and muffins are out of this world good.
Explore Walk around City Dock, the historic heart of Annapolis, where it connects with the waters of the Chesapeake Bay. Also be sure to check out the small shops around Church Circle and Main Street; many of them import their hand-crafted goods, just as merchants have done for the past 350 years.
Dinner: Galway Bay. This Irish pub has been featured on Diners, Drive-Ins, and Dives, so it can be crowded. Make a reservation if you want to sit at a table, but the best service is at the bar - their bartenders are personable, friendly, and cool to talk to. The pot roast lives up to the hype, and I’m mentioning this as a first-night dinner option because if you’re like us, you’ll probably want to go back.
Dessert: Kilwins. You may have one local to you, but we don’t, so this is a can’t-miss spot for us (even in the winter). A scoop of toasted coconut ice cream is the best way to end the day.

day two

Breakfast: Iron Rooster, which has tons of outdoor seating, and is right by the water. It’s kinda pricey, but the homemade pop tart is worth it.

Walk off brunch and check out the shops on Main Street. Before you get too far, take a little detour and check out Old Fox Bookstore, which is right around the corner on Maryland Ave. The boutique next door, Cupla, is also really cute and the owners are super nice.
Lunch: After walking back down the other side of Main Street, you’ll have completed a loop, so have lunch at McGarvey’s. Known for incredibly fresh seafood, they also have plenty of burgers and vegetarian options. Their fries are addicting, and the kid’s menu is straightforward.
Walk (or Uber) back to the room for a little downtime, and to get ready for dinner.
There are a few dinner options, depending on your vibe. Preserve is a very aesthetically-pleasing restaurant that serve small plates so it’s best to go with a group. You could also grab drinks and a pizza at Fox’s Den, which has a darker, speakeasy atmosphere and can get busy quickly. We personally don’t like to eat out a ton, so we headed to Teriyaki House for chicken bowls.
Nighttime tour: So many people rave about the Annapolis Ghost Tour & Crawl, and there are a few different options available, including pub tours and walking tours. Advanced reservations are required.
Dessert: I stay true to Kilwins, but Annapolis Ice Cream Company is a local favorite with lots of different flavors to choose from, including unique ones like lemon Oreo, plus a few vegan options.

day three

Breakfast: If you want a bigger meal, I recommend Bread & Butter Kitchen, but we went back to Bitty and Beau’s for another coffee/ muffin combo.

Explore the Maryland State House, which is the oldest state capitol still in use and once served as the nation’s capitol.
Lunch: Boatyard Bar & Grill, which is known for their crab cakes. Crowds get big on the weekends, but you’re likely to get seated quicker than you think.
Explore the Annapolis Maritime Museum & Park, which is about a 10 minute walk from the Boatyard Bar & Grill. This museum is interactive and fun, with both indoor and outdoor exhibits.
If you’re not looking to go back to Galway Bay, another great dinner spot is Davis’ Pub, another Diners, Drive-Ins and Dives alum.

where to stay in annapolis

There are lots of hotel options in Annapolis, including historic and national chain options. For the best option that’s budget-friendly and within walking distance of downtown, I recommend staying at the Hilton Garden Inn Annapolis Downtown. The rooms are modern, clean, and friendly, and it’s about a 10-15 minute walk to downtown and the Naval Academy. The showers are a little small, but for a quick trip, the location is ideal.

getting to Annapolis from BWI airport

The quickest, most cost-effective way to get to Annapolis is to fly into BWI airport, and then take an Uber or cab to Annapolis for around $40. The price seems steep, but flying into one of DC’s airport and then taking public transportation to Annapolis will set you back a couple of hours, and that’s not worth it for a quick weekend getaway.

You can also rent a car. We’ve done this in the past, and I think it’s worth it if your hotel is farther from downtown or you don’t want the extra walk. Annapolis has a downtown parking structure that will make parking much more convenient, but I don’t mind walking so the potential parking fee at the hotel isn’t worth it to me.

where to eat in annapolis

While it may not seem like a top foodie destination, Annapolis has incredible dining options. Our favorites that we absolutely cannot miss are:

Miss Shirley’s Cafe - Great breakfast, and they’ve been featured on Diners, Drive-Ins, and Dives. We loved the french toast, egg sandwich, and mini donuts. The hash browns were a little soft; we wished we ordered them more well-done.
Chick & Ruth's Delly - Even with a line, you get seated quickly and the menu is huge. They serve you pickles as a snack while you wait for your food. The club & reuben sandwiches were great, and as a picky eater, I loved being able to build my own salad. If you want a cheaper, diner-style meal that will keep you full all day, this is your best bet.
Galway Bay - Also featured on Diners, Drive-Ins and Dives, this is such a charming spot and they’re open late. The pot roast absolutely lives up to the hype. You do have to call ahead to make a reservation unless you want to get a seat at the bar, but we liked sitting at the bar more anyways (the bartenders are so nice).
McGarvey’s - Their food, especially the seafood, is really fresh and prepared perfectly; my boyfriend and dad love the fried shrimp.
Bitty & Beau’s Coffee - Make this is your go-to coffee stop while you’re in Annapolis. Love the message and everything they stand for. They serve the best chai I’ve ever had (it isn’t too sweet or vanilla-y) and the muffins are amazing.
Kilwins - We don’t have a Kilwins near us, and they make the best toasted coconut ice cream. They also have great seasonal ice cream flavors, plus fudge, caramel apples, and other treats; you really can’t go wrong with anything there. Even in the dead of winter, I have to end my night with a scoop from Kilwins.

things to do in annapolis

Tour the US Naval Academy - The academy is so elegantly designed and truly worth exploring; they offer public, private, and group tours. You won’t want to miss seeing the chapel, the Crypt of John Paul Jones, and if you time it right, formation, which is at 12:05 most days.

Annapolis Ghost Tour & Crawl - I’ve heard lots of people rave about this, so definitely look into this if you like spooky things. There are a few different options available, including pub tours and walking tours. Advanced reservations are required.

Game On Bar & Arcade - Retro games with a creative bar menu and mocktail options. Kids are allowed until 8pm.

Maryland State House - This is the oldest state capitol still in use and once served as the nation’s capitol. It’s located in the downtown area, so you’ll most likely run into this while you’re walking around. They do offer tours as well.

Day trip to DC - DC is only about 45 minutes away and definitely worth at least a day trip. Since we fly across the country to visit, we spend around 3 days each in Annapolis and DC to make the most of the longer flight. You can view my full DC travel guide here.