Annapolis, Maryland is a quaint historic town filled with amazing restaurants, cafes, cute boutiques, and the elite United States Naval Academy. We went back this October to see my dad get inducted into the US Naval Academy Athletic Hall of Fame, and had a few days to explore. The city is walkable with lots to see, and a perfect weekend getaway destination.

best time of year to visit annapolis

Early October is the best time of year to visit Annapolis. Slightly cooler and crisp in the evenings with a few warmer days sprinkled in, you get the best weather. While we were there, we had two days in the 70s, one in the 60s, and minimal clouds. It cooled down considerably once the sun set, but wasn’t cold you need to bring a full winter wardrobe when you pack. Spring weather can be a bit more unpredictable, and summer is busy season, so expect larger crowds and longer wait times. We’ve also visited Annapolis in early February and while we didn’t experience any rain or snow, you definitely want to pack warmer layers and a coat.

things to see and do in annapolis

Tour the US Naval Academy - We didn’t book a formal tour as we had my dad to show us around, but they do offer public, private, and group tours. The academy is so elegantly designed and truly worth exploring. 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 every day.

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 plan to spend around 3 days each in Annapolis and DC to make the most of the longer flight. You can view my DC guide here.

best food + cafes in annapolis

Bitty & Beau’s Coffee - Probably our favorite stop out of the whole trip. 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.

Miss Shirley’s Cafe - Great breakfast. 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.

Iron Rooster - Popular breakfast spot with tons of outdoor seating, and right by the water. Kinda pricey, but the homemade pop tart is worth it.

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.

Galway Bay - Featured on Diners, Drive-Ins and Dives and stays 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 already wants to go back for the fried shrimp.

Castlebay Irish Pub - Quick service and big portions

Teriyaki House - Nothing fancy, but one of the healthier restaurant options. If you order the teriyaki bowl, get the sauce on the side as there was a lot.

Davis’ Pub - This place has also have been featured on Diners, Drive-Ins and Dives.

Preserve - Cute place, they serve small plates so it’s best to go with a group.

Fox’s Den - Great pizza and they have a lot of drink options if that’s your vibe. It has a darker, speakeasy atmosphere and can get busy quickly.

where to get dessert in annapolis

Kilwins - They have ice cream, fudge, caramel apples, and other treats. The flavors we most recommend are toasted coconut, praline pecan, and apple pie, but you really can’t go wrong with anything there.

Annapolis Ice Cream Company - A local favorite, there are lots of different flavors to choose from, including unique ones like lemon Oreo, plus a few vegan options.

The Red Bean - The process for ordering was a little different as you pick chocolate or vanilla and then two mix-ins and they swirl it for you. We did chocolate with strawberry and oreo (it was recommended to us) and couldn’t really taste the mix-ins but it was a really good chocolate and we still talk about it weeks later. Service can be slow, so I’d go elsewhere if there’s a long line or you’re in a rush. I’d also avoid ordering coffee here if you order a non-dairy milk.