Annapolis is a short drive from DC and offers a definite change in pace and scenery. If you like Savannah, Charleston, or Nantucket, you’ll enjoy Maryland’s preppy and picturesque capital. In this post, I share everything you need to know to plan your own getaway to ‘Naptown’ (that is a real nickname, I did not/could not have made it up, but I have never heard a real human use it).
Annapolis is home to the Maryland State House, which is the oldest U.S. state capitol building in continuous legislative use, dating back to 1772. Despite Annapolis housing the Maryland General Assembly and offices for the Governor and Lieutenant Governor, most of the state agencies operate out of nearby Baltimore.
Rather than feeling like a bustling state capital, Annapolis has an historic, small town feel. There is a thriving local food and art scene and plenty to explore for a small city, perfect for a weekend but probably not enough to fill a week-long trip. The downtown area has a high density of Irish pubs and is a favored destination for celebrators of St. Patrick’s Day.
When to Go
I would recommend visiting Annapolis during the sailing season, April through October. Summer months are popular for tourists and sailors and will be the most crowded time to visit. April and September offer warm, breezy days and cooler but generally not chilly evenings, perfect for a comfortable sail and walking around historic downtown.
Cherry blossoms and magnolia blooms can be spotted as early as mid-March, but tend to peak in early April. Try to avoid Commissioning Week in mid-May, when the Naval Academy hosts graduation and Annapolis surges with families and visitors, as it will be very difficult to find a place to stay, parking, or dinner reservations. Also check dates for the United States Sailboat Show in October and the Annapolis Spring Sailboat Show, which similarly draw crowds.
What to Do
Visit the Naval Academy
Annapolis is probably most well known as the home of the US Naval Academy since 1845. The Academy was closed to visitors in 2020 due to COVID-19, but is now open for the public to walk around campus and see the spectacular Naval Academy Chapel. We visited during Family Weekend and spotted a lot of some midshipmen (upperclass students at the Academy) showing their families around town, wearing their dress whites. You can book a guided tour of the campus or walk around on your own. Park in downtown Annapolis and enter through the pedestrian entrance. Be prepared to show your photo ID at the visitor entrance. Stop for coffee at 1845 Coffee on campus, next to the Naval Academy Museum.
Annapolis is also home to the small liberal arts school St. Johns College, known for their unique curriculum called the Great Books Program.
Go Shopping
The city is full of history and we enjoyed walking around downtown and perusing the many unique shops. Downtown Annapolis is very walkable and free 2-hour street parking was generally easy to find. I recommend starting your day with a coffee from Brown Mustache Coffee, which operates out of the winsome Old Fox Books. You can grab a book and sip your coffee in the back garden or explore the two floors of the bookstore. My favorite part of Old Fox was “Blind Date with a Book”, where you could choose a mysterious book wrapped in newspaper based on a handwritten description.
From there, you can walk down Maryland Avenue to visit my favorite two of the many many antique shops in Annapolis, Blue Crab Antiques and Evergreen Antiques & True Vintage. Across the street is KA-CHUNK!! Records, perfect for audiophiles like my husband who is constantly adding to his collection of vinyl. Keep walking to find Back Creek Books, a small shop specializing in maritime and Marylander literature. Lastly, don’t miss Mills Fine Wine & Spirits, which has one of the most diverse collections of wine I’ve ever seen, from local Maryland wines to bottles from Croatia and the Republic of Georgia.
Go Sailing
Downtown Annapolis is sandwiched between the neighborhoods of Eastport and West Annapolis. West Annapolis is a little more residential, but it has some good restaurants and more shops. You can walk across a drawbridge to Eastport from downtown but you may prefer to drive. Eastport makes clear why Annapolis is called the “Sailing Capital of the World,” there is one marina after another and literally thousands of boats.
Each October, Annapolis plays host to the United States Sailboat Show, the world’s largest in-water sailboat show, as well as the Annapolis Spring Sailboat Show. These events are a great opportunity to see sailboats of every make, from preserved historical vessels to hyper-optimized racing boats and everything in between.
If you’re interested in learning to sail yourself, there are several great options in town. J World Performance Sailing School is regarded as one of the best places you can learn to sail, they have facilities in Annapolis, San Diego, and Puerto Vallarta, Mexico. At the Annapolis location you can choose from a variety of courses including FirstSail, a three-hour introduction to sailing if it’s entirely new to you. Annapolis Sailing School also offers courses for youth and adults on several time frames, generally at a slightly lower price point than J World. If you’re more interested in a recreational sail with a captain, you could book a private sunset sail for 6 people for $600. However, in my opinion the best value for a sunset sail is booking with one of the historic ships that sail out of Annapolis City Dock.
There are two main options for sunset sails on historic vessels – the sister ships Woodwind and Woodwind II or the Wilma Lee. Both leave from Annapolis City Dock downtown and have reduced their capacity 30 per cruise to allow for sufficient social distancing and comfort on board. Woodwind and Woodwind II are identical replicas of the classic wooden schooners built in the early 1900s and cut a striking profile with four sails. Public tours run up to four times a day and are operated by the private company Schooner Woodwind. Tickets go on sale 6 days prior and are currently $75 per person.
The newest option on the Chesapeake is the Wilma Lee. The Wilma Lee is an original Chesapeake Skipjack, a class of boat originally designed for dredging oysters, built in 1940 and meticulously restored in 2019. Operated through the Annapolis Maritime Museum you can book a sunset cruise ($65/person, 21+ only), or a heritage cruise ($45/adult, $20/child) which includes a museum docent sharing points of historical and ecological interest. If you want a more intimate experience, there are also several listings for private sail cruises on AirBnB Experiences. We ultimately chose the Wilma Lee because there were fewer total people allowed on, the price was slightly less, and it supported local educational and conservation efforts.
We boarded the Wilma Lee just after 5:15 PM, the captain introduced himself and the two crew members, went over what to expect and some basic safety information. The nice thing is whichever boat you don’t choose, you’ll have a great vantage point to appreciate it as you both sail around the Chesapeake Bay. Your ticket includes adult beverages and snacks and the crew was happy to answer any questions about the city, sailing, the Wilma Lee, or just chat. The night we went out, the wind was really low so we actually motored up the Severn River to see sunset rather than try to sail out into the Bay. It was still very relaxing and you get a great view of the Naval Academy from the water. We got back to the dock just before 8:00 and headed to dinner.
Where to Eat
Seafood is the star in Annapolis but there are great options for any taste and price point. There are so many restaurants to check out, I’ve only listed my ‘can’t miss’ spots. Please share any other recommendations in the comments! During COVID-19, several streets or lanes were blocked off to ensure abundant outdoor seating options, but those have largely disappeared.
Coffee and Brunch
- Iron Rooster – situated at the heart of Downtown with plenty of outdoor seating, Iron Rooster serves breakfast all day and is famous for their giant homemade poptarts. The poptart flavors rotate, we opted for the Mixed Berry. Definitely fun but I would get one to share because it’s very sweet. Also try their Bloody Mary.
- Brown Mustache Coffee – I mentioned this above, but this is located inside of Old Fox Books and has a lovely back patio.
- Ceremony Coffee Roastery – I noticed Brown Mustache said they were serving Ceremony Coffee and it turned out this local roastery is just down the street from our AirBnB. They are doing takeout only right now but you can get a seasonal latte or a bag of beans to go.
- Evelyn’s Kitchen – low-key brunch spot in West Annapolis with indoor and outdoor seating. Very popular on the weekends, so expect a wait.
- Bitty and Beau’s – Bitty and Beau’s is a North Carolina-based business with a focus on employing adults with cognitive disabilities, such as Down Syndrome. Also located downtown on Dock Street, you can grab a coffee on your way to Iron Rooster.
Dinner and cocktails
- Preserve – locally owned restaurant with a focus on farm-to-table and, as the name suggests, fermentation and pickling. The menu changes with the seasons, so expect something different ever time. Everything we’ve had there has been delicious. In 2020, we had the Chesapeake Cheddar Cheese Pupusas, the Dutch chicken pot pie, crab cakes, and bread pudding. We had never had pupusas before but they’re kind of similar to Venezuelan arepas. The chicken pot pie was tasty but threw us for a loop because it had no crust; in the South we would call it chicken n dumplings. You cannot go to Annapolis and not have crab cakes and Preserve is where I would recommend getting them, they were incredible. We went back recently and got the hamburger, pork soup dumplings, and a coffee crepe cake, which were all incredible.
- Sailor Oyster Bar – SOB is a vibe. Cool music, great cocktails, and lots of raw oysters on the half shell. Our waiter described how the taste of oysters varies based on where they’re harvested and helped us choose some local oysters that were a little sweat and not super briny. We also had the charcuterie board that featured some unique meats and cheeses and was excellent, but everything on the menu looked great. As of March 2023: SOB is temporarily closed following a kitchen fire, check their Instagram for updates on reopening.
- Flamant – this was the last dinner we had during our trip but it was definitely not the least. Be prepared to drop a pretty penny ($100-150 per person depending on drinks) and to be taken on a whimsical culinary adventure by Belgian chef Frederik De Pue. Each dish on the prix fixe menu is artful and surprising, especially the crab twists and duck lettuce wraps served as your welcome snacks. Everything was delicious but dessert was our favorite – braised figs with white cheese ice cream and raspberry wine; chocolate mousse on a bed of crushed hazelnuts with a crystallized mint leaf. If you are looking for a high-end date night in a cozy bungalow, don’t miss Flamant.
- UPDATE AS OF FEBRUARY 2024: Flamant closed in December 2023. The space is now occupied by InGrano.
Where to Stay
I rounded up my favorite AirBnB options in Annapolis, one of which was the place we stayed. All of these listings have ratings of 4.9 and above, are committed to enhanced cleaning and don’t allow smoking or pets.
Grayscale Annapolis Loft
This soothing studio apartment has everything you need for a comfortable long weekend in a convenient location. Located above a detached garage, check-in is easy and contact-free with a keypad and there’s plenty of street parking in the quiet neighborhood. Less than a 10 minute drive to Dock Street and just down the road from Ceremony Coffee Roastery.
Private Art-Filled Guesthouse
Also a studio, this West Annapolis guesthouse offers a ton of character and all the amenities. Guests really appreciate the hospitality of host Linda who goes the extra mile to make sure your stay is comfortable. Location is convenient to everywhere you’d want to go.
West Street Carriage House
Need more space? This two-bedroom apartment has plenty of room with a pull-out couch for a fifth guest and a full kitchen and living room. This private apartment also has a patio and covered deck perfect for enjoying your coffee in the morning before a short drive to downtown.
Beautiful and Tranquil Carriage House
This listing is slightly further away from downtown and a little more expensive than the others, but it’s just so pretty! Two bedrooms, 1.5 baths with a beautiful open-concept kitchen and living room, with a balcony off the living room. Both of the bedrooms also have sofa beds if you have a bigger group, I can see this being a great home base for a bachelorette party.
In addition to AirBnB, traditional B&Bs are big business in Annapolis. There are a lot of options, the Flag House Inn is probably the most well known and highly rated. It’s been locally owned and operated since 1992 and is made up of two duplexes with themed rooms.
Have you been to Annapolis, what else do you recommend?