48 hours is the perfect amount of time to explore Maryland’s waterfront capital city. After visiting recently on the hottest weekend of the year, here is everything you need to know about where to stay, what to eat & what to do. #protip: spend as much time on the water as possible!
Day 1: Arrive, Get Settled, Get Dinner
The traffic from Washington, DC & Baltimore headed to Annapolis can get a bit gnarly on the weekends, so it’s ideal to hit the road by 3pm or so. I highly recommend staying at the Annapolis Waterfront Hotel, since it’s the only property right downtown on the water & you can basically valet your car & leave it for the weekend.
After a pre-dinner cocktail at Pusser’s Caribbean Grille, which has a great view of Ego Alley (the waterway along the city dock where all the people in their fancy boats like to show off) & a fun, Caribbean vibe, head to dinner at the Naval Academy. This can only be booked through Annapolis Waterfront Hotel (unless, of course, you’re an officer in the Navy), which gives it an air of exclusivity, even if the restaurant itself isn’t as fancy as we expected it to be. When we enjoyed dinner there, we went all crab, starting with the crab dip (super cheesy & crabby), continuing onto crab cakes (almost all crab & no filler) & even made room for dessert (B had a chocolate lava cake & I had an old school root beer float). We ate way too much, so it’s a good thing that dinner at the Naval Academy is only accessible by foot.
If you’re in the mood for a nightcap, the Dock Street bar has a great, local vibe.
Day 2: Getting your Sea Legs
The best way to experience Annapolis is on the water & luckily there is no shortage of ways to enjoy getting your toes wet. Head over to Eastport for breakfast at Bakers & Co. (the croissants, oh my goodness…) & then to Capital SUP for a morning tour. Their History Tours are an awesome combination of everything you want to know about Annapolis’s storied history & a great time on the water. The tour I took with Kevin was a great mix of newbies & experiences SUP-ers. Our group paddled around on a busy Saturday morning for boats &, while I always felt safe, the water was pretty choppy for a beginner – I’m very proud to say I’m one of the few people in our group who didn’t fall in!
There are a few great lunch places in Eastport, including Wild Country Seafood, a no frills seafood shack with awesome steamed shrimp (everything in their case can be steamed on-site) & hush puppies, & Eastport Kitchen, serving up huge sandwiches. Before you leave Eastport, stop by the charming Maritime Museum, which is housed in the old McNasby’s oyster plant & shares the story of the declining oyster population in the Chesapeake Bay.
Afternoon’s in Annapolis are meant for sailing & there’s no better place to do it than on the 74-foot Woodwind Schooner (& its sister ship Woodwind II). Their two-hour public tours are the perfect intro to sailing, where guests can be as active or relaxed as they’d like. B helped hoist the sails while I leaned back & enjoyed the wonderful breeze. We sailed with full sail out almost to the Chesapeake Bay Bridge & down the Severn River. The crew was a lots of fun & were happy to answer my endless questions about sailing. There’s a cash bar on board & a non-alcoholic beverage comes with your ticket. We’ve been on various schooners around the country & without a doubt, Woodwind was one of our favorites. Sailing along, keeling, boat shoes balanced against the edge of the boat, with the wind whipping through my hair is definitely my happy place.
If the schooner sounds a bit too intense for you, or especially if you have little kids, a great alternative is the Harbor Queen. We enjoyed their 40-minute Harbor Cruise, which included a great view of the U.S. Naval Academy & narrative about the military academy. The Harbor Queen has covered (read: shady) seats on the lower deck & ample seating upstairs if sun bathing is your thing. Best of all, the boat leaves once an hour during the summer & hardly ever sells out, so you can just arrive at their ticket booth right on the dock when you’re ready to go.
Really good restaurants are a bit hard to come by in Annapolis, which is why reservations are an absolute must for Iron Rooster. Located right downtown, there’s a reason why they’ve become the most popular spot in town: the food is awesome. Start off with a handcrafted cocktail (I enjoyed the Hen House, which tasted like an adult pink lemonade), but save the “appetizer” pop tart for dessert (we had the mixed berry, which tasted exactly like a cherry Pop Tart & was so huge we had the other half for breakfast the next morning). I decided to splurge on the chicken & waffles &, although the waffle was a bit soggier than I would have liked, the chicken was so perfectly seasoned, it made up for it (be sure & ask for the gravy on the side). B had the shrimp risotto, which came baked in a cute iron skillet, & ended with a gooey chocolate dessert, also cooked in a little iron skillet.
Some of the stores in Annapolis stay open later in the summer, which make for a perfect post-dinner stroll. A nice evening is also the perfect time to check out some of the mega yachts parked along the waterfront.
Day 3: Sneaking in Some History Before Heading Home
After breakfast at Hard Bean Coffee (their breakfast sandwiches were the perfect size!), it’s time to squeeze in a little history into your stay. Wander up the back streets & enjoy all the colorful, historic old row houses that have been occupied since the 18th century.
Your destination is the Maryland State House, which serves as both the capitol building for the state of Maryland, but also served as the U.S. capitol for a year from 1783 – 1784. This impressive building on the hill is open every day from 9:00am – 5:00pm, with self-guided tours always available. Fans of the Netflix show House of Cards might recognize the House of Delegates, which was used for filming scenes involving the U.S. Senate chamber a few years ago.
The U.S. Naval Academy is also worth a stop, whether you do a walking tour or just stroll the grounds. Everyone over age 18 will have to show a government-issued photo ID & the academy is best accessed by foot. The museum in Preble Hall is especially impressive (& a nice place to cool off in air conditioning on a hot day), as is the impressive Navy Chapel.
A trip to Annapolis wouldn’t be complete without one more crab feast, so head out of town for lunch to The Point Crab House. Less crowded than nearby (notoriously touristy) Cantlers, we enjoyed crab cakes & steamed shrimp right along the marina. It’s the perfect way to end a quick 48 hours in Annapolis.
Note: Some of these experiences were provided on a complimentary basis, including dinner at the Naval Academy, the tour with Capital SUP, our sailing on the Woodwind Schooner & our ride on the Harbor Queen; however, all opinions are my own. Annapolis is really a great little town, with fantastic people working in the hospitality industry!