48 Hours in Annapolis

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.


the view from our room at Annapolis Waterfront Hotel
(C) Christina Saull – All Rights Reserved


a standard room at the property is bright, airy & nautical!
(C) Christina Saull – All Rights Reserved

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.


#TeamCarbs crab dip
(C) Christina Saull – All Rights Reserved


yummy crab cakes
(C) Christina Saull – All Rights Reserved

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!


SUP-ing through the Annapolis harbor
(C) Christina Saull – All Rights Reserved


Capital SUP
(C) Christina Saull – All Rights Reserved

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.

WIld Country

Wild Country Seafood yumminess
(C) Christina Saull – All Rights Reserved


the Maritime Museum
(C) Christina Saull – All Rights Reserved


the Chesapeake Bay has a long, complicated history with the simple oyster
(C) Christina Saull – All Rights Reserved

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.


(C) Christina Saull – All Rights Reserved


such a great view off the front of Woodwind
(C) Christina Saull – All Rights Reserved


keeling under moody skies
(C) Christina Saull – All Rights Reserved


Woodwind II & the Chesapeake Bay Bridge
(C) Christina Saull – All Rights Reserved

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.


Harbor Queen, as seen on our Woodwind sail!
(C) Christina Saull – All Rights Reserved


one of several bridges crossing the Severn River
(C) Christina Saull – All Rights Reserved


athletic & sailing facilities at the US Naval Academy
(C) Christina Saull – All Rights Reserved


one of several Osprey nests in the Bay
(C) Christina Saull – All Rights Reserved

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.


my cocktail tasted like adult pink lemonade
(C) Christina Saull – All Rights Reserved


chicken & waffles goodness
(C) Christina Saull – All Rights Reserved


mixed berry pop tart
(C) Christina Saull – All Rights Reserved

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.


yes, please
(C) Christina Saull – All Rights Reserved

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.


brekie & iced coffee
(C) Christina Saull – All Rights Reserved

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.


Oh, Maryland, my Maryland
(C) Christina Saull – All Rights Reserved

28543492532_de0fc5c95a_k (1)

the State House is visible all around town
(C) Christina Saull – All Rights Reserved

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.


the impressive entrance to the Naval Academy
(C) Christina Saull – All Rights Reserved


USNA Memorial Hall
(C) Christina Saull – All Rights Reserved


USNA Memorial Hall
(C) Christina Saull – All Rights Reserved


inside Bancroft Hall
(C) Christina Saull – All Rights Reserved

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.

the point

all of the crabs (& shrimps)
(C) Christina Saull – All Rights Reserved


right on the marina at The Point
(C) Christina Saull – All Rights Reserved

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!


Annapolis harbor
(C) Christina Saull – All Rights Reserved

Share Button

About christina

Christina is a 30-something D.I.N.K. travel writer & photographer who travels the world often wedged into the middle seat. Follow her on Twitter & Facebook.

15 Responses to 48 Hours in Annapolis

  1. Mary August 18, 2016 at 5:57 pm #

    I loved reading this review of your Annapolis weekend! I’ve been there many times but learned some fun new things I need to try😄

  2. Noemi of Pinay Flying High October 26, 2016 at 12:53 pm #

    I’ve been to Annapolis only once and fell in love with it. Learned so many new things on this post. Will definitely keep this in mind next time I’m in MAryland. Also, how are you able to stand comfortably on the paddleboard? I trieed SUP before and couldn’t stand for longer than 2 seconds. Lol.

    • christina October 26, 2016 at 1:23 pm #

      I don’t know! I think it’s a total balance issue because my super athletic husband can’t do it either. I feel completely at ease on one & yet I’m the biggest klutz in the world!

  3. Andree-Anne October 26, 2016 at 1:17 pm #

    Seems like you had an amazing stay! I’d love to visit Annapolis someday!

    • christina October 26, 2016 at 1:24 pm #

      It’s definitely a nice day trip from DC or Baltimore!

  4. Ivy October 26, 2016 at 2:01 pm #

    I’ve yet to try SUP, is it actually as easy as you make it seem? Love the nautical feel of the room and OH MAN I LOVE crab and shrimp- I’d be pigging out everyday if I ever visit Annapolis!

  5. La Vida Viva Travel October 26, 2016 at 6:03 pm #

    Looks like my kinda trip with all of that delicious food! Sounds like you had a fabulous time :D

  6. Christina October 26, 2016 at 10:22 pm #

    What a lovely weekend getaway. Annapolis looks like it has a lot to offer. I would definitely like to explore the bay by going sailing and finishing the day off by having some seafood.

  7. Erika Bisbocci October 27, 2016 at 1:10 am #

    The food looks so good! Especially the crab cakes. I can totally understand why you would have made sure to eat more crab before leaving. I’ve heard great things about Annapolis before and can imagine that it is a very nice getaway from the DC area. What a nice view of the harbor you had from the hotel!

  8. Nicki October 27, 2016 at 4:36 am #

    I was so excited to find a post about a city I love so much! My husband and I want to move here one day – but currently we live in Alexandria, VA and just visit frequently.

    We sail on that same boat every year at the sailboat show. Did they tell you that it was in the movie Wedding Crashers? I thought that was a cool story they told.

    • christina October 27, 2016 at 2:21 pm #

      How funny – I live in Alexandria!

  9. Theresa October 27, 2016 at 1:08 pm #

    I’m from MD, and Annapolis is such a great town to visit, especially when the weather’s nice. The downtown area is beautiful, the Naval Academy is super interesting, and the food is great. I’m glad you loved it!

  10. Manon @ The Dutch countryside October 27, 2016 at 5:26 pm #

    The food looks so incredible! I’ve never heard of Annapolis before but it definitely seems like a great place to visit, with all the water around and the delicious food I think you cannot go wrong there.

  11. Cory Varga October 28, 2016 at 5:08 am #

    I made the bad decision of reading this article before lunch, which means your incredible pictures made me Oh, so hungry! Would visit Annapolis for the food alone!


  1. Top 5 Day Trips from Baltimore | Mishvo in Motion - August 21, 2016

    […] info: Annapolis Tourism Board, 48 Hours in Annapolis from My View from the Middle Seat […]

Leave a Reply