6.23.16 8

24 Hours in Annapolis, MD


weAs you may have heard by now, Katie and I spent last Friday night + the day Saturday in Annapolis, Maryland. Just over 30 miles from DC on the Chesapeake Bay, it’s the perfect destination for a quick weekend getaway for those in the northeast corridor. It’s the cutest little town that’s both Maryland’s state capital and is home to the Naval Academy. Being there definitely makes you feel like you’re hours outside the city…it’s quaint and picturesque in the best way. If you’re in the DC area or anywhere within driving distance, definitely add Annapolis to your wishlist of weekend getaway destinations!


View from our room

As expected, we hit a ton of traffic on our way out of DC on Friday. Beach traffic is no joke! It took us about 2 hours but with good company and some good tunes, it wasn’t too terrible. We stayed at the Annapolis Waterfront Hotel, which gave us the warmest welcome and could honestly not have been any better.

Annapolis Waterfront Hotel

After dropping stuff off in our room, we quickly went back outside to enjoy the breeze by the water and shoot some photos. It was perfect! I mean…look at this view. We enjoyed a bottle of wine on the hotel’s second floor patio/deck area before heading out to dinner + beers at Dock Street, followed by ice cream from Kilwins.

While Annapolis also makes a great day trip, I will say that spending a night there is the way to go. I’d spent a couple nights at a local friend’s house over Thanksgiving two years ago, but Katie had just been for the day. We both agreed that staying right downtown was the ideal move!


Saturday morning, we filled up with breakfast at Pusser’s Caribbean Grille (which was attached to the hotel) and spent a couple of hours strolling around town. We walked by the water, partly through the Naval Academy, onto the grounds of the State House, and into a bunch of the boutiques on Main Street. Our last stops were lunch at Preserve and another cone from Kilwins (obviously).

Below is a little more on where we stayed + what to eat + where to browse if you have 24 hours in Annapolis! I’d say we covered a lot, minus going in depth about the town’s history.



Outfit details

Like I said, the Annapolis Waterfront Hotel was a total dream. It’s really the perfect lodging for a small coastal town– so, so well done. Guys, the décor! I can’t even! I have yet to find a hotel that was decorated so closely to what I’d want my own house to look like someday. Lots of navy + white and wood…eeeek! Some friends literally said “that was the most ‘you’ hotel ever” when I got back.

Annapolis Waterfront Hotel

When we were booking our stay, both Katie and I, the branding lovers we are, immediately caught sight of the hotel logo and fell head over heels. The robes, room keys, and even the towels were branded…something you don’t see often outside of very high-end luxury hotels. Definitely a nice touch that resulted in us sneaking our room keys into our wallets upon departure :)

Annapolis Waterfront Hotel

No detail went unnoticed, from signs at the entry of the hotel’s carriage entrance, to the box of snacks for purchase in the room, to the perfectly contrasting striped chairs and topiaries in the lobby. One of my favorite parts were the black and white photos of sailors that hung in the rooms and in the lobby. They fit in so well and like the rest of the décor, were the perfect nod to the Naval Academy and fact that Annapolis is a waterfront town.


Annapolis Waterfront Hotel


One of my favorite touches was the C.O. Bigelow bath products. They’re one of my favs companies for bath products thanks to an early Bath and Body Works intro in middle or high school, and unfortunately I don’t see them circulated as much anymore. (If you’re curious, Nordstrom carries a ton of their products, including the famed rosebud salve).

Annapolis Waterfront Hotel

In general, I can’t recommend AWH enough. The staff was friendly and helpful, the rooms were huge and comfortable, and the aesthetics were an photographer’s dream. I’ll definitely be back–who wants to go?!


View from the hotel’s patio


Dock Street Bar & Grill: A solid neighborhood bar with phenomenal crabcakes. We split one for an appetizer. I got a burger for dinner and Katie got the BLT, but the jumbo lump crab was definitely the highlight (as were our $5 Leinenkugels)! Also: friendliest bartenders ever!

Preserve: We stopped here for lunch before heading out and it was great. A very farm-to-table vibe (it technically isn’t one, but they source a lot of locally-sourced ingredients). I had the deviled egg salad tartine + fries, plus the house made kombucha, and Katie went for a BLT round two.

Kilwins: Amazing ice cream! We went twice, and I’d been once before last time I was in Annapolis visiting my friend’s family. I got s’mores the first night and chocolate chip with rainbow sprinkles Saturday afternoon.

Kilwins Annapolis

Pusser’s Caribbean Grille: Pusser’s hosted us for breakfast on Saturday and let me tell ya, the waterfront views were no joke. I had a a crab omelette– so, so good– and Katie went with eggs, turkey sausage, hashbrowns, and toast. Why can’t breakfast overlook the harbor every day? As an aside, Pusser’s is also known to be one of the best watering holes in town and are open till 2am Friday and Saturday. We didn’t make a late night stop this time around, but would definitely sample a painkiller (or two) there next time we’re in town!

Pusser's Caribbean Grille

Annapolis Waterfront Hotel


There are tons of stores along Main Street, right in the center of town. Some of my favs included:

Kokopelli: A great selection of resort brands, housewares, gift items, and everything nautical. The staff was also so nice and helpful–I could have walked out with five bags in minutes. This was probably my favorite store we stopped into, as it’s so uniquely Annapolis and carried some of my favorite brands I don’t frequently see elsewhere (Mudpie, KJP, Malabar Bay, and more).

The Lucky KnotA preppy paradise! The whole store is so colorful and just screams summer…all of your favorite resort brands in one place, (they include Sail to Sable, Duffield Lane, Gretchen Scott, and more).


The Pink Crab: A Lilly Pulitzer store–all the cutest Lilly in one place, with some Vineyeard Vines and other preppy brands sprinkled in. PS: Have you heard that the You Gotta Regatta print is back?!

Tervis: There was an actual Tervis store…how cool is that?! I don’t actually own any but went in to browse and almost came out with one. I always think it’s so cool when you stumble upon a store of a brand you see sold almost exclusively elsewhere.

Other stores:  These are just the tip of the iceberg…there are several more clothing stores (Tangerine and Lilac Bijoux were cute for the non- overly preppy crowd), art galleries, and speciality stores just along Main Street and within a few minutes walk.



I pretty much summed up how we spent our 21 hours in Annapolis, but like I said, we didn’t delve much into the town’s history. The Naval Academy has a visitor’s center, walking tours are available, and of course sailing is a popular option that we unfortunately had to save for our next visit. Schooner Woodwind was recommended to us and picks up right on the dock behind our hotel, next to Pusser’s.

Like I said, we drove to Annapolis from DC and unfortunately by car is the only convenient way to get there, as no trains run into the city. There are definitely buses of some sort, but I recommended driving if you can. That being said, Katie and I both agreed that a lack of majorly used public transportation is likely part of why the town remains as charming as it does, especially as it attracts tons of tourists during the summer month.

Definitely let me know if you have any questions regarding the city or what we did–Annapolis, I’ll be back soon! :)


The Annapolis Waterfront Hotel graciously hosted us for a one night stay and Pusser’s had us over to breakfast, but as always, all opinions are entirely my own! A huge thank you to the AWH team + Pusser’s for having us!


Leave a Comment


  1. This looks AMAZING. I was dying over the photos of the hotel! Looks like the perfect weekend getaway :)

    Published 6.23.16
    • Monica wrote:

      Thanks girl! It was perfect!!

      Published 6.26.16
  2. Victoria wrote:

    LOVE this roundup! You captured Annapolis really well and YES – Kilwins is so good :-) The hotel looks absolutely stunning with it’s nautical decor…Love the logo too! xx – Victoria | Viciloves

    Published 6.24.16
    • Monica wrote:

      Thanks, Victoria! I could totally go for some more Kilwin’s right now :)

      Published 6.26.16