This past Saturday was one for the books! First of all, whenever you find a free weekend available for four DC couples, it’s nothing short of a miracle. But more importantly, we got to spend the day with some really sweet friends who inspire and strengthen us, and we are so grateful we get to do life with them!
We started the day with a carpool to Ben and Taylor’s adorable vintage townhouse on H Street armed with Brooklyn Bagels. We took our time catching up over coffee and admiring their new place and precious 6-month-old, Callan. Eventually we loaded up in segregated guys and girls cars for the journey. 🙂
Shopping Around Town
Disclaimer: it wasn’t an entirely free weekend for all four couples, but Jeff joined us later.
But let’s talk about Annapolis. I feel like N’SYNC was singing “God must have spent a little more time on you” in my head because really, it’s that amazing. This town is equal parts Colonial, nautical, and European. I’ve said it before and I’m sure I’ll say it again, but the quality, convenience and variety of DC’s weekend getaways can’t be beat.
We started out just exploring the main street of town (I think it’s actually called Main Street?) popping into stores and such. There was a really cool cooking store full of spices, a Danish children’s clothing store, and this awesome vintage bookshop.
You know you have a good crew when the used bookstore gets the most love of all the shops.
Then we popped into a cute hipster coffee shop for some basil limeade and wandered through an art gallery. 
I want to be Taylor when I grow up. She has a baby and her hair still looks amazing.
With drinks in hand, we decided it was time for a quick strategy session to plan our next move and Yelp a lunch spot. Leslie lived here when she was a kid, so it was good to have one knowledgeable member of the crew! Ultimately we decided to show some responsibility and tour the state house before heading to lunch on the water.
Touring the State House
You might not have even known we had a baby with us for the entire day, because that guy was so, so good! He’s just the cutest, happiest baby, and he must have liked Annapolis, because he was just all smiles throughout the trip!
We learned about how Annapolis was once the capital of the U.S., and Cal was in awe.
Hanging out on the steps while Cal took the elevator.
After strolling through some more charming shopping areas (and LOTS of American flags, woooo), we had the best crab cakes of our life at Dock Street Grill on the harbor and took our time hanging out and eating lots and lots of crab things.
Kayaking on Annapolis Harbor
With Jeff in tow, we took a little walk around to the other side of the harbor for a kayak excursion! We had taken our time so much that we only had an hour, but it was all we needed. Baby Cal sat this one out with his parents, but the bar they hung out in overlooking the water looking pretty nice too! 🙂
Jeff occasionally went on paddling strike to see how Hayley would do, and it was hilarious.
Ben and Leslie crushing it!
We’ve been doing quite a bit of kayaking this summer, and this might have been my favorite view with all of the waterfront houses and boats.
Paddle boarding is so hot right now.
Can I live here? I’ll happily take the small one. Thanks.
Jeff on strike.
We had the best time, and eventually came back in ready for a drink!
Happy Hour on the Water
Having brought our boats back just in time, we found Ben, Taylor, and Cal, and took the cutest ferry to the main area of downtown again. We stopped by various yachts to pick people up, and it most definitely did not feel like real life.
Ben and Leslie on the ferry!
It was a beautiful and fairly crowded Saturday, so once our ferry navigated the “minefield of privilege” in Ben’s words, we found this hopping waterfront patio with live music to enjoy happy hour and watch the boats go by. They had an amazing drink called “the painkiller” that was all coconutty pineapply goodness, and the music was great.
Post-kayaks and happy with fruity drinks for the ladies and beer for the gents.
Sweet Callan was STILL going strong at happy hour! Isn’t he the handsomest baby ever?
Sunset sail.
And this is where my photo documentary ends, but the day did not. The Irwins took baby Cal home, and the Porters and Mostellers found Leslie’s childhood home while Will and I checked into our AirBnb. We found the most charming waterfront carriage house to stay in. The Porters and the Mostellers came over for a drink on “our” patio, and it was a great night! After everyone headed back to DC, Will and I actually snuck back into town for some very late night sushi, and who knew, everything was still open! Charm and nightlife? What a town.
Sunday Brunch, the Naval Academy, and a Birthday Party
The next day, Will and I woke up to realize that this sweet fire pit set up had been outside all along and that we could have been using it the night before, but alas, it was dark and we didn’t know, haha.
We started the day with brunch and shopping around at Lilly Pulitzer and Sperry, because that seemed fitting, not only for us but also for Annapolis.
This is an old Lilly dress, and the hat is from Tuckernuck.
After brunch we decided to explore the Naval Academy, and oh my is it beautiful. I was so pleasantly surprised by the European architecture! I did not expect to feel like I was in France, but Annapolis’s wonders never cease.
First we walked through this idyllic row of the professors’ homes, and they all had matching blue and while awnings. Be still my heart.
Is this too many pictures of this? I can’t stop.
We wandered up to the superintendent’s “quarters” which was this beautiful mansion. The mint shutters! I die!
Then we went into the preppiest chapel there ever was.
See? French. Right?
And finally, we strolled through the rest of campus and went into the dining hall, where they have all of the state flags in alphabetical order. It was another gorgeous day, naval students were milling about, and we were loving life.
We ended the trip with a first birthday party for a friend’s baby, and couldn’t believe it only took us 30 minutes to make it back for church in downtown DC! Who knew this magical place was essentially a DC suburb all along? The mid-Atlantic is magical.
