Valentine’s Day Trip to Annapolis

This Valentine’s Day H and I went on a quick but romantic trip to Annapolis, Maryland. Annapolis is less than an hour away and there was so much I wanted to do there—I can’t believe we hadn’t taken a day trip there before! This getaway was a great way to break up the dreary month of February, and I loved learning more about the historic downtown area.

We left on Saturday morning and stopped on the way to see one of my cousins who lives near downtown Annapolis. After a brief visit, we booked it downtown for an afternoon tour of the William Paca House. The house was beautiful—I was shocked that one family had that huge mansion right downtown plus another lot behind it for their garden. Inside, it reminded me of the Governor’s Palace in Colonial Williamsburg on a smaller scale: the same paint colors, floor coverings, and even the same smell (do all historic houses have that smell??). After our tour of the house, we explored the garden, which was sectioned off by hedges and graveled paths like a mini-Versailles, and walked across the picturesque bridge over the pond to peek inside the windows of the summer house. It was warm for February, so we took our time walking back to where we had parked, looking in the windows of the little shops and admiring the historic buildings.

For our afternoon in Annapolis, I wore an outfit I’ve been waiting for the right occasion to break out: a pink cable-knit sweater and white wool skirt with brown ankle boots and a pink J Crew coat. I figured if there was ever a time to have a 60s-inspired matching coat and sweater moment it was in Annapolis, which is basically preppy central. This outfit was perfect for a mild February day.

Back at the car, we drove to our hotel to check in. I was so excited to stay at the Graduate Annapolis—we’ve stayed at the Graduate Hotel in Charlottesville a few times, and I love the quirky décor. The cavernous lobby at the Graduate Annapolis had a preppy naval theme, with wood paneling, plaid chairs, and knot motifs on the ceiling. The fun vibe continued in our room, which had colorful striped walls, leather furniture, and a madras headboard (I want one of these now). Even the bathroom had wallpaper with a crab pattern!

We had researched a few options for dinner that night, and our top pick was Reynolds Tavern, which has been around since 1747. People were already waiting outside when we walked by earlier that day, so after we checked into the hotel we walked back for dinner, hoping to get a table. We got to sit in the basement near one of the old fireplaces, and everything we ordered was amazing! My favorite part was the Smith Island Cake, which is the official dessert of the state of Maryland and tastes like the best homemade birthday cake ever. After dinner, we walked back to the hotel and settled into our cozy nautical room for the night.

Dressed up for dinner in Annapolis

For dinner, I wore a black minidress with a sweetheart neckline and puffy sleeves. To make the look a little less formal for the basement pub at Reynolds Tavern, I added my ankle boots and pink coat from earlier that day. The boots were also much more walkable than the black suede heels I had brought—it was only a ten-minute walk to the restaurant but I didn’t want H to have to carry me back because of blisters.

When we woke up the next morning it was snowing, which was enchanting for a Valentine’s Day getaway. We had planned to do brunch that afternoon, but we decided to get coffee and croissants from the cute lobby café instead and then head out early before the roads got too bad. For lounging around the room that morning, I had packed navy pajamas with white trim, to match the nautical theme of the room!

Coffee in bed at the Graduate Annapolis

We had so much fun exploring Annapolis—it reminded me of Old Town Alexandria although it definitely has its own flavor! I definitely want to go back, maybe in the summer when it’s a little warmer, to see the Naval Academy, walk around the marina, and try one of the restaurants near the waterfront.

Have you been to Annapolis? What day trip/weekend away destination should we try next? Let me know in the comments!

2 thoughts on “Valentine’s Day Trip to Annapolis

  1. I’m enjoying your pursuit of history, and remembering the motto I “coined” once upon a time: “Carpe Diem, et Toga Apropos”. Obviously, I don’t “know” Latin, but it seemed like how one might say “seize the day and WEAR THE RIGHT OUTFIT”!
    Next visit to Annapolis, I recommend Sunday…so you can see all the cadets in their dress whites, walking to church or ???
    And since you mentioned Smith Island, do plan a day trip there…it’s a boat ride, a mini-tour of the very historic island & the lifestyle of the watermen who still live & work there, followed by a family-style lunch in their one restaurant. My visit was about 30 years ago and my introduction to corn pudding! That area of the Bay once had pirate activity, but none now that I know of!
    Tangier Island has a similar tour, I believe, but haven’t checked lately. Terry’s ancestors lived in that region in the late 1700’s & 1800’s; there were no roads…all commerce & travel were water-borne. 😁

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