I absolutely loved historic Annapolis! It is such a cute and charming city full of history. Oh, and the dining and shopping aren't bad either. It is just a quick 40 minute drive from DC (including a Dunkin coffee stop), making it the perfect day trip.
Originally settled by Puritans in 1649, the city has quite the colonial history. It was the seat of the Continental Congress and the site where, following the end of the Revolutionary War, George Washington resigned his commission as Commander-in-chief of the Continental Army. In fact, you can see his original letter of resignation displayed in the Maryland State House, which was also the temporary capital of the United States following the signing of the Paris Peace Treaty.
Annapolis/Maryland was also home to four signers of the Declaration of Independence, and since many of its colonial structures remain, you can do a little walking tour to admire the historical architecture and the homes of Chase Lloyd and William Paca (there is a great walking tour here).
But, Annapolis is probably best known for being home to the US Naval Academy. I have always argued that the Navy is the best dressed of all the military branches (they did give us the peacoat after all), and their stylish uniforms are on full display around the city. Hello sailor!
After lots of strolling and exploring we satiated our hunger with the most delicious late brunch at the Iron Rooster. Try the crab hash, it's amazing! We spent the rest of our day window shopping before heading back to DC.