Things To Do
Explore & Sightsee
Historic Downtown Annapolis – Walk the charming streets, browse boutiques, grab coffee, and soak in the waterfront views. The area is super walkable and full of colonial architecture. Eastport - Take a stroll through Eastport, Annapolis’s laid‑back, waterfront neighborhood that proudly calls itself the ‘Republic of Eastport.’ It’s an easy walk with great views of the harbor, sailboats everywhere, and plenty of spots to grab a drink or an ice cream. Think small‑town charm with a salty, nautical sense of humor — very on‑brand for Annapolis United States Naval Academy - If you have extra time in Annapolis, swing by the U.S. Naval Academy — Peyton’s alma mater and home to approximately 4,000 midshipmen who somehow survive on discipline, King Hall dining hall food, and sheer willpower. The campus is gorgeous, historic, and absolutely worth a stroll. City Dock – A central waterfront area where you can watch boats and enjoy the harbor atmosphere
Restaurant Recommendations
If you’re arriving early, we recommend grabbing breakfast or lunch in downtown Annapolis! - Rams Head Tavern - Lewnes' Steakhouse - Boatyard Bar and Grill - El Toro Bravo - Nano's Sushi - Iron Rooster - Chick and Ruth's Deli
Historic options
Maryland State House - The oldest state capitol still in continuous legislative use. George Washington resigned his commission here — it’s Annapolis history at its peak. William Paca House & Garden - A beautifully restored 18th‑century Georgian mansion built by a signer of the Declaration of Independence. The gardens are stunning and very walkable. Annapolis Maritime Museum & Park - for a relaxed, waterfront experience exploring Chesapeake Bay history, local watermen culture, and scenic harbor views.