GPS: 38°58'N 76°30'W
Maryland’s colonial capital is the major recreation port of Chesapeake Bay and home to the U.S. Naval Academy. Blow off steam kayaking, sailing, wind-surfing, or go crabbing for your dinner.
The Chesapeake is flooded with ships of all shapes and sizes and with a little chutzpah you can kayak right alongside them (kayak rentals $15 an hour; www.annapoliscanoeandkayak.com). But if the hustle and bustle of imposing boats and lighthouses becomes too much then head to Quiet Waters Park for a more soothing paddle (www.aacounty.org/RecParks/parks/quietwaters). Want to try your hand at crabbing? Ask a park ranger! Matapeake County Park can be hit or miss depending on the season (www.parksnrec.org), so consider renting a boat at Sandy Point State Park and up your chances with a little mobility (www.dnr.state.md.us/publiclands). Or just time your visit to coincide with the annual all-you-can-eat August crab feast (http://www.annapolisrotary.org/crabfeast) and forgo the work.
Chick and Ruth’s Delly, at 165 Main Street, is a local institution in business now for 40 years. Show up early for the Pledge of Allegiance, and stick around all day washing down your "Colossal" reuben with a six-pound shake—and win a T-shirt if you finish both in an hour (www.chickandruths.com).
The Inn at Horn Point has preserved the original features that made it a cozy home when it was built in 1902—a big wrap-around porch, double bay windows, and pine-wood floors—and added the modern amenities that now make it a comfy weekend base camp (doubles from $149; www.innathornpoint.com).