Alleys and oddly angled streets are crammed with small row houses and slivers of gardens. Cafes and restaurants offer outdoor tables in season. Mansions inhabited by Maryland’s political elite at the dawn of the nation are open to visitors. Segway riders roll en masse for tours. Yachtsmen proudly parade their boats on a finger of water, called Ego Alley, that ends at City Dock in the heart of downtown.
Annapolis, which is often choked by automobile traffic, is perhaps best reached by water. Sail or motor from the Chesapeake Bay, and you are likely to see the tops of the hilltop State House and the Naval Academy Chapel before the rest of the town is visible. Ric Dahlgren, the harbor master, said that each year 8,000 to 10,000 boats visit Annapolis, which is often called the sailing capital of the country.
Drivers (it is about 40 minutes from both Washington and Baltimore) can head to the waterfront, too, to begin a tour of the city at City Dock, a great spot for walking and browsing. Park at the Navy-Marine Corps Memorial Stadium and take a free shuttle to the City Dock area. Many visitors barely go beyond the shops and restaurants near Ego Alley.
Pop into Re-Sails (42 Randall Street, 410-263-4982), which sells a variety of goods, including drawstring backpacks for $49 and $54, made of recycled sails. Next door, Mixed Greens (410-216-9830) offers eco-friendly items, including bowls shaped from old vinyl records, sold for $28.