Under $100: Annapolis, Md.

The capital of Maryland quaintly sits on the cusp of the Chesapeake Bay where seafood reigns supreme, naval history abounds and charming old-town accents line the streets. Start your day with a coffee and pastry for less than $4 at City Dock Café in the heart of downtown. Chat with friendly locals and plan your day within the cozy café walls or outside on the patio overlooking the docks.

After a caffeine boost, head into the streets of downtown Annapolis and window shop among colonial architecture, cobblestone streets and smiling faces. A leisurely stroll along Ego Alley provides ample opportunities for window shopping, people watching and boat gawking along the water. Pop into St. Anne’s Church for a step back in history, and inquire about the seasonal free concerts held within the church. A few steps away from the church is the Maryland State House where Maryland’s government operates. There is no cost to enter and wander the halls of history and diplomacy.

Thurgood Marshall Monument, Maryland State House © Philip Rink Jr | Dreamstime

Lunchtime warrants a visit to Chick and Ruth’s Delly. Although sometimes crowded thanks to its well-earned reputation, a visit is worth it for diner favorites (burgers from $5.99 to giant sandwiches, starting at $5.99) and all-day breakfast. After lunch, visit the Pennsylvania Dutch Farmer’s Market to browse both Amish and non-Amish crafts and fresh food.

To round out the day of walking history, feed your soul at the Iron Rooster, another establishment that serves all-day breakfast as well as breakfast-inspired entrees such as Cakes on Cakes: a crab cake and a cornmeal pancake topped with fried green tomatoes and chipotle hollandaise ($24.95).