5 Days of Charm in Annapolis Maryland Itinerary

Begin your day with a visit to St. Anne's Church, one of Annapolis' oldest churches with beautiful architecture and rich history. For breakfast, enjoy a cozy meal at Bread and Butter Kitchen, offering fresh pastries and coffee.

Next, explore the Banneker-Douglass Museum which highlights African American history in Maryland through engaging exhibits. Have lunch at Mason's Famous Lobster Rolls for an authentic taste of New England-style lobster rolls.

In the evening, participate in Phantoms of Annapolis Ghost Walking Tour. This walking tour will take you through some of Annapolis' most haunted locations while sharing eerie tales from the past. Beforehand, dine at Vin 909 Winecafe, known for its farm-to-table dishes and extensive wine list.

Kick off your day with a scenic walk along City Dock where you can watch boats come in and out while enjoying breakfast at Cafe Normandie, famous for its French-inspired cuisine.

Engage in some fun with Annapolis: Private Scavenger Hunts. This activity is perfect for families or groups looking to explore Annapolis in an interactive way. For lunch afterward, visit Boatyard Bar & Grill which offers great seafood options in a casual setting.

Conclude your day by exploring Main Street where you can shop at local boutiques or enjoy live music at various venues. Have dinner at Level - A Small Plates Lounge, which offers creative small plates perfect for sharing.

Start your day with a visit to Quiet Waters Park. This beautiful park offers scenic trails, art galleries, and kayak rentals for those looking to enjoy nature. For breakfast, head to Eggcellence, known for its delicious omelets and friendly service.

After a refreshing morning at the park, visit the William Paca House & Garden. This historic home of a signer of the Declaration of Independence is a stunning example of Georgian architecture and offers guided tours. Enjoy lunch at The Federal House Bar & Grille, which serves classic American dishes in a historic setting.

In the evening, join Best of Annapolis Walking Tour. This tour will take you through some of Annapolis' most iconic sites while providing fascinating historical insights. Before starting the tour, have dinner at Osteria 177, known for its upscale Italian cuisine.

Begin your final day with a visit to the Hammond-Harwood House. This beautifully preserved colonial mansion offers guided tours that delve into its rich history and architecture. For breakfast, stop by Miss Shirley's Cafe, famous for its Southern-inspired dishes.

Annapolis: Crabtown Boos and Booze Haunted Pub Crawl provides an exciting way to spend your afternoon with ghost stories and pub visits around Annapolis. For lunch before the tour, try Davis' Pub, a local favorite known for its crab cakes and laid-back atmosphere.

Phantoms of Annapolis Ghost Walking Tour is another thrilling option for your final evening in Annapolis. Enjoy dinner at Reynolds Tavern, offering traditional British fare in a historic setting before embarking on this spooky adventure.