Annapolis is one of the Chesapeake Bay's most charming waterfront towns, home to brick and cobblestone streets and historic locales dating back to the 17th century. The city, which has been named as one of America's prettiest towns by Forbes, is located within convenient day trip distance from Baltimore and Washington, D.C. Its 17 miles of gorgeous waterfront and 200 acres of public parks make it a great escape from the hustle and bustle of the city.

Visitors can enjoy decadent dining at elegant restaurants like OB's Prime Steakhouse and the waterfront Carrol's Creek or stroll through charming boutiques and specialty shops along the city's hanging basket-lined historic Main Street.

Sunset sailing excursions from companies such as Schooner Woodwind make the perfect ending to an evening before returning to romantic accommodations.

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