Small Group Annapolis Tours

Tours in Annapolis

Discover Annapolis — the charming capital city of Maryland, USA, celebrated for its rich maritime heritage and colonial architecture. Nestled along the shores of the Chesapeake Bay, Annapolis invites visitors to explore its historic streets and picturesque waterfront. Immerse yourself in the city's vibrant culture, from the renowned United States Naval Academy to the quaint boutiques and galleries of Main Street. Enjoy scenic cruises on the bay, stroll along the City Dock, and savor fresh seafood at waterfront restaurants. With its unique blend of history, culture, and natural beauty, Annapolis offers an unforgettable experience for travelers seeking a taste of coastal charm. Join us on a guided tour and discover the magic of this historic city with Tripshepherd — Annapolis's premier small group tours. Reserve your spot today and embark on an adventure through history and beauty!

Frequently Ask Question

What are the best tours in Annapolis?

Experience Annapolis through walking tours of historic downtown, such as the Best of Annapolis Walking Tour with Boat Cruise, and guided tours of the city such as the Best of Annapolis Tour with Boat Cruise, providing insights into the city's maritime heritage and colonial history.


Why is Annapolis called that?

Annapolis derives its name from Queen Anne of Great Britain, reflecting its colonial origins and historical ties to British monarchy.


What are the most popular attractions in Annapolis?

Notable attractions in Annapolis include the U.S. Naval Academy, Maryland State House, Annapolis City Dock, the Hammond-Harwood House, and William Paca House and Garden, offering glimpses into the city's political, maritime, and architectural heritage.


What is the best time to visit Annapolis?

Spring is the perfect time to visit Annapolis, with the city blooming and sailing season kicking off.


What is the coldest month in Annapolis?

January marks the coldest month in Annapolis, with temperatures occasionally dropping below freezing. Make sure to dress warmly when you visit during this month!