Food comes first in Annapolis: Chesapeake crab cakes, oysters in season and pubs set inside old brick buildings. The tours below thread history through that appetite, from the Maryland State House on its hilltop circle to the waterfront at City Dock and the Naval Academy gates.
Related: Best Things To Do in Annapolis: United States Naval Academy & Maryland State House
Top-Rated Annapolis Maryland Tours & Experiences
Colonial Annapolis and Maryland State House Guided Tour
A guided walk through the colonial core, centered on the Maryland State House, the oldest state capitol still in legislative use. It suits history fans. Check whether the interior is part of the visit, since access can depend on the legislative calendar.
Annapolis Harbor and U S Naval Academy Cruise
A boat tour from the waterfront with views of the harbor and the Naval Academy grounds from the water. A relaxed option for families and anyone who prefers sitting to walking. Confirm the departure dock and season on the listing.
1 5 Hour Haunted Ghost Walking Tour of Historic Annapolis
An evening walk through the old streets built around ghost stories and local legends, lasting about an hour and a half. It suits groups and curious skeptics. Wear comfortable shoes, dress for the weather and expect theater more than fright.
Annapolis Colonial and Maritime History Walking Tour
A walking route linking the colonial town with its port history, useful for visitors who want context for the harbor as well as the buildings. Expect brick sidewalks, so wear flat shoes, and check the starting point.
Best of Annapolis Tour Colonial History and U S Naval Academy
A broad introduction pairing colonial landmarks with the Naval Academy, aimed at first-time visitors short on time. Check whether it enters the academy grounds, since visitor access rules change and photo ID may be needed.
Whichever experience you choose, booking online ahead of time in Annapolis Maryland means one less thing to worry about once you land.
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Eating your way through Annapolis
Annapolis is Chesapeake Bay seafood country: blue crab, rockfish and oysters appear on menus around City Dock and Main Street. If a tour includes tastings, check the listing for what is covered, and mention shellfish allergies to the guide early.
Why We Picked These Tours
Annapolis is Maryland’s capital and home to the U.S. Naval Academy, with many well-preserved colonial buildings in a compact center. That walkable layout is why walking tours dominate this lineup, with a harbor cruise and a few evening options rounding it out.
Where to Sleep in Annapolis
Staying near City Dock and Main Street puts tours, restaurants and the water within minutes on foot. Eastport, across Spa Creek, is quieter and more residential. Parking in the historic core is tight, so choose a hotel with parking or a garage.
Timing Your Annapolis Trip
Spring and fall bring mild weather and pleasant harbor days. Summer is hot, humid and busy with boaters, while winter is quiet and some seasonal cruises may not run. Commissioning Week at the Naval Academy in late May fills hotels, so book early if you visit then.
How Much Annapolis Tours Cost
Across 6 priced tours, prices run from $26 to $235, a wide gap. Most land near the median of $35. The top figure likely reflects a private or small-group format, so compare inclusions and group size. The cheapest is Ashes and Apparitions of Annapolis Ghost Tour at $26.
How the Top Tours Compare
Review counts are modest, about 312 in total, so read ratings as early signals rather than verdicts. Tipsy History Tour scores 5 from 49 reviews, while Ashes and Apparitions of Annapolis Ghost Tour has the most feedback at 92 reviews. Choose by theme: history, ghosts, food or harbor.
Before You Book in Annapolis
Wear comfortable shoes for brick sidewalks and gentle slopes. Bring photo ID if you plan to enter the Naval Academy grounds, and check current visitor guidance first.
Annapolis Tours: Quick Answers
Can you visit the Naval Academy on an Annapolis tour?
Some listings pair the academy with town history, and the cruise shows the grounds from the water. Visitor access and ID rules change, so read the listing and current guidance before you go.
How much do Annapolis tours cost?
Across 6 priced tours, prices run from $26 to $235, with a median of $35. Walking and ghost tours sit near the low end, while food and private-style tours cost more.
Is Annapolis walkable without a car?
The historic center around City Dock, Main Street and State Circle is compact and walkable, which is why most listings here are on foot. Parking is limited, so leave the car at your hotel.
Which Annapolis tour has the most reviews?
Ashes and Apparitions of Annapolis Ghost Tour leads with 92 reviews at 4.3 stars. For the best rating among tours with 20 or more reviews, Tipsy History Tour scores 5 from 49 reviews and costs $39.
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