Top-rated Annapolis Attractions, Landmarks & More
Annapolis, USA
Looking for attractions and landmarks in Annapolis? Check out reviews and photos of 8 attractions in Annapolis on Cool Destinations.
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Annapolis attraction reviews

New York City
Annapolis Harbor and U.S. Naval Academy CruiseBetsy_S, Sep 2026
The crew members were all...
The crew members were all very nice. The boat captain did a great job navigating the waterways. I would definitely recommend this excursion!

New York City
Annapolis Chesapeake Bay Bridge CruiseBarberett, Sep 2026
History with drinks and laughter
We really enjoyed the stories of history and the alcohol that they drank in their time period. The bars were amazing. All of the group enjoyed it lots of information and lots of laughs and the period drinks were delicious . I highly recommend this tour. We all enjoyed ourselves. Thank you Ryan

New York City
Annapolis Harbor and U.S. Naval Academy CruiseKim_L, Sep 2026
Nice experience
Very friendly staff. Clean boat. Very nice experience. I wish they had benches at the waiting area prior to boarding.

New York City
Annapolis Scenic Severn River CruiseRob_F, Sep 2026
Relaxing river cruise
This river cruise was very relaxing and saw a part of the Severn river we never saw before. Very well worth it.
E6145AVlc, Sep 2026
Wonderful walking tour!
We spent the day in Annapolis and decided to do a walking tour. The tour guide, Rebecca, was amazing. She grew up in the area and definitely knows her “stuff”!! What really shines through is that she really loves the area and it definitely rubbed off on us. We enjoyed the tour and learned so much. There’s so much history in the area and beautiful historic homes, and being close to the water was an added benefit. We would definitely love to come back someday.
PEGGY_T, Sep 2026
Annapolis Fan!
Our guide Priscilla was super knowledgeable about the history of Annapolis, welcomed questions and was pleasant to talk with. We enjoyed that she kept us engaged along the way with her mini-history quizzes!
We live in Maryland and have been to Annapolis many times over the years so it was great to be a more enlightened tourist for a couple of hours and enjoy neighborhood streets we had yet to visit and learn about new haunts we could try! I am sure that we will venture out again for another tour in the future. Thank you Priscilla!

New York City
Day on the Bay Cruise from Annapolis to St Michaelsjacqueb581, Sep 2026
St. Michael's sail
The weather was beautiful during this trip. We had smooth sailing and we saw may sailboats on this cruise. The time in St. Michael's could have been a bit longer to explore the town more. We did have time to enjoy a lovely meal at a local restaurant, Limoncello. The town was busy with a lot of visitors.
Susan_C, Sep 2026
Educational, enjoyable well presented
Started on time progressed at a good pace the guide obviously has intimate knowledge of the city houses and landmark’s. Open to questions and elaborates with stories and histories.

New York City
Colonial Annapolis and Maryland State House Walking TourD9815RBkristis, Sep 2026
Great Time!
We had a great time on the Annapolis tour! Our tour guide Lynn was fabulous. As locals who brought friends from out of town, we also learned so much!!

New York City
Annapolis Colonial and Maritime History Walking TourDavid_W, Sep 2026
William is absolutely...
William is absolutely magnificent. This is a must do tour! He taught us so much in such a shortime. He’s amazing
X6846WHgailf, Sep 2026
History came alive
Just had a great tour with watermark. Reine, our guide kept us moving and seemed to make the tour come to life. Her love and respect for these sites made the past personal and exciting.
Katie_M, Sep 2026
Great tour for families
We had a delightful tour with Michael! He is super knowledgeable about Annapolis’ history as well as the Naval Academy. We had mentioned interest in a few other areas of the city that he was quick to add into our tour. He was friendly, flexible, and made the whole experience great!
Russell_P, Sep 2026
I never knew so much about Annapolis history!
Michael was extremely pleasant and very thorough answering all of our curious questions. He also offered great after tour Annapolis suggestions.

New York City
Ashes and Apparitions of Annapolis Ghost Tourrsabrin, Sep 2026
Gosts in Annapolis
Guide did a good job. Interesting ghost stories and history.

New York City
Annapolis Chesapeake Bay Bridge CruiseVoyager780789, Sep 2026
Relaxing girls trip
Informative and fun. Nice way to learn about the history of the area.
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