Tours in Annapolis

Top Tours in Annapolis, MD

Annapolis Tours

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    Tours, activities and experiences bookable on Tripadvisor, ranked using exclusive Tripadvisor data including reviews, ratings, photos, popularity, user preferences, price, and bookings made through Tripadvisor.
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47 places sorted by traveller favourites
Things to do ranked using Tripadvisor data including reviews, ratings, photos, and popularity.
Showing results 1-30 of 47

What travellers are saying

  • S7821QCkellym
    5 contributions
    We loved our sail with Captain Tony! We appreciated the text morning of to help ensure we knew where to meet him and were grateful his willingness to customize our time. Very nice to have snacks and beverages provided as well. Highly recommend!!
    Written 13 October 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Larry A
    4 contributions
    Fantastic tour. Highly personalized and visited streets not on typical tourist walking tours or large group tours. Well worth the ticket.
    Written 23 April 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Elena K
    Peso Da Regua, Portugal2 contributions
    We had William as our tour guide. A fountain of historical knowledge, very personable and fun to listen to. We totally enjoyed our tour and have been recommending it to our friends.
    Written 18 April 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Darin H
    2 contributions
    CapSup community is great so much fun to explore nature on the water with. Relaxing atmosphere and knowledgeable guides and staff.
    Written 26 April 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Rachael B
    Spotsylvania, VA17 contributions
    Awesome time with my 9 year old. At first she told me she was going to be too scared . But we got her a hat and sword she got to pick out a tattoo and had a bunch of other kids to interact with. The staff was great very engaged with the kids. I do recommend you don’t forget sunblock. After it she told me it was her best time ever.
    Written 1 August 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • judyolsonann
    Annapolis, MD12 contributions
    Sailing on the Schooner Woodwind is a wonderful experience for anyone who visits or lives in Annapolis. You get a different perspective of the city from the water. The captain and crew are not only very professional, but have a lot of knowledge of the history of Annapolis and its surroundings.
    We had the unique opportunity of participating in the Wednesday Night Sailboat Races on the Woodwind. It was great!
    Written 20 May 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Rita S
    Ellicott City, United States2 contributions
    I've always wanted to go under the Chesapeake Bay Bridge by boat, ever since a failed attempt on a sailboat many years ago. This boat trip was relatively fast (90-minutes vs. the hours it takes to get to the bridge from Annapolis under sail), and even though I lived in Annapolis for many years, I learned some new things from the audio recording. The boat was CLEAN, inside and out! We left on time and returned on time.

    We talked to Colleen the bartender (great lady!), and my husband and I are already planning on doing the Baltimore cruise next weekend!
    Written 23 May 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Esther
    1 contribution
    We went on a twisted history tour on April 22nd with Melissa. She is amazingly knowledgeable and funny. We couldn’t ask for a better guide. If you are thinking about taking the tour … sign up, you won’t regret it.
    Written 24 April 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Svetla V
    1 contribution
    Awesome! I stayed for 5 days, and I sailed with 3 different instructors. They were all great! I am a novice sailor, and I had a lot of questions. They are very good at teaching and I leaned a lot! I will sign up my husband and my kids for classes! The area is also great for food - lots of good restaurants and bars nearby.
    Written 16 May 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Beth
    New Delhi, Delhi, India2 contributions
    My 5 and 7 year old kids (and 70 year old mother-in-law) LOVED this fishing trip. It is well-organized/planned, just the right amount of time (1.5 hours), and by far the best part was Captain Chris and First Mate Brent. They were SUPER friendly, fun, and engaged all the kiddos in learning about crabs, fish, the harbor... The boat is clean and safe and played fun music. It was a great adventure and we will definitely come again. Highly recommend for all ages, but clearly geared towards kids.
    Written 1 September 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Jan S
    2 contributions
    Aloysius was very knowledgeable and has done a lot of history research not in the history books. Great personality and great tour guide. We went last night and though only a few of us due to it being a Monday Aloysius gave the same effort and energy! We have taken 2 tours while here and this one was by far the better one! Highly recommend!
    Written 10 May 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • lenniemejia
    Richmond, VA13 contributions
    I highly recommend this walking tour if you visit the Naval Academy. Our walking tour guide is Roza. She is remarkably passionate and very knowledgeable about the history of the academy. She provided our group as much detail (of the past and present) as can be to make it really an interesting and informative tour. I am glad we decided to do the walking tour rather than the bus tour. Kodus to Roza! She even pointed us to the Officer's Club if we decide to have our lunch there.
    Written 19 April 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • ssa71
    Basking Ridge, NJ8 contributions
    We had a fabulous day sailing with captain Paul. The boat is comfortable and he is quite knowledgeable. Made us all comfortable and enjoy.
    Written 29 April 2022
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Debra H
    Minneapolis, MN10 contributions
    For out of town visitors, this was a great way to experience parts of Annapolis you otherwise would miss. Captain Greg gives a nice briefing on how to handle the boat and where to go, so you don't have to have boating experience. Our group of 8 was in town from all over for a family gathering, and this gave us something fun to do while visiting with one another. We chose a 2 hour timeframe. It was very much a highlight of our time in Annapolis. We highly recommend this activity.
    Written 10 October 2021
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
  • Joanne
    Cancun, Mexico46 contributions
    Absolutely love Kayak Annapolis! Frequently rented kayaks last summer from them. Had my first SUP experience today and plan on perfecting stand up paddle boarding with them this summer. The owner, Kate, is awesome. She welcomes everyone with a smile and has always been pleasant. Definitely rent from Kayak Annapolis.
    Written 14 July 2019
    This review is the subjective opinion of a Tripadvisor member and not of TripAdvisor LLC.
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