Annapolis 2026 Calendar of Events

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!

Really enjoyed the pub crawl, fast paced. Tour guide very knowledgeable and passionate about the history.

Nice cruise with great scenery

Michael was extremely pleasant and very thorough answering all of our curious questions. He also offered great after tour Annapolis suggestions.

Guide did a good job. Interesting ghost stories and history.

Informative and fun. Nice way to learn about the history of the area.

Ryan was so delightful!! He was funny and knowledgeable and told the stories in such an engaging way - not to mention he handled our sometimes rowdy group with such grace and really rolled with the punches to get us back on track! Seriously fun guy, great cocktails, turns out our history is wild and raucous and very tipsy! lol recommending to everyone!! Oh and we loved the maps Ryan!!!

This was such a fun outing! We loved seeing all of the beautiful waterfront homes and giant yachts, and the tour guide shared a lot of interesting information about the area. I would absolutely recommend this to anyone who wants to see what Annapolis and the area is like from out on the water.

Always a lovely time. Be sure to leave time to navigate to the new departure point on the other side of Ego Alley during the construction at city dock of course. Staff was professional as always and the boat was in good shape. Docking at the Maritime Museum is perfection, especially when they are setting up for an evening, outdoor, wedding like yesterday. Enjoy!

My girlfriend and I had an amazing time on the Tipsy History Tour! Our tour guide was incredibly knowledgeable and did a great job making the history interesting, entertaining, and fun. We learned a lot about Maryland’s distilleries, Prohibition, and the history of Annapolis.Every pub we stopped at had amazing drinks and a great atmosphere. It was the perfect combination of history, drinks, and spending a fun afternoon together. We had a fantastic experience and would definitely recommend this tour to anyone looking for something fun and different to do.

This was a wonderful introduction to Annapolis: a walk through town to learn the history of the city, the tour of the State House, and the visit to the Naval Academy. Our guide, Mistress Melissa in period dress, presented historical background in a way that was enjoyable and easy to follow, and answered all our questions well. We all left with some good information to use in a future trivia game. I traveled with two friends, and although two of us had been in Annapolis before, this was our first tour there, and it was excellent. The price of the ticket is very reasonable for a guided tour of over two hours.

This was a great way to learn about Annapolis and its (sometimes creepy) history. We did the 8pm tour on a night with a mostly full moon, which was perfect for the mood. Megan was a great storyteller!

Our tour lady was very knowledgeable and informative! Enjoyed the tour lots and lots of.As we walked back to our car on the dark street we thought we heard a skateboarder right behind us .. but no it’s was we thought rustling leaves . It was neither no wind nor rustling leaves . A spirit did follow us only for a moment.

Carolyn was fantastic. Such a wealth of knowledge. Great food, great experience. We would highly recommend. We learned so much history about Annapolis!

Our tour with William, in costume, was a great way to learn about the city, capital (State and Nation!), and the history of Annapolis. The tour guide was very personable and full of interesting and memorable stories and anecdotes, shared while on the actual sites where they occurred. This tour experience will have broad appeal to visitors of all ages and levels of education. Highly recommended.

I decided to spend a day exploring Annapolis, and since it was such a beautiful evening, I asked ChatGPT for a recommendation on something special to do. It suggested taking a Spa Creek cruise — and I’m so glad I did because it ended up being the absolute highlight of my week!When I arrived at the meeting spot, I met Captain Scott, who was incredibly friendly, knowledgeable, and clearly very passionate about what he does. He took me around the Annapolis waterways while personally narrating the tour, sharing stories and information about the area, which made the whole experience feel much more personal than a typical sightseeing tour.What made the evening even more special was that there happened to be sailboat racing that Wednesday. Captain Scott took me over to watch the races up close, which was such an unexpected and memorable addition to an already beautiful evening.The combination of the scenery, the sunset, the racing, and Captain Scott’s hospitality made this one of my favorite experiences in Annapolis. I would absolutely recommend this cruise to anyone visiting the city — especially if you’re looking for something relaxing, personal, and a little different from the usual tourist activities.Thank you, Captain Scott, for such a wonderful evening!