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Annapolis, MD

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Pirate Adventures on the Chesapeake

4.9 (111 reviews)
Closed • 8:30 am - 6:30 pm

Pirate Adventures on the Chesapeake Photos

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Kids spraying Pirate Pete!
Olivia M.

Such a fun experience for the entire family! Our group of ten people went ranging in age from 4-60 years old and EVERYONE had the best time. The staff are friendly, helpful, and silly! Highly recommend if you're visiting the area with family

Group picture at the end
Elaine F.

My grand children were visiting from Indiana, so I booked this adventure to give them a chance to get out on the water. What a great time they had! The staff here is so kind, enthusiastic, and great with the kids. The kids enjoyed every minute, and will remember it for a long time. It was money well spent.

Hoisting the found treasure
Josh F.

This was way worth the trip! Our kids are 7 and 5, and this was right up their alley. The staff does a tremendous job keeping the kids engaged and making them feel included from the get-go. They have several different activities they involve the kids with leading up to the ship and while on the adventure. The staff make it fun, funny, innovative, and embrace the pirate culture. I couldn't think of any suggestions for how it could be better, and I'm typically a highly critical person. This was top notch fun for my kids, and that made it top notch fun for me as a parent.

Colleen P.

The crew working were fantastic, you could tell they genuinely enjoy playing pirates and interacting with kids! Loved that it wasn't just a boat ride. Upon arrival they wanted the kids to be involved. They even include face painting.

Megan C.

We took our 9 year old nephew on this pirate adventure and he had a blast, it was $28 a person and you had to call to reserve, they knew the kids by name and paid attention to every single one. They kept the kids interested and kept them engaged the entire time, the staff was very friendly and had a positive interaction with all of us. We would definitely come back in the future!

What an amazing day we had for a 3rd birthday! The staff is incredible and I couldn't speak more highly of them. The day turned out so perfect and our daughter couldn't stop saying "it was the best birthday EVER"! Thank you again Pirate Adventures we sure will be coming back and referring you to all of our friends!

Jason M.

Super fun excursion. Our group ranged from 3 to 9 and all had a good time. The employees... er, pirates, go out of their way to ensure all the kids have a blast. We were the first to arrive and the kids had their choice of outfits before getting tattoos. The littlest was more adventurous with her outfit while the older kids were more adventurous with their pirate and mermaid tattoos. The banter with the pirate cast was very funny. Swell was our pirate guide and she was great. She catered to every kid from the youngest to the oldest, and made sure they were all having a good time, and focused on helping with the missions. The music on the boat was aligned to the story in a fun way. The kids were busy the whole time. The kids favorite part was shooting Pirate Pete with the water cannons. I believe they were playing Metallica Enter Sandman during the attack. They also liked sampling the Grog and checking out the treasure! I would definitely recommend this trip to anyone in Annapolis. It's rough to entertain a 3 yo and an almost 10 yo at the same time and they were engaged the whole time.

Our kids getting the cannons ready!!
Genna P.

Our family was looking to jump start our long weekend in Annapolis and I can't recommend this excursion more. The Pirates crew was super engaging and called our 2 yo and 4 yo by their first names the entire trip. Our two kids were completely captivated by the treasure hunt which even left many of the adults bewildered and asking "how'd they do that?!" Don't pass this up on your next family trip to Annapolis!!

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Good adventure with kids. Not much parking in front of location but we're very accommodating with another lot.

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Page 1 of 3

Ask the Community - Pirate Adventures on the Chesapeake

Review Highlights - Pirate Adventures on the Chesapeake

“Pirate Pete was dressed very casually and safely (life vest underneath his clothes) with drawn on marker beard.”

Mentioned in 8 reviews

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Free Range Improv - Post-Show @ Fed House 1/24/2013

Free Range Improv

4.3(4 reviews)
0.7 mi
•$$

An amazing group of performers. I have been to almost every show they have ever performed and have…read morenever once been disappointed. My husband and I love the fact that going to a Free Range Show is an evening guaranteed to be hilarious and unique. The show is interactive and the performers professionals. They perform at multiple venues at multiple times so it is not difficult to find a show time that fits into a busy schedule. Believe me, it is worth fitting a show in. The tickets are affordable and easily accessible through their website. Once you go, you will want to go over and over just to see what they can come up with. Because the content is based completely on audience suggestions (and sometimes the audience members even go up on stage and become part of the action!) no show is the same as the last. I cannot recommend them highly enough. I need more stars.

First time seeing them at Ram's Head in Annapolis on 1/25/2015…read more They were an enthusiastic, energetic team of performers that unfortunately just were mostly unfunny with just a few humorous moments. Their shtick is the standard "Whose Line?" game play with the audience - picking topics and keywords / using crowd interaction to try for comedic effect. Maybe they were having an off night, or maybe I was expecting more based on other reviews here, but they didn't knock my socks off, nor did they really rock the other three people I was with. Tickets were $17.50 each. I'd be interested in seeing them again maybe in an online video to see if they have a better laugh factor than I caught during my live visit. Long story short, I was disappointed, and wouldn't recommend them based on my experience.

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Children's Theatre of Annapolis

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3.8(4 reviews)
4.7 mi

First time taking granddaughters to a play. The…read moreactors/actresses were impressive. Was thoroughly entertained by their ability and singing! The cast members meet guests outside after the play, which I thought was a nice added value. The theatre itself is very impressive. Very clean and the seats seem to all have a great view. (They also provide booster seats for the little ones). You might want to bring a sweater, it is a little chilly. Be prepared as the audience is mainly friends and family of the cast - so there is considerable hooting and hollering for specific characters. (This was mentioned in a review from 2019 - so some things never change). As with bathrooms worldwide, there are not enough stalls in the women's restroom to accommodate the lines - especially during intermission. All things considered, I probably will not go back, because... being as this is A CHILDREN'S THEATRE and the play should NOT be 2+ hours! Holy Moly, how do you expect 4, 5, 6 or even 8 year olds can sit still that long? Sadly, I left feeling: set changes, a 20-minute intermission and about 6 songs too many, made me more than ready to go home.

Like every children's theatre organization I've interacted with, CTA is great!…read more From a patron perspective, their shows are high quality. My family and I have thoroughly enjoyed each musical show we've been to. From an educational perspective, they are also great. They offer numerous workshops, in addition to full productions, throughout the year. My boys have participated in numerous workshops. They have enjoyed and learned a lot from each session. I am very grateful CTA exists here in Annapolis.

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Children's Theatre of Annapolis
Children's Theatre of Annapolis
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Illusions By Vick - Laughs & Fun on stage at a fund raiser

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28.3 mi

We hired Vick for our wedding reception! I was thinking of a simple way to entertain older folks,…read moreyoung children, and everyone in-between -- he was the answer! Vick had a wonderful story line and great tricks that kept everyone's attention! We had some guests that are very skeptical of magic tricks, and he still blew them away! I'm so happy we had him! We ended up starting his show a little late, unfortunately, but he was incredibly patient, set-up, and mingled with a few guests while he waited! He then put on a 45-50 minute show for all of us, and included some guests, my father, and us in the show! I highly recommend him for ANY event -- weddings, birthdays (children AND adult), social events, etc. Thanks, Vick!

Vick performed as Professor Snape at our twin boys' 8th birthday party. He was amazing to work…read morewith, especially in light of the commute required. We were so lucky he agreed to drive well outside of his usual area to perform. His illusions were mesmerizing, and he expertly handled a room full of inquisitive and skeptical kids by getting most of them involved in his performance. He gave a great message in the end of the performance also, drawing on the themes of inclusion and acceptance from the Harry Potter stories, which the adults present also mentioned as being a highlight. We cannot say enough great things about his professionalism and performance and we would highly recommend him for any event!

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Illusions By Vick - 30th Birthday Celebration!

30th Birthday Celebration!

Illusions By Vick
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Annapolis Electric Boat Rentals

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I heard about Annapolis Electric Boat Rentals through another Eastport/Annapolis event. Greg and…read moreSherry were terrific to work with before and after I rented their boat online. At the dock, Greg gave me and my family a quick, but thorough review of the boat and its safety features. The boat itself was spotless, and silent during the cruise. Cruising Annapolis Harbor and Spa Creek was a delight. A wonderful day, and a great value on the water. Thank you Greg and Sherry!!! I will be back.

On April 5, 2026, I made online reservation for a boat at 10 AM April 6, and was charged $423 at…read morethat time. At 8 AM the following day, I received a voicemail, an email, and a text message from the company stating that they were closed Monday and I should not have been allowed to make a reservation via their own website,. Obviously there would be a full refund, and they were very apologetic. I never received the refund and contacted them twice more during the next six days. Today I received an email from Benjamin. Tiederman stating that I would only be refunded 50%, which would not be received for another five days. This is fraud and theft, Along with basic incompetence and lack of ethics. I had to eventually submit a charge back to my credit card company, which will cost them extra money in fines instead of doing what they stated they would do. I've never left a negative review on any site so congratulations Annapolis electric boat rentals.

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Annapolis Electric Boat Rentals
Annapolis Electric Boat Rentals
Annapolis Electric Boat Rentals

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Pirate Adventures on the Chesapeake - theater - Updated October 2026

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