Reviewers highlight the interactive pirate-themed activities, such as treasure hunts and face painting, which engage children and adults alike. The crew is frequently praised for their energetic performance and ability to keep groups entertained. However, some customers report issues with customer service, including unresolved refund requests after weather cancellations and complaints about staff demeanor during scheduling conflicts.
Data from Google, last updated October 25, 2026.
Reviews from Google, shown as published (original wording, unedited).
Made for kids but the grownups had fun too. Our 4-year-old had the greatest time. Highly recommend!
We bought mine tickets pre-sale, we went to use these tickets during the weekend of graduation. Unfortunately, it rained the entire time. We hope to travel back and use them, but we have been unable to make it, I called this company several times and was promised by two different people over the phone that they would offer me a refund. The third time that I called someone told me there is no refund and I have to use the tickets at another time or try to sell them. Unfortunately, this was very unclear on the pre-sale option. I wish that they would’ve made it clear. It’s a lot of money to waste and it’s unfortunate that the communication via phone has been so poor.
Thank you for sharing your feedback. We take customer concerns seriously, and we’re sorry there was confusion surrounding your Presale tickets. As a small, family-owned business, we work hard to balance affordable options with policies that allow us to operate responsibly, while always doing our best to take care of our customers. Our limited-release Presale option, unlike our full-price ticket option, offers savings of up to 20% in exchange for more restrictive terms, including being non-refundable. Your tickets received the full 20% savings. These terms are presented during purchase and must be agreed to before the purchase can be completed. Our discounted Presale Terms & Conditions can be viewed here: https://www.chesapeakepirates.com/presaleterms/ Terms for both Presale and Full price ticket options can be found here: https://www.chesapeakepirates.com/reservations/ We can’t speak to what may have been said during previous phone conversations, but we are sorry if anything communicated by phone caused confusion. As a small, owner-operated business, we personally handle our customer calls and take clear communication seriously. When we spoke today, I resent your vouchers along with the terms and documentation from your purchases showing the terms accepted at checkout. Most importantly, the money you paid has not been lost. The amount paid never expires and can be used as credit toward a future visit, even in a future season, or the vouchers can be transferred to someone else. We’re happy to honor the full amount paid whenever they are used. We appreciate your feedback and will take it into consideration as we evaluate whether our Presale option continues to provide the right balance of savings and flexibility for our families. Emily Tomasini Owner, Pirate Adventures on the Chesapeake (410) 263-0002
We had the best time on our sailing 9/20/2026. Peggy was amazing! Our kids are 3 and 5 and the younger was a little nervous but the crew was so good to her. We will absolutely sail with them again in the future.
The experience offered at Pirate Adventures on the Chesapeake was amazing. We had 5 kids with us, they were engaged and loved every second of the trip. The captain and crew were so good with the kids and kept everyone involved and having a great time. I recommend this for anyone looking for a fun kids experience or party. We will be coming back for sure.
Thank you so much! Great to hear that we captured all five kids, our crew aims to keep everyone engaged and it sounds like our mission was accomplished! We’re so glad Pirate Adventures was a fun part of your time in Annapolis, and we can’t wait to welcome your crew back aboard!
We had a great time at Pirate Adventures in Annapolis. We were there for a birthday party, and my kids really enjoyed the whole experience. The face painting and shore activities were fun, and the boat ride was a highly interactive pirate adventure with treasure hunting that kept the kids engaged. My only real complaint is the parking. Their lot fills up quickly, especially on weekends, and parking in Annapolis is difficult in general. If you are going with a larger group, I would definitely recommend carpooling. Overall, it was a fun, well-done experience and the kids had a great time.
Thank you for celebrating with us! We’re so glad the kids had a great time and stayed engaged throughout the pirate adventure. We also appreciate the parking feedback. Our main lot can fill up on busy weekends, but we do have an additional parking area available, and our crew is always happy to direct families there. We’ll keep working to make those directions as clear as possible. Thanks again for joining us and helping to celebrate a fun birthday!
an incredible outing on the water! Captain Crabby and crew were really fun and invested, they had a group of 20 kids totally immersed while us parents could sit back and watch. Really creative and interactive - our kids had a blast
Thank you so much! As owner and operator, Captain Crabby gets just as immersed in the adventure as the kids do! We’re so glad all 20 kids had a blast and the parents could sit back and enjoy the fun too. Thanks for spending some time on the water with us in Annapolis and for noticing just how invested we are!
I sailed with my daughters family- boys 9 and 5 and girl 1 with Mom and Dad. We had a beautiful day. Presail activities got the children involved and ready for the adventure - get there at least 1/2 hour before sailing for the presail fun, maybe even earlier. Captain Stretch and First Mate Lagoon kept the children involved with the treasure adventure story line. The newbie pirates learned a bit about things that need to be done to sail. The Treasure Adventure- was perfect. I loved the water cannons- each child fired water cannons. The booty was shared by all. Of course there is a store of pirate related gear and toys. Put the big big wooden puzzle together. Go, enjoy the adventure while sailing the Annapolis-Eastport harbor. Captain Stretch highly recommends using the pirate store bathrooms before boarding - there are no bathrooms on board the ship.
Thank you so much for sharing your adventure with us! It sounds like your crew took in everything from the pre-sail fun to the treasure hunt, water cannons and even the big wooden puzzle! We love seeing grandparents, parents and kids all enjoying the experience together. So glad you had a beautiful day sailing the Annapolis Harbor with Captain Stretch and Lagoon, and we really appreciate the time you took to leave a feedback!
Didn’t love the ‘captain’ telling my kid to close their eyes and then putting her feet on their face. Had a rash after that.
Thank you for the feedback. Our captains often ad-lib and use silly moments to keep kids engaged in the adventure. In this case, the Captain had the “X that marks the spot” on her bare foot for the treasure map and showed it to the kids as part of the fun. We’re sorry this particular bit didn’t land as intended and she never meant to make anyone uncomfortable. While there’s plenty of silliness aboard, our captains hold USCG Master Captain licenses and as professional mariners take the safety of our passengers seriously. Our entire crew is committed to making sure everyone on board feels safe, comfortable and has an enjoyable experience, and we appreciate feedback that gives us an opportunity to look at things from a guest’s perspective. Onward and upward!
What a fun time with the crew! Thanks!!!
Thank you! Appreciate you taking the time to leave feedback :), please join us for another adventure next time your family visits Annapolis!
Everyone there is amazing! We had Slim on our boat. He was hilarious. My 3 girls age 6 to 11 all enjoyed it. They make it interactive with kids. Adults had fun too.
Thank you so much! Slim is a good one! He just headed off to college after spending his high school years adventuring with us through spring, summer and fall, and we’re already looking forward to having him back next summer. So glad all three girls and the adults had fun too. Thanks for sailing with us!