1. Pirate Adventures on the Chesapeake

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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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Ask the Community - Pirate Adventures on the Chesapeake

Review Highlights - Pirate Adventures on the Chesapeake

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Annapolis Electric Boat Rentals

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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SailTime - Annapolis

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4.7(11 reviews)
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I'm a member of the Flyer 9 PowerTime boat at SailTime Annapolis. I love SailTime! I evaluated…read moreseveral other options when I joined and SailTime had the best fleet options by far. The Annapolis location is especially great. There are regular social events, a great clubhouse, and incredible team to support everything. SailTime is remarkable at how quickly they address reported issues. Just yesterday I reported a few minor issues during my check off and they are already scheduled to be fixed tomorrow! Sailtime is really the best way to boat in my opinion. It's so nice to not have to worry about maintenance, winterizing, and all the other things that typically come with boat ownership. It's far cheaper than owning. Some things still could use improvement. Sailtime Plus, while extremely promising, isn't the most straightforward to use/book. I didn't hear back when I inquired about using it through the site. Building a better automated system for using SailTime Plus and checking availability at other locations would be awesome. I'd even plan trips around which locations had availability. There is one thing I would change if I ran SailTime. An additional charge pay-per-use option to have the boat prepped, stocked with sheets, refueled, docked, rinsed, and covers put back on. Not sure if there is enough interest in something like this to justify it but I'd definitely use and love it! Overall, I love my membership. I was worried I wouldn't feel like I got enough time on the boat but I don't feel like I've had any issues finding availability. I get plenty of use for my satisfaction. There are lots of days (especially weekdays) when the boat is completely unused. The other members are wonderful and take great care of the boat. I highly recommend joining!

Just completed my ASA 104 with Sailtime Annapolis and Captain Gary. I can't say enough about the…read moreexperience. Everyone was superb, professional, organized, and really went out of there way to make the entire 3 day / 2 night course such a great time. Capt. Gary was the best: a patient teacher, knowledgeable sailor, a kind, humorous soul, and really instilled fun and learning into the course. The 40' boat was clean, well-equipped, and sailed great. My crew mates were excellent company. Accommodations were very comfortable -- a great sailing vessel. Upon returning to port (after slogging through a dreary, cold, rainy last day), Tammy had prepared delicious Crab Bisque and cookies! What service! Can't say enough about the experience!

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SailTime - Annapolis
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Pirate Adventures on the Chesapeake - theater - Updated October 2026

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