Went out on a whim and scheduled this party boat out of Annapolis this summer - we had never heard…read moreof them (well come to find out they are new!) and truly didn't know what to expect... It was such a FUN evening! Watching the sunset from the water, the drinks were flowing (loved that it was BYOB, we brought a cooler for us, but they already had one on the boat as well!) and being on the water... doesn't get much better IMO Can't recommend this party boat enough! The captain and the owner, Trevor, were responsive and helpful in booking and finding the location of where the boat docks. Would be so fun to bring the girls back for a gals night or even a bachelorette party. Can't wait to book again this summer and maybe even for the air show Ps - make sure you use the bathroom before you leave bc there isn't really one on the boat haha

Amazing experience for my bachelorette party with Captain Jamie and his deckhand Devin. It was a…read morevery personalized experience and Devin even helped us capture some amazing photos along the way!!! Highly recommend to anyone looking to celebrate an event or just cruise along the beautiful water. It was S O MUCH FUN and super affordable !!!

Update 06/06/26 On…read morethe water again with Captain Larry. Four hour review class. Went over all the basics, docking, anchoring, MOB, avoidance turns, trim while on plane. Another great lesson and time! Update 05/27/26 A great lesson from Captain Larry on the water for Advanced Open Water Maneuvering. Collision Avoidance Turns, and Man Overboard Drills among others. Check them out! Update 05/15/26 A great time on the water with Captain Bill for Precision Docking and Boat Handling. Captain Bill explained everything clearly to his three students, showed us how to do it, and then let us do it. Docking, (including a bonus Spring Line maneuver), Ferrying, and Pivot Turns. A great Captain and teacher! We enjoyed a 3 hour lesson from Captain Bill on our new to us boat. Sarah was great to work with arranging the training and finding such a skilled Captain. Captain Bill allowed us to feel more confident docking and maneuvering our boat at slow speeds. I highly recommend both Captain Bill and Chesapeake Boating Academy!

I took the 16-hour US Powerboating safety course at Chesapeake Boating Academy with Captain Bill…read moreand Captain Ken and learned so much. I especially appreciated the local knowledge and perspectives they brought to the course. Learning about Maryland's boating culture alongside the safety material made the experience feel much more connected to being out on the water here. Their insights were a highlight, and I'm grateful for everything they shared. Highly recommend Chesapeake Boating Academy to anyone looking to build their boating knowledge and confidence.

We booked the Fireworks from the Bay cruise on the Wilma Lee. It was the best experience ever. We…read morehave done the other sailing cruise from Annapolis several times, but this was so much more enjoyable. The boat is a historic vessel, the crew is knowledgeable and friendly, and they really put in a lot of effort to make it an amazing experience. We boarded at 7:15 pm, received the safety briefing from the captain, and learned the history about skipjacks oystering on the Bay. The ticket price included drinks (a nice selection of beers, wines, soda, and hard seltzer). Music (oldies favorites) was playing. They had prepared little goodie bags that included swag like little pinwheels and glowsticks and a bagged snack. They also passed out individual small charcuterie boxes with skewers of meat, cheese, and olives, plus a separate container of tiny crackers. The captain let people help the crew unfurl the sail, and he took us way out to see a visiting frigate. There were views of the Bay Bridge and lots of other sights. Around 9 pm, the boat was back in position for a great view of the fireworks. There is nothing like seeing the fireworks from the water. And the ticket cost goes to a good cause--maritime education and preserving this unique vessel.

We took Wilma Lee out for our rehearsal dinner and had an absolutely wonderful time. Such a great…read moreway to show people Annapolis. The staff was fantastic, it's byob and food which worked out great for us. The pricing was also very reasonable, we were impressed with all aspects. Will certainly do again.

What better way to get around than on the water. I would commute via water if there were a way to…read morewhere I live. In Annapolis, there is! So try it out. Starting out at $2 you've got nothing to lose and it is a super fun way to beat the heat and enjoy that sea breeze while watching the shoreline pass you by. They have a fairly high capacity, we were a group of 6 and all fit plus more. So go cruise Annapolis

We have used the taxi for years to ride from the boat to town dock…read more During a week long stay on mooring #17, a matter arose where I needed to drive back to Baltimore to grab some missed packed medical supplies. Unfortunately it was all ready 8pm and the last taxi stopped at 10pm. Capt. Phillis went above and beyond her service. She assured me her taxi would be waiting to take me back to the boat. It was a big comfort during my 2hr round trip drive. Thanks a million to all the fine and pleasant captains especially Capt. Phillies. ​

Boats are not well maintained. They are dirty and don't handle well. I did not renew.read more

We have been members of the sailing package for a year and have absolutely loved it. It's fantastic…read morethat J/80 reservations, for example, are only allowed a week in advance, so we have actually never had an issue reserving a boat when we wanted to go out. Boats are maintained extremely well, the staff is outstanding and helpful answering any questions (even for relative beginners like us!), and they are great at allowing independence yet will step in to help whenever needed. We have not yet been to the Baltimore location, but we plan to this spring/summer. Can't recommend this club enough. It has definitely provided us with a fantastic opportunity to practice our sailing skills, get our children comfortable on the water (easy to take a boat out for just an hour or so to maintain their excitement!), and expose us to boats that we otherwise wouldn't have an easy opportunity to sail. Love it!

Great experience! We loved the cruise around the bay and the musician was much better than…read moreexpected! Easy boarding, the bathroom was totally fine, a good variety of drinks, and views from both the top and bottom decks. If I had one note, I'd say the musician should display a qrc for Venmo so we could give him a tip.

Olden top cathedral, FDR brought remains of JP Jobes 1905, buried in there in a marble structure…read more To honor JPJ for the nation he fought for our independence

Captain Jim and his wife were wonderful! We booked a 2 hour cruise at the end of May for a team…read moreactivity. He was always quick to respond to any questions, his boat is beautiful, and his wife was so hospitable during our ride! She served us snacks and refilled our drinks, and narrated the sights for us as we cruised! They are both knowledgeable about the area and were wonderful tour guides through Annapolis and the Chesapeake. We will book a longer cruise next time. In my research, it's hard to find a boat that is NOT a fishing boat in the area. (Fishing boats are great, but are usually not for lounging and not that pretty.) Captain Jim's boat is super sleek and meant for cruising! More than enough space for 6 adults to spread out. You won't be disappointed!

Absolutely wonderful! Captain Jim was amazing, and the boat was immaculate! We did a 2 hour cruise…read moreout of Kentmorr and up to Thomas Point Shoal Light. Then we went through Ego Alley in Annapolis and underneath the Bay Bridge. We have lived in the area for decades, but learned so much about that area that we didn't know! Captain Jim is knowledgable, accommodating and wonderful! Five enthusiastic stars!

Peter was such a great guide! Boat was in beautiful shape. So clean and well kept. Fishing spots…read morewere filled with fish and my family and I had such an amazing trip. I can't wait until the weather warms up to go again!! Would recommend Wann to anyone!

I booked a 10 hour day trip for myself and my adult son . I booked the trip through fishing…read morebooker.com . I payed the security deposit and left a note for Peter Wann about how much we were looking foward to the trip . I booked motel rooms and secured the time off from work . We drove down the night before so as not to be late . We were to be at the dock for a 6 am departure . We were at the dock at 5:15 am and ready to assist or what ever. 6 am came and went as did 7am and 8am. Wann did not answer our phone calls or attemp to contact us . My adult son called numerous times and left voicemails. I called but didnt leave voice mails as I knew they would do nothing to change the situation. He did contact my son somewhere around 330pm that afternoon. My son told him he needed to contact me because I was the one that booked the trip . He didnt. I only heard from Wann Sunday night after I left a negitive review on fishing booking.com. ( they later took it down cleaning up for their clients which are the charter owners ) He offered a free trip ,a reduced cost trip , but he was unable to give back the time that he wasted ! I was willing to stop posting the reveiws untill I saw that it was being white washed by fishing booking.com.I had to get the deposit back on my own Wann said alot and I was willing to let it go but re-visiting the fishing booking.com site I beleive this happens more than just this one time. They categorized the bad reveiws as "Trips canceledby captain" .