Overall, the experience was beautiful…read more Clean boat Great crew, all 3 crew The atmosphere was welcoming. Came with my son. He had a great time

We had an absolutely wonderful time sailing on the Epiphany with Captain Jim and First Mate Josie!…read moreThey were both incredibly friendly, knowledgeable, and accommodating, making the entire experience feel effortless and relaxing. They were wonderful with our family, and our two-year-old even got the chance to steer the boat, which was definitely a highlight for him! It was the perfect way to spend the day, and we couldn't have asked for a better crew. We will absolutely be sailing with them again the next time we're in the area.

Very nice experience! We cruised on the miles River. The cruise is a total of 70 mins. Everyone was…read moreso nice. We also received good background history of St.Michael's. This cruise line has two levels. The lower deck which is closed in. It also has a small bar area for drinks as well as non- alcoholic beverages. They sell light snacks such as chips, hotdogs, etc. I tried the Miles River drink. It was delicious. She made it perfectly. We decided to let the wind blow in our hair. So we remained on the top level which was open windows. The views were amazing. Just bring a light jacket because it gets a little windy on the water. I would like to do this again. Maybe during warmer weather though. Even though I still enjoyed everything about it. If you're interested in learning St. Michael's history while enjoying the calming waters. This would be perfect.

Decent 70 min cruise up/down the Miles River. For some reason I thought it would be a curated tour…read moreof the Chesapeake Bay giving us history and landmark info, but it was just 70/80s music except a few announcements from the captain. We ended up on the lower level where its air conditioned, several tables/chairs, bathroom, and snack bar. Staff was friendly

We had a great time with Captain Tyrone. We booked about 3 weeks out for a Saturday morning in…read moreOctober. Your best bet for info or reservations is just to call or text. He told us to be at the dock at 6:30am. He was ready and waiting once we got there. Friendly guy who greeted us as we boarded. The boat is nice and big, there were about 2.0 people total and we didn't really feel cramped. His mate Brandon was also VERY helpful throughout the day. He took us up the Choptank River to about 10 different stops. You can bring your own rod or you can rent one from him. We ended the day with ~24 perch. Overall, a great experience!

Haven't been yet but will be going next Saturday ! For my first fishing trip not to shabby ! Caught…read moresome fish and spent time with some of my coworkers ! Got off to a slow start but eventually got things going ! Pretty good for fishing trip and hanging out ! Will return for another adventure next month! Good job Captain Tyrone and crew!

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!

Decided to try out kayaking before buying a kayak. Jim was very helpful and knowledgeable. Had a…read moresuper time on the river!! I am now looking to buy my own kayak. I highly recommend this place. Laid back and down to earth people.

Great experience renting from Jim, nice calm route and good service. Included water bottles and…read moreshuttled us around (even showed us local highlights like the Easton Strawberry Festival!)

First, I want to say that I have no issues with the initial class I attended at Annapolis Sailing…read moreSchool or with the instructors. Carrie and Steve were welcoming, knowledgeable, patient, and courteous with all the students. If my experience at the school had ended with them this would be a five star review. Regrettably it was not.The the class I attended fell on three windless days, which meant the sailing portion had to be deferred to a makeup class a month later. Now this is where my story takes an unfortunate turn. The day of the make up class I arrived at the school exhausted and lost in a mental fog do to a medical condition I do not feel like discussing here. I am a veteran with a 100% disability rating, I am sure you can figure out what my problem may have been. I promptly informed the instructors that I was having serious health issues at the time and they agreed I should sit out the class and suggested I return the next day if I happened to feel better. I left believing the school would work with me, since I had prepaid for two classes (ASA 101 and ASA 103). Unfortunately, the scheduling staff did not share the same views or concerns as the instructors when I called the next business day. When they finally agreed to place me in another ASA 101 class (so they wouldn't have to adjust the ASA 103 course I had already paid for), I was told during that final phone call: "There is a caveat -- you feeling sick or not well is not an excuse for missing a class." Let that sink in: "feeling sick or not well is not an excuse for missing a class." I don't think a more tone deaf statement could be said to someone living with a permanent disability. Now, I may have overreacted -- I admit I had gone four full days without sleeping. But even in my altered state, I knew that my health and safety, as well as that of every student, should be the school's top priority. Their response made me feel like nothing more than an inconvenience -- a monetary transaction that had gone wrong. Living with a disability is not a choice, and it is not something I can control. Disgusted by their attitude, I rejected the offer for yet another makeup class. For my troubles I received a partial refund on ASA 103, I kept the course book and plan to teach myself. The money I had intended to spend on additional courses will now go towards a down payment on a boat that I will be able enjoy at my own pace. This was my experience with the Annapolis Sailing School. If you have any health issues or happen to be permanently disabled, as I am, I would strongly suggest looking at other schools in the area. It's your choice -- I have made mine.

Stop thinking about it and just do it…read more Def a top flight sailing school in the Mid-Atlantic! I did the combined 101/103 course that allows you to take out a cruiser. The 101 course is great for newbies; the instructors are all highly experienced yet very patient with beginners, you'll have a great time for sure! Since I love cooking, I'm going to use the Scoville scale to compare 101 and 103. If 101 is just a mild bell pepper, then 103 is a jalapeño. Don't take it unless you're ready for a true sailing boot camp! It will kick your ass, especially if you've just come from 101, but you're going to learn A LOT that you can then take with you to digest and practice. You're going to be overloaded with a LOT of information, but just take some time at the end of each day to decompress and process what you've learned and you'll do fine. They are all very passionate about the art of sailing and push you hard to be the best sailor you can be. Def a great experience!!!

Fabulous time sailing with Captain Mark! We got a little bit of history while enjoying a relaxing…read more90 minute sail. We sat right up in front on the bow. It was a windy day but Captain Mark took it easy on us with limited spray. Gorgeous views! A must do if you're in Rock Hall.

Absolutely wonderful day on the water on this sailboat with captain Mark. Loved the Laurel Canyon…read morestyle music as well as the margaritas. So much fun!!

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 just finished the 16 hour Safe Powerboat Handling course offered by the Chesapeake Boating…read moreAcademy. The course and the instructor, Captain Ken, were outstanding! I cannot say enough good things about this course and about Captain Ken. We spent 8 hours on the water and 8 hours in the classroom. A powerboating rookie, I quickly and easily learned a vast amount about powerboating, about how to powerboat safely and efficiently and about US and Maryland rules and regulations. At the end, I successfully and easily passed the tests to receive the US Powerboating Safe Powerboat Handling certificate and the Maryland state specific certificate. I'm already planning to take other courses from the CBA.