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    The Sailing Academy

    4.1 (14 reviews)
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    Review Highlights - The Sailing Academy

    Captain Jeff was naturally funny and kind to our amateur sailing abilities.

    Mentioned in 3 reviews

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    Herrington Harbour North

    Herrington Harbour North

    (13 reviews)

    Well kept full-service marina with all the amenities! We…read morestayed here overnight twice over the summer, using Dockwa for our reservations. These are fixed, not floating piers, but tides are minimal. The pier head where we stayed (dock E) and the adjacent fuel pier head can be exposed to wind and some waves if coming from the southeast, but the waves are knocked down a bit by flats. The docks are in good repair, and the grounds are immaculate. We took advantage of the free-access propane grills up on shore for a nice picnic. There's a West Marine just a short walk away. The marina has a pool, poolside bar, ice makers, laundry, and more. Their pump-out is also free. Docking here was slightly pricy, but well worth it at a location central to the Chesapeake between two 8-hour sails, and not at all out of line for the area and quality of facilities.

    Herrington Harbour North Marina is a site to behold. This entire location is kept pristine. The…read moregrounds are well kept and the main building is immaculate. The restrooms are not only clean and well stocked, but they also have showers. Every inch of the docks are impeccable and every vessel, you could see, are well maintained. The reason for this visit was to assist with returning a family member's 47 foot sailboat back up to the Jersey shore. I cannot commend Herrington Harbour North enough on their professionalism and attention to detail with every aspect of this location. The customers of this harbour are privileged, well supported, and I'm certain....appreciative.

    Annapolis Sailing School - At the dock with the training boats.

    Annapolis Sailing School

    (51 reviews)

    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!!!

    I wanted to update my review of Annapolis Sailing School. There is one reason: my review last year…read moredidn't include Ian Morrison, the new Keelboat club director. It's been a terrific season at ASS. The winds have been so steady into August and the special events (blue angels, dinghy day, Monday night races) have all contributed to creating a real community there. Ian has helped take the club membership up a notch or two. As the club director he takes charge and delivers help and services for the club members and connects members together. "it's your clubhouse" he's said to me more than once. I've learned so much from him this year about rigging and racing. How I love Annapolis Sailing School. Thank you Rick Nelson for bringing Ian on board for us.

    Mariner Sailing School - South of Wilson Bridge

    Mariner Sailing School

    (25 reviews)

    Very rude and impersonal on the phone when I called to ask about my sailing class after I put a…read moredeposit down. I tried to give my availability and was cutoff---she said I will contact you if we have an instructor. Ok, well I can't just drop everything when you call to go sailing, please take my updated a availability? I hope other employees are better-suited to customer service and maybe kayaking and other options are still worth it, just wanted to let everyone know of my experience. I've never left a bad review, but I was excited to learn to sail, sad this had to be my experience. On to the next place!

    Learning to sail had been on my bucket list forever so when I saw that the Mariner Sailing School…read moreoffered sailing lessons for adults every week of summer I decided to sign myself up for my own "summer camp". I have to tell you that learning to sail was an excellent decision because I actually learned to sail a 19 foot flying scot independently! My lessons consisted of four 2.5 hour morning sailing lessons out on the Potomac, Monday through Thursday. The sailing school also offers adult weeknight and weekend classes and different kids camps. The instructors split my class up into groups of two or three, went over some of the materials and then out onto the water we went to learn how to rig the boat and raise the sails. My instructor Ray was awesome, he taught us what we needed to know and even pushed us to run docking drills by ourselves on the last day of classes. Yes, at times the lessons were super challenging and nerve wracking, but once you get some practice time in, you'll get the hang of it. It's worth it to learn how to sail. I myself now find sailing enjoyable and ridiculously relaxing. Everyone I have encountered at the marina either teaching lessons, working in the office or out on the dock have been super friendly and helpful. They give you a free week of practice sails after your lesson so that you feel totally comfortable sailing independently and the people at the dock give plenty of tips to help you continue to hone your beginner skills.

    Chesapeake Bay Charters

    Chesapeake Bay Charters

    (7 reviews)

    Unfortunately I call looking for this fantastic cruise for sunset. But due to Covid-19 they weren't…read moreable to do so. Although they were gracious and thankful for the inquiry. I highly recommend them. The concern was my well being and that of their crew. With that level of concern I will sail with them when circumstances change.

    My wife and I booked an evening sunset cruise for a long weekend getaway. Carmelita and Josh were…read moreable to get us a 2 hour trip on a busy weekend in Solomons. The two of them make a great team. It's obvious from their introduction that they love sharing their passion of sailing with others. Before we even got to the dock I was in contact with Josh on the phone and email. He responded quickly and was happy to offer some amenities. Josh offered me a few pick up locations and offered to drop us at our hotel marina. Once on the boat we covered a quick but thorough safety brief. We toured the river before entering the bay. Carmelita and Josh made suggestions for restaurants and other activities on Solomons and pointed them out as we passed them. Our tour took us around Solomons Island and under the bridge at sunset. Carmelita took pictures of us the whole time and shared them with us after the tour. It was great talking with them about how they got into sailing and how they learned their craft. The boat was clean and appeared to be sound. On the way back lighting storms were surrounding us. The light show was really cool to watch. The storm was about 30 miles so there was no danger and we felt safe the Josh and Carmelita were keeping an eye on the weather. I would definitely recommend their tour or charter service. They were great hosts and provide a memorable experience. You should book your tour now.

    The Sailing Academy - boatcharters - Updated June 2026

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