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The Sailing Academy

4.1 (14 reviews)
Closed 10:00 am - 4:00 pm

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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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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.

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.

St. Michaels Sailing Charters - Our guide

St. Michaels Sailing Charters

(125 reviews)

We first sailed with Captain Iris 10 years ago with our children. This year we chose to return for…read morea Monday night for a moonlight cruise. Captain Matt and first mate Mike were top notch. Informative and attentive. Weather was perfect in our eyes, clear with almost full moon. Wasn't much wind, but the Salina II sailed beautifully. Plenty of beverages, great history of a beautiful vessel, and a photograph worthy sunset. Thank you so much for a wonderful night!

I needed to get away, and saw this excursion via Eric Oranges' wine happenings. Wine tasting and…read moresailing! Right up my alley. I booked and made reservation at Harbour Inn- I love that I stayed at before. Approached by a spry lady, I was asked my name - she turned out to be the granddaughter of this 1926 New England Charter, Capt Iris. Very personable and knowledgable as she pointed out things along St Michaels banks e.g., The Perry Inn and the focal point filming of The wedding crashers. The name Selina, itself had family virtue and significance-pronounced different ways, the one I remember is as in Selena Gomez. We were also quizzed on how many tons the vessel weighed. My guess way low-16 tons!!. We marveled at the woodwork and upkeep of the ship and hours to maintain- not to mention gas cost. We were offered our choice of beverage- I had a tasty Chardonnay, although I'm not sure the brand. The first mate. Was agile at that point coasting in a nice spot to put up the sail, beautiful as the sky was starting to cast its evening glow with the sunset. It was truly relaxing as we made small talk about catfish and enjoyed the ambiance. I then had a second Pinot Noir however the water being a little choppy declined a third- we were Rockin ! a little with wind picking up. It was a very enjoyable outing and I would do it again in a heartbeat! Next time I want to be at the helm lol, if only for a photo shot. Speaking of photos...a picture paints a thousand words...btw the name means 'moonlight'

The Sailing Academy - boatcharters - Updated May 2026

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