The Captain gave very little instruction on this trip and the boat was in poor condition. The…read moresafety briefing didn't occur and the students were not treated well. Overall you'd do better to charter a boat than to go on a trip with this 'school' because you'll learn more doing it yourself.

I am sailing away.. set the open course for the virgin seas!…read more My neighbors and I went sailing this weekend with the Sailing Academy. The weather was extremely hot, but the water was really calm so we mostly laid out. I did get motion sickness for about half of the trip so I would advise students to take Dramamine before the go. Our instructor Jeff was very knowledgeable and friendly. He answered all of our questions and had great tips and fun stories. Our day of sailing was fairly brief and he allowed us to do various task like steering the wheel, raising the sails, etc.. Its a good experience for beginners but might be a little boring for the advance.

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.

The Escape catamaran experience is what being on the Chesapeake is all about. The 42' boat is…read morecomfortable, clean, and spacious. The crew is friendly and knowledgeable about sailing and the Chesapeake Bay. The Escape can manage any type of outing with the proper planning. I couldn't recommend the experience more highly.

From the owner: Sailing vessel ESCAPE is a 43’ Leopard catamaran chartered out of Annapolis, MD. Give us a call and…read morewe will help you plan a great ESCAPE on our beautiful yacht. Sailing on the Chesapeake Bay is an adventure you will remember for a lifetime. Charters can be as short as a half day and as long as you want. ESCAPE has four queen bed cabins and each has its own private head/shower. The salon is bright and includes a full galley and dining area. The cockpit is outside and covered with plenty of seating. And there is still the deck and forward trampolines to relax on. Our posted rates include all taxes, cleaning and booking fees, nothing is added at checkout.

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'

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.

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.

Stunning boat and great crew! We had a great time on the SV Eternal Hope with Captain Derek and…read morefirst mate (and local expert) Nate. Highly recommend!!!

Outstanding experience on one of the cleanest and most beautiful sailboat I've ever been on. Top…read morenotch crew and service from start to finish. I highly recommend this group. My family had a great experience and I would recommend them to others. We brought our own snacks and beverages not supplement theirs.

A friend and I sailed on Saturday and I've already recommended this outing to all of my colleagues…read moreand local DC friends! Captain Jen and her crew were great--from welcoming everyone aboard, to the safety briefing, to answering a million questions, to serving drinks--they were knowledgable and fun. Joey and Jake were great crew, too. It was the perfect day to be on the water as it was SO HOT but windy and clear for sailing. Will definitely bring my family next time!

If you need a different idea for date day look no further than the schooner woodwind. 2-hour sales…read moreout on the Chesapeake Bay out of downtown Annapolis with all the comforts of boat ownership without any of the headaches. Well worth every penny, especially if the weather is nice The cruise super nice and they serve drinks on board both alcoholic and not. It's a fair price for what you get and the capstone for any day date in Annapolis. Highly recommended as we have been three or four times now and look forward to it annually. The owner and her staff could not be more friendly.

Highly recommend. Fabulously flexible class scheduling…read more Comfortable yet responsive Catalinas; keel/ tiller. Easy going instructional atmosphere. Beautiful, wide, quiet spot on the river.

Great experience! I recommend it to everyone. Cameron is…read moregood guy to spend 2 hours on the water with. Will be signing up for lessons. 1 demerit for mediocre wind- Cameron can you do something about that next time? Thanks Cameron that was fun.

Chartered a catamaran for a week in Nov 2024 from Sailaway Key West. Booked in March…read more Unprofessional outfit: boat we chartered was not available, but an on paper good alternative was offered. Then the price of the crew was increased. Excuse was that the person who we booked with in March was no longer with the company. Lot of work to redo all the work we had done in March to find the charter we wanted - anyone who has tried to book one knows it's much smoke and mirrors, the same boats are rented out by different outfitters, everything is a little different between each and it's hard to get a full picture of total cost, and to compare apples to apples and not something else. Document every conversation and detail of what you agreed upon with Sailaway (or any other company) or they'll change the game. Arrived in Key was as agreed upon. Boat reeked of sewage. Captain had been on the boat for ten minutes several days before our charter, that's it. Said it reeked then too, but didn't do anything about it. Captain had almost no contact with Sailaway, it was the first time they worked with them. Captain ended up calling marina engineer and it turned out that half of the boat had not been pumped out. Additionally, the captain's cabin bathroom was broken, and the toilet didn't flush. You can imagine. It all got fixed but it was a stinky hassle and we started our charter several hours late. Sailaway overcharged us in their electronic system and ghosted us upon repeated request to resolve. Jennifer, owner of the company, acted unprofessionally and winged it to provide a charter boat and an ok but inexperienced crew she had never met, nor taken the time to get to know. It came out all right by helping out on the fly, but Sailaway was disappointing and there was no communication with, nor support for the crew from them either. The situation would have been salvageable if Jennifer had responded to our emails and calls to resolve the issue and accept feedback as we asked her to do. But she didn't, which leaves us with a bad feeling about her and her company.

Keegan Smith has been absolutely incredible to work with during all the stress of planning a unique…read moreand fun wedding. He has anticipated our challenges and calmed my fears. We have not even held our charter and I feel compelled to write this review. Not only has Keegan handled my concerns as the bride, he has fielded questions from other members of our charter with ease. I am sure the charter will be amazing, and I will provide an updated review after the event, but I 100% recommend Sail Away Catamarans and ask to coordinate it through Keegan!