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.

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.

My brother and his wife and and my wife and I very recently completed a three hour Sunday morning…read morecharter. We thought the charter was well worth the money. The Captain and one crew member were really excellent. They made sure to cover critical aspects of the boat and abide by all the safety precautions. I actually timed the charter and we were on the water under sail for almost exactly 3 hours. We got there a little early, and the process of familiarizing us with the boat took a few minutes, so the entire process was probably closer to four hours. The boat was clean and in great shape. Some of the electronics we're not working but that was not an issue for our charter. We were provided with basic cold drinks and bagged treats as well as a bottle of wine. We own a Catalina 22 sailboat so we were familiar with sailing, but sailing a Catalina 42 Mark II was a lot different. I was thrilled that the captain offered me the opportunity to sail and tack the boat for an extended period, of course under his watchful eye and guidance. In short it was a very memorable experience and we had a blast! The wind and weather were perfect.

The experience was great from start to finish. I mostly dealt with Keegan and he was very helpful…read morewith planning to helping work through minor issues on the boat. The boat, Lily Rose, was a beautiful, new Seawind 1170 catamaran. Keegan, and his colleague Ralph, really helped make our bareboat charter great.

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.

I also had a terrible interaction with Paul last summer. I would share more from our conversation,…read morebut it appears Airbnb finally decided to give this rude, borderline verbally abusive, and arrogant business owner the boot. I highly recommend unless you want a berating for simply asking about accommodations (what/if any were available), that you do NOT bother reaching out to Paul. Honestly, his behavior and demeanor are likely great examples of what terrible experiences and (lack of) service we would have probably received had we decided to utilize Paul's business and services during our visit.

Had an outstanding experience with Captin Paul this week. He showed my family and I all kinds of…read moreinteresting places on the Chesapeake bay. Dolphins, osprey with fish in their talons, lighthouses, a drawbridge, and a chill approach to life. He navigated us Tilghman island... let us rest, eat and swim... then returned us safely to our lives in DC. The 38 ft sloop is awesome, well cared for and handled great in some chop. I will absolutely sail with captain Paul again. I highly recommend sailing with him.

I chartered Recovery Room, a Jeanneau 51, over Memorial Day weekend 2021.  When I picked up the…read moreboat, there were a number of broken parts that were pointed out to me.  I was concerned that this boat was aging and in poor operating condition.  My concerns turned out to be true.  When I returned the boat, I was informed that a metal bar that holds down the spinnaker halyard had broken and I would be charged $400 for the damage.  This boat doesn't have a spinnaker on board and I never went anywhere near this part.  I believe that this boat is aging and the charter company is keeping it seaworthy by fleecing it's charter customers.  Beware.

From the owner: The Finest Bareboat Fleet on The Chesapeake Bay! The Chesapeake Bay is well-known as an outstanding…read morewaterway for sailboat cruising. Protected waters, great anchorages, gorgeous natural scenery, bountiful seafood, unique, historic towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. We also offer Captains, if needed. These are private charter boats, not group tours. If you are wanting to venture outside the Bay, we have affiliate locations in the Bahamas, New England and the Caribbean.