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    Sail Away Catamarans

    3.9 (7 reviews)
    Open 9:00 am - 5:00 pm

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    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.

    SailTime - Annapolis

    SailTime - Annapolis

    (10 reviews)

    I'm a member of the Flyer 9 PowerTime boat at SailTime Annapolis. I love SailTime! I evaluated…read moreseveral other options when I joined and SailTime had the best fleet options by far. The Annapolis location is especially great. There are regular social events, a great clubhouse, and incredible team to support everything. SailTime is remarkable at how quickly they address reported issues. Just yesterday I reported a few minor issues during my check off and they are already scheduled to be fixed tomorrow! Sailtime is really the best way to boat in my opinion. It's so nice to not have to worry about maintenance, winterizing, and all the other things that typically come with boat ownership. It's far cheaper than owning. Some things still could use improvement. Sailtime Plus, while extremely promising, isn't the most straightforward to use/book. I didn't hear back when I inquired about using it through the site. Building a better automated system for using SailTime Plus and checking availability at other locations would be awesome. I'd even plan trips around which locations had availability. There is one thing I would change if I ran SailTime. An additional charge pay-per-use option to have the boat prepped, stocked with sheets, refueled, docked, rinsed, and covers put back on. Not sure if there is enough interest in something like this to justify it but I'd definitely use and love it! Overall, I love my membership. I was worried I wouldn't feel like I got enough time on the boat but I don't feel like I've had any issues finding availability. I get plenty of use for my satisfaction. There are lots of days (especially weekdays) when the boat is completely unused. The other members are wonderful and take great care of the boat. I highly recommend joining!

    Just completed my ASA 104 with Sailtime Annapolis and Captain Gary. I can't say enough about the…read moreexperience. Everyone was superb, professional, organized, and really went out of there way to make the entire 3 day / 2 night course such a great time. Capt. Gary was the best: a patient teacher, knowledgeable sailor, a kind, humorous soul, and really instilled fun and learning into the course. The 40' boat was clean, well-equipped, and sailed great. My crew mates were excellent company. Accommodations were very comfortable -- a great sailing vessel. Upon returning to port (after slogging through a dreary, cold, rainy last day), Tammy had prepared delicious Crab Bisque and cookies! What service! Can't say enough about the experience!

    Sail Away Catamarans - boatcharters - Updated May 2026

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