Annapolis Sailing School

We had a nice day but I wish we had done the twilight sailing cruise, looks nicer. Still, cool experience, even without wind. I do not like the smaller boats however — make sure you are getting what you think you are and if you want a bigger boat, ask for it!

We had a great lesson today with the instructor: Ricky Nelson
He was very knowledge and delightful person too. Each of the 5 of us had an opportunity to sail the boat as well as enjoy 2 hours on the Bay

Went out on the Sunset Sail a few weeks ago and it was a great time! Captain John made sure we all knew what we were doing and made sure we had fun at the same time. We brought a cooler of drinks and just relaxed while watching the sun go down. A great evening out on the water with great people. Loved the Annapolis Sailing School!

Had a fantastic time out on an Annapolis sunset sail with some good friends, a little BYOB, and of course, the Cap himself Captain John. Can’t say I’m much of a sailor but Captain John was quick to show us the ropes so I could learn a thing or two while still just kicking back and enjoying the views. Highly recommend this sailing school to both grasp an understanding of sailing as well as just enjoy being on some beautiful boats in the bay.

I took Annapolis Sailing School up on their new «Evening Sail» option this past weekend, and boy was it a blast! We got a couple of friends together and loaded up a cooler full of drinks (BYOB) and dinner food, and set sail under the twilight sun. The cruise lasted roughly 3 hours and our captain took time to teach us little nuisances of both the Bay and the boat (Beneteau 37) we were sailing on…
I highly highly recommend this excursion and will be back to take advantage of this, and the other options offered at Annapolis Sailing School in the very near future! Thanks again Captain John!

A group of friends and I went for a sunset sail on the bay, and it was fantastic. Our captain was excellent and knowledgable and taught us about how to sail. The views were incredible. I will be back as soon as I possibly can be.

I can’t say enough good things about this place — but I’ll try.
Last week I had basically no sailing experience whatsoever, and just completed their 5-​day Basic Keelboat Certification class.
I had two wonderful instructors: John & Gary. I’m not qualified to judge their sailing skills, but they’re both great teachers — which is even more important. They’re very knowledgeable about all things saling, and have the patience and temperament necessary to the task of teaching novices.
Everyone at the school was incredibly friendly and helpful. The instruction was appropriately paced, blending classroom with hands-​on sailing.
When I finished the class and got my certification, I joined their «keelboat club» — which will allow me, for a flat fee, to rent a boat (availability guaranteed) on 72-​hours notice, anytime I want, for the next year. I got a 10% discount for signing up shortly after completing the class.
Pointers:
While they have 3-​day classes covering the same material, I personally felt I needed every bit of the 5 days to reach a point where I would even consider taking a boat out on my own. Others probably feel differently. The incremental cost of the additional days makes it well worthwhile. Also, I imagine the bay is a zoo on weekends. I took a week of vacation and was glad I did. I also stayed in town (I live in Silver Spring) to avoid the exhausting commute back and forth.
Read up in advance to get the most out of the class. The volume of information is pretty overwhelming. If you know the terms and basics going in, you’ll be way ahead of the curve, avoid wasting precious time and get the most out of the actual sailing.
As a caveat… I was extraordinarily lucky in that: 1) we had absolutely perfect weather all week; and 2) I was the only student in my class (I appreciated the fact that they didn’t just cancel it).

I’m sure this place is as good as the other reviewers say it is… if you can get an appointment. I got the groupon for the sailing lesson and tried for almost two weeks to call these people and set up an appointment. The first time I called was after hours, so I left a message. No response. The next three times I called during business hours, still no real person answering but yet another recording telling me to call back or leave a message and they’d get back to me. Which they did not. Six calls, four messages, ten days, no answer. This place is clearly unprofessional and/​or just plain rude. I will be getting a refund from groupon and take my money elsewhere.

Back in December, long before anyone was thinking about sailing on the Chesapeake, Annapolis Sailing School offered a Groupon for their 2 hour trial sail. We arrived a bit before our trip time, but when the other couple arrived they got us out on the water right away (so there were 4 of us and the instructor in a 26 Rainbow sailboat so room to stretch out).
Our instructor was very knowledgeable and explained everything as she was rigging up the Genoa sail. The purpose of the trial sail is really to see if you would be interested in taking a longer weekend course. We did get to do some jibbing and tacking, but the wind on the bay wasn’t really cooperating.
However, our instructor kept it entertaining and relaxing. It was an absolutely perfect time. I am considering going back for a longer course.

The instructors were great, you spend a lot of time on the water, and we didn’t end up rigging our boat incorrectly and subsequently floundering in the water like we saw someone from the Chesapeake Sailing School. The only thing that would have been better is if we sailed in crews of 4 instead of 3, but that’s nitpicking. I highly recommend this place if you’re looking for lessons.