Courageous Sailing

We took the 2 hour private sail with Audrey. We were 3 adults, we had a great time sailing, learning to steer a bit and understanding how to sail a boat. A great experience, to remember! I would totally recommend it! I look forward to trying it again some time

We took a 2-​hour tour with Captain Eric. The wind wasnt very good, so we didnt get very far, but he still made it an enjoyable and fun ride.
He taught us a bit about sailing along the way as well.
We would definitely go back

Had a really great time sailing with Ben! I he showed us the ropes (literally) to sailing and it was a really fun time! Looking forward to trying courageous sailing again some time!

I didn’t really know what to expect when I bought a voucher for my family to go sailing. If I had known it was going to be as amazing as it was, I would have bought more. This was a great adventure for my family. We have two girls 8 and 11, who love the water, but were more than a little nervous to go out in a sailboat. The young man who set out with us soon calmed their nerves and eventually talked them into taking over. As a family we learned a lot about the boat and how to maneuver it on the water. I could see my girls busting with pride and confidence as they took control of the tiller and guided us along the harbor. I highly recommend anyone who has an interest in sailing or anyone who just loves being on the water giving Courageous a try. It was the highlight of our vacation and my girls are already asking when we can go again. This was some of the best family quality time we’ve had in a long time.

Courageous sailing is great! Great people, great boats. The convenience of club membership and not having the costs of boat ownership, storage and transportation cannot be overstated. I like the rigorous flag ratings to really push my sailing skills. Instructors are always friendly and helpful and really know their stuff.

Great place to get a membership and sail on in the Harbor. Much more reasonably priced than other options.

This gem is located in the historic Charlestown navy yard. They offer youth the opportunity to learn to sail in Boston harbor. There is an adult program that provides access to the water for new sailors and old salts. The adult education follows the US Sailing program. They also offer a chance for non sailors to get on the water with a skippered ride.

This not for profit sailing club is fantastic ! Not only do the wonderfully friendly and knowledgeable staff offer lessons to inner-​city children and take handicapped folks out sailing, they offer sailing lessons to people, young and old! We never sailed before and they have taught us and encouraged us so much that we are out on boston harbor sailing on our own and loving every minute of it!

Jessie was an awesome guide. He had a great sense of humor. We really enjoyed our trip, however, it was a light sailing because of the wind but we are def going back and trying it out again. The staff was friendly.

Never knew this gem was there — what a find! Got a deal, so this was priced RIGHT — we had a choice of sailing lessons, or just a sailing trip. Lazy beasts that we are, the 4 of us opted for an afternoon sail in the harbor, summer of 2013, and left the hard work part to our «skipper», Liz..
She was a very entertaining young woman in her early 20s, who had been sailing since she could walk. or perhaps it was swim? In any event, she went out of her way to share humorous and informative stories with us and made those in our party who were not terribly sea-​smart, feel safe, without making anyone feel stupid.
Love that we were supporting kids sailing programs, so that was a plus. A wonderful way to see the city. Try it!

I have to say that the community of sailors at this place is amazing. A great, down to earth and friendly bunch of people from diverse backgrounds who all come together around sailing. There’s also racing just about every night of the week, which is good since I do other things on my summer weekends. Monday night team racing is a blast — I’ve suffered quite a bit of withdrawal since graduating from college! And whoda thought you could team race J/​22s? — and I’m looking forward to coached fleet racing on Thursdays. Tuesday nights are supposedly pretty epic (it’s all the crazies who sail «frostbiting» all winter!!). I can’t keep up with that crowd, but it’s good to have something to aspire too, right? They also have grills here, and after racing no one thinks twice about cooking up a few cheeseburgers and hanging out as the sun goes down. This year I’m hoping to check out the advanced cruising and coastal nav classes. They’re a non-​profit, but the instruction is top notch. The best part? All the money you spend here underwrites their youth sailing programs for Boston kids! Anyway, can’t say enough good about the place, the people, or the sailing. I love Courageous!

My uncle took me out for a sail one day and I immediately bought a membership when I got back to shore. I can’t tell you how much I love this place! It’s turned into more than just a sailing club… it’s a place to find friends and meet lots of great new people. Spend a day on one of their boats and then hang out on the pier and meet new people. I’ve always been able to just show up and find someone to go sailing with. Oh, and their lessons are amazing! I’ve learned so much about sailing and I’ve even started racing since I joined.
You can’t beat the prices, people, location, and the cause. Knowing that your money is going to teach Boston kids how to sail for free is the best part!

This sailing center is a non-​profit organization run by the Parks and Recreation Departments of Boston. It was started to try to bring sailing programs to the people of the city and offer ooprtunities for inner city youths to learn about sailing. The «Courageous» Yacht that won the America’s Cup twice, used to dock at this pier so that’s where the sailing center gets its name.
They offer kids sailing lessons and adult sailing programs which is what I took with three friends. The instructors were very nice and helpful and taught us to sail in 19 foot sail boats. It was a blast. They teach the basics and then allow you to sign out the boats without a charge as long as you have a membership.
Its a beautiful place to learn to sail, though on weekends the traffic in Boston Harbor can get heavy. The winds in the harbor shift a lot, but that’s a good thing when you are learning as it teaches you how to deal with setting up your sails correctly. You can take the boat out for the whole day and sail out of the harbor around the islands if you like.
As a member you can participate in races and they have a barbeque for members every Friday on the pier. They also will host private or corporate events.
Its a fairly economical membership fee and your money is going towards a good cause.
Its a fun day to sail on the harbor, get a beautiful view of the city, the Constitution, and Bunker Hill and then come back in and have lunch and a sangria (or two) at Tavern on the Water which is just one pier over. You can find out more about their sailing packages at their website.