Monday, June 16. By resident Challenge Blogger Judith Krimski. 

Yes, there was more of that sailboat racing stuff on Boston Harbor. Winds veering from easterly sea breeze to SW.

It never fails. Just another stellar night on Boston Harbor and my "happiness quotient" is a solid 9.99999. Every time I venture out from Courageous Sailing, whether in a motor boat or sailboat, I think "I am the luckiest person." As I park on Pier 3 and pull the requisite sailing gear out of the car; PFD, hat, jacket, sunglasses, I sniff the air, squint my eyes and search down Pier Four for the American flag perched on the top of the Courageous boathouse. Sailors like myself are always looking for breeze.

It never fails. Breeze is the first thing most sailors think of when we wake up in the morning. Slowly lifting our heads from the pillow, we come to consciousness. Yawning, we automatically pivot towards the nearest window looking for signs of wind. The flicker of leaves in the morning light. That soft rustling that heralds a light breeze. Sniffing we sense the direction: northwest = gusty clear air; northeast = possible backdoor cold front; southwest = a hot strong wind that tells us summer has arrived. I wonder what non-sailors first thoughts are when they wake up in the morning, probably stuff like, "Arrrgh, another boring staff meeting to attend today." or "I need a donut."

Everyone should spend a night hanging out on the RC Boat with our able PRO Carl Zimba. PROs are in charge of making sure races are run smoothly. They communicate with mark boats to get the course set square to the wind, they run starts and call boats who are over early. That's why Carl's voice is always hoarse at end of the night, "FOUR! FOUR IS OVER!!!!" And they record finishes which can be quite a challenge when there's more than a few boats finishing. That's why Carl is so good. He always gets it right.

"I got my mojo back." Becky Wheatland from Step Ahead Physical Therapy was happy to announce over drinks and and dinner aprés sailing. After two weeks of great finishes Becky's team came away with a second place for night three. Another team who improved tremendous was Boston Private Bank who earned a bullet in race one. I had noticed this team on the first night of sailing. They had good boat speed but were obviously struggling a bit with boathandling. That's why is great to see such a big improvement.

After three nights of racing there are five teams vying for top spot. Kudos to them. But you know what? The real story behind the Courageous Corporate Challenge is all the other teams. The BPB team who gets a bullet and says to themsleves "We got this." The Alphagraphics team whose skipper Carmine just helmed his second night. And all the other teams who are just coming out for the fun of sailing and most importantly to support Courageous programs.

It never fails. Courageous Corporate Challenge. Sailboat racing. Tons of fun and good competition. Turning non-sailors into sailors. Helping really awesome kids learn sailing and do other cool stuff. Happiness quotient? A solid 9.99999.


Apparently there was some sailboat racing on Monday night--this thing we do every year called the Courageous Corporate Challenge. Yes, I was there. Yes, I watched said sailboat racing. You’re curious: “Who raced? Was it competitive? What were the conditions? Who won?” All questions will be answered....maybe.

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Courageous Sailing is proud to announce its first cross-curriculum program with Brooklyn Boulders of Somerville! BKB Courageous Explorers is a unique program for kids ages 8 – 11 who want to embark on the quest of the summer! Who is Brooklyn Boulders?


June 16th – 20th. Each day begins at 9:30am and ends at 4:00pm. Families must take care of their own transportation to and from the program at both sites. Course fee: $550 per child. Unfortunately, we are not able to provide financial assistance for this program.


  • Monday and Tuesday at Brooklyn Boulders – bouldering, roped climbing, auto belays, slacklining and more!
  • Wednesday and Thursday at Courageous Sailing – master the basics of sailing through a games-based approach aboard a stable keelboat!
  • Spend Friday on a sailing expedition to a Boston Harbor island to explore and play team building games!

How to Register

Registration is open to all and is "first-booked, first-served." Space is limited to 15 students, so book your adventure today! Register on the Brooklyn Boulders Somerville website.

Our Staff

Our experienced staff will keep your kids engaged while they learn the ropes for climbing and sailing; building skills and confidence and making friends along the way!

Questions? Comments? Concerns?

Email the Brooklyn Boulders Somerville Youth Program Manager at  For more info about Brooklyn Boulders programs, booking and cancellation policies, and what to expect, visit the Brooklyn Boudlders Somerville website


Register for the 2014 Summer Youth Program Lottery!

Online Form Available March 10 - March 28

The 2014 summer youth program lottery registration period will begin on Monday, March 10th. Every year Courageous serves 1,000 youth from the Boston area. Space is very limited and we expect to reach capacity again this summer. It is important to note that registration is lottery based, not 'first come, first served'. Follow the links below to learn everything you need to know about courses, lottery registration and scholarship information.
Courses | Registration | Fees & Scholarships

Hello Frostbiters,

With just two weeks left in the season, Courageous is looking to continue our string of great race days with 5+ races per day. The weather is looking gorgeous! Temps will be in the mid 40s, sunny, with a steady breeze around 10 knots from the NW. I look forward to seeing you all out there on the nicest day we will have this week!

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