From the Blog

Posted by Jake DiMare at 8:39 pm

It was a gorgeous fall day on Boston Harbor and team Sparkle Pony joined some other members of the Boston PHRF fleet for a 13 mile ‘Rogue’ race around the islands. The winds were consistently blowing 17 to 20 and spirits were high.

There were a few really intense moments though. Lots of steep and deep downwind racing created a constant fear of an unexpected jibe and a couple of dramatic round ups kept the entire crew on our toes. Dan, one of our jib trimmers, almost lost his fingers when the down haul on the spin pole broke and the guy slammed into the lifeline exactly where Dan’s hand was and trapped it there until I was able to put enough weight on it for him to get his hand clear.

Posted by Jake DiMare at 11:49 am

Here’s a great shot of The Cone of Silence starting the Berringer Bowl and me, the hindmost hiker, doing my best not to screw up the job of being ballast.


Posted by Jake DiMare at 9:46 pm

Cone of SilenceSo, I’m pretty sure I’m screwed. Three years ago when I got back into sailing my goal was to work my way up to a nice, modest, slow cruiser for long distance journeys. Then I met Doug Mitchell and the crew of The Cone of Silence. They invited me to Go The Cone! for the 2013 Berringer Bowl this past weekend. Suddenly, my personal aspirations for boat ownership are trending more towards speed, agility, and (inevitably) cost…

My experience with the race was mostly about time to meditate while hanging off the rail with a lifeline cutting through my mid-section (for 6 hours). There were a lot of beautiful views as the sun slipped below the horizon, a few tacks, listening to the crew discussing various strategies (to which I added my own rookie ideas from time to time) and one nasty wipeout off Race Point at 1:30 in the morning, after setting the chute for the finish.

By the way, I’m not going to get all dramatic and say my tether saved my life on that broach, but it sure as hell stopped me from slipping into the inky black Atlantic on a dark night. What might have happened without it is anybody’s guess…Hopefully a successful man overboard drill, while wrestling an out of control, broached sport boat with it’s kite up in the dark…But we sure as hell weren’t close enough to shore for me to swim it in.

So yeah, we were topping out at 9 knots during the race…But this was all forward of the beam sailing. What The Cone is really designed for is downwind sledding…And delivering the boat from Boston Harbor to the Yacht Club in Marblehead in a 15-20 knot southwest winds was the most exciting 3 hours of sailing in my life.

Funny name for the boat really. At 9 knots she starts to hum quite audibly. Skipper told me it’s the keel vibrating. With a little more speed the hum changes pitch and at around 11 knots it starts harmonizing a chord of notes. It’s beautiful and ominous.

I could try and explain how much fun it is to Cone downwind but it would be easier to show you:

Posted by Jake DiMare at 7:44 pm

Summer 2013 is here and it’s all about racing this year. I’ve been on Sparkle Pony for Wednesday night a few times, started the R19 summer series and done weekend regattas on Sparkle Pony, Tank, (Boston Thunderbird fleet), and taken a ride on The Cone of Silence in the 2013 Hingham Bay Scorpion Bowl. (See video below).

All this racing gives me plenty of time to think, while hiked out over the rail. I’ve learned A LOT in the last 3 years. I’ve sure got plenty to learn…I’m sure that will never end…But it’s really satisfying to put all this time into a sport and see results.

Anyways, Cone of Silence is a Reichel-Pugh Super 30. You can learn more about her on Here’s a quick edit of us in yesterday’s race:

Posted by Jake DiMare at 11:35 am

I managed to score a spot last night working the mast for the first evening of PHRF in Boston with Sparkle Pony racing. The wind was brisk (consistently gusting to 20 knots) with passing rain squalls. I’m too excited to write much…Here’s some video I captured between tacks. Sorry for the shakiness, I had sailing responsibilities as well…


In this first video check out the close shave on the starting line as at :45 seconds…Sparkle Pony took the start on a port tack.


In this next video the boat off our starboard bow gets over-powered in a puff on the final downwind leg and rounds up right in front of us.


Finally, check out Cone of Silence as she accelerates past us like we’re standing still…

Posted by Jake DiMare at 4:12 pm

Last spring I decided to take up racing sailboats at Courageous Sailing in Boston, MA. At the time my goal was to get more time on the water, hopefully improving my ability as a sailor in the process. My plan was simple: Find the most experienced sailor I could and get in his or her back pocket for the season. When I arrived that first Thursday afternoon I was relieved to find most of the other sailors had done this before. But, almost everyone else was already broken up into teams. As I glanced around the field of competitors while reliving anxiety of being picked last in gym class I noticed someone who seemed to be alone.

When I first met Bob Burke he was joking with the girls at the front desk. He was an older guy and had an easy-going, confident demeanor. His hat, the kind only a Navy veteran would wear, read “USS Franklin D. Roosevelt”. I remember the absurd idea he had stepped out of a Hemingway novel just to teach me to sail crossed my amazingly self-centered mind. I walked straight up and extended my hand to introduce myself thinking “This is so perfect…”

Bob on watch

Bob on watch

As Bob and I set sail that first evening I promptly discovered every assumption I made about his sailing ability was wrong. Bob was an Intelligence Officer in the Navy and had nothing to do with the ship’s operations. In fact, he had only started learning to sail a couple of years ago. This was a disappointing setback in my master plan to latch onto a more experienced sailor. As we trailed the pack in that first race I remember thinking I was in for a summer of losing and conversations with a septuagenarian about his favorite shows on the Fox news network.

However, Bob didn’t live up to any of my assumptions on or off the water. For instance, he wasn’t slow, or pessimistic, and he doesn’t watch Fox news. Instead, Bob is an energetic, positive thinking guy, making the most of life in retirement. We quickly became good friends.

Regardless of our friendship, on the boat, it seemed evident we were not going to be doing much winning. Against a backdrop of breathtaking sunsets at the back of the pack we dubbed ourselves ‘Team Gratitude’, after deciding winning was secondary to being on the water with friends week after week.

However, as the season unfolded a surprising thing happened: when you do the work, you get the results. We slowly improved our timing and tactical ability while inching our way up the field of competition. By mid-season we were sailing consistently above average and eventually, we even placed in a couple of races.

In September we were joined by Chris, an extremely talented young sailor. Chris, who also became a good friend, had taught Bob to sail a couple years back when he raced in college. With Chris on the team we were suddenly an extremely competitive program with growing skills. Wins started to stack up, and with them came a sense of pride.

As it turned out I ended up learning more than I hoped for about sailing this year. However, I also picked up a few more important lessons:

  • It’s never, ever too late to pursue your dreams.
  • Age is meaningless when it comes to making good friends.
  • Even when the wind doesn’t cooperate, sailing is better than most other ways to spend time.
  • Time spent with friends is more important than winning.
  • Gratitude is more rewarding than winning.
  • But winning…After a season of painfully slow, incremental improvement…Is very, very fulfilling.

Check out the video below for a montage of all the action this year. I can’t wait for 2013.

I got the call yesterday to be mainsail trimmer on Sparkle Pony during rogue racing in Boston Harbor. It was a really fun night, in spite of ‘less than ideal’ weather conditions. Winds were 5-7 knots out of the Northeast with light fog and drizzle. Seas were glassy smooth.

As always, the crew, like myself, was just happy to be there. A slow night of sailing beats sitting on the couch any day. The weather added a small dimension of excitement, particularly as the sun was all the way down and darkness filled in. At that point we were rounding the windward mark out by Logan Airport and the breeze freshened.

Not sure how we ended up in terms of winning. I don’t think the race was much more than an excuse to sail…

Here are a few pictures…



This last week has been one amazing sailing adventure after another. Unfortunately, I’ve spent so much time on the water, there’s been no time for blogging. What a great problem to have…

Last Thursday night Bob and I welcomed Chris, a new crew member for Thursday night Rhodes 19 racing at Courageous Sailing. Although recently graduated from college, Chris was actually Bob’s first sailing instructor a few years back, and he knows his stuff. The weather was incredible…Steady west winds at 10+ knots, clear skies and light choppy seas.

Off the docks late, we missed the start on the first race of the night. However, this gave us a chance to get comfortable with a third man on the boat and we settled in nicely to take the win on races 2 and 4. (of 4!). We might have won race 3 as well, though most of the field was wiped out by a rookie barging maneuver at the start. This event caused us to lose a favorable position lose considerable time extracting ourselves from the pile up.

I’m pulling together a video of the summer 2012 racing season, which I hope to have completed in the next couple of weeks.

September Session

September session...

Saturday I took Jackie and friends Ben Buckman and his fiance Stephanie out for a long cruise on the J24. Winds were 15+ knots out of the East North-East and gusty. We were all really excited for a great day of sailing.

However, the day got off to a tough start after I failed to check on the specific procedure for reefing the mainsail on this boat I’ve got little experience with. As soon as we were clear of the pier and traffic, we turned up wind, raised the main sail and then attempted to reef and realized the reefing line wasn’t rigged through the sail.

Within a few minutes I figured out a solution and we got underway with what I thought was a properly reefed main. Within minutes the reefing line, pulled the cringle grommet through the leech of the sail. This caused the boom to drop down without warning and bonk poor Jackie on the crown of her head as she sat in the companionway.

Fortunately, nobody was seriously injured and another lesson was learned. I’ve yet to check in with Courageous about the repairs and not sure  if the problem was the age of the sail or a procedural error, but in either case, it was my responsibility to be prepared for such an event.

Around this time we realized the J was sailing upwind just fine without setting the jib so we proceeded under main sail alone. Before long we had some successful sailing under our belt and decided to set the jib. The rest of the day was absolutely incredible, including a long run downwind to end the day.

Our route was under the long island bridge, out past George’s Island and the up through Nubble Channel before turning back towards home. While running downwind we experimented with a preventer line which worked great and made it easy to keep the big genny filled by staying just by the lee in safety and comfort.

Monday I connected with a bunch of Courageous sailors and we took a pair of J22′s and a Rhodes 19 out to Peddock’s Island for a raft up and lunch. I crewed with my racing nemesis Gary and learned quite a few things while practicing MOB drills in heavy wind and seas out by George’s Island. More images and videos coming soon.

Nav Station

Welcome to the Nav Station

One of the most surprising things I’ve learned while training to skipper sailing yachts at Courageous Sailing is how little it has to do with basic seamanship. Don’t get me wrong, sailing is critical. In fact, one should not only know how to sail, but be pretty good at it, and really love it as well. But I think it is assumed one will know a sheet from a halyard by the time they start training for cruising, and off-shore passage making.

It is certainly true to say seamanship is important, but any novice sailor can be taught to steer a yacht and trim the sails. A smart greenhorn can also rapidly come to terms with the fundamentals of point to point navigation, and learn all their knots. But the sailing part of managing a modern yacht is a fraction of the overall body of knowledge required to get around the globe with safety, efficiency, and comfort.

Yesterday I awoke early with the windows open and noticed an old familiar crispness in the air, signaling impending changes in the weather (assuming the weather actually changes this year*). Though I love the fall season, opportunities to get out on the water will become fewer and further between over the next few months. Fortunately, there is no better time to buckle down on the vast body of knowledge a skipper must master outside of sailing then during a cold New England winter.

That’s why I thought it would be a great idea on Running Downwind to make a list of those skills (other than general seamanship) an aspiring captain must learn. So here they are, the 12 hobbies of highly effective skippers, in no particular order. I say hobbies because, I’m guessing I will need to enjoy the pursuit of knowledge of each as if it is a hobby to be successful. Any one could be an entire career path on its own…

  1. Diesel mechanics
  2. Plumbing
  3. Propane systems
  4. Marine electrical systems
  5. Basic meteorology & weather forecasting technology
  6. Traditional navigation techniques
  7. Digital navigation and chart plotting
  8. Communications
  9. Boating safety
  10. Basic first-aid
  12. Leadership

Diesel mechanics
Any yacht more than 24 feet in length is most likely going to have a diesel auxiliary engine. As captain, one will need to maintain and repair said engine. Furthermore, it is quite possible one may need to repair said engine in far-flung parts of the world with limited access to parts and knowledge. This is a rather special set of circumstances and as such warrants the special knowledge  and preparation only other mariners can share. I am told the Boatowner’s Mechanical and Electrical Manual: How to Maintain, Repair, and Improve Your Boat’s Essential Systems by Nigel Calder is the must have text on this subject. It’s definitely on my personal list of required reading.

This is one of those general disciplines for handling a variety of marine systems. The fresh water system, marine head, refrigeration, engine, through hull fittings, and more. At the very least, a captain better know how a seacock works, the location of each and every one on his or her boat, and exactly what to do when one breaks, in a hurry.

Propane systems
Comfortable cruising includes hot meals and heated cabins in colder latitudes which is why, for reasons of safety and worldwide availability, a typical yacht will usually include propane cooking and heating systems. One can not say enough about how important it is to completely understand the safe handling of any explosive gas on board. Although propane related accidents are rare,  they do occur. Proper understanding of these systems will definitely mitigate the risk of a fire or an explosion while ensuring  smooth and efficient operation whenever required. Just ask anyone who needs coffee first thing in the morning how important this can be.

Marine electrical systems
Even a basic cruising boat will have a fairly complex electrical system with both shore-side 110 volt power and 12 volt battery power. The battery charging system delivers energy via some combination of diesel generator, wind, solar, and even submerged impellers. More sophisticated boats will also have a secondary gas powered generator and/or power inverter capable of pushing 110 volts of alternating current when away from the dock.

Put it all together and it is obvious a captain must have a solid foundation with electrical systems. Then factor in the unique complications of being on the ocean. Salt water and humidity are hell on electrical systems and yachts are increasingly equipped with highly valued, sensitive, digital equipment such as desktop chart plotting, weather forcasting, radar, radios, kitchen equipment, GPS, and more. Again, Nigel Calder’s bookis a well known, and highly recommended resource.

Weather Map

NW Atlantic Wind and Waves

Meteorology and weather forecasting technology
It seems sort of axiomatic, but seafarers live by the weather. Sailors, in particular, must be constantly focused on the wind and sea conditions before and during passages. Even as one who is still shore-bound, I am working hard to get into the habit of being constantly aware of what’s going on with the weather on the coast and beyond. I am currently reading and learning a lot from Modern Marine Weather. Interestingly in the introduction they recommend reading Nathaniel Bowditch for more fundamental knowledge related to observing and understanding marine weather.

Traditional navigation
You can’t just consult Google maps for directions when you want to get from one place on the ocean to another (yet). For one thing, navigating at sea is an incredibly dynamic activity based on seasonal weather patterns, currents, localized wind conditions, tides, depths, and more. Further complicating matters when you are off-shore, there are no landmarks on the horizon. In the event of an equipment failure, which is always a possibility where salt water meets electrical systems, it is critical to know how to navigate using traditional techniques including dead reckoning and celestial navigation.

Much has been written on this topic but The American Practical Navigator is claimed as the best selling boating book ever. It is certainly on my own reading list. Navigation is complicated and my own personal development in this area has already and will continue to include multiple classes on and off the water.

Digital navigation
All that being said about traditional navigation, there’s nothing like the convenience of modern navigation systems. I have just begun to scratch the surface of this topic, which I plan to eventually dedicate many blog entries to. I’m currently talking to engineers about building a plugin for OpenCPN. I highly recommend checking it out…Much more on this topic to come.

Ship to ship and ship to shore communications on board yachts is getting more complicated as it gets more convenient. Gaining a thorough knowledge of VHF, Ham, HF, Cellular and Satellite communication systems is absolutely necessary. This is another one of those areas where reading and classes is recommended. Typical topics covered in an RYA GMDSS course include:

  • VHF communications
    • Controls found on marine VHF set
    • Channels (simplex & duplex)
    • SSB RadioVHF communication range
  • VHF DSC (Digital Selective Calling)
    • Distress, Safety and Routine Calling
    • MMSI (Maritime Mobile Service Identity) numbers
  • Ships licence and radio regulations
  • Voice procedures
    • Maydays, Pan-Pans etc.
    • MSI (Martine Safety Information) broadcasts
    • Stations
  • Portable safety equipment
    • EPIRB (Emergency Positioning Indication Radio Beacons)
    • SARTs (Search & Rescue radar Transponders)

Boating safety
Sadly, boating can, and sometimes does, have disastrous results. According to the United States Coast Guard, In 2011 there were 4588 accidents that involved 758 deaths, 3081 injuries and approximately $52 million dollars of damage to property as a result of recreational boating accidents. Only eleven percent of deaths occurred on boats where the operator had received boating safety instruction. Only seven percent of deaths occurred on vessels where the operator had received boating safety instruction from a NASBLA-approved course provider.

Long story short: Get safety training.

Even after safety training, accidents will happen. In fact, on a rolling boat you are likely to eventually experience a fall which can result in cuts, bruises, or broken bones…And you can’t simply call 911 from a boat that’s off the dock. Every captain should know how to deal with the most common accidents and emergency medical situations. With even a simple accident off-shore, knowing first-aid can make the difference between survival and death for the captain and/or their crew. All this being said, don’t be scared. A life sitting at a desk while living in a typical city is far more likely to present opportunities for serious or life-threatening injury or illness.

Further on the subject of safety is the United States Coast Guard Collision Regulations, or ‘COLREGS’. Required reading for a 100 ton Captain’s license, this is essential knowledge for anyone on the water.

This is one of my favorite topics. It has so many applications in life, business, and certainly on the water. The time when it was acceptable to rule by fear or intimidation on a boat are all but extinct in most of the developed world. They certainly are not tools valued or used by a savvy skipper, often on a boat with a crew including spouses, family, and friends. Many books have been written on the subject. I can’t think of any I recommend more than others. What I will about leadership is this should be a lifelong pursuit for anyone on this planet…No matter where their feet are planted.

In closing, this list is not meant to be exhaustive. One thing I love about being on the water is the never ending pile of things to get better at. That being said, I’m sure I’ve missed something. What do you think? I am definitely planning to create an essential reading list. What books do you think should be included?

*The winter never really arrived in 2011/2012

Though incredibly energetic and fairly coordinated, I was not very talented with sports as a child. I was, however, raised in the 70′s and 80′s and always had access to video games. Through console and computer gaming I learned the distinct pleasure of achievement, normally reserved for children engaged in more practical activities, like baseball or soccer.

Often, in the realm of gamification, we refer to achievement as ‘leveling up’ -after a fair amount of effort the player accomplishes a difficult task and is given more ability and new tools to ‘sally forth’ and discover more challenging opportunities to level up. Like most people, I like leveling up. That’s why I was quietly beaming with pride and excitement yesterday when I was given the opportunity, and responsibility, of access to the larger cruising boats at my sailing club. I didn’t waste any time seeking new opportunities…

Image of  a J24

J24 image courtesy of Sail-World.Com

The weather was absolutely perfect for a day sail. Winds were gusty, 5-15 knots out of the East. Skies clear; seas light and choppy. I decided to take out a J24, a larger and much faster boat than the club’s Rhodes 19′s I’ve had the run of up until now. The plan was to head out past Castle Island and do some tacking around the mouth of the inner harbor to see how she handles and then maybe do a loop around Spectacle Island if we had time.

It may seem like a small thing to the uninitiated, but the veteran sailor may keenly recall their first experiences with new equipment and expanded cruising grounds. First, I had to figure out how to rig a new boat, which included varied options for different sail configurations. After taking my best guess I asked one of the cruising instructors to inspect my work and discovered I had run the Genoa sheets through fairleads for a small jib sail and a ratcheting block for a spinnaker.  After some quick adjustments and orientation Jackie and I were off the dock at Courageous Sailing at 2:30PM.

We pulled up into the wind in the harbor off Pier 4 and Jackie got her first taste of keeping the boat pointed into the wind under power while I went forward to lift the mainsail. I worked at the mast, feeding the sail while hauling down on the main halyard and Jackie tailed the halyard and steered the boat. All and all, it went quite well though it felt like the J24 helped a little with a natural propensity to point upwind. The Genoa also went right up and we fell off and got underway without incident.

Aside from some fairly significant weather helm, the boat was lively and seemed to enjoy the gusty conditions. I probably should have reefed in the main but I wonder, and need to remember to ask a more experienced sailor, being stuck with the hanked on Genoa, how will reefing the main affect the boat’s performance upwind? Jackie started off pretty intimidated by the power behind the larger sails on this new, more athletic boat. She was also initially confounded by the use and timing around tacking with winches. However, after an hour or so her ability was markedly improved…Though I don’t think she was giving herself much credit for how quickly she learned.

Channel MarkerOnce outside Castle Island we settled down for a couple long tacks to round Spectacle Island. Although I’ve been on Boston Harbor hundreds of times, this was truly the very first where I was the senior sailor, completely responsible for the boat and crew. The first time it fell to me to decide if it would be prudent to take the longer planned route or turn back, based on time, currents, tides, and all the other conditions a skipper must consider. Although we had fought gusty upwind sailing against the tide to get out of the inner harbor, the J24′s speed had left us plenty of time to range out further and the wind, tide, and current would be favorable on the return trip.

The wind seemed to settle slightly and we had a truly memorable afternoon from there on out. The trip around Spectacle was comfortable and uneventful except for giving Jackie her first lesson on checking charts and figuring out our location and water depth. We sailed back in on a downwind run, the only trouble being directly into a gorgeous, setting sun…And keeping the lively Genoa winged out without a spinnaker pole. We doused sails abeam of the Custom House and motored in for a flawless docking, in spite of me forgetting an important little detail resulting in a last second ‘fender fire drill’. (-5 points)

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