Around Long Island



It is Sunday the morning after returning from the 2003 Around Long Island Regatta sponsored by the Sea Cliff Yacht Club and Mount Gay Rum. Visit for more info, results and related info.


Having recovered sufficiently to sit (on a pillow) at the computer I thought it would be a good idea to record some impressions and memories for further review, possibly to share with friends, family and other sailors.


Disclaimer: Bear in mind that these are just impressions and likely contain errors of fact and omissions of all sorts. I hope to produce a corrected version in the not too distant future. Anyway, to coin a phrase, “It is what it is”.


Some Notable Quotes:

1. “Ever seen three monkeys trying to fuck a football?”

2. “Rum, Sodomy and the Lash.”

3. “God, I love this shit!”

4. “God, I hate this stupid fucking sport!”

5. “This is a mistake.” (Followed by severe and prolonged retching)

6. “You’ve got about 3 minutes to figure it out or we’re going to have words.”

7. “If you’re born to hang you’ll never drown.”

8. “Wet paint!”

9. “Eat me first.”

10. “I always get sick at sea.” (“What?!?!?!?!”)

11. “This is the most fun I never had.”

12. “Wow.”

13. “It is what it is.”


The boat:

Indecent Proposal, a 1980s S2 9.1 (about 30 feet with a ten foot (?) beam.)

(Attach picture)


The crew:

Andrew Toomey, 35, American, moderately experienced sailor and racer

Glen Vitaglione, 50, American, master heavy air helmsman and navigator

John Dodson, 43, Australian, moderately experienced sailor

Steve Pritz, (40s), American, experienced sailor and racer


The owners:

John Shea, 35, American, former marine professional and all around sailor

Larry Boxerman, 50, American, skipper for this race

Toby Moors, 40, Australian, master light air helmsman and tactician


Wednesday Night Pre-Regatta Club Race

Additional crew:

Eric, former merchant marine, jovial wiseass and experienced sailor

John “Sully” Sullivan - Nice guy, experienced sailor and racer.



Light air. No boat in our class finished as a result.

Late finish, drinks and cheeseburgers,

Retired to Toby’s place with John D. at 0030 to sleep for a couple of hours.


Thursday AM

Awake at 0300. Shower. Depart for City Island Yacht Club.

Load boat and cast off motoring for Hell’s Gate cranking The Blues Brothers.  At this point I was concerned that we would be fighting the current as it was high at 1 AM but Glen correctly said we would catch the tail end of the ebb and we did.

I am questioned through Hell’s Gate.

“What offends you?”


“What’s your experience?”

“Done a few things, but never this.”

“You’ll do.”

Let me say right now these guys have a great sense of humor. You need one for this type of racing, as I have since learned. I never laughed as hard or as often as I did on this trip. We had a bit of barge traffic down the east river, and a lovely sunrise. We motored across New York Harbor to Liberty Landing in New Jersey to meet Hank.



Hank is a friend of John’s and a wealthy trucking magnate of some sort.

At 78 years old, having never owned a boat before, he bought a Nauticat pilothouse 44 ft. ketch with automatic everything. It is a VERY nice boat. Apparently he’s had some bridge trouble with it (Bang!) due to a construction fault in the boat, but it was impeccably (and expensively) restored. There are two throttle controls, one inside and one outside. When using the one outside the one inside would slip into reverse, but the throttle still worked. Not a pretty combination. Anyway Hank graciously provided coffee and breakfast after which we all retire for a snooze.



I awake and come on deck. Eric arrives with more fresh bagels. Larry wakes and we sit on the dock and talk a bit. John S. awakes and he and I go to the Big Red Boat for a last bathroom run and a shower. Well worthwhile.


While there I encounter my former employer George Samalot, a master sail maker from the Haverstraw Marina who will be racing his Laser 28 in the ALIR, thankfully not our division. I also ran into Greg, my first sailing instructor from SEAS. He is also racing in another division, which he later won. He is very glad to see me and proud to see that I have advanced in the sport. It is a short but friendly meeting.


We spent some additional time removing a shelf and installing a gimbaled propane stove which we used not at all the entire race, but which was something of a hazard by swinging its small metal propane tank around wildly. So much for saving unneeded weight! We all said we must have coffee during the race. It didn’t happen.

Add that to lessons learned. Bring what you know you need, not what you think you want. Dry clothes are better than hot coffee any day.



We depart across New York Harbor, followed by Eric and Hank in the Nauticat, under the Verazano Bridge, and around Coney Island. They are not racing, just coming along to take some pictures and see us off. I steer some of the way spelled by the others. We eat liberally, chowing down on delicious Subway sandwiches. I am trying to eat and drink as much as possible both to keep my energy up and avoid seasickness, which I would witness first hand very shortly.


1300 It was a lovely sunny day through to the Verazano Bridge, but then it clouded over gradually. We arrived near the start early and hid behind the breakwater off Green buoy  # 2 off Rockaway Beach from the rapidly building wind. Around this time, slowly motoring and bobbing around with our competitors showing off their colors, Larry turned green and started vomiting off the stern. This did not bode well. I drank more water and tried to think of other things and not listen. Seasickness is catching. I knew this was true from the color John Dodson’s face slowly began to turn. I suddenly realized why you need 7 guys on a 30 ft boat for ocean racing. At any time any number of the crew might become incapacitated.



We raise the sails, kill the motor and start for the racecourse in steadily building conditions. I am both apprehensive and excited.



Roughly 2 miles offshore we reach the start.

78 boats are starting in 10 divisions.

Conditions are deteriorating rapidly. 25-30 knots sustained wind gusting to I don’t know what all.  Seas are 8-10 feet with breaking waves. Glen is at the helm. We are all on the rail. Toby and John S. are trimming. It is a VERY confused start. One of the race committee told me later that they were very sick on the committee boat as well. There seemed to be an error in flag handling which caused half of our fleet to start early. I think they raised our flag (division 6) instead of division 4. At any rate we and many other boats in our division started WAY early. We realized sooner rather than later that things weren’t right. We went back and started again at the proper time. It was 1528 and 35 seconds by my watch. See race results at for actual times.



We soon see that the wave action is better on one tack, but VMG (velocity made good over the ground towards a waypoint taking into account direction, speed, and angle) is better on the other. This makes the tougher beat the better tack. This is a painful but unavoidable fact. Glen does an amazing job of surfing down the backs of big waves, but some waves have no back. We leap off the tops and drop into the troughs hard, causing big splashes which soak the crew on the rail, myself included. We start calling the waves.

“Wave in 5, 4, 3, 2, 1.”  This way Glen can time his steering to the waves.

This goes on until dark.



The sun has gone down. I am off watch wedged into one of the starboard bunks as we pound through the waves. I experience freefall just after the top of every third wave or so. Thank God for earplugs and my wool hat over my eyes. Every time we tack it sounds like the rig is coming down. Conditions are hairier than ever. It’s pitch dark, windy, and wavy in the extreme. I go back on deck having been unable to sleep. The next few watches are really ugly. Boats are crossing each other. We can hardly see. Glen gets me thinking about submerged containers. Great. I go down to take a plot. Putting lat/long on a chart while being bounced around like a ping-pong ball was surprisingly difficult. I was so cold, wet and beat that I knew exactly where we were on the map, but I thought it was a mile from shore. It was seven. My next off watch was no easier and I could hardly sleep.



No sooner do I fall asleep but I am awakened to find that I’m being called on deck early. I am not happy, but apparently Steve has done a longer hitch than he’s supposed to and needs to rest. It takes me forever to get dressed, get myself together and get on deck in the dark and bumpy cabin. Another lesson learned: Sleep in your foulies and keep your harness and tether within arm’s reach. I am on deck and mighty grumpy. Somehow we make it through the cold, wet and miserable night.



I go off watch at some point and awake to find the wind has died, visibility is low, and the seas are still very confused, but nothing compared to the night. We are trying to fly a spinnaker in light air, but the chop keeps us from sustaining any sort of air flowing over the sail. We sit there for what seems like hours. After a while I’m at the helm and Glen is trimming. I can’t maintain a course and Glen says: “You have three minutes to figure this out or we’re going to have words.” Toby wants me to steer by looking at the chute, which I can’t see behind the main. A brief exchange clears him out of the way of my view of the compass, I get on course and no one has words. We start moving slowly but surely. Finally we drop the spinnaker, put up the jib and really get moving again. We sail in progressively foggier conditions for the rest of the day. I am much more comfortable on the off watches now and am able to sleep soundly. Apparently when I snore I sound like I’m on a respirator in ICU. In fact, I felt rather like that too. Remarkably, my ability to sleep soundly in terrible conditions (!) earns me the Golden Blanket Award.



Friday has gone by more or less in a fog. We round Montauk Point in zero visibility.

We are depending completely on Glen’s navigation and he calls in our rounding time. Then he comes on deck and says “Wow! You guys really can’t see ANYTHING!”

We came all this way and never saw the Montauk lighthouse. The good news is we hit the tide just right and the current has us positively screaming through Plum Gut. We hit nine knots flying the spinnaker. The wind has picked up considerably and the rig is super tight.



I come up from my off watch an hour early and take the helm. I’m floored by the clarity and beauty of the stars. The Milky Way is brightly visible in all its glory. The wind freshens from the South and we are reaching along nicely. In fact we are flying along at a pace that amazes me. We haven’t seen any of our competitors since the night before. Now we see a number of stern lights way ahead and we can’t seem to gain on them. This fact is much discussed and lamented. As it turned out we were the last of our division to round the point, but we didn’t know that at the time. Thunderstorms begin rolling in and lightning begins flashing more and more frequently. This makes me nervous and in spite of myself I keep flinching away from wet metal, which is more than hopeless and I laugh at the thought. By the time I see it and react it’s over. Instinct is a powerful thing.



I’ve been at the helm six hours through two watches and I’m beat. The rain starts to pour down in buckets. I give up and go below. I smoke one more cigarette in the companionway as the rain pounds down. I lay down in my foulies and sleep.



I awake to light air and heavy fog. Toby’s at the helm and we are doing everything in our power to keep moving. We are sounding foghorn blasts and dodging all manner of fishing boats, crab pots, etc. On the upside the crappy conditions have kept all the pleasure boats out of our way.



As the fog lifts we suddenly realize that we are surrounded by our competitors. In the night we have caught up to all the boats ahead of us, and the last ten miles are where the race will be won or lost. We become a pack of wind sniffing dogs trying to out sail everyone else. It’s working.



The last hour consists of progressively more frequent tacks and luffing matches with several boats. We are totally focused and completely cramped and miserable sitting on the leeward side of the boat on each tack. Toby handles the boat perfectly, which later earns him Most Valuable Player award.



We cross the line. We do not get the gun. We are not the first of our fleet across. We are somewhat crestfallen at this fact but, as it is a handicap race, it’s still possible that we can do well on corrected time. We go to start the motor and realize we left our running lights on all day. The batteries are dead. Damn. Toby sails us up to a mooring flawlessly and we are done. The race is over. Phew! I can’t wait to get out of my wet clothes. We go ashore to check the results but it’s still too early to know what will happen. As we get on the dock there’s a big SCYC flag painted on it and Steve yells “Lookout! Wet paint!” I almost fall over dancing around it. Then I realize there are already people standing on it. We all have a good laugh as he tells me that one year, in the bathroom after the race, the guy at the urinal next to him just fell over. Sea legs (and land legs) are a funny phenomenon. We go to the bar and have lunch and drinks. Toby comes back a bit later and says “Sorry guys. They recalculated the results.” My heart sinks. Then he says: “We only won by 15 minutes.” Jubilation.



It’s official. We have taken 1st place for our division and 10th overall. What a rush! Of 78 boats that started 28 withdrew due to the horrible conditions. We made it! Finally we head home, unload the boat and get some much-needed rest.


Funniest moments:

Almost two many to list, but some of my personal favorites:

1. John Dodson has a life vest that automatically inflates when it gets wet. Everything is wet. I go below just in time to hear “Pop! Sssssssssssssssss!” as it inflates waking him most unceremoniously. We all burst out laughing uncontrollably. What a horrible way to wake up.


2. At some point we have the hand held foghorn in one of the winch handle holders. Unfortunately it’s in a spot where it’s too easy to step on. Several times it is stepped on causing sudden very loud bursts of sound waking the off-watchers unpleasantly. I guess you had to be there. I laughed anyway.


3. After picking up the mooring Toby says: “So you think you guys have seen it all?”

At this point John Shea comes on deck in an orange tiger striped thong and nothing else.

As we fall out laughing someone on the next boat quips “I bet they were white when you started the race.”


4. The “Wet Paint!” gag was pretty funny. I owe you one Steve.


Lessons learned (in no special order):


When ocean racing it’s a good idea for all crewmembers to take, and continue to take seasickness preventative of some kind. Wrist straps and any other mojo to ward off the dreaded mal de mer should be encouraged for the best possible chance of having the most crewmembers active and available for duty.



Know your start. Talk to the race committee. Use the radio. Know what’s happening in advance if possible. Things are too chaotic to try and guess and you can’t see a small flag half a mile away in bad conditions. Talk to other boats in other divisions. “Did you start yet? At what time?” Then make a good start. Nothing will help you win a race more easily than a really good start. Or so I’m told. I wouldn’t know.



The foremost spot on the rail is NOT the best spot in heavy seas driving hard to windward.



On a long race seconds still count and those with the ability to push through the harshest miserable conditions and stay focused on racing can prevail.



There is no substitute for good preparation. Having the right gear in good condition will not only help you win races, it can save your life. Just because none of us needed our harnesses and tethers doesn’t mean we could have done without them. For my part my foul weather jacket disintegrated halfway through the trip. I would have been a lot drier and happier if it had been in good shape to begin with. The fabulous food and drink we had sure helped make a hard trip a lot more bearable. Also, having a good strategy, as well as the ability to deviate from it when conditions require, makes all the difference.

Also, dry clothes you do have are better than hot coffee you don’t have.


6. Ocean racing can be the most miserable thing you’ve ever experienced. It can also be the most satisfying when you do it right. I’ll be doing it again.



First and foremost I want to thanks these great guys for having me along. I appreciate their confidence and their patience with my comparative lack of experience. Also, thanks to the race committee for doing their best in absolutely horrible conditions, and to all the other racers for getting out there and giving it their best. Finally, thank heavens we made it! LOL


End statement:

I am proud to have raced with these guys and I have a profound respect for each of them for their skills, their commitment and most of all because they are genuinely some of the nicest guys I’ve ever met. Salud!