2014: The Season in Review

Categories Supplemental Thoughts

Short days, pervasive overcast, coat weather, and a yard full of unraked leaves mocking me: it’s that time of year when sailing feels like it’s an impossibly long way off. But perhaps it’s an ideal time to reflect on a season well-sailed.

Given my delight in the derision that my university’s English department always displayed toward the journalism department, I’ve tried hard to think of a way to intentionally bury the lead in this log entry, but I just can’t do it: we got a new boat.

Catalina 27 Profile

It wasn’t an easy process. We had deep and genuine affection for our Catalina 22, and after our first visit to the Catalina 27, we declined to make an offer—I just didn’t have the immediate emotional connection that I expected. The weeks that followed were arduous, however, as I contemplated the decision in some kind of bizarro non-buyer’s remorse. After a lot of thought, a lot of discussion with fellow sailors, and a blown deal between the seller and another potential buyer, we got a second opportunity and seized it. Our new Fortuitous has been a giant leap for us.

One of the reasons that we wanted to move up to a bigger boat was so that we could expand our cruising range. As much as we loved the 22, I never really felt comfortable taking her beyond the barrier islands and out into the ocean. We broke through that barrier on our very first trip in the 27 when we sailed her from the Shrewsbury River, around Sandy Hook, and out into the Atlantic to get her home—and we did it blind.


While we might not have been out of sight of land in the traditional sense, we certainly were in the literal sense, because we were enveloped in a fog that required us to draw on every scrap of seamanship that we’d stashed over our previous 4 or 5 years of sailing. Dealing with invisible ships, an inlet, a canal, and the Baltimore Shrimp Box (without the advantage of a real chart plotter, radar, or AIS) made for an exciting and occasionally terrifying trial by water. The full account is still a little nerve-racking for me to read, even though I know how it ends.

The delivery wasn’t our only foray into the ocean this year though. Determined to actually see the ocean in which we were sailing, we set out again on our trip to Atlantic City. The major mental hurdle for that trip was traversing Barneget Inlet, which has a reputation as a nasty place for a sailboat. Leaving Myers Hole before dawn and watching the sun rise over the ocean as we made our way out into the infinity was amazing, and Jen has described the sail that followed as one of the best experiences of her life.

Leaving Barnegat

The return trip and some of the intermediate equipment blunders were another story, but we made it. I’m hoping that leaving Absecon Inlet on an ebb with opposing onshore gusts to 20kts was our Cattus Island Event on the 27—the moment when we earned our faith that the boat will absorb far more abuse than her crew.

Another entirely new facet of sailing for us this season was racing. I’ve been racing on other people’s boats for years, but it was exciting (and humbling) to take the skipper’s seat. I don’t think Jen was necessarily looking forward to racing—she doesn’t seem to have my competitive streak—but when I asked her for her list of sailing highlights for this year, she included the long distance race among them. Even with two reefs in, we held off the bigger faster boats for far longer than was reasonable and wound up in second place by 38 seconds in corrected time.

Distance Race

While we didn’t place as high in the Tall Oaks Challenge Cup, we did confound a couple 34 footers who absolutely could not pass us downwind.

You Shall Not Pass

In all, I don’t think we had a bad showing for our first season of racing. Special thanks to Sailor Steve for crewing with us, and we hope he can join us again next year. Here are the full racing results:

Race Result Notes
Instructional Race 2nd finished with main sheet disconnected from traveler
Distance Race 2nd still catching hell for refusing to be barged at the line 🙂
Tall Oaks Challenge 6th 3rd among WJSC
Frostbite Race DNF oops

In addition to our racing and ocean sailing, we did a lot of the typical sort of daysailing and weekending in the bay that we’ve always enjoyed, and we did it in a lot more comfort than ever before. If given a choice between being known as gritty or elegant, I’d almost always choose gritty, and there were many things that I loved about sailing a pocket cruiser with no amenities, but I’ve come to accept that there are no bonus points for sleeping in separate bunks from your wife or adopting a catcher’s stance to pee.

We did have a few setbacks. For example, I have about five outstanding tasks that are going to require a trip to the top of the mast and we still don’t have a functional boom after bending it in the Frostbite Race. I’ve been focusing on that stuff a lot lately in my day-to-day, but in going back through the 2014 boat log entries in preparation for writing this, there were a lot of good times that deserve remembering:

This has been a momentous year for us. Our new boat has exposed us to exactly the sorts of challenges and opportunities that will enable us to take our sailing skill to the next level. Despite the early trepidation, we have no regrets. We were ready.




"Prepare to fend off the bridge abutment."

3 thoughts on “2014: The Season in Review

  1. Congrats on a great season Chip! I’ve read your blog from the beginning and through your humorous, detailed writing garnered a huge respect for how you and Jen handled your entrance to the sailing world over the last few years. Pretty much 180 degrees opposite my feelings for some other beginner sailors we know. No names, of course. ***cough, cough …Rimas…cough** (I’m a LONG-time SA lurker, SA is responsible for my finding your page)

    I had an O’Day 240 on Eastern Long Island Sound for 5 years that myself and an ex-girlfriend also cruised on for a 2 month trip in Florida and up the ICW to North Carolina. I yearn for those days again (the boat, not the ex LOL), and reading your logs feeds the yearning nicely, motivating me to save more money for another boat.

    I currently live in Rayong, Thailand for work. My rental house is only 1.6 miles from the ocean, but unfortunately there are few to no 25-30 foot sailboats with the right combination of affordability/condition here. I’ll keep looking and saving, but in the meantime I will have to survive living vicariously through your posts. Many thanks for providing the content to allow this!


    1. Wow, thanks so much, Nate. Cruising the ICW for a couple months sounds awesome…I hope we can do something like that some day.

      I'm glad you're enjoying our boat log. It's great to hear that people are reading it. Good luck in your boat search.

      1. Thanks Chip! Headed back to the frozen tundra (ha!) of Connecticut for Christmas today. Bah humbug.

        You guys are totally ready to go NOW from experience standpoint. You know how to respond to weather forecasts, deal with challenging anchoring situations, kedge a boat off, and have even seen the destructive forces of a rough sea-state. Just getting out there is what you need next. But, as is always the case, I’m sure career, financial obligations or maybe kids in the future etc. etc. are not ready to go now. I was lucky and had 6 months between college graduation and my new job start date at the time. I also had a tiny amount of money and empty credit cards on my side. I’ve been sailing on all kinds of boats since before I could walk so I didn’t have the steep learning curve that you guys have so deftly scaled, either.

        Make a 5 year plan. Or 10. But plan and do it. I just know you guys will love it for at least a few months if not forever. The feeling of accomplishment during and afterwards is beyond description. I’ll cherish those memories forever.

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