Last weekend as we wrapped up an intense overnight delivery I said something along the lines of “what an awesome trip! This is probably in my top ten sails EVER”. Then, having hand steered for most of the last 19 hours, exhausted TJ decided that I should have a list of my top ten sails. So now I do.
Roughly in chronological order:
First offshore delivery
My first offshore delivery in 2015 I found myself on the sexiest race boat I’ve ever sailed. And I met some great sailors I still look forward to sailing with. And we had a 36 hour or so downwind run with plenty of surfing from the mouth of the Chesapeake Bay to just off of Block Island where I helmed the boat to 17.9 knots and the record for the night was 18.3.
I can’t imagine a more epic introduction to offshore sailing!
First Race to Bermuda
My first offshore race in 2015 really tested me as a sailor. It was a bash into rough conditions and and although FEARLESS, a Baltic 55, handled the conditions very well it was physically exhausting and mentally draining.
The upside of having this be my second offshore experience (I had planned it to be my first and was working on prepping FEARLESS when the delivery above basically fell into my lap) is that almost all of my offshore experiences since have paled in comparison.
Foul Weather Delivery to Annapolis boat show
I guess in 2015 I was a glutton for punishment. I signed up last minute as crew for an offshore delivery where the only reason they were looking for a third person is that they were expecting rough conditions. I learned a ton on this trip and this trip lead to a lot more opportunities for me to grow as a sailor.
Fouler weather delivery to Annapolis boat show
The following year I signed up for another delivery to the Annapolis boat show. On the same boat. With the same crew. With even bigger conditions expected. The conditions offshore did not disappoint!
Confirmed: I am a glutton for punishment because I’d do it again. For sure.
Doublehanded Spinnaker to Isle of Shoals
Before SavvySalt, before all the ocean racing and sailing instruction and offshore deliveries and the captains license, one of the things my friends and I did to gain experience was simply take out one of our boat club’s boats over a night or two when stronger winds were expected. We just sailed out into the Massachusetts Bay, picked a course around the bay during the next 24+ hours, sailed that course and put the boat back to the mooring. We affectionately referred to these experience building sails as our “sails to nowhere”.
2016 was my most recent ‘sail to nowhere’. It was also a bigger, better sail to nowhere because we had upgraded boat clubs: now we had an asymmetrical spinnaker to fly through the night on a faster boat that could take us further. We also had the experience to do so doublehanded. We picked Isle of Shoals as a destination and as we sailed around Cape Ann we set the spinnaker and gybed our way to the Isle of Shoals.
Guys, if you’re reading this, we should do more sails to nowhere!
Greek Bareboat Charter: Day One
Wait, wasn’t that the day that my charter boat was taking on water? Yes, yes it was. But it was the best day of sailing during our best bareboat charter trip during the last decade. I might have chosen our long sail in the Grenadines or our adventure to Barbuda; but the charter in Greece was simply an awesome trip – everything that bareboat chartering with 26 of your closest friends can be along with some pretty great sailing!
Besides, I figured out where the water was coming from and got it fixed.
Doublehanded Sail to Block Island
As the first day in Greece represents all the best a bareboat charter cruise can be the time I sailed from Boston to Block Island doublehanded represents the best of what local (for me) cruising in New England can be. Sailing out of Boston after work on a Thursday, nonstop to Block Island and then meeting up with some friends with summer weather at the end of September seems pretty awesome to me.
Of course there are so many other great weekends of cruising that could stand and represent the best of cruising but rarely do I get the challenge of a doublehanded overnight, including a spinnaker run, combined with spending the weekend with a group of my friends. And this overnight was the longest sail I’ve undertaken for a weekend cruise (though after this year, not by all that far…).
2018 FEARLESS Newport to Bermuda Race
2018 was my 4th race to Bermuda. And about 2 days from Bermuda it was shaping up to be another uneventful light air “bash”. A big windless hole right on the rhumb line stopped all the boats and we all basically restarted two days out. On my watch that night when the wind filled in a bit the navigator made the call that we needed to get on port tack. Starboard was very much the favored tack which meant that we were port tacking most of the fleet at this “new start line”. It was a very eventful watch with a lot of crossings to be negotiated in the dark. By the time I got off watch we had made it through most of the fleet but I was disappointed that during those 3 hours, my first watch that wasn’t struggling to keep way on in at least a day, we really hadn’t gotten any closer to Bermuda.
I woke for my next watch and it was a totally different world. FEARLESS was on starboard tack now and we were close reaching in 20 knots of breeze. The navigator had used the light wind overnight to get us into the building breeze before the rest of the fleet. On AIS you could see that we were bow down and faster than the fleet; we were crossing their bows and they didn’t have enough breeze to do anything about it!
Strategy paying off was one thing but on top of that FEARLESS was absolutely lit up. I tracked my watch on my phone and we averaged 10.3 knots SOG during my 3 hour watch! The short chop was still building and at 10 knots FEARLESS was basically blasting through the waves; everyone and everything on deck was absolutley soaked. It was absolutely awesome sailing and that fast close reaching was definitely the day that put us on the podium! Doesn’t get much better than this.
BVI to Newport catamaran delivery
This was my first paid offshore delivery as a Captain. This was definitely a feather in my cap in 2019 and the owner definitely got his money’s worth; the North Atlantic is always dishing out free lessons in seamanship and humility. But making the best of the conditions and the navigation once the mainsail got stuck up, and doing so without any permanent damage or injury, was a hard fought positive outcome. I had a ton of sleep to catch up on once we got the main down and finally stepped ashore.
We also had a fun crew and a really good time during our layover in Bermuda; even if at least some of that time was spent fixing some of the stuff that we broke on the first leg!
Counterpoint Rogue Beringer
In the middle of the 2019 season I bought SV Counterpoint. While I did get to do some sailing on her in 2019, including delivering her from Rhode Island to Maine for a refit, the best sails on Counterpoint have definitely been during 2020. In the midst of the pandemic Counterpoint has been a refuge from life ashore; I wish I could have shared the refuge and the season with more friends but that’s not how pandemics work.
One of my favorite sails was when we sailed from Boston to Provincetown for the same weekend as the Beringer Bowl. Leaving after work we wound up exiting Boston Harbor at sunset, pretty much with the race fleet coming from Marblehead by way of Boston. The wind was on the beam but it was very light; some of the race boats were flying kites at hot angles and some were sailing with genoa’s instead and there was no clear winning strategy.
I had sleepy crew so I was by myself on this overnight sail. Which, to me, meant I could spend the night tweaking the sails and trying to keep pace with the race fleet instead of turning on the motor and getting to P-town so folks could get to bed.
I wasn’t trying to mess with anyone’s race though so when one of the lead raceboats got stuck in my dirty air I did a quick penalty turn to let them pass; it took quite a while to get back up to speed after that one. But I kept the boat sailing through the night, availing myself of every sail control aboard Counterpoint, and arrived at Woods End in the middle of the fleet amidst flocks of seabirds bobbing around in a very light fog before sunrise.
It was at this point that the wind shut off entirely and I turned on the diesel; we motored past most of the front of the fleet between Woods End and their finish at Long Point. The fog descended as we put the main away in Provincetown Harbor and we had a heck of a time finding our buddy boat so we could grab a mooring next to them.
I went to bed very happy that heavy, singlehanded Counterpoint wound up somewhere in the middle of the fleet in a light air race.
Counterpoint Boston to Barrington
Last, we come to the impetus for this article.
Counterpoint’s 2020 season came with great bookends. Our delivery from Maine to Boston turned into a bash into 25 knots off the coast of Maine. Double reefed main and 90 percent of the jib up we were making 7s and 8s and had a great time of it.
The trip from Boston to Rhode Island was also epic. But instead of being against the wind the whole way we had all the conditions: we tacked our way out of Boston Harbor. Upwind to Minots light, close reach to Scituate, and a reach to enter the Cape Cod Canal. Then we gybed downwind all the way out Buzzards Bay to Newport. Lastly we beat our way up Narragansett Bay: starting at Newport we had two reefs in the main and as we passed Bristol I shook out the reefs in the main and we were once again under a full press of sail. The crew saw 29 knots apparent as we were gybing downwind in Rhode Island sound, before we reefed the main or rolled up any jib, and when we pulled into Barrington Cove Haven was a mill pond.
We also pushed Counterpoint pretty hard. We definitely kept the full main and jib downwind when two reefs in each would have been prudent. But the rudder always had plenty of bite to push the bow down in the puffs and surfs. A crew mistake gave the rig a good flogging. But I was looking at the entire season as a shakedown and on this familiar route I was happy to go big and finish off the season putting Counterpoint through her paces. Hard.
Then there were the whales. I’ve had dolphins play with the bow wave plenty of times but on this sail, heading south due east of Plymouth a few whales decided to swim with Counterpoint! After we saw one off of our starboard quarter two followed off our port quarter. They were matching our course and surfacing, not breathing just popping up to take another look, less than a boat length from where we stared back in disbelief from the cockpit!
Ohh, and we cemented the new delivery strategy that, whenever transiting the canal on a crewed delivery we should use the canal’s shelter from waves and wind to make a hot meal. We had chicken fajitas and they were delicious!
There I was putting Counterpoint through her paces on a windy October delivery and we had the coolest whale encounter I’ve ever had, a delicious hot meal during a chilly delivery and while we were gybing downwind with too much sail up the crew spent most of their time under the dodger working on a spotify playlist that essentially started as a joke. Two important takeaways from the trip: Counterpoint aced her shakedown and I have awesome sailing friends!
Worst sail: Destinee breaking sail
There isn’t much on the other side of the coin. I’ve got a handful of learning experiences that I wouldn’t like to repeat and two trips to the emergency room that I would recommend avoiding if possible. But by and large, looking back, most of the difficult sails I’ve done have been learning experiences; I might do things differently but I’d still make a go of it.
Sure it could have been much worse; I mean, we made it back to the mooring on our own – no emergency services were notified. The boat’s haulout was the following week anyway. But it was a sad way to bring to a close such a great sailing program that taught me so much.