A Summer Cruise on Weatherly - Part 1

(Originally posted July 27, 2021)

On June 6, 2021, I set off with 3 crew for what was intended to be a slow, 8 day cruise up to Boston.

We did it in 5 and a half days. Some crew had taken time off work, so we sped up the pace to be sure they’d get back in time. Then my one remaining crew and I spent some time poking around Massachusetts.

Day 1

Our route was a short day to start, since the crew was mostly new to sailing. We headed to Ziegler’s Cove up in Darien, CT, a short ~15 mile sail with perfect wind and sunny conditions. Ziegler’s Cove is a narrow entrance, and full of sportboats during the day, but by about an hour after sunset we had the place to ourselves. It was perfectly calm, which was good because it’s not clear how heavy the mooring tackle is there and Weatherly is a big boat.

Day 2

The next day was a longer one, about 70 miles in light conditions from Ziegler’s Cove to Fisher’s Island, just south of Mystic, CT. It was a short overnight stop, we didn’t even go ashore.

Day 3

From there we slowed it down a bit, and pulled into a dock in Newport, RI, to meet some friends ashore for a rowdy dinner. It wasn’t enough time in Newport, but our schedule demanded moving on.

Day 4

From Newport, we sailed over to New Bedford / Fairhaven harbor, and picked up a mooring. Next to us was an Instagram friend’s boat, but they weren’t aboard so we had a chill evening on the mooring.

The next morning, we packed into the dinghy and went over to the New Bedford Whaling Museum. I also picked up some spare headsails from the previous owner, who lives nearby.

Day 5

From New Bedford, we did another short sail up to Pocasset Harbor. It was gorgeous, and private, and definitely on the list of places to go explore more next time.

Day 6

From Pocasset Harbor we did a long trip up to Boston - we left at dawn, and arrived at the Constitution Dock by mid-afternoon. It was light air again, but we managed to sail most of the way.

All but one crewmember jumped ship in Boston, and we got to see a lot of friends while there. I also did a day-trip back to CT to get a new dinghy as the one I had was falling apart.

Day 7

After about a week bumming around Boston Harbor, me and one crew set off first to Peddock’s Island. It was gorgeous, and only about 5 miles from Boston Harbor - the sunset over the city was absolutely spectacular. We rowed ashore and wandered around the island for most of the day, too.

Days 8 & 9

From there, we set sail for Marblehead, and stayed at the harbormaster’s mooring for two nights. The first day, we explored Marblehead, and then taxied over to Salem for the second day and did more sightseeing.

Days 10 & 11

After a lovely stay in Marblehead, we had a short downwind sail to Gloucester. This was an old haunt of mine, having grown up maybe a 20 minute drive away. We toured some galleries, met up with my dad and saw some live music, and then made some friends at the dock and joined in at their birthday party. It was a great stop.

Day 12

After two nights in Gloucester, we started the trip back south to Boston area.

We stopped at Misery Island, expecting a quiet, serene abandoned island. It was full, full, full of powerboats out for daytrips and parties. We explored the island some, but it was so hot and crowded we left the next morning.

Day 13

After a short upwind sail back into Boston’s outer harbor, we’d intended to stay at Bumpkin Island, another island in the outer harbor area. But its reported moorings were nowhere to be seen, and we got caught in a big thunderous squall just as we were approaching the island. Wet and with few options deep enough for Weatherly, we grabbed a mooring near Nantasket Beach.

We got a good day in Nantasket, relaxing and exploring a little. But the harbormaster warned us that we’d need to get off that mooring if the weather picked up, and another big thunderstorm rolled in right around 5pm.

Day 14

We dashed off that mooring, and headed for our next stop a few hours early. After an exciting time getting out of the harbor in the middle of a lightning storm, we got to Weymouth harbor an hour or so later, and grabbed a mooring just before the next thunderstorm rolled in. Thankfully it was pretty calm, just rainy and with the ominous flash of lightning all around.

And then cleaned up the boat a bit, and dashed back to NYC for the 4th of July.