Dodging Erin
- Jimmy Lee
- 1 day ago
- 6 min read
Friday, August 15 through Thursday, August 21
40 nautical miles (NM) / 46 statute miles
We continued our westward trek leaving Block Island and moving into Long Island Sound while keeping a close eye on Hurricane Erin. We visited funky Montauk, did some hiking, detoured to Connecticut and hunkered down for a glancing brush with Erin.
Sailing from Block Island to Montauk to New London
Block Island, RI to Montauk, NY
Friday, August 15
As expected, we woke up to some good wind from the east, so after breakfast we raised the anchor and left our protected anchorage of Block Island and into Block Island Sound. We were treated to an awesome downwind sail all the way to Montauk, New York. We had put out the whisker pole before we left since we knew we would be downwind. We only gybed the main sail once while keeping the jib on the “lee” side going wing in wing. It was a great 20-mile sail, and we entered Lake Montauk and dropped the anchor right around noon on the northwestern portion of Lake Montauk, a 2 mile by 1-mile protected bay.
Thoughts on Hurricane Erin
Sailors live and die by the weather, and we have been keeping an eye on Erin for quite some time. About a week before it formed, we were reviewing the possible treks and the best way to place ourselves in a good position so we could easily move out of its way. We decided it was best to get into Long Island Sound well ahead of the storm since 1) it is protected for the most part from the Atlantic Ocean swell and 2) we would have opportunities to escape further westward if it’s path treks more to the west. We could even do an overnight trip to New York City and travel well up the Hudson River if we needed to get far inland. Luckily, Erin is tracking to the east and all we will get is some wind, but we still want to find a good spot since where we are in Montauk is still a bit exposed since it sticks out into the Atlantic a bit.
Montauk, NY
Friday, August 15-Tuesday, August 19
Once we had the boat buttoned up from our sail from Block Island, we dinghied into shore to look around and go on a walk. The dinghy dock was on Star Island which is apart from the actual community of Montauk. We walked around the marina and resort (Safe Harbor Marina and Yacht Club). Our first impression was not overly good since there were no pedestrian facilities and really nothing more than the see the marina and some fishing boats. It was not overly welcoming. The town proper is a good 2 miles away, so we plan on taking the “Hampton Hopper” free bus on Saturday.
Montauk looks like a Circa 1975 Beach Vacation

On Saturday we dinghied back to the town dock and found the bus stop for the free bus. Once we got to Montauk proper our opinions changed much more to the positive. This is a little funky beach town that reminded me of a beach vacation from the 1970s as a youngster. A bit cheesy but still very fun with an artistic flair. We walked through the shops and had a great lunch at a Latin lunch counter. We then continued our walk and ended up at the Montauk Brewery since there was a bus stop there. We then took the bus back to Star Island and dinghied back to Utopia. Highlight of the night was that Baxter almost caught a bird on the bow of the boat. Feathers flew but the bird got away.
Sunday was nature day where we ended up going on a 10-mile hike on the far east end of Long Island. We started by dinghying to a beach on the southern shore of Lake Montauk. Once the dinghy was secured we began our long walk along the bluffs of Long Island and to the Montauk Lighthouse.
Hike to Montauk Lighthouse
This lighthouse is the farthest point east on Long Island. It was the first lighthouse in New York and commissioned by George Washington in 1792. We ate a packed lunch there and continued our hike along various trails to Camp Hero State Park. This is an old military base that’s claim to fame is the abandoned Montauk Air Force Station which was utilized for coastal defense during WW II and after. After Camp Hero we continued our walk back to the dinghy. We were very tired when we got back to Utopia.

We needed to stay in Montauk at least one more day (Monday) since there was a cold front passing through and wind was quite high. We did not even drop the dinghy today since the trip to the dinghy dock would be a very wet affair. We spent the day doing boat chores and Sondra did some City of Tallahassee work.
More ruminations on Erin
During our time in Montauk, we have spent a good bit of time in the background figuring out where we will be hunkered down when Erin passes close to us this coming Thursday/Friday. Originally, we had planned to go further west to Shelter Island. We had reservation at a mooring ball for a few days at Sag Harbor. Unfortunately, that area is exposed from a northeast wind. So exposed that the marina that owns the mooring balls messaged us and said we might want to reconsider coming since it would be very bumpy even with the sea wall protecting the field.

We then started looking at other places that would be good to wait out the storm. We found several anchorages that would work but we would not be able to leave the boat for a few days. We would prefer to get on land, so we decided to leave Tuesday morning for New London, CT. It’s on the mainland side and a couple of miles up the Thames River. The wind should be diminished enough to allow us to get off the boat during the day.
Moving onto New London, CT
Tuesday, August 19 - Thursday, August 21
We woke up early and left Montauk about 7 am so we would not have an adverse current on our trip. The distance from Montauk to New London is about 20 miles and it traverses a location called “The Race”. It is a location where you enter Long Island Sound from Block Island Sound. Due to the change in depth and its narrowness, currents through the section hits 3 knots in each direction every few hours. It’s no fun to only make about 2 knots of headway so we timed going through “The Race” at slack current (meaning the current was around 0). It went off well and we went through “The Race” about 9 am. We had a great sail the entire way and entered the Thames River in New London about 11 am.
Fun in New London
We always like to stretch our legs after a passage, so we went on a 5-mile walk around New London. We enjoy unfamiliar places and we understand that not all stops will be like Newport. We liked the non-touristy vibe, and we are glad we will be here for a few days waiting out Erin. A few things we would like to do are to visit Fort Trumball and the first nuclear submarine (USS Nautilus). It should be noted that General Dynamics has a huge presence in New London since their “Electric Boat” subsidiary is here building submarines for the US Navy.
We have some friends that we met while hiking the AT last year that live in the area and they reached out to us and offered to lend us one of their cars. We met at the marina parking lot on Wednesday morning and immediately took the car to a park for a little hike and then to get a large amount of groceries that we would normally not get do to the weight. It was truly kind of our friends to lend their car for a couple of days. We then came back to the boat around noon since we knew some weather was coming in. We spent the rest of the afternoon doing chores inside while it rained into the night.
It's Thursday and the rain has ended but the winds are building a bit from the glancing blow we are taking from Hurricane Erin (i.e., closest we are to the eye is about 300 nm). As a side note it was in the 50s this morning when we woke up (Brr....). We were planning on having dinner with our friends that lent us the car tonight, but we decided to put it off until tomorrow/Friday after the storm passes. We had one trip in the dinghy to go for a walk and realized leaving our dinghy at the designated location for an extended period might be sketchy due to the waves and bouncing around the crowded dinghy dock. We spent the remainder of the day doing chores and sailing on our mooring ball due to the higher winds pushing us back and forth. Winds peaked out at around 25 knots for a few hours but overall our close brush with Erin was tolerable.
Our general plan is to leave New London, CT on Saturday and start moving west into Long Island Sound. Stay tuned!
Here is a video from our time in Annapolis, MD around Independence Day:
Good stuff...!