top of page

We Venture to Sag Harbor via Block Island

Back to our home away from home

While we were home in Southern California for our niece Bailey's wedding, I felt a bit conflicted. I was enjoying our time to connect with family and friends very much and was also concerned about our boat in Newport. Two weeks went by too fast! A good thing to know for the next time.

Fortunately, the weather was very mild in Newport for the two weeks we were away. And, you can be sure we checked daily!

After our whirlwind trip home, Steve and I got back to Relentless. We were a little road weary, but relieved to find her on the mooring just as we left her.

Our first big sail – we've got this!

Now, it was just the two of us on board. We were re-provisioning and getting Relentless ready for our first big sail by ourselves. Our plan was to depart two days later for Sag Harbor, New York, which is 56.5 nautical miles from Newport, Rhode Island.

First leg

With the weather predictions and a nice light wind sail on the Code 0, we thought we could easily manage this trip in one day. In actuality, we faced gusts of 18 - 25 knots on the nose, with pelting rain showers. We're quickly learning that predictions are just that!

It didn't take us long to realize that the Code 0 we had hoisted on the bowsprit that morning had to come down. This was not easy in challenging conditions, but we did it and got it stowed back in the sail locker. Instead, we decided to use our smaller self-tacking jib on the forestay with two to three reefs in the mainsail.

The seas were sloppy and the tide was against us. You can't always choose your tide, but we had hoped with the predicted wind we'd be able to sail across the tide and get a good VMG (velocity made good, sailor-talk for best speed toward our destination). It was truly a slog, and we weren't making good headway at all. It was getting late, so we opted to stop for the night at Block Island, just 25 nautical miles from Newport.

Our foul weather gear kept us warm and relatively dry, but we were still relieved to be out of the wind and weather when we pulled into the anchorage around 5 PM. We were safe on a mooring for the night, feeling proud of ourselves despite the discomfort and making it halfway to Sag Harbor.

Our encouraging virtual travel companion

Just as a side note, when my Dad sees we've turned on our AIS instruments (Automatic Identification System), he often follows our journey from his home. Our trip to Sag Harbor was no exception. We love that he does this, and we will often receive a text after we arrive somewhere with encouraging comments about our experiences. We know he is stalking us – in a good way – and it's kinda fun.

For our first leg, he knew the conditions weren't great (he watches the weather along with us) and that we weren't making good time. So he asked, "Why didn't you just turn on the engines?" Steve and I had also discussed this option, but Steve responded, "Because we're sailors!" My dad said to us, "You certainly are and good for you!" That was very affirming.

Second leg

A 5-AM-wake-up rewarded us with a beautiful sunrise the next morning. We exited the Great Salt Pond and Block Island with a few other early birds. Next time, we'll stay longer to enjoy all that the island has to offer.

Morning sunrise from our mooring.

Great Salt Pond at Sunrise

Early Birds leaving Block Island

Block Island North Lighthouse

Because of our early departure, we were able to time our second leg to Sag Harbor with the tide entering into Long Island Sound. Fog greeted us shortly after we exited the well-marked channel, so we watched our instruments carefully for other vessels on AIS – mostly ferries and fishermen. After a little more than an hour, the fog lifted and we regained visibility.

Long Island Sound was much smoother water, like a huge bay, as we moved from the outside to the inside waters. With Montauk and the Hamptons to the east on the long peninsula that blocks these waters from the Atlantic Ocean, we can see why boaters love this area. There is so much room and smooth water to play with sailboats! Needless to say, we motored most of the way with little wind, so sailing for us would have to wait for another day.

Sag Harbor

Navigating through the narrow, winding channel between rocks and shallows to the Sag Harbor breakwater was a little tricky. We are grateful for our Maptech Cruising Guides, paper charts, and B&G Instruments that help us become familiar with approaches and obstacles before arriving at our destination. The navigational aids (red and green channel markers, known as cones and nuns) made it easy to stay in safe water.

Arriving an hour early (it pays to go with the tide!) for our mooring check-in, we anchored just outside the harbor breakwater. Then, we notified our good friends, Jonathan and Jenny, that we arrived. They own S/V Inconceivable, an Outremer 4X, and are the reason for our visit to Sag Harbor (see our previous post entitled Fortuitous Friendship, Inconceivable).

Each summer they spend a few weeks at The Maidstone Hotel in East Hampton, which they own and operate. They invited us to stay as their guests for a few days. With Relentless in the protected harbor on a mooring, she'd be safe for a night or two until we bring Jonathan and Jenny aboard for an afternoon sail.

Stay tuned for more about their hotel, our beautiful sail to Shelter Island, and an additional surprise...


Recent Posts

See All


bottom of page