Sailing Mystic Hearts

We were eager to get a move on from Port Washington because there are countless places we have yet to explore in Long Island. Two years ago, our time on Long Island was cut short when Hurricane Henri made a direct hit in New England. We were on Block Island at the time when we learned the storm would be coming our way, so we cruised two very long days west into the Long Island Sound to escape it. We were very fortunate to be safe, but we basically bypassed everything on the eastern side that we had wanted to visit.

We’ve heard wonderful things about Port Jefferson, the next town down the island, but we didn’t go into town while there. (We didn’t go into town in 2021 either!) It’s been a reliable anchor spot for us multiple times. I guess we’ll save a trip in for “next time.” One thing to note about Port Jefferson: there’s a large passenger ferry that runs pretty regularly all day. The channel in is relatively narrow, so be sure you check AIS before coming/going to ensure you don’t encounter the ferry in the channel. There’s probably room to spare, but it didn’t look like anything we wanted to mess with!

After Port Jefferson, we finally got to visit some new-to-us spots! Only 53.6 nautical miles from Port Jefferson is Sag Harbor. We’ve always wanted to come here. We were greeted in the anchorage with a sea plane taking off close to the boat (fun memories from our time in the Dry Tortugas)! Since we arrived so late in the day, we made burgers on the boat for dinner with plans to check out the downtown the next day. So worth the wait! Sag Harbor is a very cute town. Lots of beautiful old homes, shops on the main road in town, an even an old whaling museum (it was closed when we were visiting). In our usual fashion, we took a multi-mile walk around town, checking out the main commercial district, surrounding neighborhoods to get a feel for the community, and a walk to the public beach. We had no idea what we wanted for dinner, but I found a local Mexican place called Cilantro’s that we enjoyed quite a bit. We got chicken tacos, a chicken burrito, and split a Jarrito’s guava soda at a picnic table in the park on the waterfront. We loved the town, but the next day decided we had seen enough and were ready to keep moving.

Greenport is just 11 miles north of Sag Harbor. We cruised around the western side of Shelter Island and into an anchorage that we had all to ourselves. Greenport was definitely more of our vibe. It’s hard to pinpoint how different it was, but the town had way more shops and restaurants and felt more family-friendly. We stumbled across Goldberg’s Famous Bagels and had the best bacon/egg/cheese bagels ever (super soft and not chewy) before checking out the cute waterfront park, stopping by the old jail, doing our own walking tour through some neighborhoods, and finally settling in to watch one of the most incredible sunsets from the boat. Again, we really enjoyed this town as well, but had a big itinerary ahead of other places we wanted to visit, so we didn’t stick around that long before leaving the Long Island Sound altogether.

We really wanted to check out Shelter Island, but weren’t sure where to anchor or go ashore there. We’ll need to do more research so we can visit next time.