The run from Block Island to Montauk is a short one (25 miles, 3 hours), and it was a beautiful, clear day. We pulled into the Montauk Yacht Club, on Star Island in Lake Montauk, at 12:15 pm, which gave us plenty of time to hop on our bikes and explore.
We went down to Gosman’s Wharf, which sits right on the inlet to Lake Montauk from Long Island Sound. We know from past experience to avoid any of the Gosman’s restaurants, so we settled for….you guessed it, ice cream! The only food we would recommend eating at Gosman’s would be the ice cream or the raw bar out on the deck. Gosman’s does have a fabulous small seafood and gourmet market there that is worth a visit. We had delicious sea scallops that we enjoyed on the grill. They even had some wonderful Long Island produce, truly some of the best anywhere! So, yes, we got corn 🌽 and tomatoes 🍅! It wouldn’t be a summer visit to Long Island without it!
We loved staying at the Yacht Club. When we were in Montauk with the boys we stayed at the Montauk Yacht Basin, which is closer to the wharf and inlet. However, when we were there 14 years ago the facilities were mediocre, and in researching marinas here, we read that it’s continued to go downhill. The Yacht Club staff and dock hands in particular, are great. The facility is beautiful, with two outdoor pools and one indoor (happy co-captain had the pool to herself in the mornings). There is a small beach with free paddle boards, and several restaurants and bars. And, they have a free shuttle into downtown Montauk, so we were able to run a few errands and provision.
The Montauk Yacht Club
The IGA is a short walk west from the center of town, and it’s just a block off the beach. You can walk along Montauk Highway, where there are some shops and restaurants, or take a more scenic route along the small hotels lining the beach, and take a peek at the ocean. We can’t say anything about restaurant experiences on this leg of our trip, as we ate on board, recovering from the stupid expensive marinas and moorings in New England!
The activity in and and around the Yacht Club is extremely entertaining! There is a small airport just east of Star island, and there is a ton of small craft traffic, largely sea planes (which I learned also have landing gear for dirt, not just water! Duh.) . Several excursion boats leave from Lake Montauk, and being on the T dock, we had a prime view of all the boat traffic. We especially liked the tour sailboat with all of the bean bag chairs on the deck for seating.
And then….there are the huge fishing boats and yachts. Some with some pretty crazy names.
We enjoyed a lazy morning in Montauk, leaving at 9:45 am for a leisurely run over to the charming town of Sag Harbor. It was a beautiful morning to enjoy gorgeous Gardiners Bay.
We arrived in Sag Harbor at 12:20 pm. We needed a full service marina to look at our Yamaha motor for the dinghy, as it wouldn’t start. The great team from the Sag Harbor Yacht Yard came over to us at the Village of Sag Harbor Dock, and picked up the dinghy motor for repair. Turned out we needed to replace the carburetor, which was more involved than we had hoped. They ended up keeping it for a week, as we continued exploring this area of Long Island, and got “stuck” in both Greenport and Shelter Island due to rain and high winds. The good news is that they were a pleasure to work with, got it up and running, and we just swung by the yacht yard before we left the area to pick it up. They had a crew waiting on the dock to pop the motor on so we could be on our way. The bad news is that as with most boat repairs, it was expen$ive!
Much of Sag Harbor is a National Historic Site, with a history centered heavily on the whaling industry.
The Sag Harbor Whaling Museum
The Sag Harbor Whaling Museum is housed in a beautiful 1845 Greek – revival mansion built for a whaling tycoon. We’ve been there before (several times, actually!), so we skipped it this trip, but it’s definitely worth a visit.
There are numerous adorable, fun shops in Sag Harbor, both practical and entertaining. You’ll find a cute toy and kite store, an old fashioned 5 and 10 (which smelled just like the one I grew up with, Bell’s, in Garden City, NY. Why is it that 5 and 10’s all smell the same? Just like antique stores!). There’s also the amazing Sciavoni’s Market (Check out their wonderful produce, meats and prepared foods), Provisions (a great natural foods market, perfect to grab lunch to go), art galleries, clothing boutiques (both reasonable and expensive), numerous restaurants, and an adorable tea and book store.
We enjoyed a fabulous lunch at Sag Pizza on Main Street. It’s a fun and funky place with an open kitchen right up front to watch the pizzas being made. The menu has incredible fresh, locally sourced ingredients put together in really interesting ways. We enjoyed a “Mushroom & Tartuffo Pizza”, with truffle paste, fontina, taleggio, sage, garlic (ingredients sourced from Schiavoni’s Market across the street!), and “Farmer’s” with tomato, shishito, sausage, mushrooms, farm eggs, mecum cheese (ingredients sourced from Provisions down the street!).
We enjoyed wandering all over this lovely village. The homes, churches and gardens are beautiful and a throw back in time.
We stayed at the Village of Sag Harbor Dock and loved it. It’s bare bones, and their bathrooms are a block away, but you are smack at the end of Main Street, so you can walk and bike everywhere, plus there are pretty amazing views! As you can see, we again had bad weather with rain and fog, with more predicted to come. Another reason to be nice and close to town!
We left Sag Harbor and headed over to Coecles Harbor in Shelter Island. At the far end of the Harbor is The Rams Head Inn, where we enjoyed dinner for our 25th wedding anniversary when we visited on our first Misty 14 years ago. This time, we threw our anchor on the western side of the harbor and enjoyed a quiet, beautiful evening, a delicious meal on the grill, and a gorgeous sunset.
We departed Coecles Harbor at 10 am for a quick 20 minute run over to Dering Harbor in Shelter Island. We spent one night at Piccozzi’s Marina (who also own the gas station) in the little town, and then moved to a mooring ball in the harbor. You’ve gotta love a village that has an old fashioned gum ball machine at the gas station, and a hopscotch court painted on the sidewalk in front of Jack’s Hardware & Marine (who also owns and operates the mooring field, and told us he needs to repaint the hopscotch court every year as it’s so well used)! There’s also the yummy Marie Eiffel Market, a real neighborhood spot, where we indulged in some pastries. Are you getting a picture of a quintessential small town?
After docking the boat and wandering around the village, we explored some of the beautiful surrounding neighborhoods, and visited Dering Harbor Inn, where Nancy had stayed with her parents many years ago.
Dering Harbor Inn
Out ultimate goal was to get to Greenport, but this was the weekend of their annual Maritime Festival, and there were no slips to be found. So we stayed on the mooring ball in Shelter Island and took the ferry over to Greenport to enjoy the festivities.
For 30 years, Greenport has hosted the East End Maritime Festival. The tall ships sail in, the streets are closed to vehicular traffic, the stores are open and their wares spill out on to the sidewalk, and food and craft vendors tents line the streets. To kick off the festivities on Saturday, there was a “Mermaid Parade”, with mermaids of every age, bands, antique cars and more!
A few of our favorite things: Goldens, Food Trucks and Little Libraries…all after a parade at a fair!
A visit to Greenport wouldn’t be complete without a visit to The Doofpot, a fabulous store packed with all kinds of beautiful Italian pottery.
We moved over to Brewer’s Yacht Yard from Shelter Island, but the marina was not very convenient to town, and there wasn’t much there. I did get a couple of books out of the “book swap” in the ladies room, but overall, can’t say much about the marina. So, I’ll focus on the book part of it. Nearly every marina has a spot where boaters leave books they have read for other boaters to enjoy. It’s been interesting to compare the books you get in small towns, vs. larger towns, or more “touristy” towns. As an example, I picked up hard cover copies (!) of Pat Conroy’s “Beach Music” (a favorite of mine I want to re-read) and “Devine Secrets of the Ya-Ya Sisterhood” (ditto) at Liberty Landing Marina (Jersey City, essentially the most accessible NYC marina), vs. James Patterson from a marina on the Hudson. Many others have had a heavy selection of romance novels, and books on the Royal Family. The general rule of thumb is that you leave something you have read in return for a new pick…which we do (good to unload stuff when you live on a boat!). We have also discovered more small towns with adorable “lending library” boxes that essentially serve the same purpose. Greenport was no exception. ❤️ Happy!
Our ultimate goal was to be in downtown Greenport, so we moved over to Mitchell Park Marina, right in the center of town. The weather continued to deteriorate, with increasing winds and rain. We were literally one of three boats in a marina that has 60 slips! Despite the weather, it was great to wander town, and provision, as there is an IGA a block from the marina. After quizzing some locals, we decided to have dinner at American Beech, and we’re glad we did. It was wonderful! Beautiful space, wonderful service and delicious food! While we couldn’t enjoy their outside patio due to the weather, the interior was just as nice…and the flamingo wallpaper in the ladies room…..!!!
As we enjoyed our last day in Greenport, the weather began to “lift”, so we enjoyed one last sunset before we left to head back to Shelter Island, this time to beautiful West Neck Harbor.
Throwing an anchor in West Neck Harbor, on the Southwest corner of the island, was a goal for us. We were here for our 25th wedding anniversary, and loved it. We had just set anchor in this beautiful harbor on an absolutely spectacular summer day, only to find out that our generator wasn’t working. We had a refrigerator filled with great food purchased in East Hampton for our 5 days without the kids, along with our celebratory bottle of champagne! So we ended up at Island Boatyard while the generator was fixed. Not our plan, so we were thrilled to be back in this remarkably beautiful spot, at anchor vs. being in the marina. We anchored on the south side of the harbor near the neck, and rode the dinghy over to the narrow strip of sand that borders Shelter Island Sound. There’s a dirt/sand road that runs the length of the neck, and it’s a popular spot for walkers and fisherman.
We found some wonderful shells…and, an abandoned flamingo. Sad.
If you head north past Island Marina, staying to the west, you will meander up a beautiful creek, with spectacular homes. The creek dumps out into a large pond, with charming old homes dotting the shore.
The weather (again!!) turned windy and rainy, so we stayed put. Once again, we were “stuck” in a beautiful place! And sometimes nasty weather brings beautiful sunsets!
A conglomeration of our gorgeous sunsets in icky weather in eastern Long Island.
We pulled up the anchor at 7:40 am on the 29th, and headed to Port Jefferson. The day started off cool (57 degrees) and cloudy, but the seas were calm, and the temperature rose to 74! We hadn’t been to Port Jeff in years, and never for any length of time. We had remembered it as a cute water town, with the ferry over to Bridgeport, CT., cute shops and restaurants. All I can say is that it’s not what it used to be. There’s a power plant across from the mooring field, the huge car ferries are running constantly, and harbor traffic overall was hectic. Overnight was enough. We took the town water shuttle in to town, walked around a bit, and went back to the boat.
Our next, and final stop on Long Island, was Glen Cove. En route, we took a side trip into Huntington Harbor, a meandering trip up to a lovely harbor lined with beautiful homes and a ton of boats!
My lovely friend, and former colleague, Janet Tipton, lives nearby in the adorable town of Sea Cliff. We enjoyed a great lunch with Janet and her family (Steven, Lily and Theadora), and visit on the boat.
Janet and Nancy and a lovely sunset at Brewers Marina, Glen Cove
This area of Long Island is know as “The Gold Coast”, where the wealthy built their mansions, made famous in “The Great Gatsby”. There are some amazing homes here, largely seen only from the water.
Glen Cove is very close to New York City, and yes, on a clear day you can see forever.
Oceanport Landing Marina, here we come! We’ll be there for 2 weeks to catch up with friends, doctors and dentists, and Rob’s 40th Drew University reunion. Good to be “home” for a bit!