Whenever someone from NYC says they’re “going out east”, you assume they are referring to the Hamptons or Montauk. However, nestled between the North Fork wine trail and the Hamptons, there’s another option. Take a seamless car ferry from either side and you’ll arrive in Shelter Island, an off the beaten path, beach, and nature destination in Long Island, NY. This tiny island has a lot to offer, including plentiful beaches, a nature preserve that covers a third of the island, great seafood, and a low-key atmosphere that you’ll crave if you’ve ever gotten a taste of the chic yet pretentious vibe in the Hamptons.
This was a great place to go during the pandemic because the island is sparsely populated and is a happy medium between the North Fork and the Hamptons. None of the pretension, yet it’s upscale and secluded enough where you won’t find crowds at their beautiful beaches. Although we were still depressed we couldn’t go to Greece this summer, our usual annual summer holiday, Shelter Island was a nice place to drown our sorrows, especially in times of pandemic.
Getting There
Shelter Island is about 2.5 hours outside of NYC. We decided to drive over and take the route to the North Ferry from Greenport because we figured there would be less traffic going there than the alternative of going through the Hamptons to the South Ferry. We took a break and grabbed lunch at The Halyard in Greenport before we got on the ferry, which was well worth it for its unmatched sea view alone. Afterward, it took about 5 minutes to get to the North Ferry and as soon as we got there a ferry was waiting and we drove right on and paid $14 cash (only!) on board with our car (note: if you want to visit Greenport or the Hamptons just for the day you can pay $22 for a roundtrip ticket with your car). If you’d like to get on the ferry without your car on foot it’s only $2 per ticket. The process was so seamless it felt as if we were driving over a bridge to Shelter Island as we were on and off the ferry in about 5 minutes.
I recommend bringing a car on the island as there are so many places to see that you just can’t go to on foot, and it’s pretty hilly on the island so biking all the time can get tiresome.
Stay at SEVEN Bed & Breakfast
SEVEN is a cute, yet modern Bed and Breakfast run by two lovely and accommodating ladies, Beth and Dominica, located just a 5-minute walk from Crescent Beach. The rooms were very clean with top notch linens and toiletries. They had French milled soaps, shampoo and conditioner from Cold Spring Apothecary that made my hair smell like a million bucks, and the softest sheets and towels. In addition to the room amenities, they also offered quality mountain bikes for $30 per person for the whole stay, parking stickers for the beach (these are absolutely necessary in the summer!), and an abundance of beach supplies including lounge chairs, umbrellas, big L.L. Bean beach bags, and large beach towels all ready to go straight to the beach. We also received a daily breakfast picnic basket full of breakfast goods such as berries, premium yogurt, a quarter block of manchego cheese, fresh baguette and croissants plus a thermos full of coffee. We were very satisfied with our stay and if we ever needed any help Beth and Dominica were right there to answer our questions in person or via text.
A nice alternative to SEVEN is Shelter Island House located right next door. This hotel is similarly priced and has a pool and restaurant (even though it was closed this year due to COVID-19) on site. They also have a sister hotel down the street called the West Neck Guesthouse where you can stay, but also have access to all of the amenities at Shelter Island House.
Beaches
Firstly, make sure you get a parking sticker ($50 for one week) from the hotel before you head to the beach with your car. They charge hefty parking tickets if you park there without one. Plus, there are so many beaches to see on the island, you do need your car to get to a lot of them. The beaches are mostly unorganized, some only providing restrooms, so you do need to bring your own chairs, umbrella, towels, and sustenance, which is a far better haul in a car than on foot or bike.
Crescent (a.k.a. Sunset) Beach
This is probably one of the best beaches on the island. It’s only a 5-minute walk from SEVEN and there are very calm waters there so it’s great for swimming. It’s located just across the water from Greenport and is also an idyllic place to catch the sunset. If you go for sunset, make sure you look up sunset times for the day. There’s also a little canteen/food truck there so you can get non-alcoholic drinks and food while you’re enjoying the beach. Typically there is a restaurant and hotel called Sunset Beach right there for lunch and cocktails, but this year it was closed because of the pandemic. Crescent Beach is a great place to spend the day.
Wades Beach
This is another popular beach on the island with a large stretch of sand to sunbath on. It was a bit bigger than Crescent Beach but I think the water at crescent beach was better. This beach had a little more seaweed on the shore. However, it was definitely worth going to. Plus they had a big parking lot available to park your car as opposed to side street parking.
Shell Beach
This beach seemed to be a wind surfers paradise. Located on a narrow peninsula off the island there were a lot of people wind surfing just a few yards from the surf. There’s also plenty of sand to park yourself for the day. You can drive down to the end of the peninsula to park your car and explore multiple areas on the left and right side to sun bath and swim. The waters here were pretty calm as well.
Town Landing Beach
We actually happened upon this beach after we decided to take a ride over to the charming Derring Harbor neighborhood, which has beautiful houses to daydream about. It was a very secluded and scenic beach with a small creek running through it. The beach is actually located on a dead-end street at Hay Beach Point, but this is actually not considered Hay Beach (see below). It’s a bit wavier than other beaches but nothing to be scared of.
Menhaden Lane (a.k.a Hays) Beach
This is a gorgeous beach with panoramic views of the Orient and little Ram Island. The water there was also so calm and clear. It’s a great place to spend the day, but this beach is unorganized so make sure you bring supplies.
Hike the Mashomack Preserve
The Mashomack Preserve covers a third of the island and is a great place to observe the greenery, coastal views, and even some wildlife on the island. This was a pretty leisurely hike without much of an incline, but it’s also quite the workout depending on the trail you do. If you take the Blue Trail, you could be there all day. We took the Green Trail, which was about half the distance and took us about 2.5 hours to cover from start to finish. The trails are well marked and indicate which way the trail is going from ongoing to returning. There’s some great views of the ocean and sandy beaches along the way. Make sure you wear long sleeves, light long socks, and pants on this hike. There are a lot of ticks and mosquitos in the preserve. The paths are pretty wooded so it’s definitely worth it to cover up. Also make sure you wear a hat and drink plenty of water. We were sweating it out on this hike.
Take a Kayak Tour with Shelter Island Kayak
This was well worth doing. The views of Shelter Island and the Moshomack Preserve alone from a kayak are spectacular. We took the Shelter Island Kayak tour for $60 per person, which began at 11:00am. You meet the tour guide at 80 Burns Road and you can pay for the tour there via cash or card. We started the tour by going through a pretty narrow marsh when our guide realized that us and the other two girls on the tour weren’t completely clueless on how to maneuver a kayak. It was cool, but also a little weird. At one point we were in pretty shallow water and the guide told us that if we got out of the kayak we would be in mud similar to quicksand up to our knees. Very fun!
After our marsh adventure we kayaked through Coecles Harbor and spotted several ospreys along the way. The conditions for kayaking were perfect. There were barely any waves in the harbor and our guide said that these are the typical conditions there during the summer. We also kayaked along the Moshomack Preserve as our guide told us stories about how he wrangled ducks closeby the day before.
Vineyards in the North Fork
When you’re driving home, why not grab a few bottles of some of the finest wine New York has to offer? Going back to NYC you will drive past some of the best wineries in the North Fork, which is New York’s wine country, aside from the Finger Lakes way upstate. Just make sure the driver drinks responsibly! We stopped at the following Vineyards on our way home:
One Woman Wines & Vineyard
As we drove past this vineyard on the way to Shelter Island, we were immediately drawn by the name, One Woman. When we stopped there we learned that this vineyard was started by a Calabrian woman named Claudia, who uses practices she learned from growing up in Southern Italy. You can go there for a tasting or just stop by to buy a few bottles of wine.
Bedell Cellars
Bedell has a very picturesque atmosphere where you can sit down and enjoy a wine tasting, as well as food, while overlooking their sprawling vineyard. If you’d like to just buy some wine and move on to the next vineyard, you can also go up to their tasting bar and the attendant will offer you a taste of some of the wines you’d like to buy.
Maccari Vineyard in Mattituck
Maccari offers some of the best wine the North Fork has to offer. We had been here before a few years ago and became big fans of their Dos Aguas red blend. Their tasting room was closed when we went because of the pandemic, but they do have their shop open for pick up. We just went up to the window, told the cashier what we wanted and paid right on the deck.
Where to Eat and Drink
The Halyard in Greenport
This is the perfect place to make a pit stop on your way in or out of Shelter Island. This restaurant is located right on the water. The outdoor dining area is a deck right above the surf where you can listen to waves crash on the shores as you enjoy your lunch with a cocktail. It’s such a picturesque setting, we felt like we were in Greece for a second. This year, the Halyard partnered with Death &Co., a fancy cocktail/mixology bar in Manhattan, so some creative cocktails were added to the menu.
Isola in Shelter Island
Isola is a cute little restaurant located in town with great wood fire oven pizza. This place is actually walkable from SEVEN, but it gets very dark at night and the road is not well lit so if you do walk be very careful. We shared a pizza and Kobe meatballs and were more than satisfied.
Vine Street Café in Shelter Island
This seemed to be the place to be for dinner, which made sense since it was one of three restaurants open for dinner on the island during the pandemic this summer. They had great cocktails and food. I got moules frites and Anthony got a local duck dish that tasted fresh as ever.
Shelter Island Seafood
This place was recently opened and had the freshest seafood on the island hands down. They also had a great selection of lunch items. It was just a 2-minute drive from SEVEN so it was very convenient too.
Commander Cody’s in Shelter Island
This is a very popular seafood joint on the island that’s BYOB. We stopped here for lunch after we hiked the Mashomack Preserve. When we got there, they had a sign on the door indicating that they weren’t doing regular lunch because of a catering job that day, but had lobster rolls and shrimp cocktail available. We saw a guy loading fresh lobsters into the tank, so we thought we couldn’t go wrong with a lobster roll and our instincts did not fail us. We grabbed two lobster rolls with fries and ate them on the front porch of SEVEN.
The Frisky Oyster in Greenport
Greenport is definitely a good option for dinner and window shopping during your stay in Shelter Island. However, it is a different vibe and seems to get a bit rowdier than Shelter Island with plenty of bars, restaurants, and things to do at night. We took the ferry round trip for $22 with our car, even though it’s totally doable without bringing your car to the other side. The food at the Frisky Oyster is delicious. Try their Lobster Gigli and oysters.
Tuck Shop Ice Cream in Shelter Island
Tuck’s probably has the best ice cream on the island. I got the birthday cake ice cream and it actually had bits of birthday cake in it. Stop here after dinner and enjoy dessert! They close at 10:30pm.
Greenport Creamery
This ice cream shop is a great stop on the way back to the ferry. Their ice cream is made on site and that’s pretty obvious once you taste it. Plus the ice cream there is way cheaper than the mediocre desert you’ll get at the restaurants in the area.
Ralph’s Ices in Greenport
Ralph’s Ices is a staple in Staten Island, NY, where I grew up, and is probably the original Italian ice shop in New York, as well as the best. They have a location in Greenport so go ahead and taste probably the best Italian ice New York has to offer.
Packing List
I swear by my Arc’teryx for hiking. They have great grip, ankle support, and lots of room for your toes when you’re on unsteady terrain. Plus they’re made with Gortex so they’re completely waterproof.
This Columbia shirt is amazing for hikes or warm weather activities. It protects your skin from the sun and bugs, but is also very breathable so you won’t overheat. I’ve worn this shirt from a summer tour in Egypt to the Mashomack Preserve.
I love these Columbia pants! So breathable, but also so flattering. Plus they protect you from the sun and bugs. I also have a few pairs of the same style in capri length and they fit like a dream.
This backpack is small enough to be comfortable/lightweight yet big enough to carry all of your things. It also includes a high-quality bladder so you can stay hydrated on the trails.
Make sure you wear good hiking socks when you hike the Moshomack Preserve. There are lots of bugs in there so it’s important to protect yourself. I even tucked my pants into my socks at some points to prevent tick bites. Try these socks from Smartwool. They are light enough to keep you dry, but long enough for protection.
Although SEVEN provides beach towels, it’s always nice to have your own. We love these Rainleaf towel because they are so light and easy to carry. Perfect for traveling. We’ve taken them worldwide.
Meli On The Move 