For my birthday this year, all I wanted was a few days away – child & dog-free – to spend with Thomas after a hectic summer kickoff. As most parents of young children understand, time together just us is few and far between opportunities. Add a major house move and the busiest social calendar we’ve had in a while into the mix, we NEEDED this vacation. We are so unbelievably grateful to have my in-laws nearby & willing to hold down the fort so this 3-day trip was even possible (if you’re reading this, THANK YOU x A MILLION.)

Over the years, pre-kids especially, we’ve found exploring the places 2-3 hours away via car to be the most satisfactory. There are so many places within reach to visit, which also makes traveling with younger kids being watched at home a bit more feasible. Having been to Greenport when we first started dating ~5 years ago, we recalled seeing the signs/ferry for Shelter Island and figured it would be worth checking out given our positive experience to the area. And it ended up being the perfect spot for us to get these necessary 3 days away, where our only responsibilities were to ourselves & to each other.

How To Get There

The only way to access the island is by car ferry, unless you’re willing to take a trip via personal / friend’s boat. Honestly, we hope to revisit by boat someday as its relatively the same time to travel as car (~3.5 hours, weather & water-permitting.) But for most of us, you’d get on island by road vehicle. Naturally, traffic will be your biggest obstacle as you navigate NYC/BK Traffic on Long Island – especially in the summer months or rush hour windows. So you’ll want to plan your drive accordingly.

There are two car ferries on the island – North Ferry via Greenport & South Ferry via North Haven (very close to Sag Harbor.) The ferries on either side are so frequent that you don’t need a reservation; just hop in a line that reads “Ferry Lane” upon arrival & drive onto the ferry for a short ride. There are just a few differences in pricing/duration depending on which one you choose.

NORTH FERRY VIA GREENPORT, NY

Car (with 2 passengers): $18 One-Way, $27 Round-Trip

Payment: cash/check only (if vehicle), pay once aboard

*If walking on as foot passenger, you have to buy Ferry Tokens at the site/dock before boarding (1 token = one-way)

~5/6 minute ride across | 2-3 ferries operating at a time (summer)

Complete Schedule / Per Season Here

SOUTH FERRY VIA NORTH HAVEN, NY

Car (with 2 passengers): $19 One-Way, $26 Round-Trip

Payment: cash/check only, pay once aboard

~2 minute ride across | 2-3 ferries operating at a time (summer)

Complete Schedule / Per Season Here

WHERE WE STAYED

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Seven on Shelter Island

There are several hotels on the island, but sometimes nothing beats the tranquility that you can find at a B&B situation. Especially one like Seven, which is simply luxury meets boutique in the most charming, refurbished 1902 Farmhouse. With only 7 rooms, it’s guaranteed you won’t be sharing your trip with a bunch of tourists & dealing with the cons of staying at a crowded place. In terms of location, Seven is pretty central – we were able to walk to most of our dining spots (granted we like to walk if we can – the former New Yorkers in us still reigns strong.) There’s also a fabulous pool and fire pit to enjoy – oh, did I mention it’s pet-friendly!? Definitely will be bringing Levi here with us when we visit again. Kids are welcome of course, but I’d say this is more of a couples retreat or even a place for a solo adventure away from the city. That’s just the vibe we experienced.

Beth, the owner/manager, is one of the kindest people we’ve met and so communicative throughout the booking process, as well as during our stay. She had fresh breakfast pastries & assorted grab-n-go options every morning, as well as checked-in with us to see how our stay was going & if she could give any recs we needed. I even left my sweater at the fire pit on our last evening and she mailed it back to us after I has realized it was forgotten accidentally. Truly a 10/10 experience and I couldn’t recommend staying at this hidden gem more if you’re looking for something peaceful, intimate and luxurious.

THINGS TO DO

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Island Public Beaches

You’ll need to get a beach parking pass if visiting between May 15 & September 15. You can purchase daily passes online for $25 using ParkMobile or pick one up at the Town Clerk’s Office (can purchase a weekly pass there too.) If purchasing online, be sure to refer to the correct Parking Zone for the beach your planning to visit & know your license plate #.

For all of these beaches, you will need to bring your own chairs & umbrellas along with anything else needed to enjoy a day by the sea. Most hotels on the island provide such to be borrowed, but you can also pick up anything else you may need in town.

Wades Beach

We spent a tranquil morning to mid-afternoon here and it was one of the best R&R experiences I’ve had on a beach, truly. Quiet, gentle ripple of waves and relatively shallow waters. There’s a comfort station (aka real bathrooms) & lifeguards on duty during season. You’re allowed to bring alcoholic beverages (just don’t intend to be a fool, this isn’t a party beach haha.) Grab bevs & sandwiches at Elli’s Country Store on the way to make the most of your day at this beautiful beach. This beach location would be considered the most family-friendly out of the rest.

Crescent Beach

Also known as Louis’ Beach, another lifeguarded beach located on the Northern side of the island overlooking Southold & Greenport. There are restrooms at this location as well. On top of sunbathing, the waters are generally calm enough to go kayaking or paddleboarding (rentals available nearby.) Another family-friendly spot to consider if you’re hoping to have a true beach day.

Shell Beach

This spot is more of a scenic, narrow stretch with calm waters and wildflowers – more of a nature walk with a sandy shore. If you’re looking for a quiet spot to decompress & take in nature (birdwatching, shell collecting, etc.), consider visiting here but keep in mind there are no lifeguards or facilities. So you’d probably not want to bring the kiddos here if you’re looking for a true beach experience.

Menhaden Lane Beach

Technically considered a “Town Landing” and located on the east side of the Island. This small, quiet beach is meant for those seeking tranquility. A great spot to consider for adults looking to enjoy some peaceful shores & a good book or alike.

Ferry Ride to Greenport

There’s not much of a downtown shopping district on Shelter, so you might want to venture over to Greenport via North Ferry to scratch that itch if you so desire. We opted to spend an afternoon doing so & it was so easy! It was also great to revisit some of the spots we went to on our first trip to Greenport a couple years back.

Bike Around The Island

We brought our own bikes but most places you choose to stay have ones to borrow (Seven did!) The only thing I found is that the island is pretty hilly – some of the roads were definitely on the more challenging side, especially if you don’t have a gear bike. Great exercise though! But it was a quick way to get to the ferry since Ubers are relatively limited.

Shelter Island Country Club

Golf enthusiasts might enjoy playing this public course – definitely had some challenging spots from the looks of it. There’s a bar/grille you can get drinks & a meal at afterward too. Or you can go just for the drinks. Very rarely do you come across a Country Club that’s open to the public.

WHERE WE DRANK + DINED

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Sunset Beach Hotel

If you’re looking for a Surf Lodge experience that’s slightly toned down, then this is the place to check out. I’ll say that we felt relatively older than the crowd on the mezzanine level lol but at least we fit in with our linen/elevated casual ensembles. I’m going to age myself here by saying the music was a bit loud and clubby, so probably not the best place to take the kids or try to have an intimate conversation. But the drinks & the people watching were great!

You can eat here on the bottom and 3rd floors, but will need a reservation if planning to visit on a weekend. Summer Sundays are their busiest days without a doubt, but if visiting during the week you’re more likely to be successful with a walk-in.

The Terrace at The Pridwin Hotel

Easily one of our favorite dinner spots we checked out, situated on a hill with views of the waterfront you can’t take enough pictures of. There’s a fabulous bar and occasional live music inside as well. The Pridwin is the largest, elevated hotel option to stay at if the B&B isn’t your vibe, if you’re traveling with kids/multiple people, or if you simply want that fresh towels and turndown service every day kind of experience. Regardless if you choose to stay here or not, The Terrace is certainly worth checking out!

Same as the Sunset Hotel, the weekends are most likely the busiest during the season and a reservation might be needed. We happened to get lucky and got a table right away on a Sunday evening, figuring most people had left by then.

The Chequit Hotel

We grabbed a delicious espresso martini at the bar here before dinner & shared a few small apps (delish!) This is another hotel spot that offers dining, located in the Shelter Island Heights district, which is kind of their downtown. It was pretty quiet when we were there (on a Tuesday evening) but doesn’t hurt to have a reservation made if planning to be there on a Friday or Saturday.

Léon 1909

I’d say this was one of our more expensive dinners, and the atmosphere/ambiance was the best out of them all. The menu offered a seasonal French-Italian fare with the freshest ingredients, cooked in a massive open-fire kitchen inside where all the entrees (for the most part) were prepared. If you’re prone to running “hot”, I’d ask to not sit too close to the fire if you can help it – definitely gets pretty warm. But super cool to watch everything being made. Cocktails were delicious and I recommend getting the bread to share – still thinking about it honestly.

Highly recommend having a reservation made during the summer season, unless you get there at 4:30pm like we did. Even still, the place was packed by the time it was 6pm.

Shelter Island Heights Pharmacy

Upon research, I learned there was an old-school lunch counter inside the Pharmacy offering simple breakfast plates/sandwiches. Don’t expect a 4+ star meal here, it’s very basic with the options. But I kid you not, it was one of the more tasty omelettes I’ve ever had. A hidden (local) gem for sure.

We unfortunately didn’t get to hit everything on our list, given what days they were open not matching up with our Sunday-Wednesday stay. But we’ll definitely be checking these below spots out when we go back!

*Disclaimer: Brief summaries of each spot are copied/pasted from their websites*

Chez Marie

A newly established restaurant, bar and lounge located at the Shelter Island House Inn. An ideal destination for unwinding after a long day’s work, catching up with friends while enjoying drinks, or commemorating special occasions with loved ones. Make a reservation here.

SALT Waterfront Bar & Grill

Indoor-outdoor site on the water with creative eats, cocktails & a kids’ menu, sundecks & boat dock. Offering happy hour, vegetarian options and live music. Make a reservation here.

Vine Street Cafe

Local produce, seafood & wine at a quaint American cottage spot with a food shop attached. Has outdoor seating & serves great cocktails & vegan dishes. Make a reservation here.

The Ram’s Head Inn

Known as a chic yet historic and inviting seaside getaway, with a relaxing atmosphere, gracious country accommodations, quality dining, and warm hospitality. The restaurant crafts a menu that is a love letter to Shelter Island’s bounty & for those who appreciate gourmet Coastal American cuisine. Make a reservation here.

Maria’s Kitchen

A quick dine-in or takeout lunch spot that offers freshly-made Latin-inspired dishes and healthy options. Check out the menu here.