Destination Boating on Fire Island

Share on Twitter

Share on Facebook

Destination Boating on Fire Island

The land just across the Great South Bay, adjacent to what happens to be this magazine’s coverage area, is an enchanted thin stretch of land of beaches, dunes, deer, wilderness, boating, fishing, relaxing, eating, drinking and sometimes just having a gay old time. Those of us who grew up on boats and were raised on the docks, dunes and beaches of Fire Island may forget how unique a place it really is. Boaters from all over consider the marinas destinations worth sailing for days and weeks to reach. For us, it only takes about a half hour by boat or ferry. Several towns along the barrier beach contain marinas for private boats to dock at for the day, weekend, week or sometimes the entire season. Spending a weekend on a boat is kind of like camping, except instead of a tent you have a boat. And instead of being surrounded by trees, you’re surrounded by sandy beaches (there are some trees too). Fair warning, you may still feel the rocking for up to a week after you’re back on the mainland (it’s kind of a cool feeling actually).

Though communities vary, most towns on the island still maintain the natural beauty the area has had since before we set foot on it. There are no paved roads and no cars, except for maybe an official or emergency vehicle here or there. It’s all walking along the beach, boardwalk or bicycling where allowed. Some towns (Cherry Grove, Davis Park, Fire Island Pines, Ocean Beach) are livelier, with a higher density of houses that are often rented by groups or families that help support more restaurants, bars, clubs, shops and the like. Others (Sailor’s Haven, Watch Hill) keep to the sleepy quality of a nice, relaxing weekend on the boat. The beaches of Fire Island are treasures that nary need mentioning in the individual descriptions of the towns (so we rarely do). In other words, it goes without saying that all of these destinations share the common wonderful trait of that stretch of soft sand running along their shores.

Although a few of the towns are still renovating after Stupid-Storm Sandy as well as several of bad fires (the fire at Fire Island Pines was especially tragic), we expect them all to be back to their former glory. Whether you’re looking for some lively action or a relaxing getaway that’s only a short boat ride away, our quick guide to Destination Boating on Fire Island will be a good primer to get you started.

Cherry Grove

When people from out of town have heard that Fire Island is gay (complimentary, of course), it’s primarily Cherry Grove and Fire Island Pines that have garnered the reputation. And for good reason; they’re very gay. And very fun. Cherry Grove in particular is a creative, artistic magnet with all sorts of imaginative art, landscaping and design elements that dance well with the vibrant nightlife scene that centers on several clubs, bars, restaurants (shout out to Jumping Jack’s Seafood Shack) a short walk from a nice marina for private boats. The houses really stand out here. They are all flawlessly designed and decorated with such artistic expression that a walking house tour alone is worth the visit. Cherry Grove has suffered from fire damage recently and is undergoing renovations but plenty of things are still open and operating and you wouldn’t believe some of the creative ways people have gone to make good of a tough situation or to simply augment the already beautiful setting.

Davis Park

A true boater’s destination, Davis Park sports a large 250-boat marina, full amenities, general store, snack bar, etc. There is also a vibrant residential community with share house rentals available for young slightly rowdy types as well as quieter houses for families. The Casino (a restaurant, no gambling unfortunately) is the spot to hang out after a day at the beach or your boat. The restaurant serves great food (prices are kind of high, but hey, they gotta float the grub over so we understand) and specialty cocktails are aplenty. Ferry goers arrive from Patchogue daily to visit the beach, which is part of Brookhaven Town, grab a drink at the Casino and hope to not miss the last ferry back to the mainland (water taxis are available in those cases). A quick mile-long walk along the beach or the boardwalk between the dunes (where you will encounter many many deer) will take you to Davis Park’s sibling Watch Hill where a more tranquil scene is taking place.

Fire Island Pines

Slightly quieter (emphasis on slightly) than its gay brethren Cherry Grove (and predominately more male), Fire Island Pines, with its marina and harbor serving as the social hub to the beach, bars, nightclubs, restaurants and shops. Boats of most sizes can fit into one of the many slips that provide water and electric and can be rented by the hour, day, weekend or season. This summer and next summer will see some serious revitalization here as the main commercial strip along the harbor (which suffered a huge, tragic fire a few years ago), including the Pavilion, Botel, Cultured Elephant (aka The Canteen) and Blue Whale, has been purchased by Out NYC owner Ian Reisner. He and his partner P.J. McAteer, who owns the popular Sip n’ Twirl club and several other local spots have some major plans for the next year and a half to revive The Pines back to its former glory as the mecca for gay men. The first phase of renovations should be completed over the summer and plans are to start restoring the Botel after Labor Day to be ready for summer 2016.

Ocean Beach

When it comes to hoopla on Fire Island, Ocean Beach is the place. Bars, clubs, restaurants, markets and boutiques abound, so the place is usually hopping full of Manhattanites escaping the city for the weekend to cut loose. Many of the revelers stay in one of the several hotels or rent houses (good behavior is a must on the public docks though the whole “land of no” thing has toned down in recent years). The marina is also a popular way to make your home base, spending the days gently rocking in a slip, occasionally getting up to stretch your legs and maybe pull your radio flyer red wagon around for some shopping before hitting the boardwalk for a night on the town. There are many bars and restaurants to choose from including Maguire’s Bayfront Restaurant, Matthews Seafood House, Bocce Beach, Castaway Bar and Grill and many more. When you have too much fun (which you certainly will) and miss the last ferry to Bay Shore, find yourself a water taxi or better yet, just make friends with someone and crash at their beach house. Just don’t wander onto a stranger’s boat in the middle of the night or you’ll probably end up sleeping with the fishes.

Sailors Haven/Sunken Forest

Boaters’ paradise Sailors Haven and the adjoining natural utopia Sunken Forest could be considered the crown jewels of Fire Island, harkening back to the natural wonder of the land before people discovered it. Sailors Haven marina and accompanying area are aptly named, as there are no residences in the town, boaters only. There are renovations currently taking place so the marina is closed until July 20 with ferry service (out of Sayville) limited to weekends mostly (thanks a lot Sandy). Even though the marina will be closed for the first part of the summer, the two main attractions will still be open: the beach and Sunken Forest, which features of the most magnificent nature trails in all of New York (or anywhere really). The 1.5-mile trail takes you under a dense canopy of trees into a unique underworld that seems like it’s below sea level (it’s technically not). The rare maritime holly trees are miracles of nature where the trees are only able to grow when dunes on both sides are high enough, and the salt spray keeps the tops of the trees only as high as the dunes (or something like that). Only a handful of spots along the East Coast offer these conditions. Although the first half of this summer is going to be largely sacrificed because of the marina renovations, once the work is complete, Sailors Haven will once again be one of the top boating destinations for Long Islanders as well as boaters from all over the country who have heard tell of this beautiful sunken Shangri-La.

Watch Hill

If Davis Park, with its rowdier crowd and higher concentration of houses, is this section of Fire Island’s unruly teenager, Watch Hill is its older, quieter aunt or uncle. The westernmost town of this list and part of the Fire Island National Seashore, it’s centered on a large, protected harbor that sports a 180-boat marina. Watch Hill is truly family friendly with its nature trails and guided tours, campsites, beach, snack bar, Tiki bar and restaurant. Slips can accommodate boats of most sizes (really big boats fit better at Davis Park) and offer water and electric with barbecuing areas around the bulkheads. With nice long stretches of beach on the ocean and bay, there’s plenty of sand to stick your feet into and restrooms and showers available. Another special thing many people are unaware of is that beyond the traditional-style campsites, backcountry wilderness camping is allowed in the area west of Watch Hill known as the Otis Pike Fire Island High Dune Wilderness. A permit with a $20 fee is required (available at and you can basically just walk 1-5 miles down the beach and pitch a tent anywhere you won’t hurt the vegetation on the dunes or disrupt nesting birds.

Photo: Flickr | Thom C

Share on Twitter

Share on Facebook


Follow NextStop Magazine: