Valentine’s Outing -- Pines Bluff Overlook

With the holiday falling on a weekend, consider marking Valentine’s Day with an excursion beyond city limits. Fire Island Pines and Cherry Grove, the world-famous gay communities on Fire Island, comprise one of four destinations that may romance your travel plans. Besides representing different points on the compass, we’ve chosen these places for their gay-friendliness, natch, and for their accessibility by rail and bus.

Fire Island’s Wintertime Charm
Mention Fire Island Pines or Cherry Grove and the mind immediately leaps to leisure, sun, socializing, and a goodly share of debauchery. But come wintertime, when the thousands of visitors disappear, you realize what drew crowds to Fire Island in the first place. This 31-mile-long barrier beach boasts a remarkable landscape, bookended by a chilly bay and roily Atlantic waves. The Fire Island National Seashore, which includes the magnificent Sunken Forest, is federally protected for good reason. And the area’s namesake lighthouse stands alone against the elements, probably looking very much like it did when its construction was completed in 1857.

Where to Stay
Cherry Grove and Fire Island Pines are home to several hospitality destinations, including the stylish Madison, centrally located Hotel Ciel, the Horace Gifford–designed Pines Paradise, and clothing-optional Belvedere Guest House. But open during Valentine’s Day, the lowest of low season? Nope. Try late April or mid-May.

One property does brave the winter. That’s Pines Bluff Overlook. Jim Key and Jim Wald have run this six-room Pines hotel since 2002, but they only began accepting super-off-season reservations during the winter of 2008–2009. “We always had people calling during the off-season, wanting a little excursion out of the city,” Key says. The cold-weather guests have trickled in since then -- always couples -- and their numbers consistently spike for Valentine’s Day weekend.

“It doesn’t justfy keeping the place open by any means, except that we enjoy it ourselves.”  

If a disco thump isn’t a requisite for your happiness, then, indeed, there is plenty to enjoy here on a Valentine’s Day weekend. Pairs of guests walk the beach, and enjoy the crashing waves. White-tailed deer outnumber the 50 or so residents who spend weekends at the Pines, so visitors can expect some kind of interaction, even if it’s just of the Bambi variety.

There’s more socializing back at home base, which Key and Wald have packed with board games, “good cable TV” (Key’s words), and their Boston terriers Jimmy and Sophie. Since local stores are not open, Pines Bluff Overlook conducts family meals, with everybody pitching in.

Preparing for the Trek
Indeed, you won’t starve at Pines Bluff Overlook, though you may consider bringing your own cheese, champagne, or other specialty food items. Also pack sturdy winter clothes.

But keep in mind that you can pack light. Because Sayville Ferry only services the Pines on Saturdays and Sundays, you’re limited to an overnight stay. If workaholics crumble at the thought of even that small timespan, Pines Bluff Overlook does have a WiFi signal.

Remember, too, that there is reward for your sacrifice. Rooms cost a fraction of high-season rates.  

Description
•    Pines Bluff Overlook, 362 Ocean Walk, Fire Island Pines
•    Phone number: 631-597-3064
•    Getting there: LIRR to Sayville, Sayville Ferry Service to Fire Island Pines
•    www.pinesbluffoverlook.com