Every Long Islander wants to go to the beach during the summer. And that’s the problem. Hotel rooms are expensive, roads are clogged, and all of the best restaurant tables have been booked for months. Wait until mid-September, however, and everything changes. Innkeepers drop their prices, traffic is calm, and a last-minute reservation at Nick & Toni’s is attainable even if you aren’t Steven Spielberg. Take advantage of “shoulder season” room deals from Fire Island to Montauk and discover what locals have always known — this is the nicest time to enjoy still-warm beaches, restaurants, shops, and vineyards.
Fire Island Glamping: The campground at Watch Hill (lovefins.com), part of the Fire Island National Seashore, began offering something new this summer: Four safari-style platform tents outfitted with two queen beds, linens, mosquito netting, decks, Adirondack chairs, coolers, and charcoal for the barbecue. A good deal in the summer, when weekday rates start at $150, the tents are an even better deal from Sept. 3 to Oct. 15, when they can be had for $95/night. Camp sites are a short walk to the ocean beach (the Atlantic is at its warmest in late summer). Also in walking distance is the Whalehouse Point restaurant, which features stunning water views and live music in addition to seafood, a snack bar, and beverages ranging from Long Island wine to Fire Island Rocket Fuel. National Park Service Rangers offer guided nature and canoe tours of the only federally designated wilderness in New York State. Ferries (davisparkferry.com) run from Patchogue to Watch Hill two to three times a day in September and October.
Whimsical Luxe on the South Fork: If Colonial Williamsburg and West Hollywood had a baby (and asked Stockholm to be its godmother) it might look like The Maidstone (themaidstone.com) in East Hampton. The rambling inn, a 150-year-old Greek revival mansion built on a 17th-century foundation, has been decorated by owners Jenny and Jonathan Baker in high eclectic style. The dining room features black Windsor chairs under a large-scale photo of Steve McQueen in a bathtub. The red velvet Art Deco club chairs in the reception area are lit by Arne Jacobsen lamps. Special menus for your dog and yoga in the Buddha garden contribute to the unique atmosphere, which has attracted famous visitors including Christie Brinkley, Don Lemon, Alec Baldwin and Holly Hunter. The hotel is conveniently located across the street from Guild Hall (guildhall.com), where an art gallery displays the work of locals including Willem de Kooning and a theater hosts the Hamptons International Film Festival. Also within walking distance are upscale shops (Brunello Cucinelli, Ralph Lauren, John Varvatos) and popular restaurants (1770 House, Citta Nuova, Rowdy Hall) where it’s easier to secure a table in the cooler months. Quirky glamour doesn’t come cheap. Weekend stays in August at this starry inn can cost $1850/night with a two-night minimum. Once September rolls around, the weekend rate drops to $595/night. Hold out until November and you can score a room for a measly $450, often without the two-night minimum.
North Fork Vineyard Stay: Visit the North Fork in September or October, just in time for the local grape harvest. Travel during the week to save money and avoid traffic backups at every colorful u-pick pumpkin stand from Aquebogue to Orient. To experience vineyard living, check into the Shinn Estate Farmhouse (shinnestatevineyards.com), located on bucolic Oregon Road in Cutchogue. For as low as $259/night (summer rates run between $350 and $450), you’ll not only get a luxurious room with farm or vineyard views, you’ll also enjoy a complimentary wine tasting in the rustic tasting room or on the stone patio, a farm breakfast, and a happy hour that includes wine, cheese, and charcuterie. Grab one of the inn’s bikes and head up the road to Lieb Cellars (liebcellars.com), another small vineyard with a charming tasting room, to compare their Chardonnay to Shinn’s. Also within biking distance is Castello di Borghese (castellodiborghese.com), the North Fork’s oldest vineyard. For a quick bite, check out 8 Hands Farm (8handsfarm.com), not far from Lieb, where Icelandic sheep and Tamworth pigs graze in the fields and a food truck serves up grass-fed beef burgers and pastured egg sandwiches. Amid the vineyards and farms, it’s easy to forget that the beach is close by. For fine dining with sound views, try the Halyard at the appropriately named Sound View Hotel in Greenport, where tables hover over the water and oysters come straight from the Peconic Bay. Souvenirs including canvas wine totes can be found at Wm. J. Mills (millscanvas.com), custom sail makers since 1880.
Montauk Hotel Hero: To find the Hero Beach Club (herobeachclub.com), a happy, family-friendly spot with a boho/Palm Springs vibe, look for a big yellow winking smiley face painted on the side of a large white building at the edge of town. At this thoroughly renovated waterside motel, furniture and accessories are from Bali, rattan hanging chairs outside each room look out on the ocean, and the garden is equipped with daybeds, lawn games and colorful large-scale sculptures. The hotel organizes film screenings, yoga sessions and nightly bonfires with s’mores for guests. There is a pool on site, and the hotel sits almost in the dunes and sets up puffy lounges and umbrellas on the sandy beach in the good weather. Cruiser bikes are available for a quick ride into Montauk for mini-golf at Puff’n’Putt (puffnputt.com) or tacos at Tacombi (tacombi.com). Hiking trails at Shadmoor State Park (parks.ny.gov/parks/16) offer dramatic views from bluffs that drop to the ocean. Quench your thirst at Montauk Brewing Co.’s (montaukbrewingco.com) tasting room, where beers have names like Wind Chaser and Driftwood. For relaxation, visit the Montauk Salt Cave (montauksaltcave.com), where you can sit in a zero-gravity chair and soak up the health-giving effects of 9 tons of Himalayan rock salt. Or visit the world-renowned spa at Gurney’s (gurneysresorts.com) for a sea mineral scrub and Montauk stone massage. Gurney’s also offers fine dining year-round at Scarpetta Beach, where soulful Italian dishes like lardo-wrapped prawns and short rib agnolotti satisfy as the weather cools. In August, weekday rooms at Hero Beach Club start at $496. In September and October, in contrast, rooms can be scored for as little as $195/night.