Before this past winter, I had never been to the Hamptons. I was deterred by the throngs of New Yorkers who decamp to the south shore’s tony towns for long, sun-filled weekends, by the parking-lot-like traffic on the L.I.E. and by the astronomical rates. But starting in late January, I spent six blissful weeks just outside Amagansett with my dog Charlie. It snowed a lot, which lent a magical, Christmas-morning feel to my sojourn, and crisp, sunny days were filled with treks through the woods, jaunts along barren beaches and walks into town for a cup of coffee. The crab shacks and chowder houses were closed, but many restaurants were still open, catering to the diminished population of locals and seclusion-seekers.
One night, I made my way to Bridgehampton, where Tom Colicchio’s latest endeavor, Topping Rose House, was hosting a wine dinner in the property’s rustic-elegant barn. I sat next to Bedell Cellars winemaker Rich Olsen-Harbich, who talked to me about sustainable viticulture and natural fermentation, and a couple who divided their time between Park Slope and Sag Harbor. The food — a sort of Alsatian-style feast with buttermilk spaetzle, choucroute, brussel sprouts, and a spit-roasted pig — reminded me of my German mother’s cooking. It was the sort of slow evening, I thought, that you might never get to experience in the Hamptons during the crazed summer season.
The most obvious reasons to travel during low or shoulder season are reduced rates and fewer crowds. But, as I discovered this winter, the off season can offer much more than cost savings and shorter lines. Ski towns like Aspen and Deer Valley become havens for hikers and cyclists in the summer months. And traveling to beach towns in the winter can offer both stunning solitude and a unique sense of community. Here are five types of destinations worth traveling to outside peak times.
Where: Ski towns
When: May through October
Why: “Aspen may be known primarily as a ski town, but that underscores its year-round charms,” says Pavia Rosati, the founder and CEO of next-generation travel site Fathom. Off-season activities include biking (Lance Armstrong trains here), hiking and whitewater rafting. “Culturally, the area is in a league of its own,” adds Hugh Templeman, the General Manager of the Viceroy Snowmass. “Unlike many resort towns, Aspen has a historic past that goes well beyond skiing. As a result, organizations like the Aspen Institute provide incredible programming throughout the year, especially in the summer, when the Aspen Ideas Festival takes place.”
Other ski towns offer summer attractions, too: Utah’s Deer Valley has an outdoor concert series at the Snow Park Outdoor Amphitheater, where music acts range from local performers to national acts and the Utah Symphony and Utah Opera host the Deer Valley Music Festival.
What you’ll save: At the upscale Hotel Jerome in downtown Aspen you can save $300 a night compared to high-season rates. A few miles away at the Viceroy Snowmass, summer rates start at around $200 per night (in the winter, a suite will set you back as much as $1,150). In Deer Valley, summer rates are roughly a third of winter rates—and you’ll save even more if you’re willing to visit before Memorial Day or after Labor Day, when rooms go for 25 percent less.
Where: The Caribbean
When: May, June, July and mid-November through mid-December. (The hurricane season starts in June and lasts through November, but you’re most likely to get bad weather in August, September and October. Those are also the months when restaurants, bars and even hotels shutdown.)
Why: The off season in the Caribbean is one big sale, but when to go exactly depends on where you’re going—and personal preference. If you go to St. Barts in May, you generally won’t spy as many A-listers, but you can score serious savings on chic resort wear during Les Soldes (state-regulated sales in France). Rosati loves the islands, Turks and Caicos specifically, in the summer: “The rooms are cheaper, the sun is glorious and the scene isn’t bonkers. Their off season is my only season.” Lyla Gleason, a.k.a. The Globetrotting Mommy, favors mid-November to December. “This is the time right before the high prices of peak season kick in,” she says, “when you'll find fewer crowds, better room availability and good weather. You'll have your pick of beach chairs and airline seats, too.”
In the summer (which is also festival season), hotels are more likely to include extras—from breakfast, Wifi and airport transfers to spa services and free nights. Go to Jamaica in late May/early June for the Calabash Literary Festival or in July for Reggae Sumfest.
What you’ll save: Expect rates to drop by as much as 60 percent from the Christmas-New Years rush. During Reggae Sumfest, you can get a room at the Round Hill Hotel and Villas for about $250; rates in peak season are more than three times as much. In St. Barts, the Christian Liagre-designed Le Sereno offers last-minute rates of around $600/night including transfers and a welcome amenity. For another $40/night, you get a complimentary car rental, daily breakfast, and champagne upon arrival. It’s still not cheap, but considering rack rates in the winter start at over $1,000, it’s a relative bargain.
Where: Domestic destination cities
When: Summer in New York, summer and winter in Vegas, the weeks between major awards ceremonies in L.A.
Why: In the summer, when locals make for the beach, the hills, or the lakes, New York is almost blissfully empty—but not so empty that you’ll miss out on a real Big Apple experience. You can eat at the best restaurants, get tickets to the best performances, take in the views from rooftop terraces, or just hang out in Central Park.
Summers in Las Vegas are brutally hot, but there are plenty of pools and misters for cooling off. Colleen Birch, VP of Revenue Optimization at the Cosmopolitan Las Vegas, prefers the winter: “Mid-December is a great time to visit with cool, sunny days with an average temperature of around 60 degrees. Our guests who visit from cooler climates find the weather warm enough to play golf, walk the Strip — some will even sit by the pool!”
Los Angeles doesn’t really have a down season, though the winter tends to be a bit slower, especially between the Golden Globes, Screen Actors Guild Awards and the Oscars (typically, late January to mid-February) when it’s possible to snag a great room at a reasonable rate.
What you’ll save: Spring into Summer rates, available June through September 2, at the Viceroy New York start at $279. (Rack rates during peak months start at around $499.) In Las Vegas, you can find a room at the Circus Circus for as little as $22 in the summer. At the Cosmopolitan, off-season rates start at around $195. Between awards seasons, rates at The Peninsula Beverly Hills fall from $725 to $575.
When: September through mid-December and January through March
Why: Heat waves and tourist throngs are two good reasons not to go to Europe when everyone else goes (i.e. June through August), when, adds Airfarewatchdog.com founder George Hobica, “air conditioning still isn’t a given on the London Tube.” If you travel during the shoulder season, temperatures are milder, waits for popular attractions are significantly shorter and you’ll get to experience cities in a completely different way. In December, for example, Tuscany’s medieval towns are strung up with tiny white lights for the holiday season. And Venice in the winter has a mystical, romantic feel with locals in fur coats and hats, hazy days and dark nights interrupted by the warmth of cheery trattorias.
What you’ll save: In terms of airfare to Europe, Hobica says, you can save 50 percent to 60 percent compared to peak summer prices until about December 15th and again from January 3rd or so to March 31st.” Hotels also offer deep discounts. A room at the Luna Hotel Baglioni in Venice, for example, starts at around $380 in the winter; in the summer, you’ll pay at least $625.
Where: Beach towns
When: Labor Day to Memorial Day, excluding Christmas and New Year’s
Why: Once school is back in session, destinations like the Hamptons, Cape Cod and coastal Maine go from crowded to quiet—and rates drop dramatically. In the fall and spring, it’s still possible to catch a few summer-like days, but there’s something appealing, too, about snow-lined beaches and nights by the fire. Off season events, like the Martha’s Vineyard Food & Wine Festival (Oct. 16-19) and the wine dinners at Topping Rose House, cater to locals, but are just as fun for out-of-towners.
What you’ll save: Rooms at the Harbor View Hotel on Martha’s Vineyard start at around $109, compared to summer rates of $435 and up. House rentals in the Hamptons, meanwhile, can drop from $20,000 a month during peak season to $2,000 a month in the winter—not to mention the gas money you’ll save by not sitting in traffic for hours.
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