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5 Reasons an Off-Season Vacation Is the Ultimate Hack for Travelers Looking to Recharge

Save time, money and sanity by visiting tony East Hampton over the winter.
5 Reasons an Off-Season Vacation Is the Ultimate Hack for Travelers Looking to Recharge
Image credit: MikeRega | Getty Images
Entrepreneur Staff
Special Projects Director
4 min read

Spending time at a hotel during the off season doesn’t need to be like a scene out of The Shining. In fact, if you can home in on the right destination, off-season travel can be some of the most fun, rewarding and -- yes -- cost-effective vacationing you can do. Plan your trip right, and you’ll be able to gain access to hotels, restaurants and events that are too crowded (or expensive) during the tourist-swarmed high season.

Related: 21 Ways to Get Inspired (Infographic)

Over the winter, Long Island’s East Hampton -- home to celebrities like Steven Spielberg, Jerry Seinfeld and Martha Stewart -- is chock full of activities for budget-minded travelers looking to unwind. Besides possessing some of the most gorgeous beaches on the east coast, the swanky town is packed with all the arts, shopping, eating and drinking the savvy vacationer could want.

Here are five reasons an off-season trip to the Hamptons is the perfect way to recharge.

1. Killer accommodations

A quick scan of booking.com or Airbnb will demonstrate the obvious: It’s way cheaper to find a place to stay in East Hampton over the winter. We suggest checking out Journey East Hampton, which maintains the hip and sophisticated spirit of the Hamptons without the stratospheric cost.

Image credit: Journey East Hampton

All the rooms feature a cozy lounge area, ultra-modern bathrooms and an insanely comfortable bed courtesy of Serta Simmons’ Tomorrow Sleep mattress. Guests can enjoy craft cocktails in the lobby bar or step outside by the bonfire and warm up with s’mores. You can’t do that over the summer. (Well, you can -- but people might look at you funny.)

2. Easy travel

Unless you’ve been stuck in bumper-to-bumper traffic for hours on end on 27 East, it’s almost impossible to comprehend the agony of driving out east during the summer months. But get this: Not only is the one-shot route to the Hamptons mostly clear in the off-season; but once you arrive, the town’s country roads -- usually backed up with beach-goers -- are incredibly fun to wind through. If you’re the type who finds spirited driving a Zen-like activity, East Hampton’s windy roads can be your nirvana. In fact, in her book, DrivetimeProfessor Lynne Pearce, of Lancaster University notes that driving can "positively direct and structure thought."

Related: 3 Important Changes That Can Save Yourself From Burnout

3. Unique activities

As one of the hottest travel destinations on the East Coast, East Hampton in the high season can be a touristy mess. While certain activities are off limits over the winter (now is not the time to take those surfing lessons), there’s still lots to do on the chilliest of days.

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 

A post shared by Wölffer Estate Vineyard (@wolfferwine) on

Ice skating at Buckskill Winter Club, cider tastings at Wolffer Estates and special screenings of live theater from the Metropolitan Opera at GuildHall are all totally worthy daytime options from December through February.

4. Trendy restaurants

Try to make a reservation at locals-only Italian favorite Nick & Toni’s during the summer, and you’ll be lucky if you can sit after 4 or before 11. During the off-season, however, you can rub elbows with some of the town’s biggest names. (Alec Baldwin is a regular.) Typical waits at Bostwick's Chowder House, a casual, locals-approved seafood spot, can be well over an hour from May through August. We much prefer walking right in and scoring one of their legendary lobster rolls immediately, thank you very much.

Related: 11 Habits of Truly Happy People

5. Natural beauty

Fighting for towel space on one of the Hamptons’ iconic beaches is hardly a calming experience. But a brisk, centering, off-season morning stroll on Indian Wells Beach or Atlantic Avenue -- both open during the winter and blissfully uncrowded -- is just the opposite, and sure to recharge your creative spirit. Science backs this up as well; in his research on the psychological and cognitive effects of the outdoors, neuroscientist David Strayer has found that time in nature enhances higher-order thinking, restores attention and boosts creativity. For even more inspiration, visit the 16-acre garden at LongHouse Reserve with sculptures by acclaimed architect Buckminster Fuller. It's the ideal place for smartphone-addicted cubicle dwellers to unplug, unwind and invigorate.

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