The Hamptons has a reputation for being an exclusive enclave for the rich and/or famous — and it is. However, there are also plenty of people who don't fit into either of those categories who manage to get the most out of summer on the East End of Long Island. It’s not necessarily about who you know but more about what you know. So here are 10 insider tips for how to get your own piece of the Hamptons pie this summer.
1. When to Go
Two words: Off Peak. Traveling from the New York City/Tri-State area to the Hamptons and back again for the weekend can be a nightmare if you’re not as strategic as a Navy SEAL. Leaving Thursday night is optimal. Friday morning is doable as long as you’re on the road by noon. Otherwise, wait until at least 7 pm Friday night. On the flip side, leaving the beach on Sunday morning is too depressing unless it’s going to be pouring all day, but do it if you must guarantee your return time. Otherwise enjoy the day and then have an early bite and hit the road at 8 pm. Or hightail it out before dawn on Monday morning. Painful but worth the extra night.
2. How To Go
Take a helicopter service. Kidding! Do the environment — and your wallet — a favor and take public transportation. The bus services Hampton Jitney, Hampton Ambassador, and Hampton Luxury Liner have multiple departures both ways during the season. Or take the Long Island Railroad, which is the train out of Penn Station. The Cannonball is the “express” train to the Hamptons on Friday afternoons. It can be standing room-only during July and August, but it’s usually the fastest way out east (notwithstanding a helicopter or private jet).
3. Getting Around
On a summer weekend, forget Route 27, the main thoroughfare connecting all of the towns and villages of the Hamptons. Instead, take the side roads. They may be a little longer in distance and have slower speed limits in places but they will save time and frustration when 27 is jammed. Pro Tip: Don’t use GPS to navigate because it will keep sending you back to 27. Look at the map and plot out your route in advance — you may have to go a little north to go south.
4. Beach Parking
There aren’t too many “public” ocean beaches in the Hamptons. Most beach parking lots are run by the towns and villages and require seasonal resident parking passes. A usually limited number of non-resident parking passes are available but they’re expensive, since they cover the entire season (and it’s the Hamptons). A few beaches offer paid daily parking during the week. Some towns have free shuttle service from the center of town on weekends. Check the Southampton or East Village Town websites for more information.
5. Off the Beaten Path
Even if you have a parking pass, on peak weekends, parking can be tight at the ocean beaches. But there are plenty of bay beaches to visit that are just as picturesque and are great for little kids because there are small or no waves. The Hamptons also has numerous nature preserves and miles of hiking and biking paths that lead to stunning vistas. Just be sure to wear tick repellent and cover up to protect yourself from tick bites, which can sometimes lead to Lyme disease.
6. The Early Bird Catches the Good Coffee
The one way to stay out of the fray is to get up and out early to do things like go food shopping, go out for breakfast or get coffee. The towns are quiet(er) even on weekend mornings and there’s nothing lovelier than grabbing a coffee and a newspaper (or your Instagram feed on your phone if you must) and perching on one of the many benches lining the Main Street of whatever town you’re in and watching it come to life.
There are many decent if not good restaurants in the Hamptons, but getting into any of them on the weekends can be a challenge. During the week, even Sunday nights, can be a much more chill time to dine out. The weekends, however, were made for grilling and dining al fresco. Skip the supermarkets and head to the many farm stands, farmer’s markets, and local fish stores to procure delicious local ingredients, including amazing homemade pies. A bottle or two of local rosé and you’re good to go.
8. Free Events and Activities
Yes, some things are for free — even in the Hamptons. Check local free weekly newspapers and the free glossy magazines for listings of everything from free fitness classes to shopping events to art openings to live music. Some places host free outdoor movies (check out Marders Nursery in Bridgehampton and the Square in Amagansett). Wölffer Estate Vineyard has sunset events Thursdays through Saturdays, some of which are family friendly. The Parrish Art Museum in Watermill has a number of outdoor music and art events that are free with the $10 museum admission (so maybe not technically free but a good deal nonetheless!).
This is one of those “proceed at your own risk” categories. The summer calendar is packed with day and evening events of all kinds. Most are elaborate fundraisers for good causes with steep ticket prices and some are private parties hosted by public figures. Getting in if you weren’t “on the list” used to be a somewhat easier proposition before RSVP lists moved from paper to tablets. These days, you can’t assume that just because your friend was invited that her five besties could be her plus ones. If you really want to get into one of these over-the-top soirees, budget accordingly so you can buy a ticket for the one or two good causes you support or offer to volunteer during the event.
While some treat a weekend in the Hamptons like an Ironman event, running from one social engagement to the next, your time “out east” doesn’t have to be an endurance event. The Hamptons, while they can be crowded, are simply beautiful. So don’t forget to take some time to enjoy that beauty. Go for a bike ride. Rent a sailboat. Go for a walk along a remote beach. Get ice cream and wander up and down Main Street. Watch the sunset with a bottle of wine and good friends. You’ll be glad you did — especially if it takes fives hours to drive back to the city.
Go back to The Hamptons for one more summer with the final season of Royal Pains on USA Network, Wednesdays at And Like Jet Set on Facebook to stay connected to our daily travel updates.
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