The many and various pleasures of the Hamptons scene in the summer are no secret. Anyone who’s taken the Long Island Expressway on a Friday afternoon in the summer knows that the Hamptons are a magnet for many.
Hop on a Hampton Jitney bus or LIRR train and you’ll find yourself crammed in with young, beautiful people (many still in their business attire), armed with their iPads, overnight bags and hopeful expressions, all eager to get to the pristine beaches, the farmstands, and the vibrant nightlife.
In the early 2000’s, people started coming to the Hamptons well beyond the summer season. However, the financial crisis of 2008 caused the season to revert to a three-month Memorial Day to Labor Day window of time. Which is a shame, because the area is beautiful to visit in spring and autumn.
Some argue that it’s even more appealing in the off-season because the crowds are absent and the restaurants are glad to see you. Also, don’t discount the advantages of being able to park without risking a heated encounter with another frustrated driver. Or being able to drive from Southampton to Montauk on Route 27 without resorting to the convoluted map of the back roads because traffic is bumper-to-bumper.
So here are some of my favorite things to do both during the summer season and before/after:
A Boat Ride from Sag Harbor to Ram’s Head Inn, Shelter Island
If you’re lucky enough to own a boat or, second best, have an obliging friend who owns a boat, taking a ride from Sag Harbor to the dock of the Ram’s Head Inn is a summer treat. Being out on the water is refreshing and exhilarating, even for this short ride.
There’s the different perspective afforded by looking back from the water towards the town. And there’s the feeling of being part of a summer fantasy of beautiful people doing glamorous things without the bother of wearing jewellery or high heels (although you can if you want to).
Upon arrival at the dock, walk up the broad lawn towards the verandah of the hotel, and have lunch or dinner at the tables set with flowers and candles. The food is smashing, and the view from the verandah seems more Newport or Nantucket than the Hamptons. Sigh…
The Longhouse Reserve, East Hampton
This 12-acre property is owned by Jack Lenore Larson – a big-name textile designer back in the day – who built himself a Japanese-style long house on the property along with a large and lovely lily pond. The grounds are covered in an extraordinary range of exotic trees and flowers that reflect the changing seasons – a big favorite is the Red Garden which comes into bloom sometime in May and features trees, flowers and antique statuary in varying shades of red. The entrance to the property features a large Chinese bell with a wooden mallet that you can bang away with to let the world know you have arrived.
The grounds include some perennial art works such as a deKooning sculpture, a non-competitive Yoko Ono chess set (you have to see it to understand, which is typical Y-O) and each year a new influx of works from artists from around the world but with a focus on the oriental. My favorite treat is to visit during the week when there are fewer visitors and plonk myself down under a tree on an ancient carved bench with a really good book – bliss!!!
The Beach
Yes, I know – hardly a revelation!! But I’m not talking about the summer beach which, to my mind, is overheated in more than one sense – crowded, noisy, hot and always makes me think of the movie “Suddenly Last Summer.” The summer beach is all about the people on the beach – not that there’s anything wrong with that! But I am talking about the beach in late September through April, when the people are mostly gone, and when long, solitary walks have only the sound track of birds, waves and your own heavy breathing.
The off-season beach is about the beach, not about the people on it, although you may run into a few determined joggers and the occasional muffled-up dog walker. The off-season beach is about the breathtaking glory of sunrise and sunset, uninterrupted by distractions; the smell of the ocean; the cold winter sun blazing off the ice-coated beach grass, turning it into a field of Swarovski crystals any diva would lust for. The off-season beach is mystical, especially on a foggy day when people silently appear and disappear in the mist.
The summer beach makes people think about tanning and what’s for lunch and who is that cute guy/gal over there. The off-season beach makes you think about the bigger existential questions – who am I and why am I here… That’s my beach!
Villa Italian Specialties, East Hampton
At first glance, this looks much like any other Italian deli with its trays of artichoke hearts, peppers, racks of pasta and olive oils, etc. But the nectar of the gods lies in the sandwiches prepared on warm focaccia, filled with fresh grilled chicken, pesto, peppers, home-made mozzarella and some kind of secret dressing that is orgasmically delicious.
Based on the premise that all delicious things are either immoral, illegal or fattening, I have to assume these sandwiches can inflict some kind of irreparable harm on those who consume them, but they are too good for that to matter. “Life is short,” I justify to myself as I sink my teeth in.
The best treat of all is to eat one of these sandwiches at the beach, and then walk it off. Or, on an escalating scale of happiness, you can share the sandwich (and some of the guilt and avoirdupois) with a loving friend and then walk on the beach hand in hand. The ‘Villa Tiramisu’ is pretty fab too, but that’s only for when I feel completely reckless about my waistline and my arteries.
The Lighthouse Swing
Yes, everyone knows about the lighthouse at Montauk and it is a wonder to behold. But if you search down one of the paths that wind from the lighthouse to the beach you may find a wide wooden swing (big enough for two) that positively demands you leave your adult self behind and kick your heels up in the air while gazing at the ocean that stretches away to the good old UK and our former colonial rulers.
So, what are you waiting for? Share your own Hamptons favorites with us below, in the comments!
I see alot of hotels around here but very few restaurants with options that vary. I’m very picky about food and this makes me sad.
My friends and I were planning to go here on a peak season because we wanted to meet a lot of people along the way, but we were seriously surprised at how the hotels are so expensive so we had to double up our budget and move the dates just a bit. But what really surprised us was that when we tried checking the rates again on an off-peak season, the prices were nearly slashed half! It’s crazy. We decided to just manage our expectations and just choose the half priced hotels than force ourselves to dish out more money for just a few days stay. We knew we could enjoy our vacation more when we had doubled up budget but with a cheaper hotel. We could always spend more on other things such as food and drinks!
My main problem about the Hamptons is that there aren’t many vegan options to dine in. I don’t want to not enjoy my vacation because I’m starving.
I was looking into The Sag Harbor because the houses look great and interesting. It’s also close to the village which is nice. But the problem here is that there are no weekly prices listed so I’m a little scared that we might end up getting ripped off for high prices.
The reason why there are no weekly prices is because the prices change a lot depending on the season! You can always ask them.
My favorite beach here is the Flying Point Beach in Southampton. There’s just something about it that I like better than the rest of the beaches, but my friends say that you’ll enjoy all the beaches just like any other in the Hamptons. I really enjoyed the wine tasting in the Channing Daughters too. Too bad it was too cold in the stone terrace when we visited and it would have been perfect to be sipping wine there. I was told that they are booked almost all the time because of special events so I highly suggest that you plan ahead of time if you wanna go here. I guess we just got lucky that one event was canceled so we managed to get a slot.
It’s not recommended to go to certain places without early bookings. But if you love that thrill, it’s worth it.
Villa Tiramisu already sounds so sinful. But just by the sound of it it’s delicious!
I’m currently checking out te Hamptons. Maybe sometime mid-April we’ll go here with a couple of friends.
Just a warning to those planning to go here on busy months such as Memorial Day through Labor Day, or any other peak season– the traffic here is bad. ☹️ It’s a go-to place for the rich and the famous people of NY (aka celebrities). Traffic can become really bad and restaurant reservations are so hard to book. The crowd doesn’t make it any easier to enjoy your “vacation” either. If you’re planning to go here on such a busy month, prepare for a New York-hectic vacation rather than a relaxing beach vacation. It can be the opposite off-season though, probably around September through May. So make sure you plan your vacation ahead of time to avoid the rush. I still enjoyed this place the second time around.?
The problem with going there on September is that you can’t swim on the beaches.
Celebrities go here a lot and I really want to see stars walking around like they’re just regular people! I’ll probably get so starstrucked!
I heard so much about the dressings being sold in Villa Italian. I’m planning to hoard because I love salads with different dressings.