Story 25 | Summer Getaways | The Hamptons: Broke-Bitch Weekend
Steal away to the Hamptons with your unpredictable bestie, maybe (very) loosely based on @wishbonekitchen... Plus, our first giveaway!
To set the tone for this story, I looked back at pictures from my September 2019 long weekend in Montauk and Sag Harbor with my cousin Allison, and I have to say, we did it right. I would love to head back!
If you’re also wishing for a Hamptons escape, I hope today’s story transports you.
And after the story, learn how to enter to win a copy of Annabel Monaghan’s newest title and newly crowned NYT bestseller, “It’s A Love Story.”
Happy travels!
The Hamptons: Broke-Bitch Weekend
“You know you’re old when what you want to do on vacation is look at real estate,” I huffed over the handlebars of my cream beach cruiser bicycle.
“Don’t be a little bitch. This is cultural! The fact that you called it real estate and not houses means you’re just as here for it as I am,” my bestie Meredith shouted back at me, always a few yards ahead of me, likely to keep me from stopping. “Also, I’m waiting for you to tell me I was right about the bikes, too.”
She was right about the bikes. If you’re going to peep at real estate, driving doesn’t leave you the option to linger, and walking is too strenuous and slow, she had explained. But biking, biking is breezy and perfectly paced.
It was June in the Hamptons, and we were winding our way through the tony streets of Amagansett, ogling primly relaxed shingle-style and colonial-revival mansions (per Google) and positing what estates lay down the occasional long drives that slipped out of sight. The sun was high but thankfully mild, and the shade was delicious thanks to bushy, full trees swaying overhead, so our bike excursion was more elegance than exercise.
I had flown in from Atlanta; she had jitneyed from Manhattan, for our annual “broke-bitch weekend,” started when we graduated college and had no money. Meredith had declared we were entitled to a fabulous vacation, and it was all possible if we got creative. A decade later, we’re a bit better off, but we maintain the tradition of the trip.
If I had to explain the inner workings of our trip to someone else (God forbid), it’s important to note that “broke bitch” is relative. No, we would never own one of these estates, nor could we participate in a summer share, but we could still splurge out on a modest hotel, the sunset lobster cobb salad at Duryea’s, and lunch at Carissa’s Bakery, even dining next to Ina as luck would have it.
It was Meredith who always added the razzle dazzle that made our trips so memorable. She could make anything fun, budget be damned.
And that is how we came to be cycling through the Hamptons dressed as off-duty princesses flying under the radar.
Now, it was true that I was thoroughly enjoying our real estate venture, but I was feeling a touch self-conscious in my strapless white seersucker dress, ballet flats and a Breton-stripe sweater hugging my shoulders. Meredith sported a more gamine look, in a fitted vest and matching cigarette pants, with an old-money blowout for contrast. She surveyed our looks before we went out, saying we pretty much nailed the precious end of quiet luxury, as would royalty of a lesser country – except with, like, a lot less money. I vacillated between feeling like a caricature and feeling appropriately dressed for the occasion.
I could tell we were approaching the coast, because the homes started getting further and further apart and the tree cover thinned. There was less activity here, privacy melding right into quiet. Sandy banks of wild grasses and plentiful hydrangeas dotted the thick lawns. These were not your average hydrangeas, these were manicured, magnificent hydrangeas, specific varietals selected for their architecture or complementary tones for the estate’s design esthetic.
“Do you hear that?” Meredith called back to me, as she picked up speed on her bike.
Now that she mentioned it, I did hear a little murmur of something. There were also more cars passing us, all in one direction. Nice cars.
Rounding the bend in the road, we could see the source of the commotion: a short line of cars leading to a valet station before an impressive iron gate nestled in a long row of hedges.
Meredith hopped off and started walking her bike. I instinctively did the same.
“Just follow my lead,” she whispered to me.
“Meredith…” I said, the edge of warning in my voice clear, though I knew she wouldn’t listen.
With a confident shake of her hair, my bestie strode right up to the valet and offered her bike to the first gent she encountered.
“Do you mind taking these?” she asked, the bike already in his hands. “We decided to bike over since we’re just a few blocks off. I hope we’re not too late! Did it start yet?”
I knew she was full of shit, but you could tell the valet didn’t know what hit him. I also handed him my bike; she said to follow her lead.
“You have plenty of time. The auction’s not due to begin for another 45 minutes, and the performance will follow,” he shared, juggling the bikes. “I’ll find somewhere for these.”
Meredith thanked him cheerfully and kept right on moving before anyone could catch on, snaking her arm through mine to walk us through the iron and gates and onto a shaded stone drive, lined with nautical flags to indicate where guests were to head. The house wasn’t even in sight yet. Of course, my friend had waltzed us right into a private event we most definitely weren’t invited to. But how long could she keep us out of trouble?
Ten minutes later, Meredith clinked her champagne glass with mine.
“Aren’t you glad we were dressed up?” she asked rhetorically, her eyes roving over the sights before us.
We stood on a sprawling back patio, a stately white colonial manse rising behind us, a long, turquoise pool off to the right, and ahead, a lush, never-ending lawn rolling out to the beach a couple hundred yards out.
We had deduced we were at some sort of arts benefit, what with the trio of modern art sculptures gracing the lawn and drawing a fair bit of attention from this crowd I would have guessed had surely seen it all. I swear one piece was a Jeff Koons but tried to keep my gaping to a minimum in an effort to blend in.
Which shouldn’t be too hard, given there were hundreds of impeccably dressed guests, chatting and milling about between the patio, seating areas throughout the lawn and the home, a double-height living room open to the festivities. A DJ played an energetic set next to an unplayed piano, clearly part of the forthcoming performance.
I was dying to go inside to check out the interiors and maybe discretely Zillow this place, but I had a more urgent need: Meredith had disappeared. She had just been by my side, sipping on expensive champagne but I had gotten lost in the people-watching and had momentarily lost track of who I should have been keeping an eye on. She had pulled this before, with unpredictable results.
A tray of mini lobster rolls delayed me from my mission another minute, but with the individual squirt of butter and squeeze of lemon, the appetizer had to be sampled.
As I polished off the decadent bite, a young JFK-Jr. type approached, all thick dark hair and entirely too relaxed looking, given he was in a full linen suit and knit tie.
“Countess, welcome. What province of Italy do you preside over again?”
Countess? Cool! Who could that be? I glanced around me to see who he was speaking to and turned back to find him looking squarely at me.
“Meredith!”
Next Stop
What do you think: should we see our JFK-Jr. type again, in another locale?
Summer Getaways Giveaway
One of my sweet friends surprised me with a copy of
’s latest, “It’s A Love Story,” so I’m feeling inspired to pay the kindness forward.Enter to win your own copy of “It’s A Love Story” by sharing today’s post and inviting your friends to read Plot Twists Summer Getaways.
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A giveaway! Thank you so much Elisabeth