48 hours in The Hamptons without breaking the bank

Mentioning The Hamptons conjures up a strong association for most people… New York’s summer playground, the watermelon incident in SATC, a couple of Kardashians… All of which are tied together with a big bow of glamour. Of which I am a fan. The Hamptons is notoriously pricey but going just off season, right before many establishments close and the weather is still luscious, can make all the difference…

Mentioning The Hamptons conjures up a strong association for most people… New York’s summer playground, the watermelon incident in SATC, a couple of Kardashians… All of which are tied together with a big bow of glamour. Of which I am a fan. Plus – this Concierge, living in landlocked Ethiopia, was craving the beach and some excellent seafood. So when Concierge Hubby began planning a special 30th birthday trip for me Stateside, a few days in The Hamptons just had to be on the agenda.

The Hamptons is notoriously pricey but going just off season, right before many establishments close and the weather is still luscious, can make all the difference. We hired a car from JFK (Nomads, watch out for deals with air miles as many car hires are associated with airline alliances) and set off in the opposite direction to NYC, right to the end of Long Island. We chose Montauk as our destination – the grounded sibling of the Hamptons family. On our way, we drove through village after village with pretty ship-lap homes and the manicured high streets. There were even windmills, Nomads! From the get-go, this was entirely what this Concierge had hoped for.

Our dinner stop was Springs Tavern, which combined the feel of a down to earth diner with stylish Hamptons furnishings (I see you, ceiling fan, wooden floor and warm grey hues). Locals lined the bar, whilst relaxed groups of sun-seekers occupied the restaurant and we filled our boots with an excellent burger, mac ‘n cheese and a craft beer that slid down very easily. Hello ‘Merica!

Our hotel was an inspired choice by Concierge Hubby, the Hero Beach Club. This was Boutique with a Capital B; art scattered throughout the hotel and grounds, branding to die for, an iPad in the room to connect you with reception, local rose on tap in the bar, swing chairs on the porch, pool furniture from Bali… Our veranda looked out directly over the sea with an enticing beach just feet away. No white noise machine needed for a deep sleep when the waves are that close!

Room in the Hero Beach Club Montauk

After a restful night, our morning began with a swim in the beautiful pool, a stroll down said beach, and a veer off course in the direction of coffee and pastries. Left Hand Coffee provides excellent caffeination – drip coffee, a multitude of single blends… These people know coffee. The pastry was a secondary event but hit the spot. It’s definitely a solid Montauk option for a grab-n-go breakfast.

Beach and sea outside the Hero Beach Club Montauk

After a wander through Montauk, we headed on to our lunch spot (a day revolving around food = a good day), the incredible Clam Bar. It feels exactly like being on Diners, Drive-ins and Dives, as you pull up to the high-class shack on the side of the highway and park up on chucky stones. This is where one of the Hamptons’ most loved Lobster Rolls can be found and, therefore by default, me. This roll was so stuffed full of lobster, it overflowed and was totally fresh. Concierge Hubby had heard that sometimes the lobster has literally been on the seafloor hours before. The bun was light, sweet and fluffy. I was in Seafood Heaven, Nomads! Add to that a glass of local white and this was one happy Concierge.

Lobster roll from the Clam Bar on the Montauk Highway

Post-lunch, there was a definite need to walk off the lobster and so we headed into East Hampton and then Sag Harbor to peruse the shops and dream of living the other side of one of those white picket fences. J-Crew, Brandi Melville and a Maple Pecan Frappuccino (FINALLY) were excellent features of the wandering. Not to mention getting up close and personal with one of the aforementioned windmills! We soon scooted off for the next item on our Hamptons agenda – wine tasting! At the Wolffer Estate, there’s no long tour with a blow-by-blow account of how every grape was smushed – it’s all about the tasting. We ordered a flight of wine and set about testing Wolffer’s best offerings. As you try, you sit on a sunny patio with the vineyards and blue skies right in front of you. It’s a perfect afternoon. The sharing platters looked very tempting were it not for the amount of lobster already consumed and the prospect of a fancy dinner in a few short hours. There’s a shop inside to purchase anything you’ve particularly enjoyed (alongside a range of ciders and a gin!) but refreshingly, we happened upon it by chance! There was not a single sales pitch, nevermind the reminders ad nauseam that can be part and parcel of a wine tasting. We returned to the hotel thoroughly relaxed.

A flight of wine to taste at the Wollfer Estate in the Hamptons

We headed up to the North Shore to find a perfect spot for sunset. A few of our potentials were closed for the season but we found the wonderful Montauket, a pub full of character (and people) with a great buzz and good beer & wine for sunset-watching. The North shore of the island is where to catch the sunset from and it was breath-taking. Just see for yourself…

Sunset from the Montauket in Montauk

We moved on for dinner at Scarpetta Beach, set inside the luxurious Gurney’s Resort that oozed elegance and Hamptons charm. This is perhaps the part of the post that (despite the title) could break the bank, Nomads, but it was the day of my 30th Birthday and Concierge Husband is very good to me. The lighting was low and romantic, the tables were spaced and intimate, the food was beautiful and refined. As we waited for a taxi to collect us, we sat under blankets at the most well-appointed fire pit I’ve ever seen and floated away home happy, happy, happy.

Hero Beach Club Montauk's smiley face

Waking up to the lapping of the sea, we set off for a healthy breakfast at Naturally Good Foods, with all the superfoods and wondergrains your heart could desire. From there, it was finally time to explore Montauk’s lighthouse *over excited squeal due to girlish love of lighthouses*. The light house is right at the end of Long Island (an area innovatively named called The End) and set in an area filled with nature and protected reserves. We strolled on the beach before clambering up the rocks and lapping the light house.

Montauk Lighthouse

It was time for us to start making our way back to JFK to get a shuttle into the city but we took our sweet time about it. We stopped off at Vicki’s Veggies, a picture perfect stall in Amagansett for some farm-fresh fruit for the road and then perused the town and did a little more shopping. We headed to The Village Gourmet Cheese Shoppe and sat people watching in Southampton with incredible soups, salads and cheese. And we once again lusted after all the beautiful homes and houses of the Hamptons’ villages.

Pretty street with movie theater in East Hampton

We reached New York easily after dropping off the hire car and completely relaxed after a perfect Birthday retreat in The Hamptons. Try it out, Nomads!


10am – Stroll on the beach and coffee & pastries at Left Hand Coffee

11am – Walk through Montauk

12pm – The Hamptons’ best lobster rolls at the Clam Bar

1.30pm – A wander through East Hampton and Sag Harbor, checking out the marina & the windmill

3.30pm – Wine tasting at the Wolffer Estate

5.45pm – Sunset at a North Coast pub like the Montauket

7.30pm – Dinner at Scarpetta Beach, Gurney’s Resort


10am – Healthy breakfast at Naturally Good Foods

11am – Discovering the Montauk Lighthouse and some of the surrounding trails

12pm – Explore Amagansett and stock up on fruit snacks at Vicki’s Veggies

1pm – Lunch at the Village Gourmet Cheese Shoppe

2pm – Explore Southampton and then on to JFK

Windmill in Sag Harbor, The Hamptons