Best of Southhampton: Top 10 affordable activities in the Hamptons

Beaches. Mansions. Yep, you’re in the Hamptons!

Although I grew up on Long Island I never made it all the way east to the Hamptons. As a high school student longing to escape the suburbs for the frenzy of New York City, this posh enclave was not even on my radar.

Known as the summer playground of Hollywood celebs and business tycoons, the Hamptons are a cluster of towns accessible by car, private bus and a lone train line. Located 2.5 hours from Manhattan (by car in optimal traffic), the Hamptons remain a world away. Farms and vineyards line the main highway, ice cream shops and antique stores dominate the village centers, and $30 million homes are a common sight.

While the Hamptons are becoming more accessible to non-billionnaires (the New York Times recently warned of a Jersey Shore-style invasion of drunken youths), it’s still costly to visit the area.

Fortunately, Jake and I were invited by a work colleague to stay in his Southhampton home on a July weekend. Among the tonier Hamptons towns, Southhampton boasts such celebrity residents as Howard Stern and Kelly Ripa, and is particularly closed-off to non-residents. We didn’t spot a single hotel or Jitney bus while driving around town.

Armed with our iPhones and borrowed bicycles, we explored Southhampton’s tree-lined streets and basked on its deserted beaches. This was a surprisingly inexpensive weekend for us since we weren’t paying for a hotel. Restaurant and food prices were on par with ritzier Manhattan establishments, but we sought out bargains and most of our activities were free or low-cost.

Read on for my top 10 activities in the Hamptons.

10. Biking

Biking past $30 million homes in South Hampton #latergram
Our gracious host in Southhampton gave us full access to his beach gear, including two cruiser-style bicycles. We spent our mornings biking to the local beaches, which are technically “public” but in practice are only accessible to residents. Beachside parking requires a permit and there are no public buses to ferry visitors from town. The only way a non-resident can visit a Southhampton public beach is to walk  or ride a bike there.

The town is optimal for biking; there is very little traffic once you leave the main highway. We biked for blocks without seeing anyone on the streets– walkers, runners or other bikers. Locals seem to stay within their gated compounds, which are typically surrounded by 15-foot hedges.

Biking is a great way to check out the mansions and get a feel for the neighborhood. The pace is slow enough to see through the slots in the hedges and get a glimpse at the great lawns, towers and grand driveways of the palatial estates!

9. Ice Cream

Ice Cream in Bridgehampton

Even the lactose intolerant will be craving ice cream during a Hamptons visit. There is no escaping the summer treat, which is sold in every town at upscale gelatorias, old-school ice cream shops and even at the Carvel chain.

After driving past the Candy Kitchen, a 1950s-style diner and ice cream shop, I had to make a u-turn. I savored my scoop of chocolate pretzel ice cream in a wafer cone, especially the tangy taste of what I believe was rum. The quick-melting ice cream was the perfect treat on a 90-degree day!

8. Star Gazing

Southhampton Getaway

Once we had a look at the sprawling estates in our temporary Southhampton neighborhood, we immediately took to Google to find out who actually lived in these behemoths. Some quick celeb-stalking revealed the address of Howard Stern, who has talked on-air about the Southhampton social scene. (A main activity among the jet-set is attending parties at one another’s compounds, which explains why no one is ever on the streets).

We rode our bikes past Howard’s driveway, which is marked “private,” has its own security patrol, and extends so far into the distance that no home is even visible. We had better luck when we biked to the nearest public beach and walked for about 15 minutes on the shore, gazing at the celeb homes in the distance. This stretch of beach was practically deserted, with no life guard present and only a few people sunbathing.

Jake actually saw the “King of All Media”– Howard Stern himself– while he was on a morning jog. Howard and his wife Beth were on a bike ride through the neighborhood. Jake, Beth and Howard exchanged a few suspicious glances, but Jake decided to play it cool instead of asking for a photo.

7. Caffeine Fix

Southhampton Getaway

Looking for a pick-me-up, Jake stumbled on the Hampton Coffee Company, a local chain. He savored their “estate-grown” coffee as I wondered whether this was a play on words. Were the beans grown on a multi-million dollar Southhampton “estate”?

I’ll be honest– I enjoyed sipping tea made from loose herbs (also from the coffee shop), reading a paper version of the New York Times, and smelling fresh flowers as I breakfasted in my host’s garden. After 24 hours in Southhampton, I was growing very accustomed to the lifestyle!

6. Car Spotting


You know you’re in the Hamptons when a guy in khaki shorts and loafers casually parks his Lamborghini in front of the Waldbaum’s on a grocery run. Most drivers opted for Mercedes or BMWs, but we saw a fair number of exotic sports cars in Southhampton. Uniformed guards (or police offers?) directed night-time traffic on Main Street, ensuring that Ferraris did not crash into parked Porsches. This area has the highest ratio of luxury car dealerships to residents that I have ever come across.

5. History Lesson

Montauk Lighthouse Craving some culture, we braved a clogged highway to visit the

Montauk Point Lighthouse. Located at the easternmost point of Long Island, the lighthouse is the oldest in New York State. We arrived in the evening, so skipped the $8 parking fee (only charged until 4pm).

We walked from the parking lot to the beach and started hiking across a rocky ledge that surrounded the lighthouse. It seemed to go on forever and in the absence of any signage, we started to worry it was a dead end. Fortunately, after circumnavigating the lighthouse, the rocky path finally met up with the beach.

This adventure set us back a half hour, so we quickly paid the $9 lighthouse admission fee and lined up to climb the tower before it closed. A sassy older woman in a baseball hat managed the line, only allowing a few people to climb the tower at once. This crowd control was necessary, since the narrow staircase only permitted one-way traffic.

We weren’t allowed to visit the very top of the lighthouse, but we did take in sweeping views from a window near the spire.

4. Wine Tasting

Wine tasting at Duck Walk Vineyards in the Hamptons

While driving on the main drag, Route 27, we spotted a sign for “Hamptons Wine Country.” Eager to sample Long Island wine, we stopped at the Duck Walk Vineyards in Bridgehampton, which charges $8 for a tasting of 5 wines. As a white wine drinker, I was pleased to find several whites among the couple dozen options on the tasting menu.

However, nothing about the Duck Walk experience evoked the glamor of the Hamptons. Numerous hand-written signs are posted on the entrance, reminding us that bathrooms are for “paying customers only” and warning that other wine cannot be brought to the premises. The bartender made as little conversation as possible, reciting the same exact line to every patron who asked, “What’s you most popular wine?”

We weren’t very impressed by the Southhampton White, their signature wine, but at least they gave us a chocolate when we ordered a dessert wine. While Duck Walk did not live up to expectations, we’ll be sure to visit another vineyard on our next trip to the Hamptons.

3. Farm Fresh

Local produce at Hayground Market in Bridgehampton, Long Island

Route 27 is peppered with farm stands selling locally grown produce. We stopped at the Hayground Farmer’s Market, lured by their catchy displays (including a Popeye sculpture and a pink pick-up truck). Hamptons pricing was in full effect, although some veggies seemed quite reasonable (like local green beans for $1.99/lb).

Potatoes, sugar plums and sun flowers were among their colorful merchandise. I bought a pack of homemade scones, which were tasty but quite dry since we didn’t have any butter or jam. (There is surely another market for that).

2. Dining Out

Hamptons Summer Getaway

We realized how reliant we are on Yelp when the spotty 3G and 4G service in the Hamptons left us without the ability to check restaurant reviews on our phones. On our first night in town, we drove up and down Route 27 until we settled on a crowded Italian restaurant with reasonable prices (large pizzas for about $22). The food was mediocre; we soon realized that every 2-dollar sign restaurant in the area was crowded because they were a relative bargain. On our second day, we used our house’s wifi to check Yelp and bookmark restaurants before setting out.

The best food we experienced was actually at the least expensive restaurants, and all offered traditional Mexican fare! The population of the Hamptons seems divided into two categories– wealthy mansion-dwellers and Latino workers– and this is reflected in the diversity of local restaurants.

Based on Yelp reviews, we ordered tacos at La Hacienda in Southhampton (opposite the Waldbaums), which was packed at 3pm on a Saturday. The prices were good and the food tasty; in fact, this meal was the highlight of our stay.

When our host referred to Montauk as a “hipster haven,” we decided to check it out. While no hipsters were in sight, we did come across Spring Break-style revelers. There was no shortage of 20-somethings in club wear, grasping Solo cups and sashaying to outdoor pool parties. Montauk restaurants received rave reviews on Yelp, but we were turned away at several spots due to heavy crowds. We ended up eating at a cute Mexican spot, the Hideaway, on the Harbor. The food was mediocre but the drinks were tasty and it was something of a scene for pre-gaming clubgoers.

If you are interested in spotting celebs, visit the pricey restaurants on the main strip in Southampton. An evening stroll through the area left us constantly turning our heads, wondering “is that person famous or do they just look ridiculously wealthy?”

1. The Beach

Flying Point Beach Southhampton

The beach was our favorite attraction in the Hamptons. It’s extremely rare to find beaches this empty so close to New York City. Accustomed to blanket-to-blanket crowds on Jones Beach, Jacob Riis and Long Beach, the amount of wide open space in the Hamptons was refreshing.

Unlike most New Yorkers, Hamptons beach-goers appear incredibly trusting. When we arrived at Flying Point Beach, we were the only ones to lock our bikes to the rack and were surprised to find a collection of shoes at the beach entrance. Incredibly, these beach-goers actually leave their possessions out of eyesight!

Reminiscent of our trip to Turks and Caicos, the women at Flying Point Beach in Southhampton were almost all MILFs. Six packs and blond hair seemed to go hand-in-hand with trios of bronzed children.

The surf was a bit rough for me but Jake enjoyed diving into the high waves. As with all Long Island beaches, the water was chilly but felt refreshing on a warm day. We felt comfortable leaving our blanket (after all, we probably had less valuable possessions than 90% of the beach visitors) and strolling down the beach.

We passed a photo shoot featuring Naomi Watts with wet hair in an evening gown (I didn’t recognize her until Jake gave me a nudge) and shared opinions about the architectural merits of the multi-million dollar beach homes.

The Bottom Line

If you can afford a hotel or house share in the Hamptons or luck into housesitting (like we did), then go for it! The vibe in Southhampton was laid-back, relaxing and opulent. Once you are in the area, it’s easy to keep expenses down by opting for inexpensive restaurants, visiting low-cost attractions like the Montauk Lighthouse, and spending your days on the public beaches.

What’s your favorite Hamptons activity?

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About Leslie Koch

I'm a New Yorker with a passion for travel and art. I founded after returning from a year-long backpacking trip around the world. Find me on Twitter at @leslietravel.