I Took A Celebrity-Inspired Day Trip To The Hamptons

For me, it’s never exactly been easy to get to the Hamptons. The jitney makes me car sick, the fight to get on the LIRR train is a pain, and I’m too terrified of heights (and budget-conscious) to ever even consider a Blade helicopter. All that to say, I don’t venture out east often — and when I do, I usually arrive looking crumpled, and dealing with nausea or a headache.

Blacklane’s new City-to-Vineyard service is a welcome change. The company is now offering luxurious chauffeured rides between major cities (including Boston, San Francisco, and even London) and nearby wineries. The rate varies, depending on what service you choose, but ranges between $100 to $200 each way — it’s comparable to the price of a luxury bus, which I once spotted Sarah Jessica Parker waiting for — but it’s completely private.

To experience the new City-to-Vineyard route myself, my friend and I took a day trip from my apartment in New York to one of the Hamptons’ most famous vineyards, Wölffer Estate Vineyard in Sagaponack, NY. Along the way, we stopped at some other celebrity-favorite Hamptons spots, including Carissa’s Bakery and Round Swamp Farm. Here’s a full play-by-play of our celeb-inspired Hamptons itinerary.

Stop 1: Carissa’s Bakery

Our driver for the day arrived 15 minutes ahead of schedule at 8:45 a.m., but the timing was perfect for a Saturday morning drive out of the city to Long Island. The drive was smooth and quick — we lucked out and missed most of the traffic — so we arrived at Carissa’s Bakery in Sag Harbor by 11:00 a.m.

I’ve loved this bakery ever since I first came to the Hamptons and heard (unverified) rumors that the rich and famous loved the sourdough bread so much, they’d get it sent to them back in Manhattan via jitney. I don’t know if that’s true, but I can verify that the bread tastes good enough to deserve that level of dedication. I’m not alone — it’s also one of Ina Garten’s favorites. Plus, Stanley Tucci and Justin Bieber are rumored to be frequent customers.

When we arrived, our driver dropped us off right in front of the shop, which wasn’t too crowded for mid-morning on a Saturday. We already had our coffee for the day, so skipped that line, but did make sure to buy the famous sourdough bread (which served as the base for 90% of my meals for the rest of that week).

Stop 2: Wölffer Estate Vineyard

The next stop on our tour was Wölffer Estate Vineyard, 10 minutes away in Sagaponack. Rolling up to the vineyard, it looked like it belonged in the European countryside. A bubbling fountain, rows of grape plants, and flower-filled planters greeted us.

After a quick walk through the building and gift shop, we were led to a vine-covered patio with an up-close-and-personal view of the fields. There, our tour guide, Fairley, gave us a whole lesson of wine-making and the history of Wölffer. Plus, she poured us several glasses to try. (All were delicious; even the Chardonnay was good, and I’ve never been a fan.)

Over the course of the two-hour tour, we got a chance to walk through the vines, the tanks used for fermenting, and the cellar filled with wine barrels etched with celebrity autographs. Paris Hilton, A$AP Rocky, and Rihanna all left their signatures. Rihanna’s note might have been the most iconic: “Thanks for getting me drunk!!”

A few more glasses (and lessons from Fairley) later, we headed up to the store and picked up a few bottles to take home.

The tour ran a little late, so I texted our driver to let him know our timing. He was ready to go when we were, and we headed to our last stop of the day: Round Swamp Farm.

Stop 3: Round Swamp Farm

Our final stop of the day was Round Swamp Farm, which is one of the most popular celebrity spots in the Hamptons. Former Real Housewives of New York star Bethenny Frankel is a long-time fan of the farm stand, along with celebs like Gwyneth Paltrow and Hailey and Justin Bieber. (Influencers like Tinx and Halley Kate are also big fans.)

There’s a reason for the popularity. The fresh food market offers a selection of produce and prepared meals for a hefty price tag. The chicken fingers are $25 — and yes, I bought them. I also splurged on a bag of homemade sea salt caramel chocolate chip cookies, which cost about $12 for six cookies. (Technically, though, I basically saved money by *not* buying the $18 guacamole — girl math.)

From Round Swamp, we hit the road with our (overpriced but delicious) snacks in tow. A day well spent.