Call me a snob all you want, but there’s no denying it: I’m a Southampton girl. And summertime for me means half-day summer Fridays, which presents the perfect opportunity to leave the hot, crowded city and head to my mecca of relaxation.
For newcomers to the Hamptons, it can be overwhelming. There’s East Hampton, Southampton, West Hampton, Bridgehampton, Sag Harbor, and Montauk all within a relatively short range of one another. So where do you start? Let’s break it down. Here’s an ultimate guide to my favorite little Long Island town, Southampton.
Before you start packing your bag, where are you going to stay?
Having a friend or family member with a house in Southampton would probably be the most ideal situation, but of course it isn’t always that easy. I’ve walked by some of the cutest bed and breakfast inns that Southampton is known for. I recommend A Butler’s Manor: there’s a pool, and it’s located right in the middle of the happening Southampton village. They always offer deals to take $100 or %10 off your stay. Check it out here.
How should you get there?
I’m going to be honest: I’ve never taken the infamous Hampton Jitney, but some of my family members are Vet Hampton-goers and they swear by it. One-way tickets can range from $18 to $90, depending on where you’re going and how crowded it is. Yikes! That potentially hefty price tag may be okay for my family, but it is the reason why I’m particularly fond of the LIRR’s service from Penn Station to Southampton. It’s fast—a little more than 2 hours with a quick transfer—and cheap, ranging from $19 to $26 depending on if you’re traveling during peak or off-peak hours. The best part? Taking the train will help you avoid all that highway traffic that you’re sure to hit on the Jitney.
If you’re feeling adventurous, rent a car. That way, you won’t have to worry about calling a cab company every time you want to explore the town. I’ve heard that ZipCar is both accommodating and affordable.
You’ve made it and you’ve unpacked. What next?
The beach, of course. Your gents and lady friends will love Cooper’s Beach. It is $30-40 to park the car for the day, but it’s a better deal than you think. The pass is valid all day, so you can leave for lunch and change into that linen button-up us girls love to see you in for a romantic stroll later that evening.
If you want a shorter, quicker beach trip, I’ve cheated the system by either calling a car company to drop me off or parking further down Gin Lane (near Road D) and walking along the smaller beaches to get to Cooper. You’ll get a great tour of the grandiose houses (read: mansions) along the shore, which is quite beautiful.
Then comes my favorite question: What and where should you eat?
There are endless places to try in Southampton but here are my top 3 favorite date-friendly places to get you started*:
- Breakfast & Brunch: Think of The Golden Pear as the Hamptonite’s go-to spot to get their day started. They have the best bagels, baked goods, breakfast burritos, muffins and iced coffee that I’ve come across. But be prepared to wait. On an ordinary Saturday morning, chances are the line will be out the door. It’s worth it though; one bite of anything on their menu will have you hooked. And you can feel free to get attached—they have locations in Sag Harbor, and East, South, and Bridgehampton.
- Lunch: When I was in Southampton for July 4th, I had a great time at Café Crust. Their Margherita pie is to die for, and their kale salad topped with gorgonzola cheese and fresh avocado—YUM—cannot be beat.
- Dinner: The Coast Grill brings a whole new definition to romantic, waterfront dining. I recommend their truffle fries and their filet mignon. By the time you’re ready for their amazing gelato or banana bread pudding, you’ll have a breath-taking view of the sun setting over the marina.
Pack your bags and head to Southampton for that much needed break from the city. Your mind (and your lady) will thank you for it later.