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Must-See Spots on Your Hamptons Vacation

Make the most out of your visit at these amazing must-see Hamptons destinations.

Photo by Frank Marino

There's nothing like spending your summer in the Hamptons. Between the A-list celebrities, the luscious greenery and wildlife, and the peaceful sunny beaches, you are sure to have a wonderful time. The expensive attractions are worth it because you will receive only the very best. I think of the Hamptons as my second home, since I vacationed there every year as a kid.

Because of the popularity of the Hamptons as a vacation spot, there is no shortage of things to do there. Whether it's going out drinking or napping on the sand, you will find a place to enjoy yourself. If you go for a weekend, or even the whole summer season, check out these must-see spots.

Montauk Lighthouse

An aerial view of the Montauk Lighthouse

The Montauk Lighthouse is perfect if you want to know some history about the area. It is well-known as a National Historic Landmark. The construction on the lighthouse began in 1796, making it the oldest lighthouse in the state of New York and it is currently the fourth oldest active lighthouse in the United States. The lighthouse is at the easternmost tip of Long Island and looks out over the Atlantic Ocean.

If you visit this landmark, make sure you're ready for walking! There are 137 steps up to the top of the lighthouse. The total height of the tower is 110 and a half feet. The light flashes every five seconds and is visible from 19 nautical miles away. The visiting hours change depending on the season, and admission is $11 for adults, $8 for seniors, and $4 for children 12 and under. 

Big Olaf Ice Cream Shop

photo by Kim C. on Yelp

On a hot summer afternoon, all anyone can think about is cold, melty ice cream. My favorite place to enjoy a waffle cone in the Hamptons is the Big Olaf Ice Cream Shop. They make their waffle cones right in front of you, so you can smell the cooking batter from down the street. On summer evenings, there is often a line down the block, but it is definitely worth the wait. The homemade ice cream is rich and sweet, and there are tons of flavors to choose from. The best part about this place is that it's right by a pier where multiple huge yachts are always docked. You can sit by the water and look at all the boats while eating your ice cream. The Olaf Ice Cream Shop is perfect for an after dinner treat on your vacation. 

Cooper's Beach

photo by Jane L. on Yelp

Cooper's Beach is a beautiful private that you must see in the Hamptons. There is a snack bar, bathrooms, and a lifeguard -- which is surprisingly rare as far as Hamptons beaches go. You can rent umbrellas and chairs, and you pay $40 per car to get in. It's not cheap, but for a full car and an amazing day on the beach, I think it's worth it. Many surfers go to Cooper's but it's also great for relaxing in the sand. The waves tend to get a bit rough late in the day, so it's best to be careful in the water.

The area where Cooper's Beach is located is gorgeous. It is surrounded by $10 million homes of the rich and famous, and on the other side of the street is a large peaceful bay. A little-known fact: if you don't want to pay for the beach, driving a mile or so down the road will take you to Southampton's public beach which is free. The downsides are the severely limited parking, the lack of snacks or lifeguards, and the far trek to public restrooms. If you can swing it though, Cooper's Beach is a great spot to visit. 

Pollock-Krasner House and Studio

Pollock and Krasner in their studio

The Pollock-Krasner House and Studio in East Hampton was originally the home of married artists Jackson Pollock and Lee Krasner. It is now classified as a National Historic Landmark and has been converted into a museum. Many of the pieces of furniture and artifacts that were there when Krasner died in the 80's are still there on display. Visitors can tour the artists' home and the barn that Pollock converted into his studio. Krasner used the studio after Pollock died and both of the artists' tools, along with artifacts and photographs from their lives, are on display.

This museum is one of the few places on this list indoors, making it a must-see spot in the Hamptons if you end up getting rained out. The artwork is incredible and it is fascinating to see how the artists were shaped. 

Paddle Diva

Also located in East Hampton, Paddle Diva makes stand up paddle boarding, or SUP, more accessible to everyone. Paddle Diva provides more than just paddle boarding lessons by focusing on the mind as well as the body. They offer individual lessons in addition to holding group classes. You can also book group events such as corporate retreats and bachelorette parties. Gina Bradley, the founder, created the DIVA board especially for women, as she felt unrepresented in the stand up paddle boarding world. Taking a lesson with Paddle Diva can be a great source of exercise during your Hamptons vacation. 

The Lobster Roll

The Lobster roll's iconic sign

Located in Amagansett, The Lobster Roll is a popular seafood restaurant. It opened in the 1960's as a small clam shack, but now is a main attraction of the Hamptons. Despite serving both lunch and dinner, the giant "LUNCH" sign outside the establishment has become relatively famous. The restaurant has indoor and outdoor seating, and a nostalgic look with picnic tables and umbrellas. The Lobster Roll has tons of seafood dishes on the menu, along with classic burgers and fries. And as the name suggests, their lobster rolls are nothing to joke about. This restaurant is great for tasting locally caught seafood and is definitely a must-see spot in the Hamptons for your itinerary. 

The Surf Lodge

A standard room at The Surf Lodge

The Surf Lodge is a trendy inn/restaurant/concert venue in Montauk. You can book rooms there, attend a concert or event, or simply stay for dinner. Artists such as The Head and the Heart, Lukas Graham, and the Strumbellas, and Bob Moses have played at The Surf Lodge in the past. Every concert is free admission so it's first come first serve, but for some popular shows being on a guest list is necessary to attend.

To rent rooms in The Surf Lodge, there's a two night minimum, and rooms fill up fast. It's best to book your stay there far in advance. The beachy atmosphere and surfer vibe makes for a relaxing stay. The restaurant's menu changes depending on what seafood is caught that day, ensuring the that only the freshest ingredients are used. All food is sustainable and local. As you can imagine, the restaurant's reservation book also fills up very quickly, so it's necessary to book a table early. Your Hamptons vacation will be enhanced by visiting this popular destination.

Tate's Bake Shop

Tate's in Southampton

Tate's ranks as my number one favorite place in the Hamptons. The Southampton bakery is where the famous Tate's cookies originated, initially called Kathleen's. The founder of the bakery and its popular cookies is Kathleen King, who opened the place when she was only 21 years old. I love the bakery's cozy feel, which is a refreshing change from some of the glitzy over-the-top businesses in the Hamptons. The store has various types of the signature cookies, along with freshly made pies, cakes, and pastries. They make new treats every day, with special seasonal goodies. In my opinion, their best products are their chipwiches made with homemade ice cream and the signature cookies, their super sweet coconut cake, and their delightfully fresh strawberry cake. Stop by Tate's for coffee, breakfast, or a snack and your day will be made a lot sweeter. 

Designer Showhouse

The 2016 Designer Showhouse

In the Hamptons, every year there is a designer showhouse. Famous and up-and-coming designers come together to decorate the rooms of a mansion in one of the Hamptons' towns. Each designer decorates a different room, and the end result is mind-blowing. Visitors are charged $40 to walk around the house and see all the rooms, and all the proceeds benefit Southampton Hospital. The houses are massive with upwards of 25 rooms, and often have lavish pool areas as well. The Designer Showhouse is a hot spot of the Hamptons, and sometimes celebrities are even seen there. You will be in awe of how the other half lives when you check out The Designer Showhouse

Wölffer Estate Vineyard

A wedding at Wölffer Estate

Last but not least, the Wölffer Estate Vineyard, is located in Sagaponack. It is spread across 55 acres on the huge 175 acre estate, which also includes stables and an equestrian center. The land was initially used for a potato farm, and it became a vineyard in 1988. If you visit this beautiful winery, you can participate in tastings or take a tour of the vineyard. There is also an outdoor Wine Stand which is open on weekend nights in the summer and features live music as visitors drink wine while watching the sunset. The vineyard can also be booked for weddings and events. This winery is the place to be in the Hamptons. Go there for a magnificent view of the landscape and a peaceful atmosphere while you taste only the best freshly made wines. 

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