20 Best Things to do in Montauk for Couples

Those unfamiliar with the northeastern United States would be forgiven for thinking that New York City is all there is to offer. While the city is an exciting cultural and economic center, this notion could not be further from the truth. Many smaller towns and neighborhoods around the region have lots for people to do and see. One of these places, located at the very eastern tip of Long Island, is called Montauk.

Montauk is nestled within the town of East Hampton, one of the towns collectively known as the Hamptons. The area is famous for its affluence and ties to wealthy celebrity culture. Still, it has a lot to offer everyone. Montauk is bustling with fun and exciting activities for people to enjoy alone, in groups, and especially with couples. Long Island is considered a highly romantic region on its own, and Montauk, being so close to the ocean, is certainly no exception.

Here are 20 of the best things to do in Montauk for couples in 2023:


Due to its location on the very tip of Long Island, Montauk’s biggest draws are the ocean and all of the related enjoyment that comes with it. Couples can always visit the beautiful beaches for a day of sun, sand, and surf, but the people of Montauk have also created several unique ways to enjoy the water and the surrounding area of the coast. Here are just a few.

1. Hike Through Montauk Point State Park

Couples who love to experience the outdoors together will love the views at Montauk Point, located on the easternmost tip of Long Island. The unique vantage point allows visitors to see the exact point where the tides from the Atlantic Ocean and the Block Island Sound converge with each other, creating an excellent effect.

Montauk Point also has some trails along the rocky shore where people can hike or even cross-country ski in the wintertime. Often groups of sunbathing seals are visible from the trail. For an extra dose of history, couples can also visit the historic lighthouse.

2. Experience a Historic Landmark: The Montauk Point Lighthouse

Long Islanders already know the iconic history of the Montauk Point Lighthouse. It’s the defining feature of the State Park and one of just twelve U.S. lighthouses to be named a National Historic Landmark. The lighthouse was commissioned back in 1792 by George Washington and today features a museum where couples can learn about the structure’s history and surrounding area. Unlike some other historic lighthouses, this one allows guests to climb to the top of the tower and experience a 360-degree look at the stunning ocean area.

3. Fish the Open Ocean with one of the Area’s Sea Charter Boats

Being so close to the ocean makes Montauk a great place to get out on a boat and enjoy the salty air with a loved one. To that end, many businesses offer rides for various purposes in the area. Couples who love to fish together can find many boats whose captains are ready to show guests the ropes, whether they are novices or master fishermen.

Many of the charters go beyond fishing. For instance, some boats feature nightly rides for kids or specialize in bachelor party “booze cruises.” If you’re looking for something to do with your loved one, Montauk’s charters will provide what you need.

20 Best Things to do in Montauk for Couples

Related article

11 Best Places to Live in Pennsylvania in 2024

Pennsylvania has it all: caves, mountains, waterfalls, culture and history. It is the 33rd-largest state by area and the fifth-largest by population. There are a lot of great places to live in the state. Below, you will find descriptions of 11 of them…

4. Enjoy a Romantic Sunset Cruise on a Catamaran

If fishing isn’t your thing, a catamaran ride can provide a perfect alternative. Sail along the waves in an environmentally-friendly, classically-designed sailing boat inspired by the traditional designs of Polynesia. Montauk has a couple of businesses that offer such cruises, including Mon Tiki and MTK Cruises. Couples can book in advance to enjoy a day out swimming on the sound or the romance of a quiet sunset ride.

5. Get Your Thrills with Montauk Parasail

Have you ever wanted to experience the rush of flying 500 feet through the air, gliding above the ocean, and experiencing stunning views? Couples who like adventure and excitement will want to try out the parasailing services offered in Montauk. If you’ve never heard of parasailing, it’s like waterskiing, except you’re attached to a parachute that lifts you high into the sky as you are pulled along by the boat. Careful, though; this isn’t for the faint of heart!

6. Learn a New Skill Together with a Surfing Lesson

When most people think of surfing, they think of scenes down in Florida, out west in California, or even across the ocean on the islands of Hawaii. While these are all great places for surfing, Montauk, NY, has some waves that can be great for the sport. Research and find the best business for you and your loved one. There’s nothing better than the ocean in Montauk in the summer months.

7. Take a Beach or Trail Ride on Horseback with Deep Hollow Ranch 

Hiking, boating, or parasailing isn’t the only way to enjoy the Montauk coast. Deep Hollow Ranch is a family-owned business specializing in trail and beach horseback excursions. There are services available for anyone here, but couples will find some real bonding time enjoying the spectacular riding trails along the Block Island Sound. The cowboys and cowgirls who guide the tours are ready and equipped to serve anyone, even people who’ve never been on a horse before. It’s a beautiful idea for a unique date.

20 Best Things to do in Montauk for Couples

Related article

The 10 Best Places to Live in New Hampshire in 2024

We’ve taken a look at the five most important issues for people looking to move to a new place: housing, employment, safety, health care and schools. Based on these metrics, below are the 10 best and safest places to live in New Hampshire…


Long Island itself has a reputation for high-quality business and delicious food. Being associated with New York City certainly doesn’t hurt in this regard. Couples need to get out and enjoy all that the local economy has to offer. Here are just a few ways for them to do just that.

8. Book a Relaxing Couple’s Massage 

The daily grind of work, stress, finances, and possibly children can take a toll on a couple’s relationship. All that tension can manifest in physical ways throughout the body in the form of aches, pains, headaches, and sometimes even injuries. Luckily, Montauk has several options for couples to rejuvenate together.

Couples massages are quiet and relaxing, designed to relieve stress and tension. Some highly-rated options around Montauk include Magnolia: A Wellness and Beauty Collaborative, The Spa at Montauk Lake Club, and the Deborah Thompson Day Spa.

9. Taste some Award-Winning Wines at Wolffer Estate Vineyard 

Wolffer Estate has been open since 1988, providing unique, premium wines and spirits for the local community. Their beautifully designed tasting room is built for class and quality. Whether you prefer whites, reds, or roses, your loved one will be grateful that you chose Wolffer as the date night spot.

10. Dine on Authentic Italian Food at Harvest on Fort Pond

Harvest has been serving up local Italian cuisine since 1994 and remains a Montauk staple. When you and your partner are looking for some delicious pasta, pizza, or grilled meat, Harvest will be there to satisfy those cravings.

20 Best Things to do in Montauk for Couples

Related article

The 10 Best Places to Live in Maine for Families

With such a diverse landscape and so many beautiful towns to settle down, Maine is a terrific place for families looking to put down roots. We looked at multiple factors, including safety, education, things to do, and cost of living. We put together this list of the ten best places to live in Maine for families…

11. Devour the Best Local Seafood at Inlet 

Inlet has the most authentic local seafood in Montauk because it is owned by six local veteran fishermen who know the area and the best foods people want. Their seafood is caught fresh daily and prepared by some of the best regional chefs to be served to guests either in the dining room or out on the dock. Couples who sit here can enjoy a romantic sunset while also enjoying dinner.

12. Sip on Cocktails at Lynn’s Hula Hut

If a couple wants to get the sense they’re hanging out on a tropical beach when they’re actually in Long Island, Lynn’s Hula Hut is the place to go. It operates out of a converted shipping container and is famous for its fruity drinks and tropical cocktails. At Lynn’s, couples can relive their honeymoon again and again.

13. Try Some of Montauk Brewing Company’s Local Beers

The craft brewing industry has exploded in popularity in recent years, and that’s because people tend to love beer. For couples, this means that there are plenty of places to relax and try the local offerings of brewers bringing these products to the masses. In Montauk, the local brewing company offers many different types and a great taproom to enjoy them. Just be responsible and make sure no one is driving.

20 Best Things to do in Montauk for Couples

Related article

The 10 Best Towns to Live in Massachusetts in 2024

As one of the central New England states, it’s highly desirable. According to WalletHub, which looked at the economy, education, quality of life, and safety, Massachusetts is the most desirable state in the nation. That’s some high praise! The only downside was affordability. It ranks as one of the most expensive to settle in…


They say the couple that learns together stays together. Well, maybe not. Still, taking in some local education with a loved one is an excellent way to spend time together. Montauk has a few options nearby for admiring some art and provincial history.

14. Admire some Modern Art at the Leiber Collection

Judith Leiber was a Holocaust survivor who met her husband, Gerson, in Budapest during the aftermath of World War II. Both were creative minds who relocated to New York to get into the art business. Gerson was an oil painter, and Judith mainly worked for fashion designers. Their legacy lives on at Montauk’s Leiber Museum, a place to admire their works as well as the works of modern local artists.

15. Experience the Creative past at Pollock-Krasner House and Study Center

Abstract artist Jackson Pollock and his wife Lee Krasner often worked out of their homestead in eastern Long Island when they were alive. Today, the area is available for public viewing of some of their classic works, as well as housing a library and study center. Couples who love art can walk the grounds together while taking in the influence of some of America’s most influential creative minds.

16. Observe more Modern Works and Shows at Guild Hall and John Drew Theater

Both the museum and the theater opened in 1931 to allow local photographers and performers to share their art with the public. That tradition continues to this day, nearly a century later. The schedule at the theater varies, but many nationally-recognized acts have played there in recent years, so visit their website for more information.

Related article

20 Affordable Things to do in Port Clinton, Ohio

It boasts a cost of living that’s 20% lower than the U.S. average. While Ohio does have some generally desirable cities, Port Clinton is one of the more attractive places to visit. Along with nearby Sandusky and the easily-accessible Lake Erie Islands, the area is fondly known as “Vacationland.”


Montauk is a place with a strong sense of community, which is partly built up by some exciting annual events. Fun-loving couples around the area will look forward to returning to these yearly events again and again.

17. Montauk Music Festival 

Live music always makes for an exciting date. The Montauk Music Festival is typically held toward the end of summer each year. It features nationally-recognized artists, sure to entertain the community with rocking shows! The festival takes place at the island’s eastern edge, and a shuttle is available from downtown.

18. Montauk Fall Festival 

Sponsored by the local visitors center and the Chamber of Commerce, the fall festival has been held in October each year since the early 1980s. The community staple features live music, excellent local cuisine, raffles, auctions, kids’ rides, and an annual chowder contest. As a bonus to getting out and meeting community members, you and your loved one will know you’re supporting local businesses and stimulating growth.

19. Montauk Film Festival

So many couples love to watch movies together, so the Montauk Film Festival is a beautiful way to support local artists while checking out some great cinema in the process. The outdoor film festival is planning its 4th iteration for summer 2023. Their films typically fall into four categories: environmental, social and cultural, surf and turf, and community. These socially-conscious films allow the budding local moviemakers to showcase their work and give the community something fun to do in the process.

Related article

27 Best Things to do in Canton, Ohio for Families

Canton, Ohio, a city of 70,000 located about 60 miles south of Cleveland, is often overlooked among the rest of the more significant Ohio locations. As the seat of Stark County, though, there are plenty of aspects of Canton that warrant a closer look…

20. Magic of Montauk Holiday Event

It’s a new local tradition! The Chamber of Commerce wants to bring the community together to celebrate with holiday cheer. They are hosting multiple events for this festive occasion, with a business decorating contest, a path of holiday lights, a party, and so much more. Couples will get into the spirit when they visit this annual festival.


Far from its reputation as a rich person’s playground, Montauk is a place with rich culture, deep community roots, and plenty of fun and romantic things for the average couple to get into. It’s an area that offers a quieter alternative to the bustling crowds of New York City while still providing a strong sense of values and personality. Couples looking for things to do together will find no shortage of them here, making Montauk a wonderful place to strengthen any relationship.

20 Best Things to do in Montauk for Couples

Related article

23 Family-Friendly Things to do in Akron, Ohio

Over 190,000 people call Akron home, making it the fifth-largest city in Ohio. The greater Akron area has over 703,500 people in total! With such a large population, Akron is steeped in local history and deep heritage. It’s the birthplace of American food staples like hamburgers, oatmeal, and processed cereal…

HOMEiA is a city living guide site where visitors can find detailed information about communities of interest. HOMEiA’s City Living Guides, created in partnership with local writers, are curated lists of the best, safest, and most affordable places to live. The guides feature the HOMEiA Score, a proprietary index that rates communities on such factors as housing costs, education and employment.

HOMEiA.com aims to be the premier site for people planning to relocate, providing them with insightful content and connecting them with skilled real estate professionals.

We also empower real estate professionals to establish or strengthen their web presence by highlighting their experience, knowledge and achievements. If you’re selected to join our list of certified real estate professionals, you will distinguish yourself from your peers — and earn HOMEiA’s support.

If you believe in HOMEiA’s mission, please share the site with others.