Boston Seaport Offers Dining And Entertainment For Date Night

Men's Dating

Boston Seaport: Dining, Entertainment, and a Lovely Sea Breeze for Date Night

Hayley Matthews

Written by: Hayley Matthews

Hayley Matthews

Hayley has over 10 years of experience overseeing content strategy, social media engagement, and article opportunities. She has also written hundreds of informational and entertaining blog posts. Her work has appeared in numerous publications, including Bustle, Cosmo, the Huffington Post, AskMen, and Entrepreneur. When she's not writing about dating news, relationship advice, or her fantasy love affair with Leonardo DiCaprio, she enjoys listening to The Beatles, watching Harry Potter reruns, and drinking IPAs.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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The Short Version: Boston Seaport, located between the scenic waterfront and historic Fort Point District, is an exciting place for a fresh date night in the city. The 33-acre neighborhood is filled with entertainment options, unique shops, cultural exhibits, high-quality restaurants, and plenty more worth exploring. Seaport offers more than 500 free programs and events on its schedule, so couples can plan exciting evenings year-round — even on a budget. Seaport is a fun outdoor destination perfect for a first date or couples looking to mix things up.

Netflix and chill” doesn’t seem too attractive after nearly a year of quarantines. Today, an exciting date should be something fresh, new, and — ideally — outdoors.

When it comes to asking someone out for a date during the COVID-19 pandemic, the person who asks should already have something fun and safe in mind. Asking someone on a date without a plan leaves the responsibility on the other person. In the age of social distancing, potential partners may not find that impressive.

Couples in New England have a go-to date destination that is safe, fun, and offers outdoor options: Boston Seaport. The new neighborhood, currently Boston’s largest development project, is 33 acres of transformed waterfront land filled with a welcoming mix of residential buildings, hotels, retail shops, restaurants, art galleries, and more.

Photo of the Boston Seaport neighborhood

The Boston Seaport neighborhood gives daters a wide variety of activities and a refreshing sea breeze.

“We combine the best of historic and modern-day Boston,” said Collette Corwin, Senior Integrated Marketing Manager for Seaport at WS Development. “Seaport is positioned to become the destination for fashion, culture, arts, dining, entertainment, technology, and life sciences.”

Singles, couples, and families can enjoy plenty of scheduled activities, advertised on the Seaport’s website and its social media pages, no matter the season.

When couples head over to Seaport, they’ll have plenty of options for a great date night, including a brewery tour or a walk in the park. Anyone looking for a date can easily plan a pleasant evening before they ask someone out.

The Thriving Seaport Offers Many Outdoor Activities

Visitors to the Seaport neighborhood, located between the scenic waterfront and the historic Fort Point District, will notice the area’s lively nature right away.

Along the main Seaport Boulevard, visitors can see all of the neighborhood’s interesting public art exhibits, including a mural reproduction of Frank Stella’s Damascus Gate (Stretch Variation I) and Okuda San Miguel’s Air.Sea.Land. If people want to enjoy more art as part of their date night, their next stop could be the Institute of Contemporary Art (ICA) Boston, also located in Seaport.

If daters prefer to stay outside while keeping an appropriate social distance and breathing the cool sea air, they can stroll along the Boston Harborwalk. This pedestrian promenade stretches across the Seaport and ends along the water’s edge.

Photo of a park at Seaport

Seaport has open spaces perfect for an outdoor date during warmer weather.

“The breadth of date night ideas in Seaport are truly endless and are all accompanied by breathtaking views of the Boston Harbor,” Collette told us. “There are countless ways to create remarkable memories together.”

In warmer weather, a popular outdoor date often starts with grabbing breakfast or lunch to go at one of Seaport’s casual dining spots. Daters can choose takeout from Cardullo’s Gourmet Shoppe, Better Bagels, Yoki Express, or Shake Shack to have a fun picnic on Seaport Common or by the Harbor.

Seaport offers a wide variety of outdoor activities year-round. In the winter, the neighborhood hosts free curling events with introductory classes on the Olympic sport, and festive weekly Winter Wonder Walks. Couples and families can even pick up their Christmas tree at Seaport, which is fast becoming a popular tradition.

Spend Time Together While Shopping for Loved Ones

Shopping isn’t everyone’s favorite activity, but even window shopping can help you learn more about another person. Seaport hosts a pop-up retail village called The Current that is a popular spot for anyone looking to buy or browse throughout the year. The Current has been home to a mix of national brands such as Glossier and beloved local businesses including Injeanius, Cupcake Mojo, Dove and Donkey, and Uwila Warrior most recently.

The Bumble app has frequently teamed up with Seaport to help people connect in the neighborhood. Most recently, Bumble partnered with Seaport to give free cupcakes from the local Cupcake Mojo to anyone using Bumble. Daters could even take a seat on the Bumble-branded Adirondack chairs nearby to enjoy their free treats.

Photo of Boston skyline at Seaport

Seaport offers dining, shopping, and stunning views of the Boston skyline.

Of course, the neighborhood is also home to plenty of retail stores where people often come to pick out unique gifts for their special someone. High-end shops include For Now, Everlane, Mejuri, and Helly Hansen. Tech-savvy types will also enjoy checking out the latest gadgets at b8ta.

If curling isn’t enough friendly competition, daters can head over to Kings Dining & Entertainment for more traditional games. The establishment offers bowling, billiards, shuffleboard, and classic arcade titles, and it’s also a lively destination for watching football games on Sundays. Another popular neighborhood spot is Flight Club, where couples can play a game of social darts over a craft cocktail.

Boston Seaport: High-End Dining Will Impress Any Date

Casual atmospheres can take the pressure off on a first date, but fine dining is often the key to impressing someone special. Seaport offers many fine dining establishments for couples to choose from, including Tuscan Kitchen, which offers authentic, artisan Italian cuisine and wines. Couples can even schedule a cooking class, either virtually or in-person, at the restaurant.

Photo of Seaport's Collette Corwin

Collette Corwin, Senior Integrated Marketing Manager for Seaport at WS Development, spoke with us about the neighborhood.

Many couples make a reservation at Lookout Rooftop at The Envoy hotel or Deck 12 at YOTEL Boston to take in the views of the city’s skyline over dinner. Afterward, couples can take a short walk to Taiyaki NYC for a famous fish-shaped ice cream cone, share a sundae at Ben & Jerry’s, or indulge in a crème brûlée or cocktail at the local Paris Creperie.

Every corner of the Seaport has a scenic backdrop, making it a popular place for engagement photo sessions and even wedding proposals.

“Just this past week, the Seaport team helped someone coordinate a marriage proposal in the neighborhood,” Collette said. “Our team was thrilled that this person sought out Seaport as the special place to ask the love of their life to spend forever with them.”

Of course, the neighborhood is great for singles, too. In the warmer months, the Seaport’s Cisco Brewers Beer Garden helps patrons connect while enjoying local brews, frosé, and light bites outdoors. Other neighborhood breweries, including Harpoon and Trillium, have a presence in Seaport year-round.

“The Seaport team knows of quite a few couples who met at the neighborhood’s free fitness classes,” Collette said. “That’s just one reason why Seaport is frequently cited as a great first date spot.”

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