The Best Date Ideas on Long Island

Long Island is a lovely place. It has a little of everything: from beaches to breweries, historic homes to Harbor Fest. But it can be difficult to find the gems among the suburban sprawl - anything you want to do is at least a 20 minute drive. It's not easy living in the shadow of the city. It can be just as (if not more) convenient to head into the city to do all the newest things in one place as it can be to find and travel to one great thing on the island. 

Joe and I have done a ton of fun stuff ranging from the totally dorky to the relatively hip. So, I've put together a list of a few of my favorite places for dates on Long Island. We're both from Nassau, so most of our suggestions focus on places in Nassau (sorry to underrepresent you, Suffolk!). And I've included a handy-dandy hipness rating - from the coolness of practical fanny packs at Disney to the coolness of the ironic fanny packs of Williamsburg.


MP Taverna Roslyn

1363 Old Northern Blvd. Roslyn, NY

Chef Michael Psilakis opened a few MP Tavernas in Downstate NY with a modern, Greek-inspired menu. The restaurant in Roslyn has a relaxed atmosphere with an impressive bar. On a warm night, the rooftop seating is perfect. 


  • Greek Meatballs
  • Roasted Lemon Chicken
  • Chocolate Halvah Brownie


hipness rating MP.png

A noisy gastropub in Merrick with an all-american menu and a Californian flair. We loved the popcorn instead of bread basket. The menu covers the country from southern shrimp & grits to Connecticut-style lobster rolls to the Pacific Beach wedge salad. Our server was as impressive as the beer menu! 


  • Mac LeBlanc
  • Six Hundred Degree Beets
  • LCK Burger

Upscale Mexican fare with a rustic, sophisticated atmosphere. The best thing is the tableside guacamole handsdown. But the second best thing is the specialty margaritas. And the third best thing would be the food, I suppose. Plus: churros come with the bill!


  • Tableside Guacamole
  • Mixtos Iron Skillet Tacos
  • Elotes de la Calle - Roasted Street Corn with Queso Fresco and Chile Molido

Heneghan's Tavern is one of the newer establishments in Point Lookout. It's open year-round and offers a fresh, upgraded take on pub food with an Irish lilt. There is seating in the bar or in the upscale rear dining room. The staff is fabulous!


  • French Five Onion Soup (Best I've ever had!)
  • Quilted Piglets (Pastry Wrapped Irish Bangers)
  • Jameson Braised Short Ribs


  • Buoy Bar, Point Lookout  - open seasonally
  • Dough Hut, Long Beach (not really a restaurant, but head to the boardwalk or the movies too)
  • Toast, Huntington  - breakfast all day
  • Kirsch's, Massapequa - retro diner & ice cream parlor
  • Marvel, Lido Beach - iconic window-serve ice cream & frozen yogurt (I love the peanut butter bonnet!)


Pole Position Raceway

40 Daniel St., Farmingdale, NY

So when we've gone it hasn't technically been a date, but we've been there enough where at least one visit must count as a date. Go-karting is unusual fun. And Pole Position Raceway streamlines the experience so it's accessible even to those who may not be as into racing as Joseph. There are quite a few bars and restaurants to visit nearby after a few laps. 


Huntington Cinema Arts Centre

423 Park Ave. Huntington, NY

With small theaters and older seating, the Cinema Arts Centre is not the most comfortable movie theater on the island. But they have a fabulous selection of indie, classic, and foreign films as well as special events. And a lovely cafe!

Sur La Table Cooking Classes

1468 Northern Blvd., Manhasset, NY

Sur La Table has a range of cooking classes from kitchen basics to seasonal meals. Joseph and I have done a few. My cousin Erin had given me a gift certificate for a Sur La Table cooking class for Christmas, and I used it for our first official date! Since, we've been to a handful. The classes are fun and delicious - you can choose which menu you'd like to experience on the calendar, they walk you through each step and you get to enjoy the meal at the end. 

Nature Preserves & Historic Homes

My favorite thing to do is to go on historic home tours. I realize that is totally dorky. But it also makes for a lovely daytime date.

  • The Sands Point Preserve is one of my favorites, and happens to be in the town I was raised. There are three historic homes (Castle Gould, Hempstead House, & Falaise) on the preserve, which has miles of trails, beachfront, and lawns & gardens.
  • Vanderbilt Museum is another lovely gold coast mansion museum & grounds in Centerport. And the Vanderbilt Planetarium is a total bonus!
  • The main attraction - even though the mansion is wonderful - are the gardens at Old Westbury Gardens. There is a ton of land to mosey around and different styles of gardens to get lost in. The house closes half an hour before the park, though, so do that first. 
  • Sagamore Hill, Teddy Roosevelt's summer home, is one of my absolute favorite places. Take a tour of the house guided by self-identified "Ted Heads" to see Teddy's unique sense of style (chairs made entirely of tusks, etc.). And walk the grounds in Oyster Bay.


  • A fair! There are millions. Oyster Fest in Oyster Bay, Harbor Fest in Port Washington, hundreds of church fairs, Greek festivals, Italian feasts, Irish Day in Long Beach, Liz's Day in Floral Park, and school fairs - the Greenvale School's fair this year featured a bunch of great food trucks
  • A trip to the wineries out East - although, this is usually best in groups rather than dates, I guess
  • Apple Picking (pumpkin picking...etc. picking)
  • Mini Golf - we went recently to the one in Bayville - it's spookyish

Dates We Haven't Been On Yet

Tell me your favorite spots on the island!