There are a million different things to do in NYC at any particular moment. Getting good at ignoring FOMO (fear of missing out) is crucial to sanity while living in this bustling metropolis. When planning a venture with a visiting tourist, often the same considerations come to mind for planning a good date! You want a stunning location that shows off the sexy meat and bones of this city but also is a fun thing to do that doesn’t mean you have to stare at someone the whole time. I’ve assembled ten of my favorite things to do with dates and/or friends from out of town.

1. Brooklyn Ice Cream Factory at the Fulton Ferry Dock

Okay, so the destination here really isn’t the ice cream, it’s the view. Brooklyn Bridge Park and the Fulton Ferry dock underneath the Brooklyn Bridge are gorgeous! It’s my favorite view of the city, a sweeping cityscape of downtown. You can see the South Street Seaport from there as well as all of the cute boats going by. Wait in line for the Brooklyn Ice Cream Factory if that’s a delicious addition to the outing, or just bring a picnic and sit on the benches along the pier and watch the river, the people and the lights if it’s nighttime. Skip Grimaldi’s, a wildly well-known pizza place that is pretty good but I don’t think worth a 90 minute wait for a table. Grab a pie in the middle of the workday if you must, that’s the best time to get one quickly.

If you want to take a wander nearby DUMBO has some cute shops, bookstores, chocolatiers and the second location of , a favorite cake shop of mine.

Bk ice cream factory

The view from Brooklyn Bridge Park during movies under the stars. Image from

2. Prospect Park in the Fall

Yeah, yeah, Central Park is awesome. But for something that’s easy to get in and out of and doesn’t take a huge hike, Prospect Park is amazing. Especially in the Fall when all of the super tall gorgeous trees create a fireworks show overhead and dump a gazillion leaves that you get to walk through and swoosh with your legs like a young child! It’s a great date with a dog and it’s easy to just pop in for a fifteen minute gander or take an hour to walk around the park. There are entrances to the park in lots of Brooklyn neighborhoods that make it convenient for later dinner plans if that is where your date may end up. It’s taken me years of living in Brooklyn to really understand all the awesome Prospect Park has to offer, and I definitely think that Fall is the best time in there. Also, sometimes there are food trucks and people love food trucks.


My roommate Damien thinks that the pond in Prospect Park is great for dates and I had an awesome hang out along the edge of it with a bunch of friends late last Spring.

3. Barcade on a Sunday
Barcade is a bar and arcade (clever, right?) in Williamsburg. They exclusively stock 80s video games, which works for me because Ms. Pacman is my jam and I will totally beat you at it. My BFF Brian just had his birthday party there and tipped me off that Sunday afternoon is the best because it isn’t crowded. They have really nice skylights and incredible beer if that’s your jam. When I was a drinker I enjoyed their selection and I felt like the prices were good Brooklyn prices for delicious pints. The games are still only a quarter each. I suggest Rampage as a good game to play with a team–especially a date!

Photo by Nick Andriuolo.

Photo by Nick Andriuolo.

4. The Whitney

There’s no shortage of great museums in New York City, but the one I’ve consistently enjoyed is The Whitney. There are really incredible exhibits, I am a big believer in audio tours at museums and enjoy the free with admission programs that the Whitney offers via loaner ipods. It is a lot to explore more than one floor on a visit so I suggest very comfortable shoes and a plan that involves sitting somewhere immediately following. I once went there on a date with an out of towner and we had a lovely tea afterward at a nearby Starbucks, but the cafe downstairs in the Whitney also has some snacks. It also gives you some great stuff to talk about with your date or visitor during your debrief/resting your weary legs!

5. Late night Williamsburg Pig Tour

I’ve done this date a few times so I hope my previous dates don’t find it generic that I’m laying it out here. If you’re up and partying in Williamsburg (the neighborhood in which I host Rebel Cupcake, as well as the site of three gay bars–Sugarland, Metropolitan and This N That) it’s a great idea to go get sustenance once your partying is over. And Williamsburg is that neighborhood that reminds you that NYC really doesn’t sleep. The other neighborhoods sleep, by the way.


There’s Bagelsmith, at Bedford and N. 7th, this awesome bagel shop that has my favorite NYC bagels. I love to go get one and walk three blocks to the waterfront for the amazing view! It used to be a lot less obstructed but condos got in the way in the last five years. But you can still wiggle around them and catch the view. I also like the pizza place on Bedford and N. 7th (pay attention to whether the street says N or S or you’ll get real lost in Williamsburg). The guy who takes the orders makes the same snarky jokes all the time and it can be kind of off-putting if you’re from out of town but just go with it and eat a delicious piece of pizza piled high with awesome toppings (they sell by the slice or whole pie and it’s awesome when a by the slice place has creative choices).

Legit late night pizza dining by Dana.

There’s also a falafel place open really late and a consistent taco truck. Neither is my favorite but you could really make it a pig tour and hit as many of the late night stops as you can if you’re famished.

6. DiFara Pizza

Now there’s pizza you get in the middle of the night and pizza you get really quick because it’s a dollar and you’re hungry. And there’s pizza you travel to the middle of Brooklyn to wait over an hour for and you’re grateful that you are able to put in the time to honor such an incredible masterpizza. DiFara’s is in Midwood, a historically Orthodox neighborhood well into Brooklyn, and it’s produced every time in the same methodical way by the same guy who snips basil on top of it. It’s completely delicious and my favorite pizza in NYC. It’s a great New York thing to do because standing in line for pizza! And also it’s so legit. Call ahead to make sure they’ll be open (I got burned once on a Monday) and bring a small group and don’t expect an easy shot at a seat, and bring your own tupperware to bring some home if you don’t want to lug a GIANT pizza box.

7. Sleep No More

I have written about Sleep No More here before. It’s a great show and I loved it–a choose your own adventure multi-floor vintage hotel where a version of MacBeth unfolds before you in a non-linear form. Through dance. I went to a haunted house in Times Square this weekend (aptly called Times Scare) and it cost $14 with a groupon and that was exactly as much as it was worth. I couldn’t help thinking that it was so much less scary than Sleep No More (SNM is deeply psychological). And when thinking about good Broadway shows in town, SNM blows them all out of the water. I saw it six months ago and I still think about it–that’s great art!

8. Brooklyn Botanic Garden

The Brooklyn Botanic Garden really shines during the Spring when the cherry blossoms peak. But even if you go at another time of year, it’s so gorgeous. There’s a koi pond, lots of places to hang out on a bench in nature, a super cute gift shop with great plants and seeds (I have some seeds that are actually working on my fire escape). It’s free on Tuesdays, so there’s no risk if you do it then, but I think it’s worth the ten bucks for entry. They won’t let you bring a picnic, though, so plan to eat ahead of time. Cheryl’s Global Soul is nearby and has good sandwiches for a weekday lunch. On weekends their brunch wait is epic, so I would steer clear.



9. Coney Island Fireworks

Coney Island is one of my favorite places in NYC because it marries weirdness and the beach and rides and kitsch. It’s a good place to go during the summer, I’ve tried cold weather Coney and it’s not as fun. It’s a great date, I once had a date convince me to pop my Wonder Wheel cherry in spite of my aversion to ferris wheels but I’m totally into it now. Perfect Coney date/out of towner activities include: getting a corn dog at Nathan’s, the Wonder Wheel, photo booth strips (there’s a machine at the base of the Wonder Wheel), getting a beer at the Coney Island Side Show bar (Coney Island Lager is delicious), playing whackamole, sitting on a bench watching the waves. During the summer every Friday night there are fireworks that are free! Bring a sheet for the sand, a flask and get a big soft drink to drink from.

My friend Leo snacking up before Coney Island fireworks.


Wonder Wheel at night.

10. Staten Island Ferry (+ art on weekends)

The subway doesn’t go to Staten Island so they built the Staten Island Ferry and it’s FREE! It’s a great way to get a view of the Statue of Liberty, Ellis Island and Lower Manahattan. There’s also lots of good art around the Ferry terminal on the weekends if you want to hop out of the terminal, but you could just do the round trip. The whole adventure without a side detour can be up to 90 minutes with ferry wait times but it is very cheap and worth it. Also they serve beer on the Ferry if that’s important to you.

When my mom and Grandmother were in town I took them on a sunset Staten Island Ferry tour!



photo (3).JPG
Even the wait in the terminal is pretty gorgeous!

For more great tourist spots in NYC check out What to do in NYC as a Tourist!

I’m fundraising to sustain and my art projects! Please consider supporting with a gift subscription (and getting some great prizes) if you have been touched by this site!

One Response

  1. Everything on this list looks awesome! (Including Barcade, where I’ve been on a previous trip to New York and would love to go again.) My boyfriend and I are planning to go to NYC sometime in the next year, so I will keep all of this in mind.

Comments are closed.