New York is packed with fun things to do, and you can’t go wrong with the classic attractions: rowing boats in Central Park, kissing at the top of the Empire State Building, eating oysters at Grand Central. But I’d love to share a few twists on those adventures that we’ve discovered over the years…

1. Sunset sail. Feel the crisp wind on your face while sailing down the Hudson River on a classic 1890’s style Schooner. The captain passes out wool blankets and serves wine, beer and Champagne, and you can bring snacks, if you’d like. (Think: Two lobster rolls from the nearby Chelsea Market.) Alex and I have been on these two-hour sails many times; they are always exhilarating, giddy and romantic. You sail right up to the Statue of Liberty (such a fun way to see her) and gaze at the sparkling city lights.

2. Kayaking. New York offers free kayaking, which is fun, beautiful and surprisingly not scary. On a sunny day, it’s refreshing to be out on the river; and kayaking is gorgeous way to see the city (the skyscrapers look even taller from the water).

3. Chelsea art galleries. Put on red lipstick and a cute dress, and go gallery hopping! Chelsea galleries are easy to find; they’re all clustered on the same few streets. (Here’s a handy map.) Even cooler, go to gallery openings in the evenings. The website ARTCAT lists when each exhibit will have its opening party (typically Thursday evenings), so you can stop by to sip wine and rub elbows with downtown artists.

4. Murray’s Cheese classes. During these two-hour classes, you taste stinky cheeses, drink wine, hear funny cheese-making stories and leave full and happy. What’s not to love? (This would make a great date, don’t you think?)

5. Drink wine on the Met’s rooftop. Here’s a (kind of) secret: Every year, from May to October, the Metropolitan Museum of Art features an amazing exhibit on its rooftop. Go to the back of the museum, take the elevator up, have a glass of wine, walk through the installation and look over Central Park. A perfect summer evening.

6. Upright Citizens Brigade’s Asssscat show on Sunday nights. This side-splittingly hilarious (and kind of dirty) improv comedy show features uber-talented comedians from SNL, The Office and 30 Rock. Amy Poehler co-founded it, and she still hosts a show now and again. You buy tickets online ahead of time, then stand in line outside the theatre early the night of the show, to make sure you get a decent seat (the place is a total dive and if you’re late, you sit on the floor…which is kind of fun, too). Highly recommended.

7. Walk across the Brooklyn Bridge (especially at sunset). The iconic Brooklyn Bridge takes my breath away every time I step onto it. You’ll adore the skyline views of Brooklyn and Manhattan, as well as sparkling water, sailboats and the sunset.

8. The Brooklyn Bridge Park. This small park in Dumbo (right across the Brooklyn Bridge) is spectacular. It’s on the waterfront underneath the Manhattan and Brooklyn bridges, so the views are dramatic and amazing. Lie in the grass. Skip stones in the water. Fly a kite. Ride the carousel. Pick up an impromptu picnic with neighborhood pizzaice cream and a giant chocolate-chip cookie. And if you’re in a boat-y mood, you can take the new East River ferry back to Manhattan.

9. MoMA. Three words: Raddest museum ever.

10. The High Line. This new park runs along old elevated freight-train tracks. The incredible landscape architecture makes it appear as if wildflowers are sprouting up among the tracks. You can sit on the reclining wooden benches, stroll along the meandering paths, and take in the city views. Such a lovely place to…do nothing.

Bonus tip! As you’re walking around the city, duck into one of the many cheap massage places around town. You’ll spot neon signs with massage prices listed by the minute (usually $10 for 10 minutes), and you typically have to head down a few steps. Don’t worry, though, most aren’t sketchy! :) Inside, you’ll see a row of massage tables, separated by a curtains instead of real walls; and the massage therapists will guide you to one. The massages are always surprisingly good, and it’s an awesome way to sooth your sore muscles after walking around all day–or to relax before heading to dinner.

What do you love doing in New York? Do you have any favorite tips? I’d LOVE to hear! xoxo

(Top image graphic design by HipHipGinGin for Cup of Jo. Globe, High Line and massage photos by Laura Ratliff, Murray’s Cheese photo by Jamie Beck, Brooklyn Bridge photos by Philipp Klinger, Met rooftop and UCB photos by NYTimes, Hither & Thither, and Alex; sailing photos by Bart Stiller and Marvelous Kiddo; MoMA photos by MoMA; carousel photo by New York Magazine.)