A 3-Day Weekend Exploring NYC’s Coolest ‘Hoods

New York City is special. There’s so much to do and see in a relatively compact area, you can easily fill your days with all kinds of activities. I’ve been to the city many times and every trip has been unique. This past weekend my daughter Emma and I went to visit my son Nick, who lives in Chelsea. (We left Liam home to train for his upcoming big bike trip.) We were so lucky with the weather—sunny, breezy and not too hot—perfect for touring. Here’s a recap of what I packed, where we stayed, and what we did. It was a busy weekend so I’m going to let the pictures do most of the talking, but click through the links if you’d like more info about anything.


Once again, I was reminded of the importance of traveling light. Due to severe turbulence, our flight to LaGuardia was diverted to Newark. Those of us with carry-on luggage simply deplaned there and made our way to the city. But passengers with checked bags had to wait for the plane to refuel and fly over to LaGuardia to claim them. What a hassle.

New York is chic but surprisingly casual, and you do so much walking, comfortable footwear is essential. My packing for this trip was practically perfect! I felt appropriately dressed the whole time and wore everything I brought except the shorts. Here’s what I took, including what I wore on the plane (I’ll spare you the details of my socks and undies):

  • 2 pairs jeans (white and blue), stretchy cargos, a flowy black skirt, shorts
  • midi dress
  • jean jacket, light sweater
  • 5 tops in solid colors
  • shoulder bag, small cross body bag, animal print belt and fun earrings
  • running shoes, sneakers, sandals and flats

The High Line Hotel in Chelsea

New York is expensive and our hotel was no exception. But the High Line Hotel is so quirky and charming, it was a treat to stay there. You step into a walled courtyard full of trees and lush plants…and, surprisingly, a red double decker bus straight out of London. A perfect place for a coffee or cocktail. Our room was decorated with vintage furnishings (like an old rotary phone) and was spacious by New York standards, with a nice sitting area. The hotel is a short walk to Nick’s apartment so it made all our meet-ups a breeze. Chelsea is the coolest neighborhood, close to parks along the Hudson River, lots of restaurants and cafes and charming streets.

What We Did, Where We Ate


  • Walked the High Line Park (a transformed old elevated train track), stopped for a beer and truffle fries at Hearth, then toured Little Island, an imaginative new park built on the ruins of a pier destroyed by Hurricane Sandy.
  • Cocktails at our hotel courtyard and dinner at Left Bank with Nick’s dear friend Alex from Wilmette and Nick’s adorable boyfriend, Daegan. Daegan was right—the Capricci Cacio e Pepe was amazing!


  • Left the kids to do their own thing and took the subway to Brooklyn Heights to reunite with Style Challenger BFF Laura Hine in her cool new ‘hood. The streets are so pretty and serene.
  • Walked along the waterfront through Brooklyn Bridge Park and DUMBO. Very lively with amazing views.
  • Brunch at Vineapple Cafe, Laura’s local favorite.
  • Later, did some solo window shopping in Meatpacking District—Alice & Olivia and Paige Denim were my faves.
  • Early dinner with Emma, Nick and Daegan at Loulou’s (adorable cocktails and the Cucumber Mint Gazpacho was amazing) .
  • Harry Potter and the Cursed Child on Broadway—really fun and magical, the scene changes alone were mesmerizing.


  • Grabbed a coffee and breakfast sandwich from Kobrick’s with Nick and strolled along the Hudson River.
  • Toured the stunning Whitney Museum with Emma (an art school grad and current art director).
  • Walked through Greenwich Village to meet the guys at Washington Square Park. We found the perfect intersection for my mom, Jane Hudson!
  • Brunch at Atla in NOHO with Mexican bites and yummy frozen strawberry margaritas. I must drink all boozy pink drinks New York has to offer.
  • Shopping in Nolita with Emma. Our favorite boutique was the brand new Maguire Shoes. Not only did we each buy a pair of these comfy, stylish Canadian shoes, we met the co-founder (one of two sisters) Myriam!
  • Dinner at Cookshop, just across the street from our hotel, no waiting and a delicious menu.

Tips and Trends

My advice for touring New York City is to just keep moving. Its’s amazing how much you can do in one day! It’s good to have a plan, but be open to unexpected discoveries and detours. Emma and I were shopping and heard this enticing music. There in the Elizabeth Street Garden, amidst the sculpture and flowers, were two amazing violinists performing a free concert. We sat for a little while to listen and relax. It was a lovely interlude.

I’m also definitely a fan of using the subway to get around (no special pass or tickets required, just tap your credit card) and wearing comfortable shoes. On Saturday, I walked 10 miles and was very happy for my “On” sneakers.

The people watching was outstanding. So many creative and diverse people! I saw a lot of crop tops and cut outs (not for me) but the fashion trends I coveted most were 1) casual jumpsuits and 2) oversized white shirts with jeans and heeled or flat sandals. Women of all ages were rocking these practical looks and they appeared effortlessly cool. I think I’ll explore these trends more in an upcoming post.

Okay, thanks for sticking with me, I’m obviously very enthusiastic about this weekend. Of course the best part was hanging with Nick and Emma! I’ll definitely go back soon and look forward to a completely different experience. If you’ve got some favorite NYC spots or tips to share please let me know!

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