Ask me about New York

Hi Sandy, thanks for reading! I haven't made it up to Chatham yet so I can't vouch for it personally, this list sticks to the five boroughs. A dedicated gluten free bakery in that part of New York sounds promising though. If you try it, come back and tell me how it was!

Great question, Erin! For a classic evening date I'd go to the original Dante on MacDougal, that's the one with all the history and it's pure magic after dark. The West Village location on Hudson is bigger and easier for walk ins, so it's my pick for pre dinner drinks. Have the best night!

Ha, no, not gone anywhere, just out here documenting every borough one bridge walk at a time. Thank you for the kind words, that means a lot. DUMBO's one of my favorite excuses to drag people across the Brooklyn Bridge and I don't plan on stopping.

Hi Jo, that sounds like such a good trip, camp nostalgia plus NYC with the kids first is a great combo. Follow the tips on pacing and you'll be fine, New York can be a lot if you try to cram too much in. Have fun getting reacquainted with New Hampshire after!

Oh thank you so much for the heads up! I'll get that updated right away -- really appreciate you letting me know!

Oh how fun! I hope you have the most wonderful trip -- this city really is magical. Enjoy every second!

That one's not actually on this list, I don't recommend the Gansevoort Meatpacking in this guide at all. Might be a mix up with another site. For a graduation trip I'd point you toward the neighborhoods I actually cover here, Upper West Side and Upper East Side are both solid picks.

Oh that's so helpful, thank you! I love when readers help me keep things accurate -- will update the post!

I haven't seen that one in years, honestly, but it's a fun call out. My list here is really the ones I think are the most iconic NYC holiday watches, but there's room for plenty more on the list of movies filmed here during Christmas.

Thirty years and still looking up, I love that. You're right that most people don't, myself included on a rushed Tuesday. Standing to the edge and out of the way is exactly the move, that's not being a tourist, that's just having manners while you gawk. The buildings deserve it.

I'd say no because the decorations come out in full force right after Thanksgiving, not before. Cheers!

Hi Magda, thanks so much for grabbing the guide and happy sweet 16 to your daughter, what a fun way to celebrate!

Since you’ll be here Friday through Monday, I’d recommend front-loading some of the “big ticket” holiday sights (Rockefeller Tree, 5th Avenue windows, Bryant Park Winter Village, Central Park skating) on Friday and Monday. Those are busiest on weekends, so you’ll have more breathing room if you do them on the weekdays.

Saturday and Sunday are perfect for experiences that can handle the crowds better, like exploring SoHo and the West Village, walking the Brooklyn Bridge into DUMBO, or catching a Christmas show in the evening (the Nutcracker, Rockettes, or a Broadway performance). If you’re interested in the holiday cruise, I’d book that for Saturday evening – it’s festive, special for a birthday, and doesn’t feel overwhelming even when it’s busy.

Think of it this way:

Friday (arrival/easing in): West Village brunch → Chelsea Market/High Line → Hudson Yards lights → Macy’s windows → Christmas-themed dinner.

Saturday (weekend energy): Brooklyn Bridge/DUMBO → 9/11 Memorial → holiday cruise.

Sunday (big shopping + show day): SoHo shopping → Rubirosa pizza → Katz Deli → Christmas performance.

Monday (less crowded): Central Park skate + walk → 5th Ave windows → Rockefeller Tree → Bryant Park Market → Summit One Vanderbilt for a big finale.

That way, you get the best balance – avoiding the worst of the weekend lines, while still soaking in the holiday buzz when it adds to the atmosphere.

Hope that helps and don't hesitate to reach out with more questions etc.