Our Long Weekend in New York

We just got back from spending a long weekend in New York City! Dave and I have been wanting to plan a New York weekend trip for so long. I hadn’t been back to visit since the fall of 2019, which was entirely too long! That also meant that we had never spent any time together in a place that we both love so much.

Since we started dating in the middle of 2020, this was actually one of our first little weekend getaways together. Multiple weeks-long road trips? Check. Remote AirBnB stays? Check. Traveling for concerts? Check. Family vacations and friends’ weddings? Check, check. But this was the first time we took a solo weekend trip — just the two of us, not even Marley! It was so good for the soul.

Having used to live there, we skipped all of the touristy stuff like the World Trade Center, Statue of Liberty, Times Square, Wall Street, etc. and really just lived like local New Yorkers. It was the perfect weekend itinerary for us since we’ve both spent so much time there. So if you’ve already checked off most of your list on past trips, I hope this helps with planning what to do in New York for the weekend.

Two days in New York is never enough in my opinion! A three-day weekend in NYC is probably the perfect sweet spot. We stayed for four nights (Thursday-Monday) and were absolutely exhausted by the time we boarded our flight home. Other than walking a ton and staying up later than usual, it probably had a lot to do with the fact that we were eating and drinking our way through the city for four days. It takes a toll!

Is a week in New York too long?

Of course, if you have the time to spend more than a weekend in New York, by all means, DO IT. Spending time in the city is always a good idea, but you’d have to find a room with a bigger space. I’d probably go the Airbnb route or make sure your hotel isn’t one of the typically tiny hotel rooms.

What’s the best area to stay in New York for a weekend trip?

We stayed at the Moxy Hotel in the East Village, which we actually didn’t love. I didn’t realize it was one of those ‘pod’ style hotels and our grand total for four nights ended up being $2,600, which felt outrageous considering you could only access the full-sized bed from one of its four sides.

There are plenty of gorgeous hotels uptown, but if you want to stay downtown, it’s a lot harder to find a great spot. The Marlton and The Ludlow would be my top recommendations. I also really liked my stay at Hotel Indigo on the LES, but that was back in 2016 so I’m not sure if it’s changed at all.

A few more downtown hotels I’ve been wanting to try: The Beekman, Public, The Bowery

How to Spend a Long Weekend in New York

I’ll share our loose day-by-day itinerary, but as I said, we mainly just are and drank our way through the city. If you’re a first-timer or are wanting more shows or museums, this is not your itinerary. This is for those of you that been before, but have 3 days in NYC and are wondering where to eat and what to do!

I wanted to show Dave my old stomping grounds, revisit some of my favorite old spots, and try some new finds, too!

Thursday

Once we landed at LGA and got in a cab, we dropped our bags at our hotel and grabbed lunch at Little Ruby. Cute little Aussie cafe!

We each had some work to do in the afternoon, but after we got cleaned up, we went to Rosie’s right when they opened at 5 pm. The best margaritas (only $10 during happy hour!) and I love their food, too. We had a few appetizers off the HH menu since we had a late dinner reservation.

We walked over to The Wren, one of my old go-to bars, and had a couple of cocktails there.

For dinner, we made our way over to Emmett’s on Grove. Dave actually grew up with Emmett so it was fun to hang with him and some friends at his newest spot! (Emmett’s Pizza is his first restaurant!)

Friday

On Friday, we woke up and walked over to my favorite bagel place, Thompkins Square Bagels. There are now multiple locations, but my favorite will always be the original on Avenue A. I used to live right around the corner! We sat on someone’s stoop, ate our bagels, and drank our OJ.

Swung by Ninth Street Espresso for a coffee before going on a little walking tour of the three apartments I called home in the area. It was fun to pop into shops that are still there and see what restaurants have remained the same, as well as see what’s opened up instead.

Where to stop and shop… Exit 9 Gift Emporium

We grabbed lunch at Dudley’s, which is always a favorite. From there, we wandered into NoLita, which was always my favorite little neighborhood in NYC. The best shops like Sezane, Clare V, Diptyque, and Le Labo, as well as some independent little boutiques. Faherty, Marine Layer, Everlane, and The Ordinary have all opened shops right there, as well.

I love Le Labo’s Rose 31, but finally bought The Noir 29 to add to my perfume collection!

We grabbed cereal milk soft serve at Milk Bar for a little afternoon treat before heading back to our hotel to get reading for the evening!

After getting showered, we walked to Claudette for a couple of apps and a glass of wine. Can’t beat their pommes frites and whipped chevre! They also have one of my favorite Cotes du Rhone wines by the glass — Famille Perrin.

We had dinner at Olio e Piu, which was one of my favorite casual go-to’s back in the day. I used to work on 8th Street, so it was fun to walk around the area.

We saw a show at The Comedy Cellar after dinner (where we were seated in the front row ☠️) and then caught some live music at Groove.

Saturday

We started off the day by grabbing an Uber down to Black Seed Bagels in NoLita. A second location has since opened closer to our hotel, but I wanted to take Dave to the original. It’s definitely walkable, but since it was raining, we decided to stay dry.

After breakfast, it was merely misting so we bought some umbrellas and wandered around Soho to do some shopping. I bought a few things at Mango and so wish we had a store here in Chicago! We also browsed through the Polo Ralph Lauren store, Canada Goose, and a bunch more.

I had bought tickets to the Met on Saturday and planned to have lunch uptown, but it started POURING. It was kind of miserable to be out and about so we ended up taking shelter at Dante for lunch.

We ended up going back to the hotel after lunch and relaxing for a bit. The Met would have been the perfect rainy day activity, but we were feeling beat. Getting on the train to get uptown felt like too big of an ask.

After getting cleaned up, we went to Beyond the Pale for a drink before our reservation at Jac’s on Bond. HIGHLY RECOMMEND getting a reservation at Jac’s on Bond for cocktails next time you’re in NYC! (It’s in the old The Smile space.) They had plenty of N/A mocktails on the menu, but their cocktails were out of this world. The Caprese Martini was unlike anything we had ever seen or tasted!

We had dinner at Che Li in the East Village and OMG IT WAS INCREDIBLE! We ordered a ton and every single dish was outstanding. The Shrimp was so beyond though… it was somehow melt-in-your-mouth and mouth-wateringly-addicting at the same time.

After dinner, we popped into Sing Sing next door for a little karaoke before heading home for the night.

Sunday

On Sunday, we walked from the East Village up to the Upper East Side and Central Park. Walked up 5th Avenue, past the Empire State Building, Bryant Park, New York Public Library, and Rockefeller Center on the way to the park.

Where to stop and shop… Cha Cha Matcha, Villa & House

We walked up to Ralph’s Coffee on the UES, but it was totally slammed so we ended up not waiting in line. Per Dave’s request, we grabbed lunch at a local Jewish deli, but Le Charlot would have been my choice.

We lounged around in Central Park before taking the subway back downtown in the afternoon. We grabbed a coffee at Bluestone Lane in St. Marks Square after getting off the train. I remember when the original Bluestone Lane cafe opened in the West Villag many years ago. It’s neat to see all of the success they’ve had since!

We got cleaned up for dinner and walked over to the West Village for dinner. We got a reservation at Saint Theo’s per Dave’s co-worker’s recommendation and it was honestly one of the worst dining experiences either of us have had. Very cute patio and decor inside, but the food and service left a lot to be desired. The apps were average at best, but one of our simple pasta dishes was inedible. How do you mess up pasta?? Not to mention, we waited over an hour between our appetizer and main courses. Beyond overrated!

Monday

On Monday morning, Dave walked over to get his final bagel fix at Thompkins Square Bagel’s 2nd Ave outpost, and I went over to get my favorite smoothie at Juice Generation. Joyful Almond, add spinach, no sweetener. So good!

We went to the airport a little earlier than needed so we could get situated in the Admiral’s Club before Dave had a few work calls. And then a quick flight home!

It truly was such a perfect long weekend in New York and I already can’t wait to plan my next trip back.

Getting Around During Your Long Weekend in New York

We walked pretty much everywhere, save for a few Ubers when it was raining or late at night. Luckily, I am very familiar with the subway, but I think Google Maps makes it pretty easy for tourists to navigate the Metra system these days. New York traffic can be brutal, so I’m always in favor of walking and/or taking the subway!

To view some more NYC content on the blog, head toward these posts: Spending a Weekend in Brooklyn, Row Boats in Central Park, Vueve Clicquot Polo Classic, 2013 Weekend in New York

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