If you follow me on Instagram and/or TikTok (if you’re not, you should be!), you’ll know that my mom visited for a weekend in May and a lot of content was produced. No seriously, I was worried that I was beating all of the content into the ground. This was the first trip that she was able to really see New York City, or at least Manhattan. My parents are usually here for utilitarian reasons i.e. moving, assembling new furniture for new apartments, or tournament hopping with my brother. So, as a Mother’s Day & birthday treat, I planned an extravagant (relatively) weekend in the Big Apple for my mom! Below you’ll find an NYC itinerary for four days (I did make a few stylistic changes to make this itinerary more enjoyable if you want to follow along for your own planning purposes, hindsight is 20/20.)
P.S. I also used to do quarterly NYC digests with everywhere I visited and everything I got up to in the city during that season. Should I bring that back?
The Set-Up
When
Christmas in New York City is always a popular choice. The city is decked out in gorgeous wintertime decor and the temperatures are honestly mild for New York! Fall foliage makes October and November equally stunning options. But, I have to make a case for spring in the city. Each year I become even more enamored with April + May. Flowers are blooming, the temperatures are exquisite(mostly), and you beat out the summer tour groups.
Who
I built this itinerary specifically with my mother in mind. In theory, it will be an entertaining trip for anyone who is feeling a lil’ bit fancy and likes good food, fashion, and shopping. I’d also recommend it for folks who have been to NYC at least once before. I didn’t really leave much time for the super touristy NYC bits (Statue of Liberty, Times Square, etc.)
Where
I’m genuinely conflicted about where to stay in the city when you’re visiting. I detest Midtown. Unfortunately, it might be the best area for visitors. It’s central and there are a ton of hotels with ranging nightly rates. This time around we stayed at the Hilton Garden Inn Tribeca location. It wasn’t anything crazy fancy, but the room was clean and pretty spacious for a New York City hotel room. Job done!
If you’re looking for fancy boutique hotels, I’ve been to events at the following and their amenities are truly stunning: 1 Hotel Brooklyn Bridge, Gramercy Hotel, Nomo Soho, The Roxy, Yotel, and Hotel 50 Bowery.
My family usually sticks to the Hilton brand of hotels. I’ve stayed at the Hilton Garden Inn – Park Avenue location and the main Hilton near Central Park. All are great!
How (TO GET AROUND)
The easiest way: the subway. My preferred method: the bus. For convenience: Uber or Lyft, whichever is cheapest at this point. My preference is cabs for on demand rides, but they can be hard to source in some areas. The curb app can be your friend and your foe. For views: NYC Ferry system. For kicks and giggles: the double-decker tour buses.
An NYC Itinerary
Day 1
I like getting into the city early in the morning to avoid traffic, and you’ll have an entire day for exploring.
Light Breakfast + Snack
Butterfield Market
Butterfield Market is one of my favorite neighborhood spots. It’s an upscale market with all the goods. They carry everything from coffee to local NYC baked goods to frozen yogurt. It’s the optimal spot for groups since everyone can grab what they want and go. Where to chow down on everything? There are a few benches outside the Madison Avenue location! If it’s nice out, I recommend enjoying your picks on The Met steps. xoxo and all that.
Morning Activity
The Museum Mile
A mile-long stretch down Fifth Avenue is home to some of the best museums in the world also known as The Museum Mile (The Guggenheim, Museum of the City of New York, The Metropolitan Museum of Art, El Museo del Barrio, The Cooper Hewitt– to name a few) You can expect to spend a few hours at whichever museum you choose. The Met cannot be finished in a day and maybe not even in an entire week. I always recommend checking out the special exhibitions. You won’t want to miss The American Wing, the European Sculptures, and the 19th and 20th Century European Paintings (Monet, Picasso, Degas — you know the vibe.)
Uptown Brunch
Good Enough to Eat (menu) | The Penrose (menu) | Maman (menu) | Green Kitchen (menu) | EJ’s Luncheonette (menu) | Miriam (menu) | Jacob’s Pickles (menu)
Early Afternoon Activity
My mom and I love a shopping moment even if it’s just a window shop. The stores in NYC are absolutely exquisite so if you’re into the designer scene you’ll want to take a stroll down the Upper East Side’s most upscale Madison Avenue. The iconic street is home to all your favorite designers (i.e. Bottega Veneta, The Real Real, Celine, Goyard, Fashionphile, Fendi, Ralph Lauren) It’s the perfect activity to walk off your brunch and you can grab coffee from one of my favorite coffee shops, Ralph’s.
Afternoon Activity
At this point, I would highly suggest making your way back to your hotel. If you’re staying in midtown, you could walk all the way down Madison Avenue from the Upper East Side down into the mid-50’s. You might run into your hotel on accident. You’ll also pass The Plaza if you walk back to 5th Avenue at 59th St.
After you check in, you can take a few moments to collect yourself and rest. Next up, I’d make a case for heading all the way down to the Financial District and walking around the area around golden hours/sunset. The west side is home to the stunning Brookfield Place (if you want more shopping and upscale dining options). If you go east, you can find yourself in the South Street Seaport district. One of my favorite bookstores, McNally Jackson, is located on this beautiful street.
If you plan out your walk just right, you can also pass by The World Trade Center, 9/11 Memorial, New York City Hall, Battery Park, and the Oculus. All very popular for visitors and worth a visit/look.
HAPPY HOUR | DINNER
If you want to stay in the Seaport/FiDi area: (I don’t really recommend unless you just want to do drinks and apps, the food in this area is not my favorite.) Sunday in Brooklyn @ South Street Seaport(menu) | 1803 NYC (menu) | Liberty Bistro (menu) | Industry Kitchen (menu)
If you don’t mind zipping up to the West Village: Aurora SoHo(menu) | Rosemary’s(menu) | Pinto Garden (menu) | Bobo (menu) | Joseph Leonard (menu)
Day 2
Breakfast
Some people aren’t breakfast people and I guess that’s okay. Even if you aren’t a fan of a big breakfast, I can’t recommend a good New York boulangerie enough. Grab a croissant and coffee and enjoy in any park of your choice.
If you’re a:
“I want a bagel everyday I’m in New York” person, try these spots: H&H (menu), Tompkins Square Bagels (menu), Black Seed (menu), Bagel Pub(menu)
“pain au chocolate + a cappucino, plz” person, try these spots: Gotan(menu), Orwashers Bakery(menu), L’Appartement 4F(menu), Think Coffee(menu), Dominique Ansel Bakery (menu)
“two eggs, any style + a stack of buttermilks” person, try these spots: Friend of A Farmer(menu), Clinton St. Baking Company(menu), Peaches Lewis(menu), Penelope(menu)
“oatmeal + green juice” person, try these spots: Cafeteria (menu), Union Square Green Market (info), Le Pain Quotidien (menu), Pressed Juice(menu)
Afternoon Activity
A big reason that I advocate for using the subway is it will be so much easier to quickly transverse across NYC. You can quickly get to any borough and back using your feet and Google Maps. One of my favorite neighborhoods to wander in Manhattan is the West Village. You can start at Washington Square Park (aka the unofficial official epicenter of NYU’s campus) and head west. The Friends apartment and Carrie’s Walk Up from Sex and the City are always fun to see and only a little underwhelming. There are a lot of independent shops that are nice to pop into and the neighborhood also has some of the best restaurants in the city.
If you’ve already done the West Village thing, I have to make a case for one of the Brooklyn neighborhoods. Williamsburg (the hipster capital of NYC), Greenpoint (Williamsburg’s less crowded cousin) and/or Fort Greene and Cobble Hill (where I’d want to buy a brownstone). If you’re into bookstores, check out Books Are Magic or McNally Jackson. Brooklyn coffee shops are elite simply because they are spacious and aesthetically stunning, try Devoción, Partners, or Homecoming. Vintage shopping is another popular destination. It’s not my personal expertise but I’ve heard positive reviews for Awoke Vintage, The Attic, and L Train Vintage.
Late Afternoon Activity
At this point, you’ve probably done a ton of walking and the exhaustion is probably starting to creep in. NYC has a lot to offer and one thing I don’t think visitors take advantage of is the spa. I set up a facial for my mom at Chillhouse. I did a collaboration with them earlier in the year and had a really great experience. There’s also AIRE and HEYDAY. Spa de La Mer is also a luxury destination to ward off the chaos of the city. Personally, I am here for a little bit of pampering after a long day of touristy shenanigans.
If the spa isn’t your vibe, you can also wind down with afternoon tea. My mom and I finally got the chance to do afternoon tea at the very iconic Plaza Hotel. Overall, I genuinely think it’s worth the cost if this is your kind of thing. We had the best tea, ate some delicious finger sandwiches, and wore super cute outfits …the dream afternoon. Make sure to make reservations in advance as I think they can fill up on weekends. There are some other very cute tea options in the city to check out as well: Lady Mendl’s, Prince Tea House, and Alice’s Tea Cup.
Dinner
My dinner recommendations are probably the shakiest as I’m much more of a brunch person than a 7:30pm reservation kind of gal. You can go casually iconic with Kat’z Delicatessen or its Lower East Side neighbor, Dudley’s. Ruby’s Cafe is an incredibly popular spot in a lot of the trendy Manhattan neighborhoods. Bubby’s is also my favorite restaurant in the Tribeca area.
Evening Activity
Nights in New York City are truly magical. As a permanent resident, I don’t experience nearly enough of the dreamy nights. The live music at Django is unmatched (I attended an event in this space and it is gorgeous). You can catch a comedy show, take a night time cruise around the island, or head to Williamsburg for drinks and dancing at Freehold. Musical theater fans can always catch a show on Broadway (or off). There are so many athletic teams that there’s almost always a game to catch at MSG or The Barclays. If cocktails are your speed, Patent Pending has the best cocktails.
Day 3
Morning Activity
I always recommend the Union Square Greenmarket (the Upper West Side one is also great!) to grab a quick and easy breakfast bite. You can also grab one of my favorite lattes from Devoción and a bagel from Gramercy Bagels or Bagels and Schmear.
Since we were staying in Tribeca, I routed our walk up through central SoHo, passing by the Washington Square Arch, and all the way up 5th Avenue until hitting 14th St. You’ll also find the very iconic Strand Bookstore and Chelsea Flea Market in the area. Madison Square Park which is a few streets north of Union Square and is home to the OG Shake Shack: the perfect place to enjoy lunch.
Early Evening Activity
Take it easy! You’re in for a long night. Put on something snazzy. I love to dress up for a night at the ballet, or the opera, or the theater!
Dinner
After trying very hard to find a dinner and drinks combo that didn’t make me want to gouge my eyes out, I have to say it’s just gonna be tough. The restaurants in this area are not very good. That being said: chains are a safe bet. The Smith hasn’t failed me yet and there’s a handy location in Columbus Circle that’s pretty close to the Lincoln Center. I’d heavily consider some of the restaurants in the upscale hotels in the area. It’s going to be expensive, but reliable — heavy truths! Jams at 1 Hotel Central Park, Cucina 8 1/2, and The Terrace in The Edition Hotel all look promising.
Night Activity
Immerse yourself in the arts. It’s probably one of my number one recommendations when anyone visits the city. The talent in this city is mind blowing!! Moulin Rouge was excellent and high energy. Want to see Samuel L. Jackson in a play: consider the The Piano Lesson. The New York City Ballet, American Ballet Theatre, and Alvin Ailey(Nov 30 – Dec 24) are great if you want to experience professional dance performances. If you enjoy a flair for the dramatic, consider the Metropolitan Opera.
Day 4
Morning Activity
The other activity I always recommend for visitors (even if they’ve already done it before) is a walk across the Brooklyn Bridge at either of the golden hours (1-2 hours after sunrise or before sunset). I typically recommend a ferry ride from 34th St down to DUMBO and then heading across the bridge back into Manhattan. You can jump on the 6 and head uptown super easily.
DUMBO has a few excellent coffee shops: Butler, %ARABICA, and a new Devoción(!!). The Brooklyn Flea is held on some weekends in DUMBO and is worth a trip. Los Tacos No. 1 has the best tacos in the city, seriously. And, Time Out Market has a bunch of staple NYC eats all in one spot.
Brunch
After we spent some time in the DUMBO area, we headed to a boozy brunch at BoBo in the West Village. It’s one of my favorite spaces in the city with a stunning French countryside house vibe. 110% would recommend.
Afternoon Activity
Baseball season is almost done, but if you’re catching this blog post in spring or summer. Catch a Mets or Yankees game. You are guaranteed an entertaining time. Both will take you out of Manhattan and into one of the outer boroughs I haven’t mentioned quite yet, The Bronx and Queens. Late August and Early September is also a great time to catch a tennis match when The US Open makes its yearly return to the USTA Billie Jean King National Tennis Center.
If sports aren’t your vibe, The Bronx Botanical Garden and Bronx Zoo are popular attractions. I recently made my way to the Museum of the Moving Image in Queens and had a blast.
Dinner
It’s a personal goal of mine to start trying restaurants outside my base camp borough of Manhattan. Here are some restaurants that I have my eye on and a few I’ve been to before!
Queens: Citrico Cafe – Astoria, Sugar Freak – Astoria, Loukoumi Taverna – Astoria, Casa Enrique – Long Island City
Brooklyn: Kokomo – Willimasburg, Taqueria Ramirez – Greenpoint, Lilia – Williamsburg, The Four Horseman – WIlliamsburg, Lowerline – Prospect Heights, La Vara – Cobble Hill, Elsa(drinks) – Cobble Hill
I know that there’s no way to see everything that the city has to offer and I live here. But, four days is plenty to see NYC’s top hits especially if you’ve already been here. You’ll find even more recommendations on my instagram story highlights and on my TikTok. Happy traveling!
