You can’t help but feel your most alive in a vibrant place like New York, the city that never sleeps. It embodies that feeling of endless possibilities, sprawling beauty in places like Central Park, culture on every corner, food for every kind of foodie, and a shopper’s mecca with every designer and label one could dream of. It’s the backdrop to countless movie sets and beloved shows, letting us bring a piece of it to our home. It’s no wonder my daughter romanticized this city from a very young age and it quickly went to the top of a very short list, for our mom/daughter trip. We booked our tickets months before and excitedly dreamed about Manhattan in the spring.

But I’m not going to lie; the second the tickets were booked a fear swept over me. While I have experience traveling big cities, in the last two decades, more often than not it had been with my husband. Somewhere along the way, I became a timid traveler and it was something that really bothered me. And since there’s no better way to overcoming anxiety that facing it head on, I knew I had to step out of my suburban comfort zone and navigate the streets of New York. I quickly familiarized myself with any necessary apps, put together an itinerary, and packed comfortable walking shoes because from my study abroad year in Lyon, France, I was taught to hustle through the streets of a big city, so as to always look like you have a purpose and know where you’re going.

Before I knew it, our middle of the night wake-up call chimed and we were on our way to a very early, direct flight from Portland, Oregon. After we landed at JFK, as our Uber driver drove us through Manhattan to our hotel, a curiosity piqued and our adrenaline started pumping. We immediately dropped our bags in the room and set out to explore. Having arrived in the late afternoon on a Friday night, the work day was ending, the streets were bustling, and restaurants and bars were quickly brimming with those ready to start the weekend. Staying in Midtown, we cruised through the streets on foot and soaked in the views that were starkly different from home. We saw iconic landmarks, snapped plenty of photos, and toured until our tired feet and big appetites let us know it was time to call it a day. But not without some of NYC’s most famous pizza from Joe’s Pizza! Within a few hours of landing, our hearts were already full, feet tired, and our trip had only just begun!

This trip is one that I’ll forever hold close to my heart! With my daughter we made wonderful memories experiencing the City together. It’s a place where I can’t wait to return and would recommend to any mom for a mom/daughter trip. And, it stripped that timid traveler in me and I regained a confidence that furthermore, even sparked the travel bug more than ever. Below is our experience that if you’re planning a trip, I hope you find it helpful.

 

Lodging:

Refinery Hotel

We chose to stay in Midtown and I would highly recommend this location. It was very central to many tourist spots, and easily accessible to walk, Subway, or Uber your way around town. Our hotel was recommended by a friend and for good reason. I would stay there again and appreciated its cleanliness and proximity to everything.

Food:

While I’m a self-proclaimed foodie, my daughter is not. And while there are restaurants where I’d love to dine, this trip was geared more towards sampling more traditional food like bagels, pizza, hot dogs, and simply grabbing a bite wherever looked good, so as to not be on too rigid of a schedule. In fact, one of our favorite meals, was after a long day of traveling there and we grabbed a pie from Joe’s Pizza, went back to our hotel room and indulged in that cheesy goodness while watching Emily in Paris. It was perfect!

Where to eat:

Joe’s Pizza – We ate at the Midtown location, but their original spot is in Greenwich Village.

Eataly – There are locations throughout the city; we enjoyed the one near the Freedom Tower the most, but is a great option for lunch, dessert, or to sit down and enjoy a cappuccino. Had my luggage allowed, I would have brought home all the pasta and olive oils!

 

Jack’s Wife Freda – We stumbled on this Mediterranean gem of a restaurant when shopping in Soho. The food and drinks were great, and reasonably priced.

Ralph’s Coffee – Iconic, need I say more. And yes, we came away with a couple of their green baseball hats and are the best souvenir from a memorable cappuccino break. I enjoyed coffee from their location across from St. Patrick’s Cathedral in the most darling Ralph Lauren vintage, green coffee truck, and we enjoyed a sit-down cappuccino break in their restaurant location in the Ralph Lauren store on Madison Ave. There was a short line, but since we were only two, we were able to be seated almost immediately. It would be worth the wait; their coffee is really good!

Burger and Lobster Bryant Park – We enjoyed dinner here just before we saw the Broadway show, & Julia. The meal and ambiance were very enjoyable! I only regret I didn’t get the lobster roll, but the burger was fantastic!

Zucker’s Bagels and Smoked Fish – A bagel institution of NYC, I could eat every breakfast there! The line was very long, but without a doubt, worth the wait and they get through their orders quickly. I had the Traditional on a Sourdough Bagel and my daughter enjoyed the Avocado Toast. Both were chef’s kiss!

Casa D’angelo – My daughter was adamant on having an Italian dinner in Little Italy and I easily obliged. We really enjoyed our meal there! She had the Tagliatelle alla Bolognese and it was full of depth and beautiful flavor! I enjoyed the Risotto ai Funghi Selvatici and it was equally as wonderful. The cozy ambiance was an added bonus!

Culture Coffee – This was a recommendation for the best chocolate chip cookies from someone who knows the restaurant scene in New York very well. These were truly the BEST chocolate chip cookies we’ve ever had and I only wish I bought a dozen to bring home!

Throughout the trip, we also hit up places like Pret a Manger, Ole & Steen, and a food truck just outside of Central Park, for some quick meals.

 

Where to shop:

We shopped hard! How can one not in NYC on a mom/daughter trip? Coming from Portland, which is limited in retail and I’m a brick-and-mortar type shopper, I could not wait to step into a variety of stores I’d only ever seen online. I had one rule in that I wouldn’t shop at a store that I could find back home, which wasn’t hard. I had my list and worked my way up and down Madison Avenue, 5^th Avenue, and Soho. Filling our suitcases were goodies from the following boutiques or stores:

Tiffany and Co. – This was a must and one of the first stops we made for my daughter’s 18^th birthday gift. She was living her best life in their landmark location. She walked away with not just a little blue box, but a memory I hope she’ll cherish forever! And while we were there, ahem, I had to try on a few pieces I had been eyeing for years. After encouragement from my husband to pick out my Mother’s Day gift, I decided on a lovely piece that’s been living rent-free in my head for years and years. While my daughter did walk away with her blue box and actually left the store wearing her new necklace, since we’re from Oregon where we don’t pay sales tax, I opted to ship mine home to avoid that additional 10% markup.

La Ligne – I have a couple of dresses from them that have stood the test of time, so I couldn’t wait to try on and feel some of their knitwear! I walked away with a bright red sweater, that I never would have bought had I not tried on in the store and was convinced by the sales associate that the color looked great on me. Not usually one who wears red, that sweater has already been worn multiple times since I’ve returned and is quite possibly my favorite ever.

Tuckernuck – The boutique is as cute as the name itself. The sales associates were so friendly, helpful, and I was just smitten over their East Coast accents! I came home with a couple of classic, yet unique pieces that I know will be in my closet for years!

Sézane – Bien sûr! How could I not go to Sézane in New York? On foot we raced from Lower Manhattan to the boutique’s location in Soho to make sure we could make it before closing. There was a line to get it, but the wait was short. The selection did feel limited, but I still managed to find the sandals and earrings I’d been eyeing online.

Ruti – I was delighted to stumble on their boutique. The pants are as good as the reviews are. Truly the most comfortable and flattering pants!

COS – A minimalist vibe, there were some fun options!

New York Public Library Gift Shop – As a cookbook and lifestyle coffee table book collector, the gift shop has some really great options for both, pertaining to New York of course. When you buy a book, they’ll also stamp it with the NYC Library emblem, which I thought was a nice touch.

Feste – The cutest home goods store in Soho! I walked away with a gorgeous book on New York from a favorite publisher, Rizzoli, as well as some other fun NY souvenirs.

My daughter’s shopping included Aritzia and the location we visited had a huge selection, including some fun NY Yankees baseball caps, which we spotted on so many well-dressed women in Manhattan. So naturally, in an effort to look like a chic New Yorker, I brought one home and have already worn it multiple times. She also enjoyed a little Zara shopping.

What to do:

We made sure to allow plenty of downtime and exploring, but balanced it with seeing lots of iconic sites.

 

Arrival Day:

• Times Square
• Rockefeller Center
• Explored Midtown
• Joe’s Pizza

Day 1:

• Statue of Liberty and we booked tickets through Statue City Cruises (We took the ferry out and then walked up to the Pedestal.)
• Eataly for lunch and cappuccino break
• 9/11 Memorial (We did the 90-minute tour and it was well worth it! Then we toured the museum.)
• Soho shopping and dinner at Jack’s Wife Freda

 

Day 2:

• Mass at St. Patrick’s Cathedral
• Tiffany and Co. Shopping
• Madison Ave Shopping
• Ralph’s Café for a small lunch
• Dinner at Burger and Lobster Bryant Park
• Broadway Show – We saw & Juliet and it was fantastic, I highly recommend it!

Day 3:

• Breakfast at Zucker’s Bagels and Smoked Fish
• Central Park
• New York City Public Library
• Bryant Park
• Washington Square Park (There was heavy police activity from an incident, so sadly was not able to spend time there.)
• Little Italy – Dinner at Casa D’angelo

Day 4: Departure Day

• The Today Show in the morning
• Grand Central Station
• Bryant Park

Transportation:

I always believe a city is better to be seen above ground rather than under, so we walked as much as possible. Although, to get you across town quickly, the Subway is always a good option. At night, we always took an Uber or taxi, except from the Broadway show as it was so close to our hotel. **Our hotel arranged for a taxi to take us to JFK when returning home. There is a flat fee of $84 between Manhattan to JFK and it was much less expensive than ordering an Uber.

Tip:

While we almost always felt safe, taking common safety measures for ourselves as well as our belongings, I attached my phone to a crossbody strap. This allowed for safe and easy access to my phone for not only taking pictures, but using Google Maps, as well as order Uber rides.