Valentine’s Day in the City
A Whirlwind NYC Adventure

We recently took a trip to New York City, this time for an entire week. It was Angela’s fourth visit in the last year and a half (fifth overall) and my third as a tourist. We spent most of our time in Manhattan, as we did on previous trips, but finally journeyed to one of the other boroughs. About half of our travel was booked using airline miles.

Each trip to New York City has been a unique experience with echoes of familiarity. We try some new things, we partake in some activities that are reminiscent of times past, and we return to our favorite spots. Most importantly, we try to act like we’re not tourists even though we definitely are. I love the city and Angela loves it even more than I do – that’s why we continue to visit.

Planning (and booking) the trip

Our last trip to NYC as a couple was over Valentine’s Day in 2018. It was a surprise for Angela – she didn’t know we were going somewhere until 24 hours from departure and didn’t know where we were going until we were on the way to the airport – and it was our first time traveling in luxury. We flew JetBlue Mint, stayed at the St. Regis NYC and the Park Hyatt NYC, and spent the entire time relaxing without a care in the world.

This trip was going to be different. We’d be gone for a week, meaning I’d need to work in the early mornings and evenings. I was hoarding Marriott Rewards points for luxury stays at properties that we haven’t previously visited so we’d be paying cash for lodging even though we still wanted to stay in Midtown, a notoriously expensive part of Manhattan. Finally, we wanted to maximize our time in the city so we needed to take that into consideration alongside award availability when booking our flights.

With these things in mind, and the idea that I wasn’t trying to best our previous luxury trip, I set out to start booking. As with all of our trips, I started with the flights.

Flying west to east across the United States is tough, especially on a transcontinental flight. First, you “lose” three hours because of time zone changes. Combine that with a five hour flight and you’re looking at a day that is wasted on travel. With that in mind, I knew we’d be flying direct from LAS-NYC on the outbound. There are a few airlines that fly that route with a business class cabin, but the clear winner in terms of product is JetBlue Mint. Luckily, it is generally affordable as far as domestic transcontinental premium class seats go, sometimes getting as low as $449 each way.

I didn’t want to pay cash for the flight if I could avoid it. As such, Angela applied for the JetBlue Plus credit card when we were booking a different JetBlue flight. At the time, the sign up bonus on the card was 60,000 points. On top of that, Angela earned 6 points per dollars on the flight purchase we made and eventually earned points from flying the itinerary we booked. From this activity, we had enough to book our LAS-JFK flights for 83,600 TrueBlue points + $11.20. We booked early enough that we were able to choose the throne style seats in the second row to maximize our experience.

I had a very specific itinerary in mind for our return to Las Vegas as I wanted to try American Airline’s Flagship First offering, including the Flagship First Dining experience at JFK. I set availability alerts via ExpertFlyer for February 17th to the 21st. Eventually, two seats in first class opened up on the JFK-LAX route and I was able to book JFK-LAX-LAS in Flagship First followed by a short economy segment. A few months later, domestic first class opened up on LAX-LAS and American Airlines moved us into the premium cabin after a quick phone call. This booking cost 100,000 American AAdvantage miles + $22.40 which we generated by signing up for the Citibank AAdvantage Platinum Select card, among other activities.

I considered a variety of options for lodging and looked at a plethora of different offers, including those through a Virtuoso agent. I settled on the JW Marriott Essex House. It has an executive lounge, so I’d have somewhere to work, is located on the southern edge of Central Park, and is part of the Marriott portfolio. It was somewhat serendipitous because I stumbled upon their Long Term Stay rate by accident and it was considerably lower than any other property in the same tier in all of Manhattan. The rate did not show on the comparison pages, but appeared when I clicked through to the property. In addition, I booked through TopCashback when they were running a 10% back promotion to save a bit more cash.

An excellent flight and an unpleasant arrival

Our outbound journey started early with a 4:45 AM departure from our house in preparation for a 6:30 AM flight. We scheduled car service through the company we generally work with, Personal Sedan Service, West Coast. Our driver was at our house ahead of time and we were at the airport in about half an hour. Security was empty and we were at our gate ten minutes after being dropped at the front of the airport. Unlike most of our journeys, this one didn’t start with a trip to The Centurion Lounge because they don’t start serving hot breakfast until 6AM and we knew we’d be getting good food and coffee on the plane.

JetBlue Mint continues to be an amazing product. We were the first people on the plane and, after quickly stowing our bags, were offered our choice of pre-departure beverages. I opted for coffee while Angela chose to imbibe some sparkling wine to start the day. Shortly after take off we were asked for our meal choices – in Mint you’re offered six dishes and asked to pick three. Between the two of us we sampled:

  • Fresh Fruit (which included kiwi, my favorite)
  • Red Wine Poached Pear with Yogurt and Granola
  • Chicken Sausage (which doesn’t count towards your selection of dishes)
  • Cinnamon Roll Bread Pudding (Nick)
  • Cheese & Chive Biscuit Sandwich (Angela)

Every single item we were served was delicious with the poached pear plate being particularly sublime. I chose to have my meal accompanied by an Americano whereas Angela’s beverage of choice was a cappuccino. Both were surprisingly delicious given how rare it is to receive a good espresso drink on a plane.

The rest of the flight passed without incident besides some minor turbulence on our descent into New York City. I was able to get copious amounts of work done thanks to the free and fast in-flight WiFi and even managed to play some Zelda: Breath of the Wild on my new Nintendo Switch during the journey. We arrived at JFK after an extremely comfortable five hours, walked down the jet bridge that was partially covered in snow, and strolled the twenty minutes to the Terminal 5 taxi stand. We grabbed a taxi into Manhattan, our preferred mode of transport from JFK, and quickly checked in to our room.

On the day we arrived, the streets were covered in grey slush and it was below freezing. We got splashed by passing cars because our driver refused to go around the block to drop us off at our hotel and made us get out and cross the street carrying our bags, so we decided to call it an early night after picking up some water and snacks from a nearby CVS. We ordered room service, grabbed coffee from the Executive Lounge, and watched some documentaries on Netflix as we prepared for the next couple of busy days.

Instagram friends, delicious food, and a new cultural experience

We awoke the next day to cold weather and, thankfully, no precipitation. The sun was shining as we left the hotel for our first trip to Brooklyn. We were particularly excited because we were meeting up with a friend we made via Instagram.

How exactly does one make a friend via Instagram? Well, it starts with posting pictures of our dog, Mr. Fitzwilliam Darcy, on an account we created to share photos and videos of him. Creating that account led to us interacting with other dachshund accounts on Instagram and eventually getting to know the people behind the dogs. We corresponded with Noodles and his owner, Lori, extensively over the last year and developed a rapport. I reached out to Lori to see if she wanted to meet up after I finalized our trip itinerary and she was gracious enough to say yes!

Lori sent us directions to a spot convenient for her and she warmly greeted us shortly after we got off the train. We said a gentle hello to Noodles but were careful to maintain our distance until he got to know us. While it was tough because he’s so darn cute, we knew from Lori that it was the appropriate thing to do. We took a brisk walk around their neighborhood and chatted about Noodles’ origin story and how Lori ended up with him.

Luckily, he warmed up to us by the time we finished our walk and we were graced with the opportunity to give him some pets and snout rubs before parting ways. He also greatly enjoyed the treats that Fitz sent his way from our local pet boutique.

While it was time for Noodles to rest, Lori joined us for a treat at Little Cupcake Bakeshop, our favorite bakery in the world. Angela and I enjoyed our favorite cakes, the Brooklyn Blackout and Dreaming Princess, respectively. They were delicious, as always. If you are ever in New York City, be sure to stop for an amazing dessert.

We talked with Lori most of the afternoon about anything and everything. She told us about growing up in Brooklyn and what it’s like as a native New Yorker. We told her the story of us, a story we never tire of relaying. We talked about parents and how they are all the same in their worries, whether they’re from rural Indiana or live in one of the largest cities in the country. It was an excellent afternoon of conversation and one I won’t soon forget.

To be honest, I had become a bit disenchanted by social media over the last few years as it morphed into something far from my naive vision of possibility. This afternoon restored some of my faith that it can be used to connect people rather than divide them if you put in the effort.

We hopped on the train and stopped briefly at our hotel before heading off to dinner at The Greek Kitchen. As always, I was lucky enough to dine with a one-of-a-kind beauty.

The dinner was great! Everything we ordered was flavorful and fresh. Our order consisted of the following.

  • Avgolemono soup for each of us
  • Red wine marinated grilled octopus to share
  • Grilled salmon with side salad for Nick
  • Mixed grill with side salad for Angela
  • Galaktoboureko for dessert, a sweet custard pie with a unique texture

I highly recommend any and all of these dishes if you happen to stop in to this restaurant. To finish off our meal, I enjoyed a Double Greek which I’m fairly certain made me sprout at least a dozen brand new chest hairs. After eating our fill, we walked over to Lincoln Center to see our first opera, Don Giovanni.

After seeing this show, Angela and I decided that we are fans of opera as an art form and excited to see more in the future. The story was interesting, the singing was top notch, and the music was sublime. I’m really glad that we tried something new and enjoyed it so much. A brisk walk back to our hotel ended with us in the downstairs bar. Angela ordered a Moscow Mule and it came out strong as the bartender gave her a heavy pour of vodka. I asked if there were any non-alcoholic cocktails available and he looked at me like I had a third eye before stammering that he could make me a Virgin Mojito. That’s how I ended up with a fancy $14 glass of Sprite.

Visiting the crown and a theatrical experience for the ages

We woke up the next morning excited for another adventure and one that I’ve been thinking about since I was a kid. We hopped on the train to head downtown, exited near Battery Park, and retrieved the tickets for our cruise to Liberty Island. We had previously visited the Statue of Liberty but this time was going to be different because we had secured tickets for the crown. In addition, we’d be able to explore Ellis Island together as it was closed on our previous visit due to damage from Hurricane Sandy.

The ferry ride was pleasant, if a bit cold, and the sight of Lady Liberty as we drew near to the island was just as breathtaking the second time as it was the first. We wanted to make sure we left enough time to fully explore Ellis Island so we made a beeline for the crown access stairway and immediately started our ascent. It was awesome seeing the interior skeleton and copper skin of one of the most audacious pieces of engineering of the nineteenth century.

The climb was easy for us, especially compared to some of the staircases we faced in Europe over the last couple of years. That wasn’t true for the person in front of us, though, so we had to stop four times over the course of 146 stairs from the pedestal to crown. Once we reached the top, we crowded on to the observation platform with a few other people and took some pictures. The windows are small and the viewing platform was packed with only six people on it. Nonetheless, I was glad we had chosen to make the climb and fulfill one of my childhood dreams.

After we left the crown we stopped on the pedestal for a few pictures of the Manhattan skyline and the statue herself. It was an exceptionally clear day and we were able to get some great shots.

From there, we headed to Ellis Island. The ferry ride is short and the museum is exceptionally assembled. The exhibit on the first floor shows how people came to the United States from every corner of the globe; some of their own volition, some through coercion, and some through force. It tells the stories of those immigrants and the reasons behind their journey.

The second floor is divided into two parts. The first was a recreation of the processing flow for immigrants arriving in New York Harbor from the late nineteenth century through the middle of the twentieth century. It showed how an immigrant would proceed from initial examination through admittance. The second part of the museum contained details of virulent anti-immigrant sentiments throughout American history. The more things change, the more they stay the same, I suppose.

We left Ellis Island on the last ferry that would leave us a reasonable amount of time to freshen up before dinner. After a brief stop at our hotel to change, we headed to Basso56, one of Angela’s favorite restaurants in Manhattan. The dinner was fabulous and I highly recommend the location if you’re looking for some rustic Italian dishes. From dinner, we made our way to the Richard Rodgers theater to see Hamilton for the third time. This was going to be special, though, because of the seats I’d been able to purchase during a Ticketmaster Verified Fan offering. We were lucky enough to be seated third row center.

I was excited but also a little worried that the experience wouldn’t be meaningfully different from our last visit to the theater. In the worst case, we’d realize it is better to sit higher up. It turns out that my fears were entirely unfounded. The entire experience was incredible. Seeing the actors emote throughout the show and embrace their roles in the context of the stage is something that you can’t appreciate without being so close. I can only describe the show as emotionally intense and well worth the expense.

Duty calls, but we took breaks for tacos, burgers, and cupcakes

After a few days full of activities, I needed to spend Friday working. However, Angela eventually dragged me out of the hotel to go eat lunch and, eventually, dinner. We headed to Tacombi for lunch to enjoy some tacos. We decided to visit this particular eatery because of a recommendation from another dachshund account on Instagram, Django.

That dachshund really knows his tacos because they were delicious! We tried a wide variety including chicken, beef, pastor, seared fish, and battered fish. Each taco was delicious in its own way. I highly recommend Tacombi to anyone looking for tacos in Manhattan.

After lunch, we went to Gregory’s Coffee to enjoy a CBD latte at the recommendation of our local barista, Adrian, at Desert Wind Coffee Roasters. Unfortunately, New York City embargoed CBD as a food additive a few days before our visit so we couldn’t try it. We procured some other coffee drinks and I headed back to work for the rest of the day. Of course, the embargo was postponed a few days later and we didn’t hear about it until we got home. Oh well!

For dinner, we headed uptown to procure some miniature cupcakes at Two Little Red Hens (on Lori’s recommendation) before having dinner at Hero Certified Burgers. It was a good burger at a good price with friendly staff and a reasonably convenient location. I’d go back in the future, if only for the giant slab of cheddar that was placed on my dual patty burger.

We walked back to the hotel along the eastern edge of Central Park and enjoyed the buzz of the city around us.

We visited a graveyard and ate a ton of ethnic food

Saturday was another day full of adventure and eating and started in the mid-morning after getting some work done earlier. We took the train downtown to Trinity Church to pay our respects to Alexander and Eliza Hamilton. It was interesting seeing the monument to a man who had such a consequential impact on history. It is, all at once, a reminder that everyone dies but that the things we do when we’re alive matter.

After leaving the church, we stopped by Laughing Man Cafe for a couple of flat whites, apparently the official coffee drink of Australia, on our way to buy some fancy candles. Laughing Man is a company founded by Hugh Jackman to support coffee farming communities and the families that produce coffee in an environmentally friendly manner. The coffee was good, but not the best I’ve ever had. I did enjoy the flat white’s texture, though, and I look forward to having many more on our upcoming trip down under.

After stopping at the Cire Trudon boutique and picking up a few Egyptian themed specialty candles, we were off for some grub from Angela’s childhood at Little Poland. If you walk in and are not sure what you’re in for, they have this article hanging on the wall by the door.

We each enjoyed a hearty bowl of chicken noodle soup and split a combination platter of kielbasa, potato pierogies, gawumpki, and sauerkraut. It was intensely delicious and Angela said it brought back memories of her childhood and her great-grandmother.

We passed on Polish dessert in favor of , a cookie dough boutique. We sat in Washington Square Park and enjoyed people and dog watching while we imbibed our sweets. We even saw a pair of dachshunds come by and give us the stare down while we were lounging. Afterwards, it was back to the room for an afternoon and evening of work.

Around 9PM we started getting hungry and I decided I wanted to try Tim Ho Wan’s Hell’s Kitchen location. I have read such amazing reviews about the restaurant that originated in Hong Kong that I couldn’t wait to try it for myself. The food was, unfortunately, not very good. Many of the dishes seemed to be overcooked and really lacked the meat I’d expect them to have. Some of the items just tasted bad, in my opinion. To say I was shocked would be a bit of an understatement given the rave reviews the restaurant has received for its Hong Kong and Tokyo locations. I was glad we tried something new, but disappointed in the dishes we were served.

Pondering abstract art and steakhouse delights

In case Angela hasn’t informed you yet, she’s a member of the Metropolitan Museum of Art. As such, we try to make it there every time we’re in the city. There’s always something new to see or experience. On this trip, we were treated to The Daguerrotypes of Girault de Prangey, Epic Abstraction: Pollock to Herrera, and Jewelry: The Body Transformed.

Each exhibit was interesting in its own right. We particularly enjoyed the daguerrotypes because many of them were produced in locations we’d recently visited in Italy. It was interesting to compare our recent memories of the landscapes with the nineteenth century portraiture.

Abstract art is always fun to look at. Some pieces are certainly easier to appreciate than others, but I think we can all agree that it is extremely easy to enjoy the conversations of people who are looking at a piece of art and eventually giving up and saying “I don’t get it.”

After closing down the museum, we wandered down to Benjamin Steakhouse and had an absolutely incredible meal. From start to finish, the dishes and service were both exceptional. We opted for the following:

  • Caprese salad
  • French onion soup (Angela)
  • Porterhouse for two
  • Sauteed mushrooms
  • Apple strudel a la mode

We sat at the bar because I didn’t make a reservation. Even with that caveat, the dining experience was great and the bartender, Andrea, took great care of us throughout the night. This is one of those restaurants that I’ll return to again and again and again.

Amazing doughnuts and a late night experience

Monday was a big day for us and one we’d been anticipating for a few months. It started off with a visit to The Doughnut Project for some of the best doughnuts we’ve ever had. I chose a Peanut Butter & Jelly and Angela chowed down on a Chandonut Rose.

Then, we were on the way to the Ed Sullivan theater to wait in line for our visit to The Late Show With Stephen Colbert. Stephen Colbert has long been one of our favorite comedians so it was a real treat to see him live. The show itself was free, but getting tickets and attending is a whole process.

First, you need to request tickets from the ticket vendor for the show. I started monitoring availability about six weeks out from when we’d be in New York City and, as soon as the dates that we would prefer became available, I created an account and made a ticket request. About a week later, I was notified that my request for two tickets had been accepted and that I could claim them. We were lucky enough to get Priority tickets.

The tickets you get outline a deadline for when you have to be present in order to gain admission to the theater. However, I’d read on several different blogs and on TripAdvisor that it was best to show up a few hours before the deadline to get in line and make sure you got good seats. We arrived at the theater around 2PM even though check-in wasn’t supposed to start until 3PM. I’m glad we did – we were the 10th and 11th people in line.

We waited outside in 39 degree weather after receiving our admission wristbands and had to wait until 3:30PM to enter the theater. At that point, we were all herded into a line and people were allowed to use the bathroom. It is highly recommended that you go when you have the opportunity because you are not able to leave the taping once it starts. After everyone has a chance to use the restroom, you are herded into the theater after being informed multiple times that you need to turn your cell phone off and cannot take it out, even to check the time, or you’ll be escorted out of the taping.

Once in the theater a comedian, Paul Mecurio came out to warm up the crowd and get us loud, the Late Show’s stage manager came out to show us the signal for when we’d need to be on our feet, and then Jon Baptiste and Stay Human came out and played a bit. Finally, Stephen Colbert came out and took some questions from the audience before the show started taping in earnest. The rest of it is pretty much what you see on your screen with some modifications for time.

It was a great experience. I loved it and loved being in the crowd. Colbert is just as charismatic and funny in real life as he is on the screen and I’m so glad we spent the afternoon and evening attending the show. I don’t know if I’d go through it all again, but I was happy to do it once.

After the taping we ventured to Pazza Notte for pizza. The service was friendly and the toppings were fresh and tasty, but the crust was mediocre. There are much better pizza places in New York City and wouldn’t recommend a visit here.

A relaxing morning and the long journey home

On our final day in the city we spent the morning and early afternoon relaxing and decompressing. We hit the gym, drank some coffee, did some work, and packed up for our journey home. Before long, we were in a cab on our way to JFK with a taxi driver telling us how hospitals poison everyone’s blood. It was an experience.

Once at JFK we made our way to American Airline’s Flagship First Dining area inside the Flagship Lounge. It was everything I hoped it would be. The dining is a la carte and it was amazing. In fact, the food was better than most restaurants I’ve eaten at. We had the following:

  • Crab stuffed shrimp (Angela)
  • Duck confit egg roll (Nick)
  • Demkota ranch filet mignon
  • Chocolate brownie sundae

The steak was cooked perfectly medium-rare which is not always the case when we go out to eat. The service was exceptional, with Richard, our waiter, taking a particular interest in my laptop such that we ended up talking technical specifications for the new desktop I had recently built alongside discussing which mechanical keyboard is best. After dinner we relaxed at our table with copious refills of espresso and sparkling water before heading to our gate.

If you have access to Flagship First Dining at JFK, do not skip it! It was worth jumping over Las Vegas on the way to Los Angeles and doubling back.

The seats in Flagship First on American Airline’s 32T were extremely comfortable and the in-flight service was great. I ate again on the plane and the food was better than the average that you’d have at 30,000 feet. Furthermore, I was able to get some sleep on the lay-flats and stretch in the aisle when needed because there was so much space.

After arriving in LAX we took the airport shuttle to the Renaissance LAX, where we have stayed previously for quick overnights. We checked in, got our five hours of sleep, and headed back to the airport for the short domestic first flight on an American Airline’s 32S to LAS. The seat was comfortable and there was tons of leg room on this flight.

In all, I was quite pleased with this trip and I look forward to a return to New York City.

4 responses to “Valentine’s Day in the City
A Whirlwind NYC Adventure”

  1. That sounds like an awesome trip! I’m going to have to pick your brain about getting Hamilton tickets when we go in July.

  2. I love that your dog has its own instagram account! My son created one for our dog a few months ago. That Brooklyn Blackout cake looks so delicious. And, I’m jealous that you’ve seen Hamilton 3 times! My husband would love to go to the Colbert show taping.

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