How We Chose Our Hotel In Times Square (And Wound Up Somewhere More Expensive Than We’d Usually Pay)


We had managed to acquire tickets to see Hamilton and I scored some great airfare to New York. Now it was time to decide where to stay. In this post I’ll be going over my usual procedure to find hotels around Times Square. We left on a Friday morning and returned late Sunday night. I’ll break the trip up into segments because I think each one is interesting on its own merits. I’ve listed the other posts about our very quick trip to NYC below. The one in boldface is the one I’m focusing on today.

Why yes, I do have a Google Maps set up for all the hotels we’ve stayed at before.

When booking a hotel in Times Square, we need to make sure it meets certain criteria. Since we always seem to visit New York in the winter, Sharon insists that the hotel MUST be within short walking distance from the shows we are seeing, “because it’s too cold out to walk very far” (she’s a wimp when it comes to cold [Edit by Sharon: True story! That’s why I moved to Florida!]). Preferably we should be somewhere between 42nd and 50th and from 6th to 8th Avenues. So you see I have a lot to work with. 😉

I find New York to be one of the most frustrating hotel markets in the country to work with. Every chain hotel is usually way overpriced because everyone from all over the world knows what a Marriott or Holiday Inn is and feels safe booking a room there. However, many of the hotels in New York City are not major chains but individual properties. Picking hotels is even more difficult because places will be bought, renamed and otherwise changed to keep people from knowing where they are staying (Did you know the Row NYC hotel is actually the old Milford Plaza?).

We’ve stayed in our share of hotels in Midtown Manhattan and have developed our list of  hotels where we have stayed in the distant past, like the Casablanca Hotel (they were nicely priced when they first opened) and the Marriott Marquis (we’ve occasionally seen a good deal on it), but the prices are almost always too steep for us. We also have our go to hotels. I’ll always look to see what rates are at the Crowne Plaza Times Square Manhattan or the Distrikt Hotel. The prices there are usually competitive and we’ve had pleasant stays at both of them.

Booking a room for this trip was vexing me to no end. The Distrikt Hotel had some good rates (around $500 for 2 nights) but Sharon still isn’t thrilled about staying there as it is on 40th St and a little further than we (well, she [edit from Sharon: shut up, Joe ;-)]) like to walk in the cold. I found another hotel on my go to site for hotel reviews, TripAdvisor, which I determined would fit our needs and would only cost us around $400. Heck, we had already spent enough money on tickets for Hamilton; I didn’t want to drop a whole lot of money on a hotel. Then it happened. I saw this headline on one of the blogs I read:


OK, Deal of the year is major clickbait to me. What is this offers to end all offers.

The offer that was so good it only lasted 24 hours before it was pulled.

Wait a minute. Does that say that when you book a stay at any Waldorf=Astoria hotel that you’ll get a night free? Everyone seemed to think so. Book one night and get the second one free. Well, I had a stay for 2 nights coming up in New York City. They have a Waldorf=Astoria there. They have THE WALDORF=ASTORIA there; the original! The grandaddy of all Waldorf=Astorias! I went to the Visa Luxury Hotel Collection website and found a room at, not only the Waldorf=Astoria, but at The Towers of the Waldorf=Astoria. This is the hotel within the hotel that consists of only the upper floors. The standard rooms here start at 600 sf (which is MASSIVE for New York). I’m interested.

Not only do you get the fancy hotel within the fancy hotel but because I’m booking through the fancy hotel website I also get:

  • Room Upgrade, subject to availability
  • Free in room internet
  • 3PM late checkout, Subject to availability (FWIW, it wasn’t available)
  • Complimentary Continental Breakfast
  • $25 food and beverage credit

I checked the rate on the website for the nights we were looking for. The total for the 2 nights after taxes came to $1000. Wow. That’s why we’d never stay there. However, with this offer we would only be paying half of that. $500 for 2 nights at the Waldorf=Astoria tower. Not counting the $25 food credit and free breakfast. Oh, I also forgot to mention the other offer which Visa had where you might get a $75 gift card REBATE after your stay. For the regular price it would be the same as the hotel we liked but was too far away. For the price after rebate, it would cost the same as the hotel we’d never seen before and had “good enough” reviews.

I took a deep breath and got ready to make my presentation to Sharon. The hotel is on 50th and Park. Way out of our usual neighborhood. I need to book this now because a deal too good to be true usually is and won’t last (as it was the deal was pulled after 24 hours). “Um, honey? How would you feel about staying at a fancy hotel? ‘Which one?,’ you ask. The Waldorf=Astoria. There’s this great deal…yeah I know, more miles and points stuff. But I need to book this now. Yeah, I think I heard something about it closing for renovations too. You’d be OK with it? Really?? Thanks!!!”

Off to book, crossing my fingers the whole time that the deal is still there. It is. Now looking at comments of other people who booked and everything looked OK. It’s a refundable reservation and we have several months until our stay. I can see if other people had problems way before we’d be going. BOOK IT ALREADY!! Done.

I hit the “reserve” button and I got my confirmation. I still kept my other two reservations for a while. I read on the message boards how other people had completed their stays and were greeted with the offer and how the last night would be free and received all the upgrades. Eventually people even got the $75 gift card. I finally cancelled my other reservations. There was no turning back now. We’re going to be staying at the Waldorf=Astoria. This is gonna be so cool! Stayed tuned for Sharon’s review of the Waldorf=Astoria…

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This post first appeared on Your Mileage May Vary



How will we get to New York? Oh, hello companion ticket!

Sharon and I just finished a very quick trip to NYC. We left on a Friday morning and returned late Sunday night. We don’t usually take such short trips but we had snagged impossible-to-get ticket for the Broadway show Hamilton. I’ll break the trip up into segments because I think each one is interesting on its own merits. The one in boldface is the one I’m focusing on today.

Now that we had tickets to see Hamilton, it was time for me to book our plane tickets to New York. I have a great deal of freedom in making airline choices to New York, as at least 6 different airlines fly there from Orlando. I also do not have any status with any airline so I don’t have to worry about upgrades, segments or mileage earning. Our only real requirement is that we will not fly an ULCC (Ultra Low Cost Carrier) such as Spirit or Allegiant (I’ll discuss that in another post sometime in the future).

I usually start searching using Google Flights, as this gives me a really quick look at what prices are available. Just be aware that Southwest Airlines does not list their prices anywhere but on

Quick Tip: you can type in airport code NYC and Google Flights will search all 3 major airports. (LaGuardia, Kennedy and Newark). If you aren’t renting a car (which is not necessary and very expensive if you are only going to stay in and around Manhattan), then you can even fly into one airport on one airline and home from a different airport/airline, depending on price. Unfortunately, the days of cheaper pricing for round trip tickets are long gone.

It is usually at this time when I’ll also do a quick search to see if there are there are any award tickets available to book with frequent flyer miles. Hint: It is possible to book a one way ticket from Orlando to New York for only 7,500 miles. I’ll cover this in a later post. 

Well, there was no award space available and tickets were more than I wanted to pay. In cases like this when I’m not in a rush to book tickets, I’ll just wait. Airfares go up and down all the time. Patience is a virtue. You can even use websites like Yapta or Hipmunk to track specific flights and notify you when the price drops.

Since I knew the most likely flights I’d book, I did a quick look every day or so. Then it happened – a flight to LaGuardia Airport on Delta showed up for $166 round trip. BINGO! That’s well under my acceptable price. IMPORTANT REMINDER: If you know you are taking a trip and see an airfare which is great for you, BOOK IT NOW! Prices can change in an instant. Feeling unsure? In most cases airlines will let you cancel within 24 hours with no penalty. Taking my own advice, I stopped what I was doing and booked the ticket.

Getting to the payment page, I saw there was a prompt for me to click on for coupons/vouchers. I didn’t remember having any but I clicked on it anyway. Delta then reminded me that I had a voucher for a free companion ticket from having the Platinum Delta SkyMiles American Express card. While this card does have a hefty $195 annual fee, I picked it up when I got a special offer for 75,000 Delta miles in the mail. I didn’t plan on keeping the card for much longer but why not use the Companion Ticket I had earned. Sharon’s ticket was suddenly free (I just had to pay the taxes which came to $28). The total we had to pay for both our plane tickets to New York was $194.

Step one of planning our trip was complete: we knew when and how we were going to get to New York City. Now for the next step: where were we going to stay?

Trip Report: Because……Hamilton

16114094_10154045741360974_5686568030597608705_nSharon and I just finished a very quick trip to NYC. We left on a Friday morning and returned late Sunday night. We don’t usually take such short trips but there was one reason we went to New York just for a weekend.


That’s right. While I confidently say I do have the greater tech skills in the family, Sharon has GoogleFu skills which outshine mine. When we saw Hamilton on Broadway a year ago last November, we decided we needed to see it again. That became quite a difficult task since it had become the hardest ticket to get since……well since we were alive.

My schedule currently gives me alternate long weekends off from work. So our plan was that when/if Sharon found tickets available, she would get them for a weekend I was off. It was then up to me to make the trip work.

Well, Sharon got tickets and I started planning. I’ll break the trip up into segments because I think each one is interesting on its own merits.

Keep following for the updates.