How I scored a lie-flat bed on American Airlines for $106.20

Did you know that American Airlines uses lie-flat bad in its first class between New York City (JFK) and Miami?

When I was looking at booking a flight between these cities, American Airlines has the best deal, coming in at $106.20 after taxes for June travel. When I went to pick a seat, I noticed that the plane had lie-flat beds (notably, the flight on American leaving later in the day did not), and decided that I would request a 500-mile upgrade for the flight.

For those who don’t know, American Airlines has a unique feature where, once you obtain premier status on the airline, you’re given around 500-mile upgrades to use for future flights (with Gold, I was given 10). For each 500 miles that you fly, you need to use 1 of your 500-miles upgrades. If you want to purchase more upgrades, it costs $40 for each one.

I generally like this system, as it makes it so you only request an upgrade when it’s most beneficial to you – and I’ve found I’m much more likely to get a 500-mile upgrade when I use it, compared to complimentary upgrades on United, where I also have status.

Unfortunately, the flying distance between JFK and MIA is 1,090, meaning it cost 3 500-mile upgrades (if it was just 90 miles less, it would have been 2!). Still, I decided to try for the upgrade because of the flat bed.

The flight was fairly empty, and I got confirmed for my upgrade at check-in. Because I’ve yet to go through all 10 500-mile upgrades (and I’ve upgraded on 3 flights now, including Turks & Caicos to Charlotte), I was able to score a flat bed for cheap!

The flight wasn’t particularly amazing, but, despite the short flight time, I actually used the bed and took a nap. Since I doubt I’ll maintain my American status, the good news is that the flight was around $300 to book directly for the flat bed; which, although not ideal, isn’t totally unreasonable.


How I scored 3 nights in an ocean-view room at The Ritz-Carlton in Miami for $337.30 total

I spent a lot of time going to Florida as a kid. As a Jew from New Jersey, many of my relatives made the “Jewish Migration” from the northeast to South Florida, and I would (generally) love my visits down there.

As I grew up, I became less in love with Florida, but always managed to have fun whenever I went. That’s why I knew I had to hop on this amazing deal I found at The Ritz-Carlton in Key Biscayne.

I was first alerted to the deal by an e-mail from I definitely recommend singing up for their newsletter – while most deals will likely be unavailable simply because of location, a few pop-up, like this one, which are incredible.

The original deal was $49/night (before fees) for an Ocean View, 1 Bedroom Residential Suite, so I booked the first dates I found available, which were in mid-June. After fees and taxes, this came $261.03 for 3 nights. I was in heaven. I even made sure to book on The Ritz-Carlton website directly, thinking there was a better chance they would honor this deal than a website like (which, in my experience, almost never honors these mistaken hotel fares).

But my dreams were short lived. A few days after I booked this deal, I got an e-mail from hotel itself, saying that they had to charge me full price for the room. Being a lawyer, I fought them on it. In fact, I had a back-and-forth with one worker for around a month, and finally got him to give me less nice, but still great deal – instead of what I originally booked, I was offered 3 nights (over the same dates) in an Onceanfront View Guestroom at a rate of $674.61 after taxes. The actual rate for room (according to the hotel’s website) is $1,974.11 for the same dates. So, although I am paying much more than I had anticipated and am losing a suite, I am still getting an incredible deal.

Even with my deal, I was still feeling too cheap to pay it. Miami can be fun, but Key Biscayne is a little slower and it’s in June, when weather down there is far from ideal. But not wanting to give up on my hard work of securing a great price, I reached out to an overworked friend of mine, easily convincing him of his need for a weekend away. He agreed to split the cost with me, making my total damage $337.30 for 3 nights on an ocean-view room in The Ritz-Carlton in Miami.

I’ll be sure to update you after my stay to let you know how it was!


Flight Review: Air Canada 787 Business Class | Santiago, Chile to Toronto

A few weeks ago, I took one of the best flights I’ve had in a long time.

I was hoping to spend a week in Kauai, but my plans fell through and I was in need of a destination.  Late at night, I checked the availability of flights to and from South America – perhaps my favorite continent to work remotely from – and found a business class ticket from Santiago, Chile to Toronto and then onto SFO for 55,000 United miles one-way.

Usually when it comes to South American award miles, United features Copa and Avianca which, although decent airlines, do not have lie-flat seats, although the tickets cost the same amount of miles. There was only one available date for the Air Canada flight, so I snatched it up, later booking a $235 flight from SFO to Cartagena, Colombia and then using miles to get from Cartagena to Santiago, Chile.

My first part of the journey was to head to the lounge in the Santiago Airport. Unfortunately, I didn’t take pictures, but the lounge was only decent. Notably, Air Canada does not have its own lounge in the airport, but you do have access to the Avianca lounge.

The lounge itself was just okay — the food was pretty bland (small sandwiches and some pastries) and they ran out of Diet Coke, so I had some beer and orange soda while waiting for my flight. There are a lot of power cords, though, so if you are need of a charge, it’s definitely a good place to relax.

As my flight approached, I headed towards the gate. When I got there, I found that it was my least favorite boarding method – the one where you board by group, but where you get onto a bus, and it’s a free-for-all once you get off. Luckily, most people on the flight were Canadian, so everyone was very nice and no one was shoving.

When I made it onto the plane, I was greeted with perhaps my favorite sight when entering a plane: a seat (that’s mine) that I know can turn into a bed!

Air Canada 1

It was glorious, particularly as it was a 9:30pm flight, and I was already starting to feel tired.

As I got comfortable in my seat, I noticed the complimentary Air Canada bag, containing goodies like lip balm (a really nice one, which I still use), a toothbrush, toothpaste, and an eye mask.

Air Canada 2

The flight attendant asked me if I was thirsty, and although I wanted to scream “YAS QUEEN!” I instead politely told her that I was, and asked for some champagne. When she came back with my champagne, I was handed a menu for dinner, breakfast, and with the specific drinks they were offering on the flight.

Air Canada 4

I decided to order the spinach and cheese filled chicken breast because, well, I love cheese and chicken.

Shortly thereafter, we took off. The TV/movie selections were great, and I couldn’t believe they had almost an entire season of The Mindy Project available to watch. I was in heaven. I kept drinking and laughing and watching TV until my first course arrived.

Air Canada 5

This was just okay. Really, it’s my own fault because I’m not much a fish person and, on that flight (and usually), I wasn’t really feeling like a salad, so I mostly just ate the bread and drank my alcohol.

I must have gotten kind of tipsy, because I forgot to take a picture of the main course. It was delicious, though, and I was already full when the flight attendant offered me some ice cream.  How could I said no?!

Air Canada 7

After finishing my dessert, I did what most sane people would do on a red-eye flight in business class with a bed – I popped an Ambien and got horizontal.

I can’t say enough good things about how comfortable the seat was, how nice the pillows and blankets felt, and the rest I got on this flight. The flight time was around 10 hours, which I think is the perfect amount of time for an overnight flight if you’re lucky enough to snag a seat in business class. It gave me time to watch some TV, drink, eat, and still have enough time to sleep to catch 6-7 hours of solid sleep.

I woke up to the smell of breakfast, and when the flight attendant saw that I was awake she asked me my choice – I picked the omelet.

Air Canada 8

It was decent, but not amazing. More than the breakfast, I needed the coffee to come to life, and their coffee was pretty delicious.

About 1.5 hours after breakfast service, we landed. The flight was uneventful, but sometimes that’s just what you need.

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One of my favorite parts about this flight was listening to the passengers talk who were on it. I know that might sound weird, but Santiago to Toronto is an interesting route, and there were a lot of people on the flight who traveled regularly between the two cities for work. I love hearing Spanish spoken with a Canadian accent, and that the flight connected two cities literally a world apart.

I very much hope I have the chance to fly this route again and would totally recommend it to anyone thinking of trying it!