How I scored 4 nights in an overwater bungalow at a 5-star resort in Tahiti for $319.87 total (including airfare)

It’s not enough that I travel to cool places — I need to get a great deal going there.

Growing up, I was obsessed with finding travel deals. As a kid, I would hang out at the local travel agency and read up on foreign destinations. I would also study the Sunday travel section and insist to my parents that we needed to go places when the airfare was obviously on sale (spoiler alert: they never gave in).

To quench my thirst for travel, for my 10th birthday, my parents got me a subscription to Condé Nast Traveler. While it took almost 15 years from that point for me to get a passport, reading the magazine gave me a ton of travel goals — and staying an overwater bungalow was always near the top.

Finally, after capitalizing on some amazing deals, in a few weeks I’ll be able to make that dream come true in Moorea, French Polynesia. While you can sometimes spend over $10,000 for a trip like this (including air and hotel), using a number of travel hacks, I was able to score the room and plane ticket for $319.87.

Airfare

Thanks to discount-carrier French Bee offering cheap, direct service between SFO and Tahiti (airport code: PPT), United has joined suit in offering the same direct flight at competitive prices.

The round-trip airfare for the flight was $618.57, but I used 49,665 Chase points which were obtained through a credit card sign-up to book it. This resulted in a total cost of $0 for the flights.

Total price paid so far: $0.

Hotel

After discovering a way to book Hilton hotels at 25% off, I decided to look into the Hilton Moorea Lagoon Resort and Spa, a beautiful property located a short boat ride away from the main airline in Tahiti. Using the tricks in the previous link, I was able to find a cheaper fare than what was listed on the Hilton.com website, which qualified me for the 25% discount. While the room would normally go for ~$600/night before taxes, I was able to score a room for $359/night before taxes. With taxes, this came out to a total of $1,454.29 for 4 nights, which is already a steal for this type of room.

But I wasn’t done yet — I’m far too cheap to spend that on a vacation myself (and, plus, what’s the fun in going to Tahiti alone?). So, I messaged a friend who previously joined me on another killer deal I got (that time, to the Ritz-Carlton Key Biscayne) to see if he’d be interested. Luckily, he was.

This cut my total price paid to $727.14. But it gets better.

Because of my Hilton business credit card, I have Gold status which means that for each dollar that I spent at a Hilton property, I get 18 points for every dollar that I spent at a Hilton property. Additionally, if I make the purchase on my Hilton business card, I receive an additional 12 points for every dollar spent at Hilton property. Because of this, I’ll receive 43,628 points for my stay (at a valuation of $0.006 per point, this comes out to $261.77 worth of points). Since Hilton points are pretty much redeemable at face-value (meaning that your redemption will almost always be at the $0.006/point rate, similar to Delta with their points being pegged at $0.01/point), this brought my total down to $465.37.

But it gets even better.

Hilton recently ran a promotion where for bookings between January 4, 2019 and May 5, 2019, you’ll receive an extra 2,000 points for each stay, which is a $12 value. Additionally, Hilton will be doing repairs on the pool during my stay and will be $66.75 property credit each day during that time, which comes out to $267 (but, for purposes of my calculations, I’m cutting that in half to $133.50, since I’ll be splitting the credit with my friend). I was aware of the pool closure when I booked and didn’t really care, since I plan on swimming in the ocean anyway.

Deducting the bonus points and resort credit, my total for the stay, including air and hotel, came out to a whopping $319.87.

Conclusion

This may be the best travel deal that I’ve ever snagged. While Moorea certainly won’t be cheap, as a Hilton Gold member I’ll get free breakfast (it’s actually served directly to my bungalow by a staff member in a boat!) and can use the resort credit towards a meal. So, I’m taking this concept of balling on a budget to a new level and can’t wait.

New York Trip Deal: $638 round-trip business class from JFK to Panama City, Panama on Avianca

Avianca, which is part of the Star Alliance, is putting its business class flights from JFK to Panama, City on sale! Flights start at $638 round-trip, after taxes with great availability through December 2018, with many routes including an angled-flat seat.

This is a really great deal — economy tickets will cost you around $568 for the same flights.

Last year, I flew Avianca’s business class from Bogotá, Colombia to Santiago, Chile and wrote a review about it. Although it wasn’t my favorite flying experience ever, I’ve heard the U.S. to South America routes have better service and that, coupled with the lie-flat seat, definitely make this a fare worth checking out.

To find this deal, use Google Flights and search for business class flights between JFK and PTY.

New York Trip Deal: $669 round-trip business class (lie-flat seat!) from JFK to Lima, Peru on Avianca

Avianca, which is part of the Star Alliance, is putting its business class flights from JFK to Lima, Peru on sale! Flights start at $669 round-trip, after taxes with great availability through December 2018, with many routes including a lie-flat seat.

This is a really incredible deal — last year, Avianca ran a similar promotion, but with business class seats costing around $992.

Last year, I flew Avianca’s business class from Bogotá, Colombia to Santiago, Chile and wrote a review about it. Although it wasn’t my favorite flying experience ever, I’ve heard the U.S. to South America routes have better service and that, coupled with the lie-flat seat, definitely make this a fare worth checking out.

To find this deal, use Google Flights and search for business class flights between JFK and LIM.

New York Trip Deal: $992 round-trip business class from JFK to Lima, Peru

Avianca, which is part of the Star Alliance, is putting its business class flights from JFK to Lima, Peru on sale! Flights start at $992 round-trip, after taxes with great from July through May, and most routes include a lie-flat seat.

Earlier this year, I flew Avianca’s business class from Bogotá, Colombia to Santiago, Chile and wrote a review about it. Although it wasn’t my favorite flying experience, I’ve heard the U.S. to South America routes have better service and that, coupled with the lie-flat seat, definitely make this a fare worth checking out.

To find this deal, use Google Flights and search for business class flights between JFK and LIM.

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 extremehoteldeals.com. 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 booking.com (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.

Planning ahead has it's perks. Book early and members save 15% or more!

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!