Boston to Dubai, via Toronto: 40k United Mileage Plus miles redeemed per person

First leg of our trip to Dubai was on an Embraer 190 flown by Air Canada. This redemption cost 40k miles per person. When I signed up for the Chase Sapphire Reserve back in September, they had a limited time offer of 100,000 bonus miles upon spending $4k in the first 3 months. Thanks to tuition, I hit that threshold pretty quickly. If you have the Chase Sapphire Reserve or Preferred, you can transfer your points on a 1:1 ratio to United and then use one of their Star Alliance partners to fly. This is exactly what we did.

 2^nd leg: Toronto to Dubai

This leg of our trip was on the Boeing 787 Dreamliner flown by Air Canada in economy class.  This was part of the redemption above. Air Canada is a Star Alliance partner of United.

Abu Dhabi to Male, Maldives: 30k American Airlines miles redeemed per person

My wife and I both signed up for the American Airlines Platinum Select credit card by Citi a few years back and received the bonus 50k miles after hitting the minimum spend threshold (that tuition again). American Airlines is part of One World Alliance but they also have several partners outside the alliance where you can find great redemptions. Etihad happens to be one those partners outside of One World. Others include, Hawaiian Airlines, Jet Airways, Alaska Airlines, and WestJet. One World partners are all below.

Male to Rangali Island: TransMaldivian Airways.  Partial cost offset by 55,000 American Express points.

When you book a trip to Maldives, there are two ways to get your island: by an expensive speedboat transfer or a ridiculously expensive seaplane transfer. Unfortunately, the sea plane transfer is offered by a single company, TransMaldivian Aiways,  which allows them to price the 30 minute flights for as much as they desire. They are not affiliated with any airline alliance so you can’t book them using miles. And it costs $546(!!) per round trip ticket to get to your island if it is only accessibly by seaplane. Since we booked the Conrad in Rangali Island, Maldives using Hilton points, our only option was taking the seaplane transfer. Since I couldn’t use miles and I wanted to reduce the cost burden of the seaplane transfer, I redeemed 55,000 American Express Premier Gold points for $550 in statement credit. AMEX Premier Gold has 20 airline transfer partners as well as the highly coveted Starwood hotels program as a transfer partner. Transferring to almost any of the programs would have given me significantly more value than the 1 cent per point I received by redeeming the points for statement credit. But I also hated the idea of spending $1,092 in cold hard cash for a 30 minute round trip flight. Redeeming the points made it a more palatable $273 round-trip per person. As for the experience itself, it was a very unique and scenic flight. The plane seats about 14 passengers in relatively narrow seats. The plane flies at around 4,500 feet so you get a great view of many islands with their over-water villas on the way to Rangali Island.

Conrad Maldives, Rangali Island: 620,000 Hilton Points

I’m not quite sure I’ll ever have another redemption in my life that will require as many points as I needed for the Conrad Maldives. This redemption took a lot of planning and required meeting multiple Hilton Card bonuses to have enough points for an award redemption. Back in 2015, My wife and I both applied for and got the Hilton Honors American Express credit card. It had no annual fee and the bonus was 75,000 Hilton points for spending $1,000 over the first 3 months. In 2016, we both got the Citi Hilton Honors Visa card. This offer was 75,000 points if you spend $2,000 over the first 3 months. I timed my car maintenance expenses and college expenses in a manner which I was able use the Citi Hilton card and get the bonus. My wife’s card was used in a similar manner. So if you’re keeping track, that is now 320,000 Hilton points we have accumulated between the two of us. Then earlier this year, American Express had a 100,000 point offer on their Hilton Surpass card. The annual fee was $75 but it came with automatic Hilton Gold Status. The benefit of having Gold status was significant. It ended up paying for the annual fee many times over. Both of us were able to achieve the 100k bonus due to miscellaneous spending + partial tuition.  Point count: 535,000 between the two of us. At this point, we had enough for 3 nights but due to the unpredictability of the weather (it was technically going to be rainy season in July), we really really wanted to get that in that 4th night. It was around this time that Hilton started a new feature in their Hilton Honors program in which you were now able to combine your points with 10 other people.  This was the break we needed. I asked my mom and dad if one of them was willing to apply for the no annual fee Hilton Honors AMEX card and get the 75k bonus after spending $2k in the first 3 months. Since they had a relatively large expense upcoming, they obliged and received the bonus. I was able to transfer those points into my account. Point count:  ~ 620,000.  Now we had enough points for 4 free nights at one of the best accommodations in the Maldives. Nightly rate if paid for in cash? $670. But the best part of this redemption is the Hilton Gold status that came with having the AMEX Hilton Surpass card. As Hilton Gold members, Conrad upgraded us from the superior over-water villa that we had booked to a retreat over-water villa. The cash value of the upgrade per night is about $130 a night. Multiply that by 4 and the upgrade is worth about $520. Hilton Gold members also had other benefits at the hotel such as free tea, biscuits, and lunch sandwiches between 4 and 5 pm and free mocktails between 5 and 6 pm. Buying lunch or mocktails at the Conrad with cash is not cheap. I’d peg this value at about $60 per day between two people. Multiply that by 4, that’s an additional $240 in value. For paying a total of $150 of annual fees between the two Hilton AMEX Surpass cards ($75 each), we derived about $760 in value. In addition, we both get a free night during our card member anniversary.

Male, Maldives to New York City, via Dubai

This was the part of our trip that really helped in reducing the overall miles/cash expenditure of our entire vacation. Sometimes you just get a little lucky. Back in early May, one of the travel blogs I follow sent out an alert on twitter about a mistake fare for a 1 way ticket from Maldives to NYC on Emirates. The mistake fare was $201 per person (!!!) for the 1 way ticket with dates extending as far out as December. Since Maldives was a trip I had been planning anyway, I thought I’d book the ticket and wait and see if Emirates would honor it. 24 hours after booking, I received an e-mail from Emirates that our tickets had been cancelled and that they would not be honoring the mistake fare. I was slightly disappointed but was prepared for this outcome. One week later, I received a call from Emirates asking me if I was still interested in that one way ticket. I told the rep I absolutely was. The booking/reservations agent informed me that there was a reversal in their decision and that they would be honoring the mistake fare. $201 per ticket from the Maldives to NYC is a steal. To put this into context, this flight would have cost $1,400 in cash per person or 70,000 Emirates miles (which I did not have)  and additional $100+ in taxes person.  Once this domino fell, everything else fell into place. Sometimes you just get a little lucky.