We are Headed to Havana!

Ultimate Rewards
Written by Dustin

In December, we are finally headed to Cuba. I was able to use our points and cash back to reduce the cost significantly.

For a couple of years, I have wanted to travel to Cuba. Unfortunately, I haven’t been able to make the trip happen. Just the other day, Kristin and I were looking at our travel plans this fall/winter and December was wide open. After discussing a few locations and flight options, I was finally able to book the trip to Havana. With travel to Cuba potentially becoming more restricted, I felt this trip was going to happen now, or it might not happen.

We are Headed to Havana!

Piecing Together Our Flights

I actually could have made this a little easier, and cost fewer miles, but decided to spend a few more miles to try Jetblue. I’ve heard nothing but good things about the airline and thought this was a great time to try them out. Hopefully it will be worth it!

Flight #1: Bangor to Havana

Instead of my usual tactic of booking Bangor to JFK, I was able to book Bangor to Havana (still connecting in  JFK) on the same ticket. This actually made more sense since it was only about $40 more from Bangor.

headed to havana

The total cost for 2 round trip tickets was $327.20.

If I were to use Skymiles, the cost would have been:

Headed to Havana

The total cost would have been 33,000 Skymiles, plus $61.20.

I opted for the cash price of the ticket, but I didn’t pay that price for my ticket. One of the benefits of the Delta credit cards is the statement credit (either $50 or $100). When I opened my Delta cards (and Kristin’s) I bought Delta gift cards since they have no expiration date.

You can only use 3 gift cards at a time for a Delta reservation. I ended up using $200 in gift cards to pay for the flights.

I also had $171 remaining on my American Express Business Platinum airline credit. Since the gift cards took off $200, that left me $127.20 remaining. I decided to book the rest on my Business Platinum to use my airline credit.

Headed to Havana

A day after my transaction posted, my airline credit posted.

This flight was not only the cheapest, but also the quickest to Havana. With my time in JFK, we will probably head over to one of the lounges and relax until our flight.

Flights from Havana

I actually had reduce my flights to 2 options. I could either:

  • Use my 50% rebate with my Business Platinum for 32,100 and pay no taxes on Delta.
  • Transfer 28,000 Membership Reward points to Jetblue, then use 15,000 miles on Delta to finish flights + pay taxes. T

One of the deciding factors was travel/flight time. The Delta option was 2 layovers, and would take 10-11 hours to get home.

If I decided to fly Jetblue, it was non-stop to JFK and left later in the day.

Life’s tough decisions!

I opted to fly Jetblue, because it was less flight time and I’ve been wanting fly Jetblue for some time now. I’m actually excited to try a new airline and it was reasonably priced for the flight.

Trouble Booking with JetBlue

Looking at my flight options:

headed to havana

A 3 hour was definitely worth the extra points. This reduces my flight time and gives me a few extra hours in Havana.

In order to book my Jetblue flights, I had to move points 28,000 from my Membership Rewards account to give me 22,000 Jetblue Miles.

Membership Rewards transfer to Jetblue at a 250:200 ratio, and although some people might not transfer them because they are less than 1:1, I have no problem with this option. It makes my travel cheaper and I get to see another country.

In addition, I paid $82.92 in taxes, which I put on my Citi Thank You Premier to earn 3x points.

The cost of this ticket would have been $412 total.

After I made my booking I realized I didn’t receive any email with my confirmation number. When I checked my flight status and it showed my flight was canceled. I was definitely puzzled since I answered all the necessary fields to book my ticket.

I decided to call in and see why this occurred. For some reason, because I booked a one way ticket from Havana to JFK, this caused an error in their system and cancelled the ticket. (according the Jetblue Representative). This is interesting because when you attempt to book a one way you receive this message:

headed to havana

I would think if their was an issue booking a one way ticket, the system would block any attempt to book tickets.

After feeding the flight numbers to the representative, I was initially told I didn’t have enough points in my Jetblue account.

The representative told me the flight priced out at 24,000 points plus taxes. I didn’t see any possible options to make that total possible. After a few more minutes, I was put on hold.

I was told it was “an internet special” and they will honor the price but that price was not accurate. I checked a few days later and the price was the same, so I think it was an error with Jetblue computers.

A few minutes later, I finally booked my ticket from Havana to JFK.

Booking JFK to Bangor

I typically book my tickets to Bangor to JFK (and from) as there is a lot of availability for 7,500 miles one way per person.

headed to havana

As with my previous awards this was only going to cost 15,000 miles total and $11.20.

I booked this with Kristin’s American Express Premier Rewards Gold, as she still had her Delta Airline credit.

headed to havana

Again, a day after the transaction posted, the airline credit posted.

Total Cost for Flights:

We used 28,000 Membership Reward points,  $16.50 for taxes to transfer points (get rid of that American Express!), 15,000 Delta miles, $200 Delta gift cards, and our airline credits for these flights. Had we paid for these flights, the total would have been $1011.60, so we saved quite a bit of money using our points for our flights.

The airline credit from Kristin’s Delta card is “free” since the card’s fee is waived the 1st year. That is not the same for my Business Platinum, since the airline credit is essentially prepaying our travel. I still paid $127.20 for my initial Delta Flight.


We have been using Airbnb more often when we travel. Since earning cash back is my typical game plan, this offsets our Airbnb cost. If only Airbnb had a loyalty program….Maybe, someday.

I had actually purchased a $50 Airbnb gift card for $25, when there was that great deal using 1 Membership Reward point on Amazon. Also, a friend helped me grab a $50 Airbnb gift card for $39.50 on Prime Day.

On top of that, I had an Amex offer for $50 off a booking of $150 or more.

Since Airbnb won’t allow you to use a partial gift card credit on your reservation (can you guys fix that, please), I had to find a place totaling $250 to trigger my Amex offer.

Luckily, I was able to find a nice apartment in Old Havana that met my requirement:

headed to havana

At $252.18, this was right over my $250 goal.

In the end, I was able to book my Airbnb for $165.50 after all my gift card savings and Amex Offer.

I also booked this through the Delta Airbnb portal where I earned 1 Skymile per dollar spent on Airbnb. I have used this portal for my other 5 Airbnb bookings this fall. This isn’t earth shattering earnings, but since it is my airline of choice (not by choice) it will help me towards my next free flights.

Other Items Needed:

Tourist Card:

We will need a tourist card to visit Cuba, which we will purchase from Delta at the gate for $50 per person.

Kristin still have $55 credit remaining on her Premier Gold Rewards card. That will also earn 3x Membership Reward points. ‘

I have $43 remaining on my Business Platinum, so I will use the remaining portion of that for my tourist card.

Medical Insurance

Another requirement to enter Cuba is medical insurance. We’ve been looking at options before this trip for travel medical insurance since we take anywhere from 4-8 trips per year, including a few international trips.

These seem to range from $20ish dollars for single trip up to $400ish dollars for multiple international trips per year. Not only would this give peace of mind, it would also protect us financially if something were to happen when traveling abroad.

There are so many options and I am still doing research, so if anyone has any recommendations, please leave a comment.


After a couple of years of waiting, I am very excited to visit Havana later this year. I look forward to seeing what Havana has to offer and visiting before entrance to Cuba becomes (possibly) harder.

Have you traveled to Cuba? If you have, what did you like or not like about it?

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About the author


After completing 6 years of pharmacy school, I finally had the time to travel. I started investigating ways to travel for less and when I redeemed my first award flight for my honeymoon, I knew I was hooked! Fast forward a couple of years and places I had never dreamed of visiting like Budapest, Honolulu, Bermuda and many other places where all within my reach, and for little to no money out of my pocket. Now, I have collected well over a million points and miles, and try to help people travel for less on their wallet.


  • I’m right behind you on Cuba travel. We’ll be visiting in March 2018. I look forward to seeing a trip report of yours to read any tips, etc for when we go. Thanks for the post

    • Hey Antonio,

      Definitely be on the lookout for a trip review. I’m sure I will have plenty to write about! 🙂

      Thanks for reading! I appreciate it!

    • Hey Ramez,

      I will have to check out your site. Also thanks for the info on the medical insurance, I’ll have to see what Delta’s medical insurance covers.

      Feel free to email me some tips and must see places 🙂

      Thanks for reading! I appreciate it!

  • Take advantage of this ASAP. The Trump administration will be making drastic cutbacks to the ease and legality of traveling to Cuba. Unfortunately all good things come to an end. Sad Times!

  • Aaron, regarding your post Making America Great Again will require drastic changes to Cuba U.S relations. We need to support and believe in our comandor and chief.

  • What ever Mr. Trump does regarding U.S Cuba relations I’m sure it’s the right choice. Mr. Trump Is easily one of the most brilliant minds our nation has ever had. We’re fortunate to have him as our leader.