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Emily: When I learned about America’s more relaxed policy towards travel to Cuba, I jumped at the opportunity!
Cuba has a lot to offer. My friends and I were drawn to the classic cars, the Art Deco architecture, and, of course, the friendly people! We also love music and dance, which is one of Cuba’s specialties! Rick Steves recently produced an excellent video on Cuba that’s fun and informative.
The US and Cuba reached an agreement for direct flights. Flight availability to Cuba from various US airports and search engines is ALWAYS changing, so be sure to try multiple search engines and cities, if possible. Readers have reported that some flights to Cuba from the US may be opening up. When I went to Cuba in December 2015, flights were not scheduled yet. My friends and I flew via Cancun, and continued our journey to Havana.
Note: Regulations surrounding US travel to Cuba are always changing, so make sure you check the current rules before planning your trip. There are limited opportunities to use miles & points, but you can save some money. I’ll show you how later in this series!
My travel partners included many of the same friends who accompanied me to Croatia!
Robbie (pink hair) is a professional dance instructor who teaches salsa, kizomba, and bachata. Sarita is also a dance teacher, as well as a graphic designer. Gissell teaches fitness classes and loves rock climbing.
On this trip, I went with 3 new friends – Diana, a local art teacher, Chelsea, who manages a hostel, and Antonio, who works in IT design. Traveling as a group of 7 was fun, but definitely challenging at times! We had a great time together, and can’t wait to return!
Viva Cuba! Trip Report Index:
- Part 1 – Viva Cuba! – Introduction & Planning
- Part 2 – Viva Cuba! – The Basics: Visa Requirements
- Part 3 – Viva Cuba! – The Basics: Cash Planning
- Part 4 – Viva Cuba! – The Basics: Internet
- Part 5 – Viva Cuba! – Flights to Cuba
- Part 6 – Viva Cuba! – Where to Stay & How to Book
- Part 7 – Viva Cuba! – Where to Stay: Casa Particular Overview
- Part 8 – Viva Cuba! – Where to Eat
- Part 9 – Viva Cuba! – The Best (Cheap) Food & Drink Options
- Part 10 – Viva Cuba! – What to Do in Havana Part 1
- Part 11 – Viva Cuba! – What to Do in Havana Part 2
- Part 12 – Viva Cuba! – What to Do – Day Beach Trips from Havana
- Part 13 – Viva Cuba! – Return Flights to the US
- Part 14 – Viva Cuba! – Conclusion & Blog Giveaway
Flights to Cuba
Update: Flight availability to Cuba from various US airports and search engines is ALWAYS changing, so be sure to try multiple search engines and cities, if possible. Readers have reported that some flights to Cuba from the US may be opening up. It did seem possible to book a flight out of Chicago through kayak.com. Kayak redirected me to kiwi.com. In this example, you still have to fly through Mexico.
However, I tried searching for flights out of Austin, Miami, and Chicago through Google Flights and Hotwire.com, but Havana is not supported. I get an error message that says, “Sorry, flights to Havana (HAV) are not currently supported from Chicago (all airports).”
My Flight to Cuba Back in December of 2015
My friends and I flew from Austin to Cancun, Mexico, on Southwest Airlines. Booking ~1 month prior to my trip, it cost ~25,000 points plus ~$75 in taxes and fees to fly round-trip in coach on Southwest. I could have flown for ~18,000 Southwest points if I had chosen later travel dates when the airfare was cheaper, but we couldn’t wait to go!
After flying into Mexico, you will need to take another flight to Cuba. I booked a Cubana Air flight for ~$350 round trip in coach. In December 2015, this was the fastest and cheapest option available to us. Again, flight availability is always changing, so check multiple sources before booking your flight.
Stopping Over at Playa del Carmen
We decided to stay a few nights in Playa del Carmen before heading to Cuba.
We had a lot of fun in Playa del Carmen, but next time I’d rather spend the extra days in Cuba. There’s so much to see and do, just in Havana alone! I was there for 9 nights, and it still wasn’t long enough to accomplish everything on my to-do list!
We arrived in Cancun safely and quickly collected our bags.
Once we arrived in Playa del Carmen, we went shopping, tried different restaurants, and gave ourselves a lot of beach time! My favorite activity was scuba diving in the cenotes, or underground caves.
It was soon time to leave for the airport. We could hardly wait to get to Cuba! A shuttle bus picked us up at our flat.
After our short stay in Playa del Carmen, we took a Cubana Air flight from Cancun to Havana. The total cost to fly coach round-trip was ~$350. You can’t use miles or points because Cubana Air is not part of an alliance. I used the Chase Sapphire Preferred® Card card to pay for the flight and earn 2X points on travel.
A Go-With-the-Flow Attitude
We were advised to arrive at the airport 3 to 4 hours before our 4:00 pm departure. We needed enough time to receive our Cuban visas and check in for our flight. So we left our flat in Playa del Carmen around noon.
We got our Cuban visas in no time! Nobody even asked why we were going to Cuba. We just filled out some personal information on a small piece of paper while we were waiting in line at the Cubana Air counter.
After we checked in, we went through security.
And forget about bringing fuzzy handcuffs!
After passing through security, our flight was delayed 4.5 hours. But we made the best of it!
The Cancun airport seemed more like a mall with a few restaurants thrown in. We spent our time shopping and eating! We received free meal vouchers for the delayed flight.
After being at the airport for ~8 hours, we finally started boarding. Yaaayyy!
After a quick ~1 hour flight, we landed in Cuba. Then, we waited for our luggage at the carousel.
Leo (the casa particular employee) told me about folks never getting their luggage, so I was a bit worried. He advised to pack an overnight bag with necessities for this very purpose. We still aren’t sure why it took so long, but we imagined 1 guy doing all the work!
Instead of focusing on our delayed luggage, we kept our spirits high, and made new friends with anyone we could find. We had made it to Cuba, after all!
It was interesting to see some items passing on the conveyor belt. Many basic supplies are either hard to come by or very expensive in Cuba.
Finally, after 2.5 hours, we all got our luggage!! It was now ~1:00 am and we were all pretty exhausted after traveling all day. But we had each other to lean on. And we were in CUBA!!!
Our Cuban vacation had begun! Woo hoo!
You Can Do It, Too!
It’s easy to get to Cuba via Mexico on Southwest Airlines. Direct flights MAY open up to Cuba in June, so check to see which flights have the least expensive award seats. Until then, I recommend going through Cancun or Mexico City.
You can get lots of Southwest points by transferring your Chase Ultimate Rewards points to Southwest! And if you have the Southwest Companion Pass, you can bring a friend for (almost) free! I also like that Southwest doesn’t charge for checking a bag.
You can earn lots of Southwest points by signing-up for the Southwest Rapid Rewards® Plus Credit Card, Southwest Rapid Rewards® Premier Credit Card, and the Southwest Rapid Rewards® Premier Business Credit Card.
You can NOT fly directly from the US into Cuba, but instead must use a gateway city in another country. My friends and I used Cancun as our gateway city. We took a pre-vacation trip to Playa Del Carmen while we were there.
We used Southwest points to reach Cancun, then Cubana Air to Havana. Cubana Air is not part of an alliance. But you can use the miles you get from the Barclaycard Arrival Plus to cover your flight!
Lots of things can go wrong while you’re traveling, like flight and baggage delays. But that doesn’t have to stop you from having a great time! Learn to go with the flow, and you’ll find the aggravations can make for great stories later! And to appreciate the positive experiences even more!