Signing up for credit cards through partner links earns us a commission. Here’s our full Advertising Policy.
Update: One or more card offers in this post are no longer available. Check our Hot Deals for the latest offers.
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
Leaving Cuba Was So Hard!
I had such a great time in Cuba. It was very hard to leave. My friends and I stayed for a total of 9 days. I think you need 7 to 10 days if possible to really acclimate yourself to the differences and enjoy it.
On the morning of our departure, we said goodbye to our host family.
Our cab was waiting for us downstairs. We piled in and talked with our driver during the 30 minute drive.
It was a gorgeous drive to the airport. There are so many cool things to see in Cuba. My eyes were never bored!
We stood in line to check-in for our flight. Little did I know how stressful the next few hours would be!
We checked our bags, and proceeded through security. I was asked about the art pieces I was bringing back. I was charged ~6 CUC to leave Cuba with art.
We then grabbed a table and sorted through our leftover money.
In the Havana airport, there are a few shops and restaurants, a money exchange counter, and a business center.
Finally, we boarded our on-time flight. The views were fantastic!
The trouble started when we arrived in Cancun. Our bags took almost an hour to come off the belt!
This prevented us from getting in line for customs & immigration at a reasonable time. We decided it was better for one of us to wait in the customs line, and one of us to wait for the bags.
The Mexican government conducts random bag searches, and I was lucky enough to be selected. I had 3 bags with me, and the lovely customs ladies took out each and every souvenir. They unwrapped them, exclaimed how pretty or cute everything was, and even tried playing the instruments I bought!
I politely explained that I had a plane to catch that was leaving in 30 minutes. But they continued to take their sweet, sweet time. Eventually, everything was taken out and unwrapped from my bags.
Then, they let me through. I was so scared all of my souvenirs would break, so I tried my best to wrap them quickly and repack.
I tried re-checking my bags, but Southwest said I had missed the cut off window, and that I’d have to remove all liquids from my luggage so they could gate check the bag.
This was devastating, because I had the maximum number of bottles allowed in the form of our favorite Mulata rum. You can’t get it in the US!
I pleaded with them, but they said it was too late. So, I started taking out the bottles and lining them up on the counter.
At that point, an employee made a call. Another employee came over and said they could check my bag after all, and to re-pack my stuff. I was elated!!
I thanked Southwest profusely, and had a big smile on my face. They said I needed to run to my gate, so I went as quickly as I could. When I reached my gate, I found out that the flight was delayed!
All of that worrying and stress for nothing! I wondered why the employees at the Southwest counter didn’t mention it, but I was more relieved that I didn’t miss my flight.
They gave me a voucher for free dinner, so I used it on a pizza. It tasted so good!
My friend Gissell and I decided we needed a drink after the fiasco, so we ordered some of the hard stuff on the flight. And I had chocolate in my bag, so us ladies were set!
The flight was just a few hours, but we had so much fun during that time! The Southwest flight attendant took a liking to us and only charged us for 2 out of the 6 drinks we had.
You Can Do It, Too!
You currently need to go through a “gateway” city if you want to enter Cuba, because no US cities fly directly to Cuba. Direct flights to Cuba will be opening soon, but until then you’ll have to first fly to another country, like Canada or Mexico, before continuing on to Cuba.
My friends and I flew from Austin, Texas, 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.
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.
And you can use the Barclaycard Arrival Plus World Elite Mastercard to erase the cost of your Cubana Air flight!
Cuba is one of my favorite countries because of the energy, diversity, color, and history. There’s so much to explore in Havana alone. I can’t wait to return to explore the rest of the country!