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Why I’m Off To Cuba Again (So Soon)

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Ever since my spur-of-the-moment trip to Havana, Cuba with TPG International Contributor Lori Zaino back in January 2015, I’ve been wanting to head back to Cuba and explore more of this charming, complex country–the largest in the Caribbean, with newly relaxed restrictions and a lot to offer tourists aside from its capital city. Visiting only Havana is like going to Times Square and feeling confident you’ve seen the whole U.S.

Though I just got back from a whirlwind trip to Asia, I figured it would make sense to take a quick trip to Cuba before it became unbearably hot. By the time you read this, I’ll already be in Cuba with little access to Internet, but I’ll be updating Facebook, Twitter and Instagram as much as possible—so please follow along for updates!

I am so excited to head back to Cuba again! Photo by Lori Zaino.

Last time I went to Cuba, I winged it, booking a last-minute hotel from A Nash Travel, flying via Grand Cayman and buying a $20 tourist visa there. This time around I did things with just a bit more organization: I enlisted the help of expert Cuban luxury travel agent Johnny Considine (who actually lives in Cuba, his contact info is at the end of the post) from Esencia Experiences, who was instrumental in helping me book charter flights, organize a three-day set of activities, transportation and casa particulares (homestay rentals). All of our trip reports, resources and recommendations are listed and linked below in case you are planning your own trip to Cuba, and stay tuned for more coming your way as my second trip begins.

I can’t wait to visit the colorful Cuban town Trinidad. Photo courtesy of Shutterstock.

My trip will start by flying into Santa Clara, a town right in the center of Cuba with an interesting revolutionary history. Then I will head to picturesque and colorful Trinidad, a UNESCO World Heritage site that I’m super excited to explore. It’s not a visit to the Caribbean without a little beach time, so I also plan to see the Bay of Pigs beaches, Playa Giron and Playa Larga, as well as the mountainous Topes de Collantes park.

I’ll end my trip in Havana, which I’m thrilled to see more of. On my previous visit, I had the pleasure of meeting friendly people like artist Damian Aquiles and his fascinating wife Pamela (who hosted an incredible dinner party in their home, a piece of art in itself), and I’m looking forward to seeing and doing some of the things they suggested. TPG Photo Editor Julio Gaggia will be joining me, so I’ll soon be able to share some amazing trip photos along with my reports.

It’s important to note that the rules for traveling to Cuba have recently become much clearer, making it easier for US citizens to visit. If you fit into any one of 12 very broad tourist license categories, you can basically approve yourself for a trip without needing to apply for a license from the Office of Foreign Assets Control (OFAC). One of these categories is as simple as planning to see a public performance (check out Cuba Absolutely to find events happening in Cuba or consider going for the Havana Biennial, an international art festival happening late May). I’ve spoken to some friends and contacts who work in visas and international policy, and they are unaware of any incident of someone going to Cuba under one of the 12 general licenses being scrutinized or penalized by the US government.

I am really hoping to have better luck this time using my credit cards in Cuba, but who knows! This time, I will try my MasterCard first.
I am really hoping to have better luck this time using my credit cards in Cuba, but who knows! I will definitely be trying my MasterCard again.

The US is also moving to taking Cuba off the state sponsored terrorism list which should also help banking relationships—supposedly, as of March 1, 2015, MasterCard can be used in Cuba, but while American Express is planning on initiating business activities in Cuba, it hasn’t yet set up merchant relationships or terminals; they don’t have a timeline for when all this will happen or when Amex cards will be able to work in Cuba. It’s still unclear if any US-issued cards will actually work there, especially in smaller cities or beach towns around the island, but I’ll definitely be trying my own, and I’ll report back to let you all know if I’m successful!

One other important thing to mention is that hotels sell out extremely quickly, so planning ahead is strongly recommended. If you find yourself out of luck in the hotel route, don’t forget the casa particular, or homestay option, as well as the brand new option of Airbnb rentals in Cuba.

Also check out these related posts and resources:

Travel Tips For Cuba
Who Can Go to Cuba?
How to Get to Cuba (and Back): Flight and Award Options.
Where and How to Book Hotels in Havana, Cuba
What To Do and See in Havana, Cuba
Hotel Review: Occidental Miramar, Havana
Inside the Super Exclusive VIP Lounge at the Havana Airport
Airbnb Now Open in Cuba
10 Things We Learned On Our First Trip To Cuba
Book Flights To Cuba With CheapAir

For just flights: Travel Services

For just booking hotels: A Nash Travel

John Considine of Esensia Experiences can help you plan a full-service luxury trip, and you can email him here:

Jose of ACJourneys puts together trips for people who are Miami-based, and can be emailed here: (For better deals and service, be sure to mention Brian Kelly sent you.)

For private Havana city tours, contact Osvaldo Nicolas at:
+53 53257200

Keep an eye out for my (possible) updates from Cuba on Facebook, Twitter and Instagram—and let me know if you’re planning to go to Cuba this year, as well!
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