How to travel to Cuba & what it’s like:

I’ve been getting a lot of e-mails recently about the Cuba Diary I wrote a few years ago. People seem to be more interested in traveling to Cuba now than at any time since the embargo. There have been some amazing changes recently in the US policy towards Cuba: relaxing of restrictions, opening of embassies, etc. It’s now fairly easy to travel to that amazing country. I’m going to briefly tell you how I did it and how you can too!


01. Why did I want to go to Cuba? Why should you?:

In the quiet early days of October 2012 I went to Cuba and it was everything I wanted it to be and it was everything I was told it wouldn’t be. I had been dreaming about Cuba for years. So close and romantic and dangerous and completely irresistible, it was just right there. I thought about flying to Mexico and going illegally, my friend Paul and I wrote up a business plan to export cigars post-embargo, but I went on a people-to-people trip and I’m so glad I did.

I grew up in South Florida. Cuba was 90 miles from my house. When we first moved from New England, we would go for dinner in Miami and Ft. Lauderdale, at that time a popular restaurant lawn decoration were rafts Cuban refugees used to get to America. I remember seeing Cuban expats living under the bridges of I-95. What was going on over there? I knew I had to go and see it one day.

I want you to forget about everything you’ve heard about Cuba in the past 50 years. It’s not that prison island. It’s not that Communist nightmare. You should go because you’re a curious person. You should go because you want to see things with your own eyes. You should go because Cuba is bigger than you think, it’s more beautiful than you can imagine, and the people reflect that beauty. They will be curious about you too. They’ll smile and want to shake your hand as you walk down the Malecon.

Most importantly…you should go to Cuba because you can.

02. How did I pick a tour provider?:

There weren’t a lot of options when I decided to travel to Cuba legally. I saw some very expensive tours sponsored by universities in NYC, some obscenely expensive tours sponsored by National Geographic, etc. I’m not sure how I got on their mailing list, but Insight Cuba came to my attention and I was sold.

Here’s where my story get’s complicated. At the time, the State Department stopped issuing licenses to tour groups. Insight Cuba seemed perfect, but for reasons beyond their control they had to postpone my trip month after month. Finally, they decided to team up with Road Scholar (a company that did have a license), and see if I wanted to transfer my reservation to them.

I was hesitant at first. I was 30 years old at the time. Road Scholar specializes in trips for older retired people, but… I didn’t have a choice. Do you want to go to Cuba or not? YES! Of course I wanted to go. Both Insight Cuba and Road Scholar were so helpful and I can’t recommend either of them enough. That’s easy and done. Use one of those.

03. How do you actually get there? Do you need a Visa?:

I’m lucky enough to live close to Miami, the gateway to Latin America. For those of you that live in other states, you’ll need to book a ticket to Miami International Airport and that’s about it. Both Insight and Road Scholar provide a charted flight to Cuba from Miami. It’s still fairly difficult to do this on your own.

You will meet with your tour guide at a hotel close to the airport and that’s all you need to do. If you made it this far, you’ve already signed up and paid, they take care of everything else for you. You don’t need to worry about getting your own Visa. You just fill out the paperwork and everything will be ready for you when you arrive in Miami.

Just drink a beer in the hotel lobby with your new friends and wake up early for your 30 minute flight to Havana!

04. What is like taking a people-to-people trip?:

The trip I took started in Havana, went to the outskirts of Havana, down to Trinidad, Santa Clara, and ended in Cienfuegos. That’s a typical route for an 8-11 day trip. I recommend making sure you hit Trinidad or Santa Clara on your trip if you can. Both are amazing cities you’ll fall in love with.

People-to-people trips are heavily regimented, but that doesn’t mean you won’t have free time. You’ll attend morning lectures, you’ll visit with local people, but you’ll also get to wander around on your own. Honestly, the trip was so amazing because of all the required stipulations. If I went to Cuba by myself I wouldn’t have seen a fraction of what I saw.

You’ll stay in amazing hotels like the historic Hotel Nacional. You’ll eat at the best restaurants. You’ll get to go off on your own at night to a paladre and sip daiquiris where Hemingway sat. Don’t be scared of the educational element.

05. Is it safe? Can I bring my mother? What should I pack? Etc etc etc.:

Cuba is beyond safe. I’ve never felt safer. Bring your mother, bring your children. There were people in my group in their 90s and they had just as much fun as everyone else. Pack how you would pack for any other trip.

You won’t be allowed to go to the beach, but there will be opportunities for you to swim, so pack a bathing suit. You could also bring some gifts for the local people you’ll meet (soap is always beyond appreciated).

Pack an open mind and you’ll have the time of your life.

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