After a family trip to Havana in March 2015, I returned home and added a Cuban title to the 101 Ways to Rock Your World book series. Since that time, many changes have taken place, the US Embassy has opened, and direct flights between the US and Cuba are schedule to begin on major airlines this fall. (The video at this end of this piece is my husband seeing his grandfather's home for the first time since 1959.)
Want to go? Things are changing fast in Cuba but the more they change, the more some things stay the same. Here are some of our favorite tips from Havana: 101 Ways to Rock Your World - 101 tips that still hold true in this Caribbean gem:
2. CHECK YOUR PASSPORT.
If your passport is going to expire within the next six months before you complete your travel, you can't travel to Cuba - and many other places. Your passport must have at least half a year left before the expiration date. Cuban authorities are professionals at bureaucracy, and while you can talk your way out of some problems, immigration law is not one of them. On the same note: don't overstay your Cuban visa, which is still required at this writing. Renew it at least a week before it expires.
5. SET REALISTIC EXPECTATIONS.
For many of us, the idea of a Caribbean vacation means being able to shut off the part of our brain controlling moderation and assume everything will be fun and easy. Havana is not so forgiving. The city is almost 500 years old, and it looks it in many places. Lights go off, even in nice hotels, and your water might not always be hot, or even running. Similarly, 57 years of communism hasn't exactly created a service industry that makes the customer feel valued or even wanted. And, if you consider yourself punctual, you should prepare yourself for "island time."
8. LOOSEN UP.
The reason Cubans can tell you are a foreigner, besides the fact your shoes are probably a lot newer than theirs, is you are a bit stiff. Cubans have a swagger when they walk, a sway when they dance, and even their Spanish sounds so loose it's about to fall apart. So, before you leave home - take a stretch, shake out the kinks, and loosen up. A lo Cubano.
22. DOUBLE AND TRIPLE-CHECK YOUR RESERVATIONS.
Cuba's travel infrastructure supports millions of tourists each year but behind the scenes it mostly operates in the pre-digital age. Your reservation could be lost when a less-than-enthusiastic, underpaid hotel employee writes your name down on a scrap piece of paper (because their computer is out of service) and then someone else uses it as a napkin. When you arrive at the check-in desk there will be no record of your reservation, and you will be lucky to get a no es fàcil from the receptionist. Nip this potential problem in the bud; send emails and make phone calls confirming your reservations when you make them and again before you leave. Arrive in Havana with printed copies of all of those email confirmations.
62. ASK SOMEONE WHAT HIS OR HER OTHER JOB IS.
Due to low-paying state jobs and high-paying tourist jobs, Havana is full of doormen who have doctorates in engineering, taxi drivers who are also emergency room physicians, and waiters who could explain the more complicated aspects of quantum physics. Strike up a conversation with a hotel, restaurant, or transportation worker and ask them what their other job is. You might be surprised to find the person unloading your luggage at the hotel could also be designing Havana's next skyscraper (if any were being built).
70. GET OFF THE TOURIST MAP.
Popular guidebooks often come with maps of the most visited areas of Havana. However, there are other neighborhoods that have hundreds of years of history and represent the reality of the present day city. Municipalities such as Cerro, La Lisa, and Boyeros are examples of parts of Havana where thousands of people live but hardly anyone visits. Surprise your convertible driver and tell them you want to go to one of those places as you cruise the streets of Havana. They will probably be impressed by your local knowledge and willingness to get off the beaten path.
84. GIVE UNUSED INTERNET TIME TO A LOCAL.
If connected to the digital world in any way, you probably bought Internet time in the hotel or at an Internet café. If you have any time left, give it to a Cuban. If your hotel has Wi-Fi just look for the young local kids hanging out in the lobby; they are there precisely to use the Internet. Hook them up with more time by giving away your leftover minutes. They will be stoked.
95. FIND A LOCAL CUBAN CONNECTION.
Almost two million Cubans and their families live outside of Cuba. That means in your hometown, no matter where it is, you are likely to come across someone who once called Havana home. Maybe your short taste of the island left you with a hankering for rice and beans or braised pork loin. Perhaps you want to take up salsa lessons to impress the locals when you make a return trip. You might be surprised to find you can fulfill your Cuban-inspired desires by looking up a local Cuban restaurant or dancing lessons. Cubans are just as curious about what you think of their country as you are about what they think of their homeland.
Need More? Pick up a copy of Havana: 101 Ways to Rock Your World. A lo Cubano!
Others in the book series:
101 Ways to Rock Your World: Everyday Activities for Success Every Day
Welcome to College! 101 Ways to Rock Your World
On the Golf Course: 101 Ways to Rock Your World
In the Classroom: 101 Ways to Rock Your World
Dayna Steele is the creator of the 101 Ways to Rock Your world book series. She's a popular business keynote speaker. Her other book titles include Rock to the Top: What I Learned about Success from the World's Greatest Rock Stars and Surviving Alzheimer's with Friends, Facebook, and a Really Big Glass of Wine. Her Havana co-author Graham Sowa is finishing his medical degree in Cuba and is also running quite the Airbnb franchise in Havana! See more here.