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Visiting Cuba for the first time: Baby Boomers go exploring

What Happens When Two Baby Boomers Go Visiting Cuba For The First Time

When my brother and I surprised our parents with a Christmas gift of a trip to Varadero, Cuba in January, there was some encouragement needed. For two Baby Boomers visiting Cuba for the first time it was something scary as well as exciting.

After their trip, I talked with my mom and dad about their experience. They had some interesting points to share about why this was a cool trip for them.

Not All Baby Boomers Travel

Despite many trend reports about globetrotting Baby Boomers, not all in this demographic travel on a regular basis. For many years my parents (ages 59 and 61) were the “Sandwich generation“, taking care of us while also taking care of my mom’s parents who lived with us. Short car trips were the only kind they were able to indulge in from time to time. Nor did the thought of a vacation at a resort really appeal to them, even though they never had been to one.

So when my leading-edge Baby Boomer parents finally had a true vacation courtesy of myself and my brother, it was a treat. Visiting Cuba for the first time was also an adventure they would never forget.

Baby Boomers visiting Havana

My dad (centre) checking out Havana’s architecture and people on the street.

We secured them one week at the five-star Iberostar Varadero. It was the first time they had traveled anywhere in the Caribbean, so there was apprehension as to what to expect. They didn’t know how to dress, how to get around and what to do while there.

That changed once they got there.

Tips for Baby Boomers Travelling to the Caribbean

Being the resilient people they are, my parents learned quickly how to have a great time while on a resort.

In speaking with them both, they shared these recommendations for fellow Baby Boomers, visiting Cuba for the first time or any other Caribbean.

  • Travel shots are important. Take the time before your trip to get them from a travel doctor. They can be painful and somewhat costly, but at least you travel knowing you won’t be affected by Hepatitis A or B. You might avoid “Montezuma’s Revenge” if you take Dukoral. Take Pepto Bismol with you just in case, as it might come in handy.
Visiting Cuba for the First time

My parents enjoying dinner at the resort with a glass of wine.

  • Don’t plan to just stay on the resort. Be open to taking resort-organized tours and doing things you normally would never contemplate doing. Set aside at least CAD $800 in cash if you plan to do at least one or two activities/tours that aren’t part of our all-inclusive deal. If in Varadero for the first time, do the trip to Havana as it’s worth seeing the historic buildings and to experience true Cuban culture. If you have time, splurge on a fancy meal at one of their best restaurants.
Baby Boomers visiting Cuba

Do something out of the ordinary. I’m surprised my parents went out on the catamaran, but it makes for a great story!


  • Travel with cash on hand. Sometimes your credit card in countries such as Cuba, will not be useful. While the resort exchange office claimed to accept it, they were having technical difficulties. Nothing beats clean, crisp dollar bills. Avoid taking any bills that are old or with writing on them. Local banks and exchange offices may not accept them. As well, if you are Canadian, don’t take along your loonies and twoonies as tips. They aren’t useful to the locals.


  • While resort staff are very courteous and nice, be nice to them from the start and they will treat you like gold. With tips and a friendly, sincere attitude towards them, they will make your stay even better. Resort staff in any country observe the behaviour of guests from different countries. As such, they will have preconceived notions about what to expect from a Canadian, American, Brit etc. If the general view is unfavourable to your nationality, change it by being courteous.


  • If you are traveling alone with your spouse/partner, engage others in conversation to build acquaintances that can make your experience more fun. This is not a time to be shy. The lobby bar of any resort is a great place to start. The easiest questions to ask are, “That drink looks interesting, what is it?” or “What do you think about this resort?
Visiting Cuba for the First Time

When in Rome… Enjoy a Cuba Libre in the resort lobby and strike up a conversation. Photo by Ashley Kirk on Unsplash

  • Pack for all eventualities as sometimes there may be a cold spell, particularly in December or January. For two days during their trip, my parents had to bundle up and layer their clothes to keep warm in 13 C evening temperatures. Packing at least one sweater, pants and a light jacket can take up space in your suitcase, but also can keep you from shivering the day and night away.


  • Be aware that if you visit a five-star resort on your first trip, you are spoiling yourself. Future trips may not be to five-star resorts, and you will need to adjust your expectations. As well, not all five-star resorts are run at the same level of luxury.

Their final piece of advice: leave all worries at home and have a good time.

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