Homestay Hopping: Amazing Cuba Road Trip

*This Cuba road trip article is the cover story in the Spring 2018 issue of Vacation Rental Travels Magazine (pages 34 – 47)*

It’s been one of the most controversial destinations for Americans since the 1960s. But love it or hate it, no one can deny that Cuba is intriguing.

Starting in January 2015, President Obama opened legal entry to Cuba for twelve new categories of American travelers. That’s when I started dreaming of going, and this year, that dream became a reality.

Some of the hype about Cuba is false; there are no old women smoking cigars on every street corner. In fact, I never saw a single one. Some of the hype is true; American classic cars are everywhere.

We wanted to see the “real Cuba,” now, before it changes. The licensed “people-to-people” tours are expensive and adhere to a tightly-controlled, government-approved itinerary. Since we qualified under one of the allowed categories, we opted to go on our own and rent a car to drive around the entire eastern half of the island.

We also opted to stay in casa particulars – private residences that have been tailored and licensed to operate as bed and breakfasts – rather than the hotels which were widely reported to be run down.

There are different ways to experience a casa particular:

Entire house, owner not present.
Private room with private entrance.
Private room in the owner’s house, shared entrance.

We tried all three, six homestays in all, in five different cities, with a range of hosts from those that spoke fluent English to no English at all.

What we lovingly call “The Mother of All Road Trips” started in Havana. The capital city is almost indescribable. It simultaneously assaults all your senses – the exquisite architecture now crumbling under your touch; the smells of cooking food wafting out from shops and homes mixed with scent of garbage and dog excrement on the street; festive Latin music blaring from open windows compelling me to dance in the streets; the frozen daiquiri that slides all-too-quickly down your throat. Read more of the Cuba road trip: