One of the questions I get asked a lot is, “How can I go to Cuba on my own?”

Eight years ago, I started one of the few US-owned (and woman-owned) tour companies specializing in small group tours in Cuba. After numerous trips and the classes I’ve taught on Cuba, the number one thing I have learned is that it is a complex (and ever-changing) system to navigate.

I’ve adventured on my own plenty in Central and South America and am fluent in Spanish, but after years of travel to Cuba and hearing the nightmares of independent travelers to Cuba, here are the reasons I swear tours are the way to go if you want an enjoyable, stress-free experience.

Waiting in line for hours for gas. As Cuba emerges from the pandemic, its economy is very slow to bounce back. Our friend whose business is classic car tours in Havana tells me that in the last year there have been times where the gas station runs out of gas, so he parks his car in line and it is the next day before he can fill up and resume work. The shortages apply to other necessities as well; the corner market where I used to buy bottled water in Havana hasn’t had it for months. Our driver and guide tap into their network of locals to know which store in Havana has water and they buy enough for the whole trip, so I never have to think about it- and neither do our guests!

woman in red vintage vintage car with building in the background

Public transportation is unreliable. The bus schedules are often more of a suggestion than a guarantee. Right after President Obama lifted the restrictions on commercial flights to Cuba, I was in Viñales, a popular tourist destination a couple of hours from Havana. It is a quiet tobacco farming community with one main street in town with restaurants. I met a young couple who were backpacking around Cuba and ended up sleeping in someone’s car. The next morning they went to the bus station to buy a ticket out of town but were told it was uncertain whether the bus would come that day.

Elderly man in hat with an oxen. Blue house and mountains in the background. Partly cloudy sky.

US banks don’t work in Cuba. Due to the embargo, credit cards and ATM cards for US banks don’t work in Cuba. This means you have to bring all your spending cash with you, in pristine dollars. If a piece of artwork catches your eye or you end up having more mojitos than you anticipated, your spending money can go faster than you might have anticipated. One benefit of our tours is that if you end up short on cash, our guide will make sure you get the money you need.

Getting a visa. This is the clincher- the process of getting a visa to Cuba can be a real hassle. Plus, the rules change under every U.S. president. While the Cuban government is happy to have U.S. tourism, Americans are prohibited from participating in “tourist activities” as defined by the U.S. government. You can find the link to the State Department’s Code of Federal Regulations (515.560) on the Vive Mas Tours FAQ page. Our tours are created for the Support for the Cuban People visa and are designed with a full agenda of activities that provide meaningful interactions with individuals in Cuba, thus “unique cultural experiences” is our tagline.

Very safe. Despite all these obstacles, there are still plenty of U.S. travelers that have positive experiences on their own, thanks to the incredible warmth and hospitality of Cubans, and that it is an extremely safe place.

Consider how you want to spend your valuable vacation time. The advantages of a group tour can be compelling, so I encourage you to find the right company to travel with so you can relish this fascinating island and its culture.