On August 31, 2016, history was made as the first commercial passenger flight from the U.S. mainland to Cuba in over 50 years embarked from Ft. Lauderdale to Santa Clara. That flight was the one of a series of events over the course of two years intended to normalize relations between the former Cold War enemies.

In the few short months since the flight, which took off amid much fanfare, even more restrictions between the countries have been loosened. However, the rules surrounding travel remain vague and complicated for Americans hoping to visit our neighbor 90 miles south. This guide is intended to make the process of traveling to Cuba as clear and coherent as possible for independent travelers.

Update June 2016: As recently reported, the travel restrictions on Americans will soon be reversed to reflect pre-Obama era rules and regulations. Americans will still be able to visit Cuba, but with designated tour companies. It is not yet clear, according to the State Department website, exactly when the reversal will be in effect.

Step 1: Meet Entry Requirements

I’m fully supportive of on-a-whim travel, but even as visiting Cuba has become more accessible to Americans, there are a few regulatory stipulations that need to be met. If you want to travel Cuba independently, that means at least a minimal amount of itinerary planning needs to be done to meet the requirements for obtaining a visa.

Taking a step in Cuba is taking a step back in time. Spend some time learning about its tumultuous history, and how that has shaped some of its many UNESCO World Heritage cities. Plan out which cities you want to visit, whether that means a long weekend in Havana or a two-week drive along the length of the verdant isle. Map out an entry and exit plan, then book your flights.

Your in-country itinerary needs to meet a few requirements to apply for a visa, I’ll get to that below. 


By January 2017, 10 U.S. airlines will operate daily or weekly service to 10 cities in Cuba. Flights will depart from Ft. Lauderdale, Miami, Orlando, Tampa, Atlanta, Charlotte, Houston, Los Angeles, Newark and New York. Prices are currently low, so book your ticket now! Check out the airline webpages for more details:

DeltaAmericanUnitedAlaskaJetBlueFrontier, Silver Airways, Spirit, Southwest, Sun Country

Note: The Cuban government requires proof of travel insurance, including medical coverage, to enter the country. The “flight insurance” offered with our airline tickets covered all manner of unanticipated need, medical included. If your airline doesn’t offer such a package, make sure you purchase travel insurance to cover the duration of your visit.


The official license and visa application is where it gets confusing for Americans trying to plan independent travel. The regulations, as written, are somewhat vague. In recent years, before the commercial flights opened, most American travelers wanting to visit Cuba could only sign up with one of a handful of government-approved tour companies offering “people to people educational exchanges”. People-to-people travel is one of a list of 12 official reasons Americans are allowed to visit Cuba; “tourism”, by definition, is still considered illegal. Prior to early 2016, visitors needed to write to the Office of Foreign Assets Control (OFAC) under the U.S. Department of Treasury to obtain an individual license based on their planned itinerary, which needed to meet the strict guidelines to qualify as a people-to-people tour; more often the tour agency would do this on their behalf, included in their sometimes lofty prices.

Earlier this year, as one step in the process of loosening restrictions, OFAC re-designated the 12 reasons as “general licenses”, and stipulated that travelers no longer needed to write in to obtain an individual license prior to travel. The catch, for lack of a better word, is that travelers still need to plan (and maintain) a full itinerary meeting the guidelines of one of the 12 licenses in order to apply for their visa and legally travel in-country.

The good news is that travelers are no longer required to travel with a tour company, lending more independence and flexibility to their trip. The downside is the traveler needs to plan out their itinerary prior to applying for their visa. In my opinion this trade-off is in the favor of most travelers, with adequate planning.

Check out this official OFAC page, specifics about the regulations, and this FAQ for more details on the general licenses. Most travelers will want to develop a people-to-people itinerary, although official religious organizations, journalists and other designees can design different kinds of itineraries that fit their needs.

Tip: When planning our trip, I visited the websites of a handful of government-approved tour companies to review their published people-to-people itineraries. While the websites used ambiguous activity descriptions rather than specifics, such as “Today you’ll visit a coffee plantation and talk with the farmers about how the beans are roasted…”,  I used the approved itineraries to guide one tailored to our group. I’d basically take an idea that sounded interesting, then do research to find a similar activity in the cities we planned to visit. The Lonely Planet Cuba (Travel Guide) was a valuable resource at this stage. I’ll post our actual itinerary, with our personal recommendations, in the coming weeks.

When you’re ready to apply for the visa, fill out the online application through Cuba Travel Services (CTS). I spent 4 solid weeks calling and emailing the Cuban Embassy in Washington, hoping to apply for my visa directly through them, but months after my trip I have yet to receive a response. I chatted with a helpful representative at CTS who expertly answered a few questions I had, submitted my form online, and within 3 business days my visa arrived via FedEx.


  • You’ll need to have your flight information, including confirmation number, before applying for the visa.
  • You’ll sign an affidavit claiming which of the general licenses you’re applying under, so it is important to do your research and have your itinerary planned prior to applying.
  • While misleading, the visa you are applying for is a “Tourist Visa”, despite the fact that the regulations specifically state “tourism” is illegal. I told you the regulations were confusing!

Step 2: Reserve transportation and accommodations before you go

While not mandatory, booking your in-country transportation and accommodations will not only save you precious time on the ground, but gives American travelers the convenience of using their U.S.-based credit or debit cards, which they can’t use in Cuba (get those airline miles!). That means needing less cash in hand while traveling, but do make sure your reservations are flexible enough in case you want or need to change them at any time.


Car rental

The car rental was probably the most difficult step in the planning process. There are only a few national car rental companies, and depending on time of year availability can be severely limited. We worked with WOWCuba, who were very responsive, but even with plenty of lead time we were already in country before we had a confirmed reservation.

Prices will vary based on size, but assume between $50-70 USD per day, including mandatory insurance. A cash deposit will be required, which will be reimbursed at drop-off assuming no damages are incurred. A small fee will be charged for pick-up and drop-off at a different location.


Travel by bus is an affordable option, though on longer routes you’ll lose more time than driving. Viazul offers convenient routes at amazing prices, their buses seem to be in good condition, and booking can be done online with a U.S.-based credit card. Transtur is an option if your Viazul route is sold out.


When you get into the cities you’re visiting, your best options for getting around will be on foot or by vintage car taxi, bicitaxi, or occasionally horse-drawn wagon. Regardless of the vehicle, negotiate the rate before getting in. Ask your casa particular host or hotel desk to help gauge the price. For reference, a 15 minute drive in Havana shouldn’t be more than $8 CUC. Legitimate car taxis will have signage, so be wary of drivers without a sign.

travel cuba independently


Travelers have long adored Cuba’s casas particulares, which are rooms or apartments rented in a local’s home. It was a natural fit then for AirBnB to launch in Cuba, enabling travelers from the States to book reservations and process payment with U.S.-based credit cards. Meals cooked by the casa hosts, still some of the best you’ll find on the island, will typically be an additional charge. Breakfast tends to run $5 CUC, and dinner $10 CUC.

Cuba’s many UNESCO World Heritage cities also boast some beautiful colonial hotels, though hotels will tend to run higher than casas.

Here are a few of our recommendations:

Santa Clara – B&B Señora Olga Rivera

Sancti Spiritus – Hotel Rijo

Trinidad – La Casa Terracota

Havana – La Rosa de Ortega and Casa Margarita

Step 3: Plan out the details


This is likely to change in the coming months, but currently U.S.-based credit and debit cards will not work anywhere, for any purpose, in Cuba (hence my earlier comments the benefit of services you can book online). You can exchange USD on island, but there is a 10% fee. Depending on the rates you can find, exchanging USD to Canadian dollars or Euros before you leave the U.S. may fetch you a better conversion.

There are two currencies in Cuba, the convertible (CUC) and moneda nacional, or pesos (MN). The CUC is the denomination of choice for travelers, though you’ll find some street vendors asking for pesos.

Cuba isn’t the most budget-friendly destination in the Caribbean, but savvy travelers can make it affordable with some planning. Here’s a breakdown of our costs during the trip:

Cuba costs

Phone and Internet

Phone and internet connectivity is limited for travelers. Cards can be purchased at ETECSA stores, but be prepared to wait in line. A $10 phone card will get you just under 10 minutes of talk time. Phone booths that accept ETECSA cards are easy to find in the cities. A $2 internet card will get about 10 minutes of connectivity anywhere WiFi is available, but those spots are few and far between. Public spaces that offer WiFi may not always have adequate signal to connect. You’ll know where to find internet when you see a group of people huddled all near one random spot on the street staring into their smartphones.

Access to fast internet connections for businesses and individuals can be expensive, so do expect that if you reach out to casa particular owners, hotels, or other businesses, response times can be longer than normal. Give yourself a few weeks to get all your reservations in order if you’ll be doing a lot of traveling.

Rum and Cigars

You can’t truly experience Cuba without enjoying her most beautiful fruits. When we visited, there was a $100 USD limit on bringing back alcohol and tobacco…combined. In the last few weeks that limit was lifted, so prepare to stock up. As with most cigar destinations, do not buy off anyone on the street.

If you’re in Havana, Tienda del Habano on Mercaderes near the corner of Obrapia has a good quality selection and prices. Don’t purchase cigars from the adjacent Museo del Tabaco.

Driving in Cuba

We loved the freedom and flexibility renting a car afforded us, but it might not be for everyone. Potholes are ubiquitous, even on the national highways, and in some areas the poor condition of the road may warrant searching for an alternate route. Bicycles, bici-taxis, and horse-drawn wagons rule the road, so be careful when passing. Keep an eye out for horses and cattle who may be freely grazing on the side of the road. Signage is limited to non-existent, so print out driving directions and maps before you go. Try to buy an official map as soon as you can, although we found their availability to be limited.

Tip: I saved Google maps of the routes we needed to take on my phone. While you likely won’t be able to use the app, we could usually get it to pick up our location on the map to reference where we were and figure out which way we needed to go. It was a bit old-school and high tech all at once.


In general we felt safe, and were lucky to have no incidents, but precautions are always in order while traveling. Like always, keep your head on a swivel when walking the streets, and avoid wearing flashy jewelry or handbags. Only take with you the cash you’ll need for the day, and keep money stashed in various locations in case of theft.

In some areas jinteros, or hustlers, are common. They are particularly bad in Trinidad, where a popular scam is to try to stop you saying the road you’re driving is closed, or perhaps the casa particular you’re searching for is full. They’ll offer to show you another way or find another casa, either to get money from you or a commission from the owner. Simply ignore them, or firmly shake them off if they get too aggressive.

Why go?

A trip to Cuba requires a little more forethought than other destinations in the Caribbean, so why bother? For starters, few other places in the world are as frozen in time as Cuba, but that’s already beginning to change. Here history is not a dead remnant of the past, memorialized only in monuments and museums; it is a living testament that can be seen and felt and heard everywhere, every day. It’s one of the most unique destinations I’ve visited, and I’m already craving a return.

Besides living history, Cuba has something to entertain everyone. History buffs, art enthusiasts, baseball fans, motorheads, conservationists, equestrians and coffee, rum and cigar aficionados will all find something to fall in love with in Cuba. It has a rich culture all its own, unrivaled by the rest of the Caribbean.

Cuba is an enigmatic place, at once as dazzling as it is disheartening. This vibrant world, one of our closest neighbors, has been out of reach for so long. We don’t know what the future is going to hold, as a very long era has recently ended in Cuba and a new one begins in the United States. Take advantage of the opportunity to learn her history, her culture, and her beauty firsthand, while the door remains open.

It’s likely some of the information in this post will change in the coming months or years. I’ll update here as needed. Disclaimer: As always, opinions and recommendations made in this post are my own. I will earn a small commission if you purchase the Lonely Planet book linked on this page. If you sign up with AirBnB using the link in the post, we’ll both receive a $25 travel credit!

Have you been to Cuba since the restrictions have loosened? Are you planning to go this year? Leave a comment and tell me all about it!