Last updated on January 13, 2023

Less than a hundred miles off the coast of the United States, Cuba is a step into a seemingly lost era. Travelers dreaming of visiting Cuba conjure images of classic fifties cars set against crumbling Spanish colonial facades. They picture lively street-side musicians and miles of gorgeous coastline. And that’s largely what you find when you visit the country. The country boasts some of the best Spanish-Colonial architecture in the Americas, the most pristine coral reefs in the Caribbean, and a fascinating, vibrant culture. Cuba is one of the more intriguing places in the Caribbean. Although the decades-long U.S. embargo shielded Cuba from much American influence, Cuba hosts millions of travelers from Europe and Latin America each year. Many tourists opt for luxury resort hotels, but it’s possible to independently travel the country on a much lower budget. Particularly if you plan to travel independently, it’s important to understand Cuba’s complex history, as well as the current political situation since these will crop up in small ways throughout your visit.

I visited Cuba in 2010 and had mixed feelings about the country; the locals were in a downswing on trusting the government and were afraid to talk with tourists. Recently, travel friends reported that much has changed and independent travelers will find opportunities for fascinating conversations and local experiences all over the island nation. Cuba is safe for travelers, including families—a big factor for indie travel. And there are a lot of fun moments to discover: the local obsession with baseball, the fluidity of time, the love for soul-satisfying beats. Also, all travelers should realize that the transportation infrastructure in Cuba is rough, and you should make a strong commitment to understanding responsible travel considerations unique to Cuba.

This travel guide focuses on helping those taking independent route through Cuba’s major travel spots, and it highlights the most important historical situations and pressing issues you’ll need to know. It also includes city recs and responsible travel options, too!

Things to Know Before Traveling to Cuba

Understanding these pieces of Cuba’s recent history is an important part of ensuring that conversations with locals are undertaken with thoughtful and considered opinions.

Present day Cuba has a fascinating mix of centuries-old history combined with decades-old history. Both are equally important in modern Cuba. Cuba’s ancient history shows the island was inhabited as far back as 3,000 BC, but little is actually known about the country’s pre-Columbian history. Once Columbus landed in 1492, there is a clearer timeline to present day. The Spanish colonized Cuba for 400 years, only leaving in 1899 and it’s that occupation that gives the island it’s unique and fascinating aesthetic. Postcolonialism, Cuba became a top global producer of sugarcane and used African and Chinese immigrant labor to meet demand. These two immigrant groups have had a lasting impact on the culture. Today’s Cuba is known the world over for the unique sound blend of Afro-Caribbean Latin music.

A Cuban revolution in 1959 overthrew the U.S.-backed military dictatorship led by Batista. Che Guevara—a revolutionary hero depicted all over the small island in everything from posters to graffiti—and Fidel Castro led the revolution and their win secured Castro as the country’s Communist dictator. The Cuban Missile Crisis had two major effects. It triggered the U.S. to sever relations with Cuba and sign a trade-embargo. It also secured Cuba’s relationship with, and dependence on, the Soviet Union. With the fall of the Soviet Union, the nineties were tense and tough for Cubans. Food shortages, power cuts, and the continued repressive regime had many Cubans fleeing the regime to the U.S. From then until now, the quality of life in Cuba has fluctuated with the government’s shifting policies. It’s also in the nineties when Cuba opened to tourism. It’s this period of time, post-nineties, that has many Cuban-Americans leery of the enthusiasm tourists have for visiting Cuba and thus tacitly supporting the government. The thawing of the U.S.-Cuba relationship began in December 2014 and will take many years to fully implement planned changes to the relationship between the two countries. The thawing has stalled a bit, however, with U.S. policy changes after Obama took office, but it’s still a vastly different scenario than it was before 2014.

For travelers, understanding these pieces of recent history is an important way to ensure that conversations with locals are undertaken with thoughtful and considered opinions. The Wikipedia page has a full history. For a quick overview, I rather like this BBC timeline or this Vox piece.

Fast-Facts About Cuba Travel

Pre-Trip Reading Inspiration: Books About Cuba

Fiction and Nonfiction Books About Cuba

• The Other Side of Paradise: Life in the New Cuba. Makes a good history read, but a little more accessible. Published in 2014, it’s the most recent and gives a great overview of the modern Cuba visitors will find.
• Cuba, What Everyone Needs to Know. If you’re interested in a deeper accounting of Cuban history, this is accessible and thorough enough to flesh out any gaps in your understanding—while still being compact.
• Dirty Havana Trilogy. Tales from a former journalist on some raunchy (mis)adventures in Havana. Published in 2002, it’s a good contemporary read about modern Havana.
• Adios, Happy Homeland. A collection of stories, the author uses modern myths and Cuban commentary to build a fascinating and unique complementary collection of stories.
• Dancing to “Almendra”: A Novel: If you like getting a dose of history through fiction, this story weaves together fascinating characters and elements of 50s Cuban history.

Podcasts and Online Reads about Cuba

• RadioLab: Los Friskis: A fantastic podcast episode about a group of eighties Cuban misfits who found rock-and-roll and created a revolution within a revolution, going into exile without ever leaving home.
• Our Human Planet: Cuba: A long-time traveler and filmmaker explores the various facets of Cuba now that it’s opening to tourism, and offers a niche look at everything from transportation to traditional games.
• NPR’s Brief History of U.S.-Cuba Relationship: NPR takes all the highs and lows over the past 100 years and makes it easy to understand and consume.
• Claimed: Fascinating profile on Slate about the claims U.S. citizens and companies have over property in Cuba. I didn’t know that these unpaid claims were the foundation of the U.S. embargo—it’s a good read.
• In Pursuit of the Wild Cohiba: This is narrative presents backstory on Che Guevara, cigars, and an intriguing, unseen side of Cuba.
• Cuba, in Clothes: This presents an interesting way to use the lens of fashion to learn about the Cuba that is just now emerging after the U.S. lifted the embargo and more money is flowing into the country.
• Word of Memory Stick: Without email and Facebook, how would you communicate? This article looks at how Cubans share their lives and stories when the rest of the world uses technology.
• Cinefilia en Habana: A look at how one Cuban filmmaker bucks the revolution and reimagines Utopia.

Read all my Cuba travel blog stories and find more regional fiction and nonfiction books and long-reads.

Best Things to Do in Traveling in Cuba

Unlike other guides on this site, this one won’t break down the recommendations by city, but instead present a list of activities and where you can partake. Cuba is quite small, so some travelers choose to take weekend or day trips from Havana. I spent a week in Trinidad and a week in Havana—with better weather (boo February, boo) we would have ventured further. Here are the highlights!

My 5 Favorite Experiences

1. Slurping down a cone from Coppelia Ice Cream in Havana—it’s a Cuban institution.
2. Starting each day with delicious guava juice and a plate of mamey fruit.
3. Watching kids play baseball in every open space.
4. Wandering the colorful streets of Trinidad and learning salsa to the beats of Afro-Caribbean music.
5. Photographing the crumbling colonial buildings in Habana Vieja. 

Traveling Across Cuba

• Wander Havana and explore with this detailed laminated city map, updated in late 2016. Since Cuba is changing quickly, it helps to have a solid map for exploring. This company also has a detailed map for all of Cuba, ideal if you are road-tripping across the country.
• Museo del Chocolate in Havana. It was unseasonably wet and cold when I visited so I took refuge in this delicious smelling shop and loved their hot chocolate and various treats (churros!).
• Pass through Callejón de Hamel in Centro Havana to see the quirky street art and murals from Salvador Gonzalez, a local artist. Go at noon on a Sunday for an experience that you’ll remember forever—drums, rhythms, and Afro-Cuban music for hours.
• The long stretch of Havana’s Malecón is quintessentially Cuban. Like a lot of the country, it’s best to plan for a stroll and give yourself time to relax and just enjoy. Cubans have a sidewalk culture—life is lived in the open, so give yourself time to soak it in.
• Walk from Old Town to the National Hotel along the Malecón and plan on finishing here just before sunset so you can grab a drink and watch the sunset over the water.
• Wander the streets of Trinidad and shop the tiny side roads. Seriously beautiful and low-slung colonial town.
• Museo Nacional de la Lucha Contra Bandidos in Trinidad. Fascinating and has gorgeous views.
• Book a tour before you leave; if there’s something you just absolutely need to do, book that experience ahead of time. Companies like Cuban Adventure and WoWCuba allow online booking and that will ensure your adventure actually happens (since the internet is scarce to research and book one you are there). For everything else though, day trips are easy to book and your casa particular owner is often very amenable with recommendations for things in the area.
• Visit the Valle de los Ingenios with a local man running ethical horse trips. You can also board a vintage 1907 American steam train to travel through gorgeous UNESCO recognized valleys outside of Trinidad and end at the sugar estate of Manaca-Iznaga. The train ride is more touristy, the horse day trips are an amazing way to get out and explore the region.
• Use the Viazul bus network to easily visit anywhere in Cuba. In the height of tourist season you may need to book ahead.
• Head to Cienfuegos for the El Nicho Waterfalls and revel in the pretty, lush green as you hike and swim.
• Remedios is a quaint enough town on it’s own, but if you find yourself in Cuba over Christmas, no where else can you experience something like their celebrations, called Las Parrandas.
• An eco-tourism project done right, Las Terrazas in the Sierra del Rosario Biosphere Reserve (a UNESCO site) offers everything from hiking to ziplining.
• Head to Viñales; friends of mine count this as one of their favorite spots to visit. You can swim in caves or just enjoy the pretty scenery.
• Visit Baracoa, the first settlement in Cuba. I didn’t make it here but I will return for it. From here you can raft, hike, or just enjoy El Yunque Biosphere Reserve and Parque Nacional Alejandro de Humboldt.
• Plan a scuba dive at María la Gorda—it’s a popular spot because they have a perfect combination of clear waters, gorgeous dives, and a great dive operation.
• Find a way to be among the mere 500 annual divers permitted on the pristine reefs of Jardines de la Reina.
• Book a bike tour to experience the rural Cuba—although you could theoretically bike the country yourself, companies like WoWCuba have bike routes that take you through the highlights, while stopping in family-run guesthouses and restaurants, which offers a great way to infuse money directly into the local economy.
• Hightail it to Santiago de Cuba for a different slice of Cuban life. It’s quite far from the tourist trail but pairs well with a visit to Baracoa. You’ll find a bit gritty and less touristy side of Afro-Cuban culture.
• Go off the path at the gorgeously placed Hotel el Salton, which is two hours from Santiago de Cuba. An ALA reader says this spot has “everything you can possibly want for some authentic experiences, getting lost in the jungle, and getting away from the city.”

Best Places to Eat and Sleep

• Head to the National Hotel on Havana’s Malecon for sunset drinks.
• Gorgeous Seaside Havana Airbnb. Sleep seaside in a beautiful white apartment located on Havana’s Malecon. With seaside views and a very reasonable price tag, it’s the best deal I’ve seen online. I often use Airbnb on my travels; if you’re new to it use this link a free credit for ALA readers. :)
•  Hostal Cuba in Trinidad. This spot is top-ranked and I’ve never heard a bad word about it. It’s well located in Trinidad and makes a great base for your stay.
• Casa de la Músíca in Trinidad. So enjoyable to pass the evening here. Locals come out to interact with tourists, play music, and just salsa.

Cuba Travel Blog Stories

Discover all my Cuba travel stories written as I blogged my way across the country—and my thoughts in the years since my trip.