Last updated on July 29, 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.

Cuba 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 had mixed feelings about the country when I first visited; 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!

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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.

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Fast-Facts About Cuba Travel

How to Travel Around Cuba

Cubana Airlines offers easy flights from Cancun, a popular route to Cuba. You can arrive in Cancun and usually book a Cuba-bound flight for the next day—give wiggle room in high season of a couple extra days.

Commercial flights from the U.S. began in August 2016 with several major airlines. The bulk of flights still leave from New York and Miami, but there are now direct flights for a dozen other U.S. cities, too. Departure taxes are now included in your air tickets, which is handy.

Within the country, tourists should only use marked tourist taxis. Buses between all the cities are great for independent travelers. Roads lead to all the major towns, but Cuba’s infrastructure is crumbling so expect poorly paved roads outside of the popular towns. You’ll use Viazul to get to anywhere in the country. Hitchhiking is also common for the adventurous, but can be an exercise in futility for those traveling in Cuba on a visitors visa.

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Is Cuba safe for travelers?

Cuba is safe. You can walk around at night and the country is proud of the very low rates of violent crime and theft. Be wary of hustlers in Havana, however. There are a few tourist scams, and they will surely recommend places where they get a commission. Just exercise normal caution when meeting new friends.

That said, you should absolutely have travel insurance to be sure you’re covered if something happens. I recommend IMG Global, here’s why.

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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.

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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 in each one. 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 Favorite Cuba 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. 

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Things to Do in Havana

Wander Old Town Havana

Old Town Havana is like stepping back in time to the colonial era of Cuba. This historic neighborhood, also known as La Habana Vieja, is a UNESCO World Heritage Site. Havana just oozes charm, and there’s unique architecture and sights around every corner. You’ll spot Baroque, Neoclassical, and Art Deco buildings, and each reflects different periods of Cuba’s history. And as you admire the buildings, it’s hard not to feel a hit of nostalgia when vintage American cars from the 1950s roll by you.

Plaza de la Catedral is, perhaps, the most iconic landmark in Old Town Havana. The majestic Havana Cathedral (Catedral de San Cristobal) dominates this vibrant square.

Explore the city with this detailed laminated city map, updated in late 2016. Since Cuba is changing quickly, it helps to have a solid map to get around. This company also has a detailed map for all of Cuba, which ideal if you are road-tripping across the country.

Visit the Museo del Chocolate

It was unseasonably wet and cold when I visited Havana, so I took refuge in this delicious smelling shop and loved their hot chocolate and various treats (churros!).

Shop Havana’s Street Markets

If you’re in Havana for a few days, it will be hard to miss one the city’s lively street markets. These are not only good fun just for the vibes, but you can find handmade crafts, cigars, and Cuban souvenirs. Don’t miss the chance to engage with the friendly locals, who are often eager to share stories about their city and way of life (but brush up on your Spanish, because you’ll need it to truly get the most out of your market visit.

Walk the Malecón

The long stretch of Havana’s Malecón is quintessentially Cuban. Like a lot of the country, it’s best to plan for a long stroll and give yourself time to relax and just enjoy. Cubans have a delightful sidewalk culture—life is lived in the open, so give yourself time to people watch the locals as they socialize, and soak it all in as you stroll this seven-kilometer long stretch of promenade that passes everything from Baroque to Art Deco architecture—and a lot in between.

The route you should take is a 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.

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Things to Do in Trinidad

Photograph the Charming Historic Center

Trinidad is renowned for its beautifully preserved Spanish colonial architecture. The city’s historic center, known as the “Casco Histórico,” is a maze of narrow cobblestone streets lined with colorful houses, grand mansions, and stunning plazas. The architecture reflects the city’s prosperous past as a center of the sugar trade during the 18th and 19th centuries.

Admire the Cobblestone Streets and Colorful Houses

Wander the streets of Trinidad and shop the tiny side roads. This is a beautiful, low-slung colonial town. The picturesque cobblestone streets are lined with houses painted in vibrant pastel colors, adorned with wrought-iron grilles, and often featuring beautiful courtyards filled with flowers. Explore Calle Cristo and hang out at Plaza de Armas—walking this area is a delightful way to soak up the city’s unique atmosphere.

Hang Out in Plaza Mayor

Plaza Mayor lies at the heart of Trinidad as a vibrant central square surrounded by buildings significant to the city. It’s a UNESCO World Heritage Site with a lot to admire. Visit the neoclassical-style Iglesia Parroquial de la Santísima Trinidad, an impressive church dating back to the 19th century. You can also explore the Museo de Historia Municipal, housed in the Palacio Brunet, which showcases Trinidad’s history and exhibits artifacts from the colonial era.

Beat the Heat and Take in a Museum

Although there are several museums and galleries where you can delve deeper into the city’s history and cultural heritage, I really enjoyed the Museo Nacional de la Lucha Contra Bandidos. The museum tells the story of the Cuban Revolution and the guerilla warfare against counter-revolutionary groups. It’s a fascinating place to stop, and also offers really gorgeous views.

If that’s not your speed, the Museo Romántico, housed in the Palacio Cantero, provides a glimpse into the affluent lifestyle of Trinidad’s past. You can also visit art galleries featuring local artists, showcasing traditional and contemporary Cuban artwork.

Take in the Sun at Playa Ancón

If you’re looking for sun, sand, and turquoise waters, head to Playa Ancón, which is pretty close to Trinidad. This pristine beach stretches for several kilometers and it’s a relaxing way to spend an afternoon. You can swim, sunbathe, and splash about in the beach, or even go snorkeling or diving to explore the coral reefs teeming with marine life.

Visit the Valle de los Ingenios 

A local Cuban man runs ethical horse trips to this area just outside of Trinidad. 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. Climbing the Manaca-Iznaga tower provides panoramic views of the valley and its surrounding landscapes, allowing you to appreciate the area’s natural beauty. The train ride is more touristy, the horse day trips are an amazing way to get out and explore the region. Either way, you get to explore more deeply a beautiful area that was once a major sugar production.

Seek Out Live Music & Dancing

Trinidad is known for its vibrant music and dance scene. You’ll find phenomenal live music performances at Casa de la Música or Casa de la Trova—talented musicians play traditional Cuban music such as Son cubano and salsa. The best part is that you can also join in on the dancing and learn salsa steps from the locals. It was so enjoyable to pass the evening here. Locals come out to interact with tourists, play music, and its just a big salsa party.

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Things to Do Across Cuba

Visit the Artwork of Salvador Gonzalez

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.

Take in the Waterfalls near Cienfuegos

Head to Cienfuegos for the El Nicho Waterfalls and revel in the pretty, lush green as you hike and swim.

Experience the Holidays with Las Parrandas Celebrations in Remedios

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.

Hike and Zipline in a UNESCO Biosphere Reserve

An eco-tourism project done right, Las Terrazas in the Sierra del Rosario Biosphere Reserve (a UNESCO site) offers everything from hiking to ziplining.

Relax in Viñales for a Few Days

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 Cuba’s First Settlement

Baracoa was 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.

Find a Slice of Cuban Life in Santiago de Cuba

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.

Splurge on a Stay at Hotel el Salton

Go off the path at the gorgeously placed Hotel el Salton, which located in the n the heart of Sierra Maestra mountain range and a short 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.”

Dive Pristine Reefs

Plan a scuba dive at María la Gorda—it’s a popular spot because it has a perfect combination of clear waters, gorgeous dives, and a great dive operation.

You should also find a way to be among the mere 500 annual divers permitted on the pristine reefs of Jardines de la Reina.

Bike Across Cuba’s Interior

Book a bike tour to experience 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.

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10 Best Cuba Travel Tips

1. Book a Tour Before You Leave Home: If there’s something you just absolutely need to do when traveling to Cuba, book that experience ahead of time. Companies like Cuban Adventure and WoWCuba allow online booking and that is one of the only ways to 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.
2. Get Familiar With the Viazul Bus Network: Use the Viazul bus network to easily visit anywhere in Cuba. Viazul is a reliable option, but in the height of tourist season you may need to book ahead.
3. You May Need to Exchange Money: Cuba has a dual currency system. The Cuban Convertible Peso (CUC) is primarily used by tourists, while the Cuban Peso (CUP) is used by locals. Exchange your currency to CUC, but carry some CUP for small purchases and interactions with locals.
4. Don’t Count on Using a Card: Cash is king and credit and debit cards from non-Cuban banks are not widely accepted. It’s essential to carry enough cash (preferably in CUC) to cover your expenses throughout your trip.
5. Don’t Count on Having Reliable Internet Access: Internet access can be limited and expensive in Cuba. Wi-Fi hotspots are available in certain public areas, but you’ll want to purchase an internet access card from ETECSA, the state-owned telecommunications company, and use it at designated Wi-Fi zones. That said, you should embrace the chance to disconnect from constant connectivity and enjoy the slower pace of life in Cuba.
6. Understand the Layers of Accomodation Options: In addition to hotels, budget travelers will stay in casa particulares, which are privately-owned bed and breakfast accommodations. These provides a more authentic experience and an opportunity to interact with local hosts.
7. You’ll Need Some Spanish: Spanish is the primary language spoken in Cuba, and although you’ll find English-speaking locals in the most touristy areas, once you step a bit off-the-beaten path it becomes a lot less likely. Learn a few basic phrases to ease your travels—it will also enhance your interactions with locals and show your appreciation for the culture.
8. Carry Your Own Toiletries Into Cuba: Due to limited availability, bring essential items like toiletries, medications, and sunscreen from home. It’s better to have them on hand than rely on finding them in local stores.
9. Take Your Time and Don’t Rush It: Cuba operates at its own rhythm, so patience is essential. Service may be slower than what you’re accustomed to, and be prepared for transportation delays or schedule changes. Flights, buses, and even taxis may not always run on time, so it’s best to have some flexibility in your travel plans. Basically, relax and embrace the laid-back atmosphere.
10. Don’t Flash Your Money: Cuba is generally a safe country for travelers, but you’ll want to take normal precautions. Keep an eye on your belongings, avoid flashing valuable items, and use reputable transportation services.

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Cuba Travel Guide: Stories from the Blog

Read through all of my Cuba travel stories—each one written on my travel blog as I traveled through the country. I share detailed guides and stories about cultural quirks, fun activities, and things I enjoyed doing in every area.