The Best Cuba Travel Itinerary: One to Two Weeks

Welcome to our Cuba travel itinerary! At this stage you’re either thinking about traveling to Cuba, or you’ve already booked! Either way, congratulations, you’ve come to the right spot! Cuba is a magical country, full of rich history and all the idealistic aspects of a country truly stuck in a time warp. But, things are beginning to change quickly, so now really is time to travel to Cuba! (If you’re an America and worried about how to travel to Cuba, we’ve got you covered for that as well in our Americans Traveling to Cuba Legally Guide.)

One of the biggest questions we get about traveling to Cuba is “where should we go?” And while it might seem like a pretty straight forward question (anywhere because the country is amazing!), it really all depends on how much time you have and what interests you.

Cuba has something for everyone, whether your a backpacker on a budget, or a luxury holidayer. But regardless of your style of travel it’s important to have a solid itinerary mapped out before taking off on your trip. And although internet is slowly becoming more accessible in Cuba, that doesn’t necessarily mean a lot of places/people have access to it. Because of this it’s important to do plenty of research before you go.

So with that being said, “how much time do you have?” Whether you’re planning on a week, two weeks, three weeks or over a month, you’ll easily find a number of destinations that will give you the true Cuba travel experience. Check out our Cuba travel itinerary to see what suits your schedule best, and if you haven’t already, we’ll show you how to book cheap flights for Cuba travel right now!

7 Days in Cuba

Experiencing this incredible country within the week is a tight squeeze, but if you haven’t got a lot of time it’s definitely better than no time in Cuba. The key to planning a short trip is being able to find a balance between visiting lots of destinations and spending your whole time on a bus. With only a week you want to take the time to actually see things properly, because there’s no point cruising past everything just for the sake of saying you went there.

This really applies to Cuba, because you need to live it to really understand how special it is. Sure, Cuba is a beautiful travel destination, but the real appeal to Cuba is being able to experience authentic life. The more places you jump between, the less you’ll be able to see the real games of dominoes happening in the backstreets of Havana; the men tinkering away on old Chevys, breathing life into them for another couple of years; and the old buildings that have yet to see the restoration coming from tourist money.

Exploring Havana

If your first stop into Cuba is Havana, then you’ve picked a great place to experience Cuba at its best. Between leisurely days on the cobbled streets of Old Havana, and lively nights at the Malecon, you could spend weeks in Havana and still have plenty of places to explore.

The Malecon, the waterside esplanade that runs along Havana, is a highly recommended activity if you want to see some authentic Cuban nightlife happening most nights, but particularly on the weekends. All along the stretch you’ll see all kinds of people congregating over a couple of beers, a bottle of rum and most likely a guitar or pair of speakers.

During the day walk the streets (which are extremely safe) and take in the old architecture, the vibrant street culture and, of course, the classic cars. Get lost among the backstreets and stumble across authentic Cuban life that you can’t see along the main tourist strips. For history buffs, or those interested in learning about the Cuban Revolution, you can check out the Museo de Revolucion to see plenty of memorabilia from the battles.

Another top locations to explore is the second hand market set up in the Plaza de Armas in Old Havana, where you can find legit remnants of Cuba’s past, including watches from the Soviet era, old Communist literature/propaganda and Revolution memorabilia.

After taking a time warp through old Cuba take a walk down to Plaza Vieja (Old Plaza) and grab a cocktail or beer La Factoria Plaza Vieja, Cuba’s moderate attempt at brewing a craft beer. There’s usually live music going on in the evenings jamming out anything from Cuban salsa classics to old American rock (which of course is exactly what you came to Cuba for no?).

Honestly if we only had a week in Cuba we’d almost be tempted to just stay in Havana for the whole time. There’s no shortage of classic Cuba on offer. Cruise around the streets and sample some of Cuba’s best street food, which is not only delicious, but also incredibly cheap. You’ll feel like a real local sipping tiny little coffees on the side of the road, watching men play checkers and kids kick soccer balls around the streets.

Day Trip to Viñales

After your time exploring Havana you can take a day, or overnight, trip down to the tobacco fields of Vinales. Here you’ll get to see the year round process of growing, cutting, drying and preserving tobacco leaves (depending on the season you’ll only get to see one or two of these processes). Cuba is famous for cigars and it’s one of their top exports around the world, so even if you’re not into cigars it’s an interesting process to observe.

If you’re thinking about picking a few up for souvenirs be sure to stick to the official government run shops. It’s a common scam in Cuba to sell tourists fake Cuban cigars made from a little tobacco and a lot of banana leaves. And unless you really know your cigars it’s very hard to tell the difference.

If cigars aren’t your thing there are plenty more activities to do in Viñales. The whole countryside that surrounds Vinales is a beautifully scenic sight of lush green fields of crops and rustic dirt trails. You can take a hike through the countryside, experience some caving and enjoy the quiet life compared to Havana. If Havana is the bustling city life, then this is definitely the country getaway.

Alternatively, if white sand beaches and tropical Caribbean coast is more your thing, you can take a bus out to Varadero to experience a very different side of Cuba. Here you’ll find high-rise resorts, fancy restaurants and lots of tourists, but the beaches are spectacular. It’s not exactly what you’d picture when thinking about classic Cuba, but the beaches are superb and the atmosphere is exciting.

Varadero could be visited on a day trip, or you could stay for a night or two if you wanted to take in the sun and sand. Personally for us we found Varadero to be a lot like any other beachside resort town, and not a true reflection of the Cuban culture. But it all depends on what you’re looking for on your trip.

Two Weeks in Cuba

Like the first week in Cuba you’ll most likely start and base yourself in Havana. Along with spending some quality time in this bustling city, you still have the options of Vinales and Varadero, but this time slow down the pace and spend an extra night or two in each spot.

For Varadero, if the tourist scene is too much, stay in nearby Matanzas for a quirky little Cuban city that has a couple of historical forts and landmarks. There isn’t anything spectacular about this city, but it’s real Cuba life and fun to explore without the busy tourist scene.

The main plaza in the middle of the city is always buzzing with locals dashing around, going about their daily business. It’s also great for people watching! In Matanzas you’ll also find the famed Hersey Train Station, where an electric train runs between Matanzas and Havana. It’s famous for transporting sugar to the refineries and being the only electric train in Cuba. The train trip gives you an authentic insight into real Cuban life.

With extra travel time, when you’re in Viñales, go and explore the outer area with hikes to the ‘pre-historic mural wall’ (which isn’t pre-historic, but instead a massive painting of dinosaurs). There is a $1 entrance fee to see the wall, but you can probably view it better from the road without paying! Either way it’s a beautiful walk out there.

Also, while in the area, search for the illusive and slightly exaggerated powers of the ‘water healers’ that reside in the mountains. Apparently they have been residing in the mountains performing miracles (as the story goes), but the locals don’t buy into it too much.

The walks aren’t strenuous and it’s really nice to just cruise the countryside and take in the culture. The main street in Viñales is a surreal contrast between tourist restaurants and residents kicking it on rocking chairs selling guava jam sandwiches and cheese pizzas from their porch.

In addition to Vińales, Havana, Varadero and Matanzas, you can now find time to take a trip down to the gorgeous colonial city of Trinidad. In Trinidad you’ll get to explore the cobblestone roads lined with houses painted in all different shades of pastel colors. Drink fresh mojitos in the street, while dancing the night away at free salsa shows. You can also party the night away in a cave, how cool is that!

If you feel like getting out of the city for the day hire a bicycle and take a trip down to the gorgeously isolated beaches of Playa Ancon. It’s about an hour to the beach (mostly downhill), but the ride back takes a little longer. For those wanting to get back quickly there are conveniently placed taxi drivers along the way (with bike racks) who know you’re over it. Trinidad is a city that shouldn’t be missed during your trip to Cuba.

Bare in mind, although you’ve only got two weeks, don’t underestimate the amount of time you should spend in Havana. It is not only the capital city by location; it’s the capital of all that’s Cuba. We’ve spent a lot of time there and still feel like we could have had more to explore, but that’s always the nature of travel. Any amount of time in Cuba is going to be awesome, so what are you waiting for?

Convinced you need to spend longer in Cuba? We think so too! Click to read the Cuba Travel Itinerary for Three Weeks or More!