Cuba: Making the Most Of Your Vacation Days

Cuba: Making the Most Of Your Vacation Days

Where to start? Get oriented here.


More of a visual learner? Check out our gallery of epic Cuba pics.

If you’re going back and forth on deciding whether or not to go to Cuba, we think it’s a no-brainer that you should go ASAP. If you’re already all in on Cuba, let’s talk about what you should do there.

First off, know this: you need to get outside of Havana to really see Cuba. Cuba is a trendy destination right now, and many people we know have been ticking the box by visiting Havana, sipping a few overpriced daiquiris at a Hemingway watering hole, and then flying out. Don’t do this – the best parts of Cuba are not in Havana! Also: stay in casa particulares, not hotels. Way cheaper, and way better. These casas are B&Bs run by real Cubans, and help you get a sense for what real Cubans are like.


  • DO: Stroll the Malecon – Havana’s oceanfront drive – with a bottle of Havana rum in hand. This is a magical thing to do when the weather is nice, particularly in the evening when it starts to cool off.
  • DO: Drive the Autopista Nacional and get a sense for what Cuba is really like. You’ll see hints of Cuba’s new economy, as ‘small business owners’ repeatedly step out in front of your car, trying to sell you bread, snacks, or produce. You’ll realize that the old cars are not for show and are 100% the locals’ workhorses (not to be confused with the real horses you’ll see pulling carts on the main highway). And you’ll be fascinated by the officially regulated first-come-first-serve hitchhiking regime that’s been set up by the government.
  • SEE: Valle de Viñales. UNESCO and the New York Times know what’s up – there’s a reason this valley is UNESCO recognized and on the Times’ Places to Go in 2016 (#10 on the list). Don’t miss this.
  • SEE: Central Trinidad bathed in the last rays of a gorgeous sunset. This colorful city is positively radiant. Follow it up with dinner at La Ceiba and a show at Casa de Musica, perched on the steps right next to the main square.
  • EAT: Ropa Vieja. This Cuban classic is a go to for restaurants across the country. The two best ropa we had in Cuba were in Havana – one at El Litoral and the other at Mama Ines.
  • EAT: A full dinner at your casa particular in Viñales. Endless courses, local produce, and masterfully cooked chicken and pork. We couldn’t recommend staying at Casa Andres y Mary more highly.



Havana is a gem of a city, rich in history and contradictions. State-run industries meet an upswell of capitalist enterprises – private restaurants, casa particulares, and knick-knack shops.

Your first full day should be dedicated to hanging out in Havana Vieja. There are four main plazas – Catedral, Mayor, Vieja, and San Francisco – that you should orient around. Check out each one, wander, and explore. Eat dinner in Vieja at least one night as well – the city’s blemishes soften at night and you can almost convince yourself you’re in Madrid. We highly recommend Mama Ines for the ambience, location and food – get the ropa vieja! Another excellent dinner option, further out in Vedado, is El Litoral.

One of the first things you’ll notice is the sheer number of classic cars on the streets. This is not a for-tourists thing – much of Cuba still gets around via pre-Revolucion classic cars. Appreciate it, because it might not last. Cold War buffs might also recognize quite a few Soviet-produced Lada cars tooling around.

Classic cars, Havana, Cuba
Classic cars lining the street in front of the Hotel Saratoga

As for where to stay in Havana, the two primary options are Havana Vieja – where all the old buildings are – or Vedado – a trendy, up and coming neighborhood on the West side of the city. Everyone recommends avoiding Centro Havana, the neighborhood in the middle. We took a different approach and stayed in Centro – we recommend it! Get a feel for what Havana is really like. Get your money into the hands of locals by staying at a B&B in Centro. Avoid the government or multinational owned hotels in Vieja or Vedado.

Spend at least one afternoon or evening strolling the Malecon. The locals come out as the day cools down and you’ll get a sense for what living in Havana is really like. Buy a 6 pack of Crystal – watery state-produced beer – and a bottle of Havana Club Rum and strike up a conversation with the locals.

Classic car, the Malecon, Havana, Cuba
Classic car, the Malecon, Havana, Cuba

Also worth a visit:

  • The colonial forts east of the city. Awesome view back of the city and truly impressive fortifications. If you only have time for one, visit Castillo de los Tres Reyes Magos del Morro. Check out the signal station in this fort and have a chat with the older gentleman working there – he’s full of stories.
  • Grab a daiquiri at one of Hemingway’s haunts. We’d recommend El Floridita over Bodeguita del Medio – significantly less crowded and (slightly) less expensive.
  • Likewise, grab a drink at the Hotel Nacional. Perched above the Malecon, the hotel commands a beautiful vista and a sense of grandeur that has been only slightly squandered.

A word of caution – don’t expect much from the museums in Havana. We won’t sugarcoat it: the exhibits are overall not very well maintained and are laced with propaganda. Worth seeing one or two for the experience (consider el Museo de la Revolucion), but don’t expect much.


Trinidad is a low-rise colonial town that time has passed by. The buildings are riotously colorful, and the main square is something to behold, particularly when sunset rolls around.

Trinidad, church
Trinidad’s iconic church and colorful buildings, just a block off the main square

Trinidad has literally hundreds of casa particulares to choose from. Book ahead or find one that looks great when you get there. Prioritize finding a spot close to the central Plaza Mayor. A roof terrace for breakfast or a sunset drink is also a plus. Beware of hustlers who offer to lead you to a B&B (or restaurant) – they’ll be taking a cut and you’ll be paying more than you should be.

What to do while you’re there? Consider a few options:

  • Do a self-guided walking tour of the blocks immediately surrounding the Plaza Mayor. We’d recommend heading northwest, past the yellow and red church and into the no less colorful, but much more local oriented neighborhood. Appreciate the cobblestone streets, cowboys coming back from a day’s work, and the inexorable sense that you’ve been plunged deep into Cuban life. Do it in the late evening and be amazed as the soft light of sunset makes the experience even more magical.
Sunset over the Plaza Mayor, Trinidad
Sunset over the Plaza Mayor, Trinidad
  • Grab dinner at La Ceiba (get something with lobster in it, you won’t regret it) and sip a canchanchara (local drink with rum and honey) or two or three. Then head over to the Casa de Musica, where live music spills out across the Plaza Mayor and the night quickly turns into a party. “Bottle service” is achievable for about $11 CUC.  

Definitely do a day trip outside of Trinidad city. You have a lot of options here – beach, hiking, or history. We’d recommend checking out the sugar plantations in the Valle de los Ingenios and grabbing a view at the mirador just outside of town. If you’re looking to hit the beach, head out to Playa Ancon – supposedly the best beach of Cuba’s entire southern coast – and grab a spot under an umbrella. If you’re looking to hike, check out the waterfall in Topes de Collantes park or the much less traveled swimming hole above the town of Banao on the road to Sancti Spiritus. The road up there is rough (very rough), but we made it happen in a Peugeot 208 so you should be fine…

We found it fun to visit the town of Sancti Spiritus, just over an hour away from Trinidad. The town has almost as much charm as Trinidad with a negligible fraction of the crowd. Scenic streets, colorful churches, and an incredibly impressive public library. Check out more pics in our gallery.

Just one of many picturesque roads in Sancti Spiritus
Just one of many picturesque roads in Sancti Spiritus

Valle de Viñales

This epic valley contains some of Cuba’s richest tobacco-growing land and is framed by sheer, jungle-wrapped limestone mountains. More than anything we saw in Cuba, Viñales made our jaws drop.

Our favorite activity here was a guided walk up into the mountains from the mirador below Los Aquaticos. Stop at the Mirador (1km past the Mural Prehistorico on a dirt road) and ask about getting a guide for the walk up into the hills. Normally we’re less into guided walks, but this was definitely the right choice. We had a phenomenal experience, threading through local homestead farms, getting a lesson in Spanish agricultural vocabulary. We headed up into the jungle, rewarded for our effort with a mountainside mojito and a sweeping panoramic view. We ended the tour with a 1km cave swim in an underground river – quite the adrenaline rush. $15 CUCs a person was a price everyone was happy to pay and our guide was happy to get.

Viñales, no further detail required

Another highlight was catching sunset with a mojito in hand just up the hill from our B&B. It’s worth the effort to leave your casa’s porch or balcony behind to get an unobstructed view. We did some sleuthing to find the best spot – check it out here. If you’re looking for a specific place to stay, we couldn’t recommend Casa Andres y Mary more highly.

Vinales Sunset
Viñales sunset, from the best spot in town


Consider a side-trip out to Cienfuegos, the “Paris of Cuba.” This is a misnomer – it’s nothing like Paris. However, it is a beautiful bayside city, the former hangout of rich Cubans in the time before la Revolucion. Think historical yacht clubs, beautiful old houses, a stunning Malecon, and a city center packed with beautiful old historical buildings. The beach isn’t far either and the snorkling is excellent. It’s about an hour and a half west of Trinidad, on the coast.

We recommend getting a feel for the town in the central Parque de Jose Marti, stopping by the pool at the Hotel la Union, strolling the Malecon in the late afternoon, grabbing a drink atop the Palacio de Valle, and watching sunset from the gazebo at the tip of Punta Gorda. If you have another half day or so, the snorkling at Rancho Luna beach (15 minutes outside of town) is excellent and the Castillo de Jagua just across the bay is worth 45 minutes of your time. If you’re lucky, you’ll catch a beach volleyball game or two – the Cuban players are world-class.

Sunset, Punta Gorda, Cienfuegos
Sunset from the Malecon on Punta Gorda, Cienfuegos, Cuba


Getting there: President Obama has made the logistics of getting to Cuba straightforward. Simply book a flight there through Mexico City or Cancun. “People-to-people” education is a valid reason for travel now – aka just talk to a few Cubans while you’re there and you can credibly fit in this category. Fill out the paperwork and you’ll be fine. We told U.S. Immigration that we’d been in Cuba when we reentered the States and they didn’t bat an eye.

Car rental: We strongly recommend renting a car when you take your trip outside of Havana. Roads in Cuba are in surprisingly good condition, although the potholes are vicious. Having the freedom to go where you want, when you want made our experience a lot better. That being said, prepare for some logistical delays day-of when you go to pick up your car. We’d recommend booking ahead to ensure you get a car. Your only options are state-owned companies – Havanautos, Transtur, or Via Rent-A-Car. Insurance is $10 CUC per day, non-negotiable, and expect a $200 CUC security deposit that you’ll get back.

Taxis: If you decide not to rent a car, taxis are a viable alternative. From the airport to Havana, expect a $25-30 CUC fare. You can get anywhere in Havana for $10 CUC, which seemed fairly non-negotiable. For longer trips, you can hire a car and driver for the day for less than $100 CUC, depending on how far you drive.

Where to stay: AirBnb is operating in Cuba! Huge word of warning – just because a house allows instant-book does not mean it’s actually available! Check with the host directly after booking to confirm availability. The site CubaAccomodation is another great site for finding places to stay. For this we recommend sending them a list of places you are interested in and not just one because it takes a day or two for them to get back to you each time. In either case, allow 24-48 hours of response time.

How to spend: The two currency system is a bit confusing – check out this explainer here for an overview. You’ll be spending entirely in peso convertible, or CUCs (pronounced ‘kooks’), which are anchored to the US dollar. You’ll get ripped off on the exchange rate, but no official outlet will give you a better deal than what they offer at the airport. The main thing to look out for is getting scammed by a local – you’ll go to pay in CUCs and they’ll try to give you change in their much less valuable peso cubano.

Itinerary: How many days in each place? It’s up to you, but here’s our guess:

  • Havana – 3-4 Days
  • Trinidad & Around – 2-3 Days
  • Valle de Viñales – 3 Days
  • Beach time – 2 Days

Curious why we call this Making the Most of Your Vacation Days? Want more? Stay tuned!

Cuba Gallery


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