The Best 2-Week Cuba Itinerary For Top Sights & Experiences

There’s more to Cuba than rum and cigars. Stroll the crumbling streets of Havana, hike lush scenery, laze on palm-fringed beaches and explore colourful colonial towns on our 2-week Cuba itinerary.

LAST UPDATE: 21 Nov 2023

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“If you’re eating beef in a private home, it’s probably illegal.”

Midway through our 2-week Cuba itinerary, we listened intently to a guide who was educating us on the intricacies of the Cuban economy. Keen to manage the lack of supply since the fall of the Soviet Union, the Cuban government has imposed restrictions on the purchase of beef. Pregnant woman, children and people on special diets are the select few.

“It’s up to a year in prison for anyone caught buying beef on the black market, so never eat it in your casa particular”

We listened as we remembered the tasty beef served in our casa particular the night before.

It is this intriguing communist economic system that makes Cuba such a unique destination. Many of its cities are a joy to visit.  Covered in atmospheric crumbling buildings they recall a grander time. But it’s not all old and decaying because modernity is starting to raise its head. Flat whites can be found in modern cafes and its art and music are cutting edge.

Further afield, the mogotes of Viñales float over picturesque tobacco crops: 90% of which is confiscated by the government at below market prices. A similar fate is in store for the lush coffee plantations near the beautiful natural parks around Trinidad.

Yet when this strange economic system becomes all too much, it’s easy to escape. Just head to the miles upon miles of soft sand sitting next to warm blue azure seas.

This is a destination to learn and experience. On our 2-week Cuba itinerary, we hiked in beautiful scenery and relaxed on powdery white beaches. We encountered endemic wildlife and glimpsed inside one of the few remaining communist economies in the world.

Here’s all you need to know to help plan your own Cuba itinerary, but if you need more inspiration, read our favourite things to do in Cuba first.

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To begin this 2-week Cuba itinerary, fly into Aeropuerto Internacional José Martí just outside Havana. Your accommodation will be able to book a private taxi for you. Metered taxis also wait outside.

DAYS 1 TO 3 – HAVANA

Days 1 to 3 of your Cuba itinerary are spent in the truly unique city of Havana. We had 3 great days strolling the crumbling buildings, touring in vintage cars and popping into galleries and museums. All followed by cheap mojitos accompanied by some of the best live music we’ve had the pleasure of listening to anywhere.

For a run-down of our favourite bars and cafes, see our quick guide to Havana. All the detailed information is in our 3 days in Havana guide.

DAY 4 – VIÑALES

After enjoying Havana, grab a colectivo (shared taxi) and make your way to Viñales. You can read more about how to get around Cuba here.

Viñales is a stunningly beautiful place. Floating above a patchwork of carefully tendered tobacco fields, craggy limestone mogotes (flat-topped hills) provide Cuba with some of its best scenery. Good enough to earn it a UNESCO listing. Yet, despite its popularity, Viñales manages to retain a slow rural way of life.

There are caves to explore, fantastic trails to hike, windy paths to bike, horses to ride, and rural farms to discover. In the centre of town there are a number of decent cafes and a wealth of art galleries.

After arriving today, grab some lunch at Los Narra – a private family restaurant tucked away in a residential area.

If you have the energy after lunch, hire a bike and take off to explore the valley. Watching the sunset from the farms that fill every patch of Viñales was a highlight during our 2 weeks in Cuba.

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Viñales Stay – Budget  Casa el Isleno | Mid-market  Casa El Porry 

Travel – 3 hours: colectivo from Havana to Viñales

DAY 5 – VIÑALES

Another great way to explore the remarkable scenery and tobacco farms of Viñales is to hike. Unfortunately, paths criss-cross the region and there are very few signs. Finding your way can be tricky. So either get a guide or follow our self-guided hiking post which has detailed instructions and a map. In our opinion, this is one of the finest walks in the area.

Whatever you decide to do, start the day at the Los Jazmines hotel for sunrise. It has the best views early in the morning as mist hangs in the valley with the mogotes floating on top. Slowly the sun burns through and a remarkable vista is revealed.

From there. our self-guided hike leads down into the valley and passes tobacco fields and farms. After a brief stop at the Mural de la Prehistorica, we complete the loop around Palmarito Mogote. The hike takes about 5 hours and ends at Café Mogote in town, where you can have decent late lunch.

After recovering, spend the afternoon exploring the town, and checking out the art galleries that line the street.

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Viñales Stay – Budget Casa el Isleno | Mid-market Casa El Porry 

Travel – 5-hour hike around Palmarito Mogote

Full Guide – Hiking in Viñales

DAY 6 – PLAYA LARGA

The bus from Viñales to Playa Larga is a tortuously long affair. So take one of the regular colectivos that plough the route. The journey takes 4 hours, 30 minutes plus a half-hour stop for lunch. You may be asked to change cars just outside Havana so that the drivers can get home. The colectivo will leave between 8:00 and 9:00 and arrive about 14:00.

Playa Larga is the gateway to the Cienaga de Zapata National Park – an outdoorsy addition to our Cuba itinerary. This flat swampy area, has mangrove forests, seagrass beds, coral reefs, underwater canyons, wetlands and lakes. It is a nature lovers paradise where you can snorkel in the Bay of Pigs, hike through forests packed with endemic birds, or boat along wetlands staring at swathes of pink flamingos.

You need a guide to visit the wetlands and forests. So on arrival, head to the Cienaga de Zapata National Park office and get a low down on all the guided tours they offer.

Spend the afternoon relaxing on one of Playa Larga’s beaches. End the evening at Sol y Caribe on Playa Caleton where the cocktails are tasty and lilting music wafts through the air. The mix of local and tourist creates a cool vibe.

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Playa Larga Stay – Budget Casa Caribe Star | Mid-market Hostal Enrique

Travel – 4 hours, 30 minutes: Colectivo from Viñales to Playa Larga

Full Guide – Things to do in Playa Larga

DAY 7 – BAY OF PIGS

In the early morning, the still and tranquil waters of the Bay of Pigs is the perfect spot for snorkelling and diving.

The reef is only a few meters offshore so you can simply wade in with flippers and mask and explore. The reef has suffered under years of tourism and is not what it once was. But, search hard enough and you will still find coral alive, plenty of fish and a number of sunken boats.

Each day a tour runs from Playa Larga that departs about 8:30, stops at Octopus Dive Centre to pick up snorkelling or diving equipment before heading off to two destinations along the bay. You get over an hour to explore each before heading back in the early afternoon.

It’s a fun way to spend the day, but make sure you treat the coral with care.

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Playa Larga Stay – Budget Casa Caribe Star | Mid-market Hostal Enrique

Travel – 30 minutes to Bay of Pigs

DAY 8 – CIENFUEGOS

Today, take one of the bird-watching tours that you signed up for when you arrived. Try to get one that leaves early in the morning and does not involve too many people: if you’re at the back of the line, the birds may be gone before it’s your turn to be front and centre.

If we had to recommend just one during our 2 weeks in Cuba, then it would be the Bermejas forest walk. It usually leaves about 7:00 in the morning and finishes before 11:00. There is the chance to see up to 15 of the 28 species that are endemic to Cuba. On our tour, we saw 11, including the bee hummingbird, tocororo, Cuban tody, Cuban parrot and Cuban pygmy owl. We were happy with this, but apparently, the guide was hoping for more.

Grab some lunch and then take the 2-hour bus journey to Cienfuegos. This town has a French, rather than Spanish influence, and it is a joy to stroll the main square and stroll the interesting art stalls.

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Cienfuegos Stay – Budget Bella Perla Marina | Mid-market Palacio Barón Balbin

Travel – 2 hours: Bus from Playa Larga to Cienfuegos

DAY 9 – TRINIDAD

The waterfalls of El Nicho are the most tranquil and picture-perfect in Cuba. They are not on any bus route but an excellent colectivo runs from Cienfuegos to Trinidad stopping for 2 hours at El Nicho – more on that here. This is the perfect amount of time to walk up to the falls and take a dip in the icy waters.

It’s a beautiful way of travelling between the two towns.

Arriving in Trinidad in the early afternoon gives you a few hours to explore this magnificent colonial town. Colourful buildings line the cobbled streets as locals play dominoes on the pavement or fix the latest problem with their carburettor. The centre may be a bit touristy but just a couple of hundred meters away you can find a genuine slice of Cuban life.

As the afternoon light fades make sure you head up to the viewing platform at the Museo de Historia Municipal for fine views over the town. Take a stroll around Plaza de las Cruces for a taste of local life. As the sun goes down head to Café Fortuna, a pint-sized bar, serving cool drinks in an even cooler atmosphere. Then grab dinner at Vista Gourmet, a beautiful rooftop restaurant serving the best food in town.

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Trinidad Stay – Budget Hostal Casa Mia | Mid-market Casa de la Trinidad

Travel – 5 hours: Colectivo from Cienfuegos to Trinidad including 2 hours at El Nicho

Full Guide – Best things to do in Trinidad

DAY 10 – TOPES DE COLLANTES NATURE RESERVE

The Topes de Collantes Nature Reserve stretches across the Escambray mountains to the north of Trinidad. It is packed with natural beauty. Caves and grottos hide amongst the ferns, palms and banana trees. Rivers cut through the valleys and waterfalls drop into crystal clear pools.

The nature reserve comprises 5 smaller parks. Each park has at least one short well-defined hiking trail that is easy to follow without a guide. While most trails wind their way through misty forests and end at a jungle-clad waterfall or a natural swimming hole, each park is slightly different.

We collected several different things to do in Topes de Collantes during our Cuba itinerary. If we were to recommend one, our pick would be the Trinidad Travels tour to Parque Guanayara. Lenya, our guide, was full of beans and gave us a fascinating insight into the daily life of coffee farmers in a communist country.

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Trinidad Stay – Budget Hostal Casa Mia | Mid-market Casa de la Trinidad

Travel – Trinidad Travels tour leaves at 9:00 and returns about 14:30

Full Guide – Visiting Topes de Collantes

DAY 11 – PLAYA ANCON

30 years ago Cuba made its money from sugar. They produced tons of it and the Soviet Union gobbled it up at above-market prices. When the cold war came to an end in 1990 the Soviet Union collapsed and Cuba was left with vast quantities of sugar they couldn’t sell. The remnants of Cuba’s collapses sugar industry can now be seen just to the east of Trinidad.

You can take a tour of the area but it is also easy to go on your own. Flag down a taxi from Trinidad and ask them to take you to the Valle de los Ingenios. They will know where to go but there are three stops on the standard tour: the mirador; San Isidro ruined hacienda and factory; and the Torre Iznaga. Visiting all three takes about 2 to 3 hours. It’s a good way to learn about Cuba’s history of slavery and changing economic fortunes.

Get the driver to drop you back at Playa Ancon to spend the rest of the afternoon lazing on the beach. Ranchon Ancon – right on the sand – does excellent BBQ fish. Spend the afternoon soaking up the sun and the cheap mojitos. There are usually plenty of taxis waiting to ferry people back into Trinidad.

Our best recommendation for dinner back in Trinidad is La Botija, serving good hearty Cuban fare. The vibe is rustic and the live music excellent. Arrive before 7:00 to avoid the queues.

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Trinidad Stay – Budget Hostal Casa Mia | Mid-market Casa de la Trinidad

Travel – Taxis or tours to Valle de los Ingenios – around 30 mintues

DAY 12 & 13 – VARADERO

Varadero has a magnificent swathe of white powdery sand, lapped by warm turquoise seas. It’s a beautiful beach but, unfortunately, much of it is backed by ugly 1960s all-inclusive hotels.

Luckily, there is still the odd spot at Varadero that manages to feel like an inviting Caribbean beach.

One of these spots is at the Hotel Dos Mares beach bar. Rent a chair and umbrella and soak up the local-feeling beach vibes. Hidden behind the bushes protecting the beach, there’s not a building to be seen – just miles of turquoise water. It’s an ideal way to wind down after 2 weeks in Cuba.

You can order some pretty good cocktails from the guys working the bar, but the food is routinely terrible. We’d go so far as to say that all the food in Varadero is decidedly average: greasy, American-inspired, heart-attack-inducing slop.

There is, however, one exception: Varadero 60. They buck the trend in the area with excellent, innovative food and 50’s Americana decor. It’s expensive – even by Cuban standards – but it’s worth treating yourself once while in Varadero

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Varadero – Budget Casa Ileana y Ray | All-inclusive Royalton Hicacos

Travel (Day 12) – 6 hours, 30 minutes: Bus from Trinidad to Varadero

DAY 14 – FINISH

Varadero has an international airport and if you are lucky you might be able to organise your flight home from there.

Otherwise, make your way to Havana international airport. There are three buses a day from Varadero to Havana bus station where you can pick up a taxi to take you to the airport.

Another option is to get a colectivo direct to the Havana airport (if you can find one running at a time that is convenient for your flight). Otherwise, get a private taxi and pay the higher fare. You’ll save yourself some time and awkward bus and taxi connections.

GETTING TO CUBA

International flights to Cuba are more expensive than most places and less regular so it is worth playing with your dates of travel, shopping around and looking for cheaper indirect options. Most flights arrive at Aeropuerto Internacional José Martí but the Aeropuerto Internacional Juan Gualberto Gomez in Varadero also has some options.

Arrival – To start your Cuba trip, arrive at Aeropuerto Internacional José Martí just outside Havana. You can’t bring cash into the country but the airports have a number of ATM, banks and CADECAs (money exchange desks). Your accommodation will be able to arrange a private taxi for you. Metered taxis also wait outside. More information about money matters in Cuba is in our article, 14 really useful travel tips for Cuba.

Departure – It’s easiest to depart from Aeropuerto Internacional Juan Gualberto Gomez near Varadero if you’re following our 2-week Cuba itinerary. But there are only a handful of flights, so you may have to head back to Aeropuerto Internacional José Martí just outside Havana.

GETTING AROUND CUBA

Your big choice is whether to hire a car or use public transport. We have put all the information we think you might need to make that decision in our getting around Cuba post. We used mostly public transport which saved a lot of money and stress. Here are the journeys you’ll need to take for this itinerary if you decide to use public transport.

VIAZUL BUS 

The Viazul buses in Cuba are reliable, comfortable and air-conditioned. Make sure you book all the buses in advance, especially in peak season. A full and comprehensive timetable of routes and prices are available on the Viazul bus website, where you can also make reservations. You MUST bring printouts of your bookings and arrive at the bus station an hour before departure to check-in.

COLECTIVOS

Colectivos (shared taxis) have set routes, usually leaving between 8:00 and 9:00 from your accommodation and completing their journey between lunch and early afternoon. They can be arranged as you make your way around Cuba. Just ask your Casa Particular or hotel to make a reservation a day or two in advance.

PRIVATE TAXI 

Taxis are ubiquitous and can be found almost everywhere. They are not particularly cheap but very useful for short journeys or quick visits. The driver will be happy to wait for you to complete an activity before taking you home.

For all the details on getting around Cuba, including some tips for hiring a car see our guide here – Getting Around Cuba.

BEST TIME TO GO TO CUBA

Cuba is baking hot in the summer so plan your visit in the dryer and cooler months of winter. December to March is ideal but try to avoid the Christmas holidays if possible.

Even then it can still be hot in the afternoons. So, to help with that, we have planned this itinerary to do most of the activities in the morning. This frees up the afternoons to spend in air-conditioned comfort (museums, buses), relax in wild swimming (El Nicho, Parque Cubano) or chill on the beach.

WHERE TO STAY IN CUBA

We chose to stay in casas particulares for all our accommodation in Cuba. Run by inventive locals, a casa particular is a villa, small guest house or a room in a local family home. They usually provide you with a mini-bar and offer to make you breakfast and dinner for a small charge.

The easiest way to book a casa particular (and with the widest range) is via booking.com selecting “homestay” from the filter. A good host will be invaluable during your stay, so spend a bit of time searching for properties with good reviews. We would pay a bit extra for air-conditioning too.

Unfortunately, due to government regulations and internet restrictions you will not be able to book online while in Cuba. So either book before you arrive in the country, use a VPN to get around the restrictions or phone or book in person after you arrive.

TOURS TO BOOK FOR YOUR CUBA ITINERARY

Booking tours in Cuba is very easy, particularly with a good casa particular host who will be more than happy to take care of any arrangements for you. Here are a few that we recommend you either check out directly with the provider or ask your host to book for you.

Cienaga de Zapata – There’s a huge selection of tours on offer at Cienaga de Zapata Park National Park Office including snorkelling, bird watching and forest walks. Book in person when you arrive in Playa Larga. | Hours: 8:00 – 16:30 | Location: On the main, just north of the junction to Playa Larga.

Bay of Pigs – Snorkelling or diving tours are available around the Bay of Pigs. Book through your casa particular host up to an hour before it departs. | Hours 8:30 depart, 14:00 return | Location: pick up spots around town.

Topes de Collantes – Various tours are available from Trinidad Travels to Topes de Collantes Natural Park including guided walks to wild swimming spots. | Hours: around 9:00 to 14:30 | Location: Pick up and drop off at your casa particular | Bookings: in person from their office at 613a Calle Antonio Maceo or online

Valle de los Ingenios – Private taxi will take you to the 3 stops on a well-trod tour through Cuba’s sugar-growing region from Trinidad.  | Location: Pick up a taxi in town allow 2 – 3 hours.

MORE CUBA READING

Cuba is a unique place. Years of Soviet-funded political ideology created a strong- if slightly confusing – sense of national identity. Soviet, American, Spanish, Caribbean and African influences fuse together to create a fascinating place to visit. Here is some more of our reading about this fascinating place.

Top experiences in Cuba not to be missed

3 days in Havana – a city of decaying grandeur

Quick guide to Playa Larga

Viñales Valley – cycle routes through Cuban tobacco farms

How to visit Cuba’s Ciénaga de Zapata National Park

Explore the best scenery in Cuba on this Viñales Valley hike

Impressions of Havana – a story from the streets

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