Make the most of two weeks in Cuba with this suggested 15 day itinerary for independent travel around the island’s west.

Sipping a mojito at sunset, watching vintage cars cruise Havana’s seaside boulevard, time seems to slow to a crawl. Two weeks in Cuba could easily stretch to two months, wandering the evocative streets of the cities, and watching rural life play out in the serene countryside. Ernest Hemingway came for a visit and stayed twenty years.

The fact is though, most of us have limited travel time and Cuba is a deceptively big island. Two weeks might feel like a good amount of time to explore most of the country, but when travel between some of Cuba’s cities can take the best part of a day, having a realistic itinerary can mean the difference between a great trip and one you need a vacation from.

With 15 days to play with, our plan for Cuba was to seek out the country’s distinctive history and culture, spend some time outdoors and get underwater on a dive.

After plenty of research, we decided to focus our two weeks in Cuba on the island’s western half, flying in and out of vibrant Havana and travelling by bus and collectivo (share taxi) to rural Viñales, beachside Playa Larga, and the historic, World Heritage cities of Cienfuegos and Trinidad.

With this itinerary, we had time in each place to immerse, explore, get active and relax as well.

Sound like your kind of travel? Here’s what we got up to and our recommendations for a 15-day itinerary travelling independently in Cuba.

4 Days In Havana (Days 1 – 4)

Cuba’s 500-year-old capital city is crumbling, eclectic and incredibly photogenic. We arrive in the early afternoon on day one and, once we’ve dropped our bags at our charming Casa Particulare – a private home that rents rooms – in the suburb of Vedado, we set out to explore by foot.

Havana is a city to be walked. While the old town of Habana Vieja is the city’s tourist heartland, the colourful streets of Vedado and Centro are buzzing at all hours as locals go about their business and socialise on their front steps. On your first afternoon, wander the streets and take it all in.

Two weeks in Cuba starts with a walk through the streets of vibrant Havana.

Explore Havana’s vibrant street life on foot.

As the sun drops, make your way to the Malecón, the city’s eight-kilometre seaside boulevard on the north side of town. The strip comes alive in the late afternoon and early evening as locals gather and classic cars cruise the stretch. Grab a mojito in one of the bars on the street and soak up the atmosphere.

Over the next couple of days, immerse yourself in Cuba’s cultural highlights. The city is full of diverse period architecture, historic forts, vintage cars and a range of museums. Many museums are in beautifully-restored colonial mansions worth a visit for the buildings alone.

Get beyond the façade of historic Habana Vieja on a guided walking tour of the old town (we recommend the tours run by San Cristobal Agencia de Viajes).

Afterwards, make your way back through the colourful streets and squares of the old town, popping into the small galleries and peeking into the courtyards of shops along the way. Stop for a cheeky craft beer at microbewery Factoria, in beautiful Plaza Vieja.

Havana's secret courtyards are a highlight of two weeks in Cuba.

Search out secret corners in the old town’s galleries and shops.

On another day, explore the outer reaches of the city aboard the hop-on-hop-off bus. It’s a great way to navigate to highlights such as the Plaza de la Revolución, and the Necrópolis Cristóbal Colón, Havana’s sprawling, marble-mausoleum-filled cemetery.

At some point during your time in Havana, book your onward bus ticket to Viñales. Viazul and Conectando (through Cubanacan) both do the run. Or you can arrange a collectivo (share taxi) through your Casa.

For more Havana highlights, check out our post on ten awesome experiences in this amazing city.

3 Days In Viñales (Days 5-7)

On day five of your two weeks in Cuba, hop on your booked morning bus from Havana to picturesque Viñales; it’s a journey of around three to four hours to the south-west.

Life moves more slowly in this small rural town, and you can too. But there’s plenty to do in the beautiful surrounding countryside. Three days gives you the chance to do both.

On your first afternoon, enjoy a wander of the town. Stop for a spot of people watching in the main square and swing by the small handicrafts market.

On your second day, set off into the countryside on a horseback riding tour to the evocatively-named Valle del Silencio. On our tour, we visit a small cave, a coffee farm and, of course, a tobacco plantation, where we learn the art of producing and rolling a classic Cuban cigar. Wrap up your day with a home-made mojito on the porch or rooftop of your casa.

A 15 day itinerary in Cuba offers time for pursuits like horseriding into the countryside of Vinales.

Explore Cuba’s rural scene by horseback.

If the skies are clear, be sure to pop outside at night while you’re in Viñales. With little light pollution, the stargazing here is amazing.

Kick off your third day with a cave tour. Viñales is scattered with mogotes, limestone outcrops that are riddled with caves. We taxi out to Gran Caverna de Santo Tomás, just 15 minutes from town, where we don head torches for a two-hour tour of Cuba’s largest cave system. Tours can be organised through the local Infotur office.

If you’ve still got energy, consider an afternoon hike through Viñales National Park, or hire a bike and explore the valley by pedal power.

Explore the Vinales countryside by bike during your two weeks in Cuba.

Pedal your way around the countryside on a bike.

We cycle out to the region’s unusual Mural de la Prehistoria, stopping at a couple of tobacco fincas and drying houses on the way.

Afterwards, we bike our way up to the spectacular lookout at Los Jasmines. It’s a solid ride uphill; if you’re after something less strenuous, take a taxi or the hop-on-hop-off bus to the top but don’t leave town without checking out the valley vistas from this viewpoint.

2 Days In Playa Larga (Days 8-9)

You could easily spend more days enjoying the country life in Viñales, but it’s time to move on. The easiest way to reach our next destination, Playa Larga, is by collectivo. We organise this through our Casa in Viñales and it’s a journey of five hours, door-to-door.

Playa Larga is one of two beach towns on Cuba’s infamous Bay of Pigs (the other is Playa Giron). By all accounts, the beaches aren’t as spectacular as those on the north coast at Varadero but if you’re after a low-key stretch of sand in Cuba, this is it.

Our Casa Particulare is right on the beach and while we’re here to go diving, our two-day stay ends up feeling like a mini-holiday.

Check in, take a walk along the shore, and chill. Watch the sun set and then enjoy a delicious home-cooked feast of fresh lobster at your Casa.

Peaceful sunsets at Playa Larga are on the agenda in this 15 Day Itinerary for Cuba.

Take time out with sunset on the beach at Playa Larga.

On day two, spend the morning diving or snorkelling in the Bay of Pigs. Trips including gear can be organised through your Casa, which is what we do, but if you’re after specific dive sites, it’s best to make your own arrangements direct.

We dive two different sites in the bay and spend the rest of the afternoon chilling on the beach back at our Casa. It’s a perfect rest stop ahead of our return to the city and our next destination, Cienfuegos.

A diver enjoys crystal clear water and soft corals in the Bay of Pigs in Cuba.

Explore crystal clear waters in the Bay of Pigs.

2 Days In Cienfuegos (Days 10-11)

Founded by French migrants in 1819, the World Heritage city of Cienfuegos is just 90-minutes from Playa Larga and an easy collectivo ride. We organise the share taxi through our Casa and make the journey in a beautifully restored vintage Chevrolet Bel Air, one of the random perks of travel in Cuba.

Historic Cienfuegos is centred around Parque José Martí. Spend an easy afternoon strolling the streets around the park and the wide, column-lined Paseo del Prado, snapping the French-inspired neoclassical architecture, and admiring the historic buildings that line the square.

If time allows, wander the Malecón around the bay to Punta Gorda, a neighbourhood of beautiful, eclectic old mansions.

For impressive views over the city and the bay, wind up your day with a drink at the rooftop Bar Terrazas at the Hotel la Union.

During our two weeks in cuba, we take in historic views over Cienfuegos from Bar Terrazza.

Take in the views over Cienfuegos from Bar Terrazas.

On day two, explore some of the highlights surrounding the city. Hire a taxi for the day (easily organised through your Casa) and plan an itinerary to suit your interests.

We visit three sites over the course of the day, starting at the mangrove-lined Laguna Guanaroca, where we enjoy a guided hike to the lagoon and then board a row-boat for a trip out to see the site’s famous pink flamingoes.

Next, we ferry over to the Castillo de Jaguan, a beautifully restored 18th-century fortress built to protect the coast from pirates.

Views towards Castillo de Jaguan from the ferry.

Head to Castillo de Jaguan for a history of pirates and invaders, and views.

Our last stop is Rancho Luna, a pretty beach resort, for a late lunch and some time on the sand.

There are lots of small family-run restaurants in the backstreets around the main square in Cienfuegos offering simple, hearty plates of meat, salad and rice for small change.

3 Days In Trinidad (Days 12-14)

The last destination on our 15-day itinerary for Cuba is Trinidad, another World Heritage site and the second oldest city on the island.

Trinidad is only 90-minutes from Cienfuegos. It’s an easy bus ride (buy tickets at the Infotur or Cubanacan offices in Cienfuegos), or organise a collectivo ride through your Casa.

Three days is plenty of time to explore this charming town, and to get out into the surrounding countryside.

Spend your first day wandering the cobblestone streets of the city itself. More than five centuries of history weave their story through the town’s brightly painted homes, colonial mansions and towers.

Our two weeks in Cuba includes three days in Trinidad, starting in historic Plaza Mayor.

Settle into a seat in Plaza Mayor and take in the scene.

While hordes of tourists visit during the day, walk a couple of blocks from Plaza Mayor, and you’ll find yourself in Trinidad’s quiet backstreets, just you, a handful of locals, maybe a horse.

Climb the bell tower of the former convent, now the Museo Nacional de la Lucha Contra Bandidos (a curious museum in its own right), for beautiful views over the town.

Take in views over Trinidad from one of the city's towers.

Climb one of Trinidad’s towers for views over the colourful town.

On day two, hire a taxi for the day (again, you can organise this through your Casa) and head out to see some of the sights in the Valle de los Ingenios, a stunning landscape scattered with sugar mill ruins, the source of Trinidad’s once-great wealth.

On our trip, we stop at a lookout for valley views, tour the historic sugar mill ruins at San Isidro de los Destiladeros with a guide, and climb the soaring watchtower at Manaca Iznaga. You can also take a tourist train through the valley, or join a horse riding tour.

Two weeks in Cuba: Climb the tall tower at the historic sugar mill ruins of Manaca Iznaga near Trinidad.

Admire views over Valle de los Ingenios from the top of the tower at Manaca Iznaga.

Choose your adventure on your last day in Trinidad. You can hit the white sands of Playa Ancon like we did and enjoy a day chilling on the beach, just 15-minutes from town.

Our 15 Day Itinerary includes beach time on the white sands of Play Ancon near Trinidad.

Soak up some rays on the white sands of Playa Ancon.

Or you could hire a taxi again and head into the mountains of Topes de Collantes for some hiking. While we didn’t get to do it ourselves, we heard great things about the 7-kilometre round-trip hike to Salto del Caburni, a 60-metre high waterfall with a natural pool to cool off in.

There are plenty of eating establishments in  Trinidad but we end up spending a couple of nights enjoying tapas and wine at Taberna La Botija, a busy and atmospheric pub with live music in the evenings.

As buses departing Trinidad fill up quickly for all destinations, we suggest sorting out your bus back to Havana the day you arrive in town at the local Infotur office, or at the Cubanacan desk in the back of the Dulcinea bakery.

One Last Evening In Havana (Day 15)

Our last day in Cuba is back where we started, Havana. The bus ride from Trinidad to Havana takes around 6-7 hours so if you take the morning bus, you’ll arrive in Havana mid to late afternoon.

As soon as we check into our Casa, we make our way to the public ferry terminal a couple of blocks south of the Basilica San Francisco de Asis in Habana Vieja.

Take the ferry to Casablanca across the bay and walk up to the Cristo de Habana statue. Time your visit right and enjoy the views over Havana as the sun sets behind the city.

The sun sets over Havana: A fitting end to two weeks in this unique country..

Watch the sun set over Havana: A fitting end to two weeks in amazing Cuba.

Back in town, wrap up your visit with a daiquiri at Hemingway’s old haunt, La Floridita, or a mojito overlooking the Malecón at Havana’s famous Hotel Nacional, and reflect on an amazing two weeks in Cuba. Then start planning your return visit to explore the island’s east.


For more tips, tools and insights for planning a visit to Cuba, check out some of our other Cuba posts:

Setting The Scene For A Visit To Cuba

A Flashpacker’s Guide To Budgeting For a Trip To Cuba