1: Learn to dive among shipwrecks, Santiago de Cuba
Santiago de Cuba (Dreamstime)
In July 1898, the entire Spanish naval fleet was sunk in a battle in Santiago’s bay during the Spanish-American Civil War, leaving a trail of diveable debris, including the 6,800-tonne cruiser Cristóbal Colón.
Learn the basics at Scuba en Cuba, then head below to spy relics like the USS Merrimac, sunk by the US navy to stop the Spanish from escaping, concluding both the battle and independence for Cuba.
How long: Five days to complete Scuba en Cuba’s ACUC Open Water Diver course; one day minimum for wreck diving (some wrecks for advanced divers only).
Get started: Scuba en Cuba offers ten-night Santiago wreck-diving from £1,635; six extra nights all-inclusive stay at Brisas Sierra Mar Hotel from £485, including ACUC course.
2: Christmas at Las Parrandas, Remedios
Colourful light display at Las Parrandas Christmas celebration (Dreamstime)
Join Cuba’s most riotous annual festival, Las Parrandas, when every Christmas Eve sees the tiny town of Remedios transforms into the biggest one-night fiesta in Cuba.
The origin of this party lies, unusually, with the town’s priest, who in 1820 noticed his parishioners dwindling as the weather got colder. To make them attend mass, he rallied all the townsfolk together and encouraged them to make as much noise as possible to get the adults out of the house.
Over the years, it has become a full-scale party, and now the town’s districts compete with vibrant floats, towering illuminated sculptures, music, dancing and all-night fireworks.
How long? It’s one-night-only, but be sure to book your accommodation months in advance, as rooms tend to fill up fast.
Get started: Víazul buses run from Santa Clara to Remedios and take around one hour.
3: Coast and culture, Gibara
Coastal view from hill in Gibara (Dreamstime)
Gibara, a once neglected fishing port in eastern Cuba, is having a renaissance. As well as the lively street parties that accompany its annual film festivals – one of which screens movies in the nearby Panderos caves – its culinary reputation is also growing.
In town, there are plenty of chances to slurp down Taíno (indigenous Caribbean) food such as cassava bread and shellfish soup. Afterwards, work it off on the trails to Gibara’s biggest lure: its cave network. Explore its limestone caverns on foot, splashing in underground lakes and admiring ancient Taíno rock art.
How long? Three days.
Get started: Fly from Havana (1.5 hours) to Holguín; Gibara is an hour’s taxi ride. Víazul buses also go to Holguín (11 hours). To explore the caves, guides can be found in town. To dive Tanque Azul, Cuba’s largest flooded cavern, advanced open-water PADI (or equivalent) certification is required.
4: Paddle the southern coast, Bay of Cienfuegos
Lake Hanabanilla (Dreamstime)
The southern coast of Cuba serves up a wealth of waters easily explored by kayak. Inland, Lake Hanabanilla takes centre stage: a vast reservoir cradled between the peaks of the Escambray Mountains, which also offers great hiking.
But the highlight is surely negotiating the turquoise waters and limestone cliffs of Guajimico, a slice of the Caribbean Sea riddled with plenty of hidden caves and coves to paddle.
How long? Eight days. No previous kayaking experience is required, with conditions usually moderate to easygoing.
Get started: For an eight-day trip to the above locations, contact Cuba Adventure Company; prices start from €1,729 (£1,507), excluding flights.
5: Take a wildlife cruise, Bay of Pigs
Tree on the shore at Playa Girón (Dreamstime)
The Bay of Pigs is infamous for a failed 1961 CIA-backed invasion by the US, which attempted to oust the recent government of Fidel Castro. What many travellers don’t know is that it’s a birding and snorkelling paradise. The area is hinged to the Zapata swamp, a protected wetland cut with forests rivers and crocs.
Boat down the Hatiguanico to spot manatee and jumping tarpon, then scour its woods for endemic birdlife, such as the rare bee hummingbird, the smallest bird in the world. Finish in the blue-black waters of the bay, snorkelling the coral wall that are just-off shore and the sink holes along the coast.
How long? A couple of nights, with day trips to the Ciénaga de Zapata NP and snorkelling off the coast. There aren’t many good hotels, but lots of beachside B&Bs (who can rent snorkels) dot the bay. Snorkelling and diving is accessed from the shore.
Get started: Independent travel is possible. Hostal Luis is run by Luis, who has an excellent contacts’ book and can organise snorkelling and diving trips.
6: Ride on the chocolate train, Havana to Matanzas
Casablanca railway station, Havana (Dreamstime)
In 1917, American chocolate baron Milton S Hershey built a sugar mill in Cuba, then set about constructing an electric railway to transport materials. It still runs today, and is not only a cheap way to depart the capital and travel the 84km east to the port of Matanzas, but a great way to glimpse local Cuban life.
Trundle out of Havana past fields of brahman cattle and busy villages, and visit the clapboard town of ‘Hershey’ (now Camilo Cienfuegos) to see how sugar changed this island forever.
How long? From Havana’s Casablanca Station, the train runs 1.5 hours to Hershey, and 3.5 hours to Matanzas. Bring snacks.
Get started: Head to the local ferry terminal in Old Havana; from here a ferry crosses the Bay of Havana to Casablanca (five minutes), where you’ll find a ticket office and station. The train goes three times a day; be sure to turn up at least 30 minutes before departure.
7: Taste the real Cuba in Havana
Traditional Cuban dish (Dreamstime)
Cuba hasn’t always been known for its sensational food. In fact, until the mid-1990s, paladares (privately run restaurants) were illegal here, and even when this law finally loosened, chefs were still restricted in what they could serve and what ingredients were available.
Since late 2010, however, this has relaxed a lot – as has government control of farming – meaning the sudden availability and variety of fresh produce has seen a surge in creative new restaurants, and nowhere more so than in Havana.
Still, the good ones aren’t easy to find and sourcing good street food isn’t all that simple either, so it pays to grab a guide like Irish restauranteur-turned-Cubaphile Tanja Buwalda, who offers insider tours that shine a light on the capital’s street food and family-run joints, as you sample intense Cuban coffee, cakes, churros, hamburgers and guarapo (sugar cane juice).
How long? Tours can last between three and five hours.
Get started: Food tours with Tanja Buwalda start from around CUC$130 (£100) and are for two-to-eight people; contact her on email@example.com to arrange.
8: Explore central Cuba like a cowboy, Ciego de Ávila Province
Cowboy in Cuba (Dreamstime)
Most horseriding in Cuba takes place in the limestone mountains of the Viñales Valley, where the west is still very much wild. But for something different, the plantation country of central Cuba is a raw delight.
The rugged reserve of Loma de Cunagua offers rare high ground, with a stay on a private farm (with rodeo) in nearby El Peñón a must. Then ride lush fields and bathe in waterfalls en route to the coffee plantations of Rincón de Maguyá.
How long: Trips last 12 days. Riders should be comfortable walking, trotting and galloping.
Get started: Contact Riding Cuba to arrange a horseriding trip in Central Cuba, including the locations mentioned above; from €2,360 (£2,057).
9: Swim with sharks, Jardines de la Reina
Swimming with reef sharks in Jardines de la Reina (Dreamstime)
This archipelago off the southern coast of central Cuba is the country’s (and one of the planet’s) top sites for shark diving, as well as arguably one of the last pristine underwaters world left in the Caribbean.
Amid a necklace of coral keys, dive among scores of silky, reef and nurse sharks, and goggle at mammoth giant groupers, turtles and colourful coral.
How long: Visits usually consist of weeklong liveaboard trips; diving requires open-water certification, with a minimum of 50 dives.
Get started: Seven-day liveaboard boat trips (or stays on a floating hotel) with Avalon cost from around US$2,585 (£2,010). The price excludes all park fees ($200/£155), the conservation fee ($100/£78) and gratuities.
10: Take better photos, Trinidad
San Francisco de Asis church in Trinidad (Dreamstime)
Few places lend themselves to the camera’s lens like the Spanish colonial city of Trinidad. Its mansions and lavish interiors were fuelled by the cash the sugar boom brought to the island, but they’re no secret.
To see them from a new angle, away from the crowds, try a tour with Julio Muñoz, who runs photography classes that introduce local street life and culture, and show you how to capture it.
How long? Tours last two hours; the photography workshop consists of four sessions (up to two sessions per day). Both are for photographers of any level.
Get started: Contact Julio Muñoz to arrange a workshop (CUC100/£77pp) or two-hour walking photography tour (CUC25/£15pp).
11: Ride Cuba’s rails, across the island
Steam train in Valley de los Ingenios (Dreamstime)
In 1837, Cuba became the first country in Latin America to open a railway line, linking Havana to Bejucal. Despite little investment down the years, it’s still the most authentic way to travel today, as it’s affordable for most Cubans.
The main line, an artery that runs the island from Havana to Santiago, offers ever-changing views, but enthusiasts should seek out the steam train rides at the old sugar mills of Remedios, Central Australia, Morón and Rafael Freyre, all long closed down. The railway and Marcelo Salado Sugar Museum, near Remedios, are particularly worth a visit for their engaging exhibits and daily rides.
How long? The longest single route is from Havana in the west to Santiago de Cuba in the east (tickets from CUC50/£39), taking from 16 hours. When it comes to timings, try to leave some wiggle room as delays are common. Bring snacks, drinks and toilet roll.
Get started: Tickets can be bought a couple of days in advance, albeit only from the station you are travelling from; bring your passport.
12: Go wild on the eastern coast, Baracoa
View of Baracoa (Dreamstime)
Baracoa, Cuba’s eastern capital of adventure, is arguably also its most scenic spot. Beaches, rivers, mountains, cocoa and coffee make it a dreamy escape.
Explore UNESCO-listed Alejandro de Humboldt Park and stay next to the wild bay. Surf at Yumurí’s beaches, then make for the surrounding area’s scooped-out coves.
You can now also visit the easternmost point of Cuba at nearby Punta Maisí, a former military zone that was, until recently, off-limits; explore its lighthouse, beaches, and swim in the Pozos Azules de Maisí sinkhole.
How long? Set aside several days to explore.
Get started: Baracoa can be reached by Víazul bus via Santiago de Cuba (five hours). Stay at Villa Paradiso, which can organise bikes for guests, and has commissioned a series of biking maps taking you off-road; doubles from CUC20 (£15).
13: Escape to the country, Arcos de Canasí
Countryside near Havana (Dreamstime)
Some 60km east of Havana and its urban hustle lies the countryside bungalow of MontECOrales. Situated a short walk from the tiny coastal fishing village of Arcos de Canasí, it makes for a serene base, with trails winding the surrounding palm forest and down to the coast where you can snorkel its sapphire sea coves. Just be sure to return to your country getaway at the end of the day for delicious home cooking and piña coladas.
How long? Two nights. Bring waterproof sandals for wading across the bay.
Get started: Combine with a trip onboard the Hershey train and get off at Canasi (2.5 hours from Havana). To reach the resort of MontECOrales, walk the 30-minute journey from the station.
14: Stay with an eco-community, Las Terrazas
Las Terrazas, Sierra del Rosario Nature and Biosphere Reserve (Dreamstime)
The mountains of the Sierra del Rosario were at the centre of Fidel Castro’s 1968 ‘green revolution’, as Cuba set about reforesting land stripped by the Spanish conquistadors and ravaged by plantations. More than 1,000km of terraces were built here, and six million trees planted. But in the 1990s Cuba’s economy crashed and the people of Las Terrazas were left facing poverty.
So locals opened up an eco-hotel (Hotel Moka), drawing visitors to their UNESCO-listed biosphere. Today you can zip-line through the forests around Las Terrazas, bathe in the pools of the San Juan River, wander ruined coffee plantations and stay with the community in lakeside bungalows, or at the hotel that started it all.
How long? Many come for day trips, but overnight stays give you more chance to explore. Bring sturdy shoes for forest walks.
Get started: Víazul buses run from Havana to the village of Las Terrazas, taking about one hour. Doubles at Hotel Moka start from £96.
15: Make for the real Wild West, Viñales
Viñales Valley (Dreamstime)
Viñales, a vast green valley pocked with rocky pinnacles and sprawling tobacco fields, is now the tourist capital of western Cuba, but that doesn’t mean you can’t find ways to escape the crowds.
Head deeper into this mogote-prickled, UNESCO-crowned area for a taste of rural Cuba, horseriding in the lesser-visited Palmarito Valley, bathing in cave pools or climbing one of Viñales’ 250 climbing routes. Pause only to chew the fat with the odd local farmer, while hiking, riding and scrabbling this wild wonderland.
How long? A couple of days.
Get started: Stay with Idania in El Bostezo, whose B&B (tinyurl.com/el-bostezo) offers horse-riding trips throughout the valley. Alternatively, Omar and Mayra (firstname.lastname@example.org) live in a quiet, off-centre house that also offers eco walks; doubles from £18pn. Cubaclimbing.com is an authoritative source on Vinales’ climbing routes, while local guide Jorge Luís Pimental Morales (aka Tito; email@example.com) can take you on climbing trips in the valley.
16: Have a cigar adventure, across the island
Man holiding a cigar in Havana (Dreamstime)
You don’t have to smoke to immerse yourself in the fascinating world of tobacco farming in western Cuba. Join an insider on a guided tour of its famed plantations. Matteo Speranza has been travelling to Cuba for 15 years and there isn’t anything he doesn’t know about Cuba’s cigars and this artisanal trade. His passion has now translated into the business of guiding people to some areas otherwise unknown or ‘quasi forbidden’.
How long? Negotiable.
Get started: Contact Matteo (firstname.lastname@example.org) to arrange a tour; from US$200 (£155) per day, excluding transport/expenses.
17: Discover the forgotten coast, Western Cuba
Magroves at Cayo Jutías (Dreamstime)
When it comes to the western coast, most travellers will visit Cayo Jutías or skip offshore to the idyllic Cayo Levisa, but few explore the western peninsula’s backroads and coastal routes.
Spread along the fringes of the island lie tiny beach communities like Playa La Mulata and the unspoilt Playa La Altura or Playa Banes (not to be confused with the eastern town of the same name), with plenty of hiking and cycling to be had. Trekkers can also summit Western Cuba’s highest rise, Pan de Guajaibón (699m), overnighting in the protected forests of the Mil Cumbres area.
How long? Set aside a few days to explore.
Get started: Independent travellers will need their own car. Stay at Villa José Otaño y María (Playa La Mulata; +53 5254 9810), which can arrange local guides for guests. Cubania also run weeklong cycling and trekking trips here from £885.
18: Go island hopping, Canarreos archipelago
Loggerhead turtle (Dreamstime)
The scattered islands of the Canarreos Archipelago slumber peacefully off Cuba’s southern coast. Postcard-perfect white sands, coconut palms and gin-clear waters greet the few sailing boats that loll through its snorkel-friendly shallows.
Join a sailing tour and pit-stop at the islands of Cayo Largo del Sur, home to pristine shores and nesting green and loggerhead turtles, before sailing on to the friendly iguanas and manta rays of Cayo Rico and the forests of Cayo Cantiles, where wild monkeys and jutía (a giant rodent) bustle among the trees.
How long? Most trips last between eight and nine days.
Get started: G Adventures run eight-day Sailing Cuba trips around the Canarreos Archipelago from Havana via Cienfuegos; from £959. Intrepid Travel’s nine-day Cuba Sailing Adventure similarly starts in Havana and includes stops at a half-dozen islands in the archipelago; from £1,480pp.
19: Live the life of a Campesino, Havana & Mayajigua, Sanctí Spiritus province
Farmer harvesting sugarcane near Varadero (Dreamstime)
If you’re looking for a quick taste of rural life, volunteer for the day at organic farm Finca Tungasuk, near Havana, where you can help plant, weed and learn about how sustainable agriculture is transforming Cuba.
But for something a bit more intense, head to the island’s centre for Mayajigua’s La Picadora, a farming community that accepts visitors into its fold on agritourism stays, allowing them a true taste of life as a Cuban campesino (farmer) and to see another side to the island.
How long? Minimum one day. Be prepared to weed (at Tungasuk) and get your hands dirty.
Get started: Contact Finca Tungasuk (email@example.com) to arrange a day visit from Havana; from CUC45 (£35), including transport and lunch. La Picadora costs CUC32 (£25) per night, including all meals and activities (firstname.lastname@example.org).
20: Become a Cuban castaway, Isla de la Juventud
Beach at Isla de la Juventud (Dreamstime)
This undeveloped island (‘The Isle of Youth’) off the southern coast of Cuba once housed both Fidel and Raúl Castro, back when it was little more than a prison. Since then, scuffles with the US and a failed ‘university’ have seen progress stall here.
For visitors, however, that all feels like a bit of a blessing as you explore its crocodile-packed swamps, pine forests, pre-Columbian rock art and white-sand beaches said to have inspired Robert Louis Stevenson’s Treasure Island. Its waters are just as rich, and if you venture to the island’s southern extremity of Cocodrilo, you can volunteer to work on its green and loggerhead turtle conservation programme.
How long? A few days is plenty, though volunteering lasts for one week minimum.
Get started: Regular NCC ferries leave Batabano (50km south of Havana) for Nueva Gerona; tickets can be bought in advance at the NCC kiosk at Havana Central Bus Station and the crossing takes three hours. Volunteer stays in Cocodrilo can be arranged through the Intercultural Outreach Initiative.
21: Wake the dead, Santiago de las Vegas
Young people celebrating in Santiago de las Vegas (Dreamstime)
Every February 5, Cuba’s quirkiest festival unravels in the small town of Santiago de las Vegas on the outskirts of Havana. ‘Pachencho’s Wake’ involves the live mock-burial of a man (Pachencho), accompanied by his ‘widow’ and presided over by a scolding ‘priest’, all to a background of fake mourning, copious amounts of rum and an afternoonlong conga. This faux funeral was launched in 1984 and has been entertaining the locals with a great party ever since.
How long? One day. Marathon dancing is required, as is drinking stamina.
Get started: Get a shared taxi (almendrón) from Havana to nearby Santiago de las Vegas (CUC20/£15). The ‘ceremony’ starts at 7.30am, the ‘funeral’ is mid-morning at the cemetery, and the conga wake lasts all afternoon.
22: Hide out like a guerilla, Pico Turquino National Park
Sierra Maestra Mountains (Dreamstime)
From Santo Domingo, hike the 9km to the Comandancia de la Plata, Fidel Castro’s 1950s rebel hideout. It lies in the high-altitude forests of eastern Cuba’s Sierra Maestra Mountains, where you can wander Fidel’s old hut (with its several escape routes), hike up to the rebel radio station, then visit the hospital hut (kept far away, so the guerrillas’ screams wouldn’t draw attention), gaining an insight into one of the 20th-century’s most divisive figures.
For the fit, it’s an 18km hike to the top of Pico Turquino (1,972m), Cuba’s highest peak.
How long? It takes at least two days to hike up Pico Turquino, with mountain huts en route; La Comandancia can be visited in a day.
Get started: Treks to La Comandancia (from CUC27/£21) and Pico Turquino (from CUC57/£44 for two days, including accommodation) must be done with state guides; these can be hired on site (minimum two people).
23: Pedal the isolated southern coast, Marea de Portillo to Chivirico (Santiago)
Beach on southern coast of Cuba (Dreamstime)
Cuba’s most dramatic cycle pedals you past where the sheer edges of the Sierra Maestra Mountains meet the wild Caribbean sea. The road rises, falls, flatlines and has even broken off into the sea in places.
It’s totally thrilling and the views are majestic, as you cover 105km between Marea del Portillo and Chivirico, though stops are few and far between.
How long? One or two days. You need to be fairly fit to cycle in shadeless Cuba; Nov-Feb is the coolest time. The bicycle-shy can hire a car (about eight hours’ drive from Pilón to Santiago de Cuba; 185km); take advice on road hazards before setting off.
Get started: Make sure you bring water and food, as there’s little help or traffic en route. Explore’s (explore.co.uk) 15-day Cycle Tour of Cuba covers this section, with back-up jeeps offering support to the weary and exhausted; from £1,895 excl flights.
24: Spend the night in Guantánamo Bay, Caimanera
View over Guantánamo (Dreamstime)
To Cuba’s irritation, a US naval base has been stationed in Guantánamo Bay since 1903 (at an annual rent of just $4,085). The closest you will get to it, however, is Caimanera, a remote fishing community on the western shore of the bay. Here, the Hotel Caimanera is the only place for curious visitors to stay, and getting there is a surreal experience, passing control points and barren salt pans.
Locals are intensely interested in travellers, while hotel staff are keen to show you their tiny museum on the US occupation. Less welcome are the base’s control towers, sea barrier and nightly patrolling searchlights, as seen from the hotel’s lookout point. But as a front-row view on a piece of modern history, it’s compelling.
How long? One night is enough. Note that three days’ notice is required to organise a permit (free) to stay in or visit Caimanera.
Get started: Minimum two people can spend the night at the hotel; solo travellers can visitby day. Permits/trips to Caimanera can be booked through Islazul or Infotur in nearby Guantánamo City; you must enter the area with a guide. Hotel Caimanera costs from CUC40pn (£31).
25: Ride into the Valley of Sugar, Trinidad
The Valley of the Sugar Mills (Dreamstime)
Just east of the gorgeous mansions and facades of colonial Trinidad lies the Valley of the Sugar Mills, a UNESCO-protected area that was once the heart of Cuba’s colonial sugar boom.
The best way to explore it is on four hooves, as local guide Reinier Toscana Orbea takes travellers out on horseback to trot the fading relics and ruins of its former plantations, steering along a scenic route into the heart of the Cuban countryside.
Combine your ride with a cerdo asado en púa – a spit-roast pig lunch – and cool off by bathing in natural pools along the way.
How long? Rides last around 6.5 hours and begin from 8.30am.
Get started: Reinier’s Trinidad Travels runs horseriding trips throughout the valley that begin in Trinidad; from CUC60 (£46) per person.
Main image: Vintage car in Havana (Dreamstime)