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Cuba small group tour TOP038_1

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Cuba Small Group Adventure – for solo travellers

This Cuba small group adventure is 12 days of the best that the country has to offer.  A small group tour with like-minded people mostly travelling solo that hits all the highlights and then some.  You’ll see both natural and historical sights, connect with the Cubans around their food, music, and zest for life, and explore the island from front to back. And when you’ve done all that, relax on some of the most awesome beaches.  Ever.


  • Hike around the Sierra Maestra Mountains
  • Stay in family run casas throughout the country
  • Cruise Havana in style – a classic American convertible
  • Learn ballet and Flamenco dancing in Camaguey
  • Explore colonial Trinidad
  • Enjoy Cuban night life as you search for the best live music you can find
  • Relax in Santiago with music, mojitos, and dancing
  • Take a bike taxi through the side alleys of Baracoa
  • Discover Cuban cuisine and have a foodie fantasy everywhere you go
  • White sand beaches. Enough said.

With some incredible local guides, you’ll get tapped into the Cuban heart beat from the moment you touch down in Havana.  You can do the Ernest Hemingway pub crawl or meander down to the Malecón sea for a romantic walk among the fishermen’s’ boats. Don’t miss Fusterlandia – a vibrant neighbourhood packed with the fantastic art of native Jose Fustia.

In Trinidad discover colonial architecture and visit museums, churches, and markets along the way. Climb to the top of Museo Historico’s watchtower and fall in love with the city views. There’s also time for a waterfall trek, great nightlife to experience, and a sunset on the beach at Playa Ancón. You’re going to get lost in  Camaguey, designed specifically to confuse pirates and undesirables from navigating the city back in the day.  And in Santiago de Cuba, visit the Moncada Barracks, the site where Fidel Castro’s army ignited a revolution.

The adventure winds down in the Sierra Maestra Mountains as you tour some of the historical areas nearby.  See where Che Guevara broadcast his Radio Rebelde messages and enjoy a nice long and relaxing hike through the mountains. Baracoa is where Columbus first landed when he encountered Cuba and you can feel the pulse of the country here like nowhere else.  It’s a foodie hotspot (as if the rest of the country wasn’t) and you’ll wind down with days on the beach, cooking classes, and cocktails.

History tells us that Columbus didn’t want to leave Cuba, and after these 12 days, you’re going to feel exactly the same.  Enquire today to learn more.


Day 1: Me casa es su casa in Old Havana

After touchdown we’ll whisk you away to your Casa in Old Havana where you can wander around the charming cobbled streets at leisure. Admire the decaying beauty of the city before taking a stroll down by the romantic Malecón sea wall and feel your cares slip away as you watch the waves rock the bobbing fishing boats. Later in the evening you’ll meet your guide for an orientation meeting and eat dinner at an upscale local paladar, a privately owned restaurant often housed in locals’ homes. And if you aren’t too jet-lagged then our guide will show you the local hot spots for a mojito or two!

Day 2: Cruise around in a classic convertible

Spend the morning acting like a Hollywood star, cruising the broad boulevards of Havana in a genuine American classic convertible car. This is one of the coolest places to drive on the globe, and we’ve made sure you’ll be kitted out with a candy-coloured set of wheels to match the occasion. Spend the afternoon sampling the potent local rum, visiting the amazing mosaic-covered neighbourhood of Fusterlandia, or salsa dancing your way through the streets whilst puffing away on a hand-rolled cigar. It would be rude not to. Wrap up your 48 hours in this incredible city with a special farewell dinner in one of our favourite Havana restaurants.

Day 3: A feast on the beach in Trinidad

Trindad time! Bathed in pastel colours of sunset yellows, sky blues and mint greens, the colonial city of Trinidad is eye-wateringly beautiful. Step back in time to walk its narrow cobbled streets, where the occasional 1950s car or even a horse and cart will pass you by. Explore its numerous churches, museums and all round architectural splendor and, if you like your culture served up with a mini workout, climb the Museo Historico’s watchtower for the best views of the city. Trinidad is situated close to the stunning Valle de los Ingenios (Valley of Sugar Mills) and the gorgeous Playa Ancón, where you can enjoy long stretches of pristine, white beaches later in the afternoon. We finish the day off with a delicious home-prepared feast of traditional Cuban cuisine – if weather permits, we may have our meal on the glittering shores of Playa Ancón with the colourful sunset as our backdrop.

Day 4: Dive into waterfalls and dance up a storm

After we’ve stuffed ourselves with a huge Cuban breakfast and a strong cup of coffee, we take a half day trek to a natural waterfall at Parque Guanayara for a dip in the crisp cool waters and a chance to spot Cuba’s national bird – the iridescent tocororo. The nightlife in Trinidad is hot on live music and latin dancing, all cooked up together before an enchanting colonial backdrop. It’s an amazing experience not to be missed, so get ready to leave your inhibitions at the door and party like it’s 1999. Don’t miss a visit to the famous Casa de la Musica, set in the open-air on an old colonial staircase.

Day 5: Top up your Trinidad tan

Enjoy a day of leisure here in paradise and hit the unspoiled, white sand shores of the gorgeous Playa Ancón. Spend the day sipping mojitos and topping up your tan without a care in the world. Pure bliss.

Day 6: No pirates allowed in Camaguey

Half way between Havana and Santiago de Cuba lies the country’s third largest city, Camaguey. Designed in the 17th century to disorientate pesky pirates and plunderers, the city is a characterful jumble of narrow pirate-puzzling alleyways. Like many of Cuba’s cities it’s a colourful mix, where blue, green, pink and yellow colonial splendour stands next to elegant churches and charming low-rise houses. We’ll spend the day exploring the twists and turns of these streets the local way, in our caravan of bicitaxis. It’s then time for more dancing, but this time we’re swapping salsa for ballet with a visit to a ballet school where some of Cuba’s finest dancers began their training. And if you love jazz as much as we do then be sure to check out the many jazz bars this trendy little town has to offer.

Day 7: History and hip-shaking in Santiago

Santiago de Cuba can be found on the south east tip of the island and is known as the ‘Hero City’ for its leading role during the revolution. The city’s half million residents are (quite rightly) proud of their cultural traditions, and you’ll take a fascinating walking tour around the many museums, cultural associations and clubs dotted around the city. This is by no means a dull history lesson, there’s plenty of cool sounds too! If Cuba were a car, music would be its engine and Santiago would be the fuel; this city is where much of Cuba’s famed music such as the Son originated. It has a vibrant traditional music scene, and culturally has a different feel to the rest of Cuba. Tonight we’re treating you to an interactive night with local musicians and dancers — join in with some hip shaking and salsa steps, learn the art of Cuban percussion with the band or simply sit back and soak it all in with a mojito in hand.

Day 8: Trekking the Sierra Maestra Mountains

Time to lose the maracas and break out the adventure gear. Today you swap salsa dancing for hiking and trek to the historical area of the Sierra Maestra Mountains. In one day you’ll do around five hours of moderately easy hiking and see the former rebel headquarters where Castro’s quarters have been preserved as a museum. The epic views of the undulating Sierra Maestra mountain range are nothing short of spectacular – make sure you’ve got plenty of space left on your SD card! Home for the night is a simple but beautifully located casa, perfect for sipping back rum as you watch the sun slip behind the mountains.

Day 9: Wake up to the mountains (and roosters!)

Be prepared for an authentic alarm call this morning from the roaming roosters and farmyard animals. This may interrupt your lie-in yet it creates the perfect setting for a leisurely breakfast at the foot of the Sierra Maestra mountains. Take a morning stroll looking out for the fresh water swimming spots, before travelling back to Santiago de Cuba to dance the night away.

Day 10: Hot coastlines and smokin’ cooking lessons

A spectacular six hour drive through Eastern Cuba’s diverse landscape brings us to the Cuba’s first capital, Baracoa. On the way we pass by the city of Guantanamo and its infamous bay, and the Mirador los Malones provides a lookout point to the highly controversial U.S. Navy Base. Once you think you’ve fallen asleep and are are dreaming of paradise, you’ll know you’ve reached Baracoa. Shimmering white beaches are surrounded by lush mountains, with winding rivers and plunging waterfalls thrown in for good measure. We’re exploring the city today with visits to the Catedral de Nuestra Señora de la Asunción, the 19th century Fort Matachin and La Punta Fort, which is now a delicious restaurant. This exploring is hungry work, but before you can tuck in you’re gonna have to earn it with a Caribbean cooking lesson from a local chef. You’ll learn how to prepare scrumptious Cuban staples such as black beans and rice, along with local specialties like fish in coconut sauce. Your dinner parties will never be the same again!

Day 11: Yumuri River and yummy food

On our second day in Baracoa, we can no longer resist the spectacular scenery so will spend the day cruising down Yumurí River, boating in between its tall cliffs and frolicking in the gorgeous waves of Maguana Beach. As well as its stunning natural beauty, Baracoa is a foodie favourite and well known for its excellent Creole cooking. Stuff yourself with as much as your stomach can handle, the seafood in Baracoa can be described as nothing short of sumptuous.

Day 12: Havana round two

All the best movies are worthy of sequels so it’s time to head back to good old Havana on a domestic flight to maximize your final hours. Retune in to the buzz of the capital and spend your remaining time exploring its many museums and historical sites. If you can squeeze it in, why not visit the Cuban cigar factory to see how this most famous of exports is made, or browse the excellent works on display at the National Museum of Fine Arts? You won’t be disappointed!

Day 13: Time to check out of Cuba…or is it?

When Christopher Columbus discovered Cuba he didn’t want to leave – and it’s easy to see why! Once you’ve arranged your taxi to the airport, the time has come to return to reality. Or if you can’t bear the thought of going home yet, why not ask us about a stunning beach extension to Jibacoa?

Itinerary disclaimer

From time to time our itineraries may be amended, either for operational reasons or in response to feedback from customers. Please ensure you have read the latest Trip Notes before booking or travelling on your tour. Please note that while we operate successful trips in this region throughout the year, some changes may occur in our itineraries due to inclement weather and common seasonal changes to timetables and transport routes. This can happen with little notice so please be prepared for modifications to the route.  

Dates & Rates

15 – 27 January 20 – 1,995 GBP
12 – 24 February 2017 – 1,995 GBP
13 – 25 March 2017 – 1,995 GBP
13 – 25 April 2017 – 2,045 GBP



  • All Breakfasts, 3 Dinner, 2 Lunch


  • Traditional casas, B&Bs and a basic trekking Hut


  • Air conditioned mini bus
  • 1 flight from Baracoa to Havana


To cruise around anywhere in a classic convertible is pretty awesome, let alone when it’s the colourful boulevards of Old Havana. Bringing shabby-chic to a whole new level, the candy-coloured streets of Cuba are timeless pieces of magic fuelled by their fascinating history and endless Latin music. Whether you’re salsa dancing to the beat of live music or dining in an authentic paladar, this tour grabs Cuba by its Flamenco sleeves and dives straight into its buzzing culture. It’s not all rum and dancing though as we’re talking beaches, waterfalls and mountains too. Hike the Sierra Maestra Mountains and enjoy wild water swimming in Parque Guanayara, or there’s always the beaches of Trinidad to fall back on (quite literally) for a white sandy paradise, palm trees ‘n all.

Included Activities

  • Tour the charming streets of Old Havana in a classic convertible
  • Dine in a traditional Cuban paladar
  • Explore the romantic, colonial city of Trinidad and its beaches at Playa Ancón
  • Take a dip in a waterfall and enjoy wild water swimming
  • See some of Cuba’s finest ballet dancers in Camaguey
  • Learn to salsa like the locals with your guide
  • Hike in Che Guevara’s footsteps in the Sierra Maestro Mountains
  • Enjoy a Cuban cooking lesson in Baracoa
  • See Cuba’s best local night spots & live music venues
  • Stay in locally run Casa’s – the best way to experience Cuban life

Beach Extension:

Not ready to leave? We can arrange a beach extension to stunning Jibacoa for you. Just ask!  


Been backpacking when you were younger and now looking for something just as fun but with a bit more luxury and style? You’re in good hands. These guys are all about crafting travel experiences that infuse the soul of a backpacker with the style of a jetsetter.

Experts in small group travel they offer smaller-sized trips especially designed for 30-40 somethings. Their travel style is about getting under the skin of a country, hunting down secret locations. Its adventure but with style and comfort!

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