Highlights of Cuba

CubaHistory & Culture

Highlights of Cuba from SGD 2,351 per person

It’s amazing to travel to a new destination and feel like you belong there, but this is exactly what will happen when you come to captivating Cuba on our 9-day Highlights of Cuba Tour. So much has been said and written about Cuba that the country will seem wonderfully familiar. There’s also the warmth of the Cuban people who are so friendly that you will wonder if they’ve mistaken you for a long lost friend! So what can you expect on one of our Cuba private tours?

We are dedicated to providing you with an authentic and unforgettable Cuba tour experience. We can help you achieve in one adventure what has taken us years – to go inside the country in a deeper, more personal way. With Locally Sourced Cuba Tours you will have unrivalled access to local people from all walks of life while you experience an island that simply has so much to offer. Our tours are focused on introducing you to the Cuba that we know and love. You will spend time getting to know the locals, immersing yourself in Cuban culture, and supporting the Cuban people through your responsible tourism efforts.

9 Nights
From SGD 2,351Per Person

Highlights of Cuba

Bienvenido! Welcome to Cuba!

Havana is the jewel in the crown of Cuba. She’s a dishevelled beauty, and while this is all part of her charm, the burgeoning tourist trade is allowing more and more of the city to be restored to its former beauty, courtesy of those tremendously timely tourist dollars. The heart of the city (Havana’s Old Town) is a UNESCO World Heritage site, helping to solidify Havana’s ongoing maintenance efforts.

You’ll have plenty of time to explore Havana during your tour. Your first evening in Cuba is an ideal time to get acquainted with the city, even if it’s just the streets immediately around your accommodation. You will quickly see that many of the things you assumed to be true about Cuba are just as you thought, although these are more than superficial charms. You will wander past enticing doorways with salsa music wafting out, intermingled with the pungently sweet aroma of cigars. Bold characters will march down the street, clad in luridly beautiful colours while having passionate conversations with each other. And everywhere those antique cars prowl the streets, crunching their gears as they sail past you. Havana can be a beautiful sensory overload, and it’s a lot to take in on your first day. Today you have the option of meeting your tour guide for introductions and to ask any burning questions you might have. Depending on your arrival time, you might like to accompany your guide for dinner, to discuss your itinerary, interests and expectations.

A Note About Your evenings in Cuba

Our expert tour guides would be happy to arrange a wide variety of evening activities for you, during your time in Cuba. Evenings are generally free time, allowing you to explore at your leisure. Although of course, if you become stuck for ideas, we would be delighted to make some suggestions, and your guide will be available to organise tickets, reservations and accompany you out if required. Your guide will have some fantastic ideas and recommendations based on your tastes and preferences.

Meals: On your own.

Today you will really get to know Havana, and the heart of Havana is its Old Town; the village that essentially gave birth to the modern city. The best way to see this part of Havana is on foot, and we’ll spend the morning walking through this sumptuously beautiful district. Your guide will be with you every step of the way, perhaps encouraging you to keep moving when you inadvertently stop and stare at your surroundings every few minutes or so. Like much of the New World, Havana was once a walled fortress, although the growth of the city meant that it would soon need to sprawl beyond these original boundaries.

There’s an abundance of cultural riches on offer, and you’ll walk past the El Capitolio, the Museo de la Revolución, and the Gran Teatro Habana. This Old Havana Walking Tour also takes in some of the most stunning squares you will ever see – the Plaza de Armas, Plaza de la Catedral, Plaza San Francisco de Asis and Plaza Vieja. There is much to see on the walking tour, and you’ll think that the beauty of Havana has been squeezed into a relatively compact area.

There’s plenty of people watching to be done too, as you get to know the people who make up this vibrant city. There will be a rather welcome break for lunch after an engrossing morning of walking, and you will definitely appreciate some fantastic Cuban hospitality while you eat at a Cuban paladar (a stunning example of the culinary scene that has flourished throughout the country in recent years).

Now you can take a break from walking and you are no doubt itching to take a ride in one of those classic cars that parade through the streets of the city. This iconic method of transportation is synonymous with Cuba, and it sure gives your legs a rest! You’ll be whisked out of Old Havana and will clearly be able to see the contrast with the newer parts of central Havana and the faded grandeur of Miramar. We will also take you past the Colon Cemetery, Revolution Square and the once affluent Miramar district. You will then be taken to the Hotel Nacional in Havana Vedado for a drink and a wonderful view of the Malecon for sunset.
You have a few options for the evening if you can handle more stimulation by this point! You might wish to enjoy a cocktail and a meal at one of our favourite Paladars (family-run restaurants). There’s also the option to visit Havana's most famous jazz club (the memorably named The Vixen and the Crow), right on La Rampa. Entry is via a red English phone box, where the stairs then lead you down to a lively basement where freestyle jazz is played nightly.

Overnight in a Casa Particular.

Meals included: Breakfast | Lunch

It’s time to make our way to the dramatic beauty of the Pinar del Rio province and the rural town of Viñales. The landscape is dotted with mogotes - steep rounded hills that contrast the flat plains around them. A rich, fertile valley of the Pinar del Rio province is where you will find Viñales. This compact and authentic village is one of the most breath-taking spots in all of Cuba. In the heart of Cuba’s prime tobacco growing region, Viñales is deceptively industrious, and many of Cuba’s trademark cigars are made from tobacco that is grown here. Upon arrival, you will have the chance to have a look around the township and experience the lively music and dance scene that Viñales excels in.

As you are arriving into Vinales, there will be time to stop at the Los Jazmines Look-out point to admire Vinales and the Pinar del Rio province in all its splendour.

With the compact size of Viñales in mind, your guide will take you on a gentle walking tour of the township and surrounding farmlands, including a delicious lunch at a local organic farm.

There is also the option of exploring the surrounding farmland by bicycle.
As you spend time in the Viñales Valley will visit the many different plantations of the region: manioc, arrowroot, sweet potato, tobacco, tomato, banana, mango and pineapple. Crossing small private farms, you can see the farmers working with their oxen and their traditional methods of cultivation. The mogotes (rounded hills) are a particular landscape that can only be found in this area. There is also the opportunity to taste delicious sugar cane juice mixed with grapefruit juice, known as guaratón.
Next, you will travel 4 kilometres west of Viñales to a 120-metre long painting designed in 1961 by Leovigildo González Morillo, a follower of Mexican artist Diego Rivera. On a cliff at the foot of the 617 metre high Sierra de Viñales, the highest portion of the Sierra de los Órganos, this massive mural took 18 people four years to complete. The huge snail, dinosaurs, sea monsters and humans on the cliff symbolize the theory of evolution and are either impressively psychedelic or monumentally horrific, depending on your viewpoint.

That rich red earth that you see is ideally suited to the cultivation of tobacco, and you will learn about the birth of cigars. To learn about the local tobacco-growing process we visit a tobacco plantation and see a fully operating secadero (drying house) in which tobacco leaves are cured from February to May. The evocative scent that wafts out of the secadero will forever be associated with Cuba.
The fertile soils around Viñales aren’t just good for tobacco (the fresh fruit here is simply delicious) and you can take full advantage of the many outdoor activities available to you. The tranquil natural beauty sits comfortably alongside a lively and jaunty nightlife which will surely make your stay in Viñales a memorable one. This town is the perfect opportunity to experience an authentic slice of Cuban rural life.

Meals included: Breakfast | Lunch

Cuba can be a country of indulgences, and today you will familiarize yourself with two of these indulgences in particular. When anyone mentions Cuba two of the first things that come to mind are cigars and rum, immortalized by Hemingway.
There is a rich, cultural tradition when it comes to producing the world’s best cigars and rum, and on this tour you will gain an insight into just why these famous exports are so intertwined with Cuba herself.
Your guide will pick you up in the morning, before making your way to the Havana Rum Museum. If you think this museum looks palatial, you are correct since it’s housed in a converted old palace. Naturally you will have the chance to learn about the rum making process and even do some tastings.
Next it’s time for a drinks break at El Floridita, one of Hemingway’s favourite bars. There’s even a life-sized statue of him at the bar. He enjoyed the daiquiris here, and you can do the same.
The next stop is the Partagas Cigar Factory where the mystique behind cigar making will be revealed, allowing you to gain a sense of the significance of these beauties. You will also witness first hand the amount of effort, care and tradition that goes into making these Cuban treasures (even non-smokers will find this tour very interesting).

This afternoon you can choose between a range of activities.

  • If you are interested in Hemingway, you can take a short drive to La Finca Vigía on the outskirts of Havana. This sprawling estate was the Cuban home of Ernest Hemingway, where the great man lived and worked. Next stop is Cojimar (14 kilometres from Havana), where Hemingway was inspired to write The Old Man and the Sea. There’s another unique statue of Hemingway here, and we’ll also show you the restaurant Las Terrazas, the preferred Cojimar hangout of the author and the late Captain of his boat (Pilar); Gregorio Fuentes.
  • You might like your afternoon to be rapturously occupied by Havana’s Museum of the Revolution, and even the building in which it’s housed has a story to tell. This grand building, deliberately impressive in scope, was the Presidential Palace prior to the Cuban Revolution. After the government was overthrown in 1959, the building was home to the Government and the Council of Ministers until 1965, when it hosted Central Committee of the Communist Party of Cuba. In 1974, it became a museum dedicated to the Cuban Revolution, and two years later, it witnessed the approval of the 1976 Constitution. It was awarded national monument status in 2010.
  • Another option is the Museo Nacional de Bellas Artes (Arte Cubano). This is where the crème de la crème of Cuban art is proudly displayed (and the museum exclusively displays Cuban art). Works are displayed in chronological order starting on the 3rd floor and are surprisingly varied. This ordering allows you to easily take in the development of Cuban art throughout the centuries. Amongst others, you will see the works of Guillermo Collazo, considered to be the first truly great Cuban artist. There is also Rafael Blanco, with his cartoon-like paintings and sketches; along with Raúl Martínez, a master of 1960s Cuban pop art; and the Picasso-like Wifredo Lam.

Next, we will take you to the unforgettably psychedelic Callejon de Hammel. This small alleyway in the central city is where the Cuban artist fraternity congregates and is a wonderful place to experience day-to-day Cuban life, albeit with an artistic twist. The art has quite literally spilt out of the studios and onto the street.

In the evening you might wish to visit La Taberna in the heart of Havana’s Old Town (this is optional and not included in the price of your tour). La Taberna offers the best traditional Cuban music as popularized by the Buena Vista Social Club.

Meals included: Breakfast

Your first stop today is Santa Clara. Rather unsurprisingly, there are many tributes to the Cuban Revolution in Santa Clara, and while it’s a troubled past, the events here are what led to the ultimate victory in the struggle and led to the formation of post-revolution Cuba. The city is often called The City of the Heroic Guerilla. The town is extremely significant, and while it’s not as visited as Havana or many better-known spots in the city, its place in modern Cuban history cannot be denied.

Contemporary Santa Clara is an important commercial hub and home to one of Cuba’s largest universities (giving the whole town a youthful and energetic vibe), but is probably best known as the resting place of Che Guevara. It was Che Guevara who led the revolutionary forces in that final victorious battle.
Naturally, we will take you to meet this iconic historical figure, or at least to his final resting place. The Che Guevara Mausoleum and Memorial was originally intended as a memorial, as Guevara’s final resting place was still a mystery when it was constructed. He was executed in Bolivia in 1967 and his body was placed in an unmarked grave beside a military landing strip, where they would remain for 30 years. Upon their discovery, his remains were transferred to Santa Clara and interred in the memorial that bore his name. There is also an interesting museum, and here you will learn about how Guevara played a pivotal role in the demise of the dictator Batista and the rise of Fidel Castro, a turning point in the Cuban revolution.

Santa Clara is a beautifully maintained city, and while its existence is hardly a secret, it’s not a place that all that many visitors to Cuba get to experience. Its history might be dark, but its present is bright.

Now it is on to the favourite destination of many a traveller to Cuba. Trinidad was founded in 1514 by Diego Velázquez and is considered a jewel in Cuban colonial architecture. The town is sublimely beautiful and (much like Havana’s Old Town) the area has been maintained as a result of its designation as a UNESCO World Heritage site.

On your guided walk around the town, you will come to understand why the term “living museum” is often utilised when it comes to describing this part of Cuba. It really is like time has stood still here.

To live in Trinidad was once to a symbol of prestige, even given its isolated nature (before highways and mass transit). This prestige came at a cost, and this cost was carried by the efforts of the thousands upon thousands of slaves who worked the sugar plantations at the adjacent Valle de los Ingenios during the early 19th century. The wealth of the town came from this sugar, and while the town lost some of its sheen in the subsequent decades after the abolition of slavery, it has retained its distinctive grace.
While its former key industry is but a distant memory (and this is obviously a good thing), Trinidad has slowly found a new identity, much of which is based upon the number of visitors who are drawn to its narrow streets and preserved colonial architecture. There is also a key drawcard for visitors some 12 kilometers away from the heart of the city. The white sands and placid azure waves of Playa Ancón is the cherry on the top for Trinidad, and if this wasn’t enough, some 18 kilometres to the north the dramatic and dense Sierra del Escambray (Escambray Mountains) begin, offering a beguiling change of pace from the town and the beach.

Today is the perfect day to do a township walk with your guide and visit some of the town’s museums. There is also the option to have a Salsa lesson if you are feeling energetic! Your time in Trinidad would not be complete without at least one evening sitting on the steps outside the open air Casa de la Musica. Every night the area beside the Cathedral in Plaza Mayor comes to life with a live salsa band. There is no cost (although tipping is generally encouraged), the drinks flow freely and inexpensively, and this all takes place under a beautiful, balmy, starry sky.

Meals included: Breakfast

Today you will explore Trinidad and its rather stunning surroundings
There are three fantastic tour options to choose from, and you will have time to fit two of them into your itinerary.

  1. Valle de los Ingenios
    We can take you to the Valle de los Ingenios, which simply has to be seen to be believed. The name of the area translates as the Valley of the Sugar Mills. It was here that the bulk of Cuba’s sugar production took place, although this came to an end around the time that slavery was outlawed in Cuba. There are dozens of old sugar mills from the 19th century, along with slave quarters and manor houses, all dotted throughout the valley, which gives you an idea of the scope of the sugar production that once took place in the valley. You’ll get to see Manaca Iznaga, an estate purchased in 1795 by Pedro Iznaga, who became rich by trafficking in slaves. It’s both deeply interesting and somewhat unsettling.
  2. Sierra del Escambray mountain range
    It wouldn’t be a valley without a border of mountains, and might like to venture into these rugged, impressive peaks (Topes de Collantes). These are the Sierra del Escambray mountain range, which run for some 90 kilometres. They’re located just 20 kilometres from the centre of Trinidad. If you want to hike, you’re looking at around 2.5 hours for the most popular hike that showcases the natural beauty of the region. It’s around 2.5 kilometres in length and takes you to the Salto del Caburní, a 62-metre waterfall cascading into cool swimming holes.
  3. Playa Ancon
    From the mountains to the sea, you might like to visit Playa Ancón, and feel that some white sand beneath your feet. Playa Ancon is one of the most beloved beaches in Cuba, and is considered to be the best on the southern coast. This white beach in the Sancti Spíritus region can be reached in less than 15 minutes in a car, although if you can muster the energy, you might want to ride a bike from Trinidad (which will take about 40 minutes, depending on your pedal power). There are some resorts right on the beach, but the area has certainly not been overdeveloped. But if you’re craving an authentic beachside village, then we’ve got you covered. There is also the option to visit the sleepy old fishing port of Casilda, 6 kilometres due south of Trinidad, which offers a pace of life that is relaxed even by Cuban standards.

Back in Trinidad your guide will be able to suggest the very best restaurants and music venues to visit for an evening of fantastic Cuban entertainment. You might wish to sample the delights of Palenque de los Congos Reales. A must for rumba fans, this open patio on Trinidad's music alley has an eclectic menu incorporating salsa, son (Cuban popular music) and trova (traditional poetic singing). The highlight, however, is the 10pm rumba drums with soulful African rhythms and energetic fire-eating dancers. You might also be perfectly content to simply sit in Trinidad’s main plaza and watch the city life unfold around you.

Meals included: Breakfast

Today you will travel back to Havana via Cienfuegos and the Bay of Pigs.

While it was primarily the Spanish who settled Cuba, there were other European powers that made their mark, and this is particularly obvious when you see the rich French-influenced architecture of Cienfuegos. A number of French settlers influenced the development of the city, many of whom came to Cuba after being dissatisfied with their fortunes in other French territories in the New World. Founded in 1819 by Don Luis de Clouet, Cienfuegos largely managed to remain free of pirate attacks (although this was primarily a matter of chance) allowing the settlement to prosper unhindered.

Along with your guide, take some time to explore the wide streets and promenades, visit Parque Jose Marti and enjoy a walk along the Malecon, the longest promenade on the island (which is not to be confused with the Malecon which snakes along the waterfront in Havana).

“Cienfuegos is the city I like the best”, wrote Benny More, one of Cuba’s most important musicians in the first half of the 20th century. Clearly, this is a subjective opinion, but it’s one you might come to share. Your guide will lead you on a city walk before taking in the grand, crumbling architecture over a cocktail at the very impressive yacht club.

Cuba is not immune from kitsch, and you will find an amusingly impressive example of this at the end of Calle 37. Cuban nights? More like Arabian Nights with this ostentatious structure (the Palacio de Valle) which was built in 1917. Used for varying purposes throughout its more than 100 years in existence, the Palacio de Valle is now an (aspiring) upscale restaurant with an inviting terrace bar.

Next stop on the itinerary is the Bay of Pigs. There has been much turmoil in Cuba’s history, the majority of which is hard to spot since it took place in areas that now seem to be the definition of tranquillity. One such place is the infamous Bay of Pigs/ Playa Girón - the staging ground for the failed US-backed invasion of Cuba, which was a catastrophic failure. It’s now a place of peace and profound natural beauty and is extremely popular these days with snorkelers and divers due to the distinctive cave systems, coral formations and an abundance of sea life. Now the aquatic creatures that populate these waters are used to inquisitive human visitors.

After some time spent relaxing at the Bay of Pigs, it will be time to make your way back to Cuba’s capital city.

Meals included: Breakfast

Today is a free day to relax or to explore Havana independently. Your guide will be available to organise a host of optional activities for you, if requested.

Meals included: Breakfast

After breakfast, we will organise an airport transfer for you to catch your departing flight.

Meals included: Breakfast

Trip Cost

Price per person in SGD

  • SGD 2,351 ~ Adult Twin
  • SGD 338 ~ Single Room Supplement


  • Return airport transfers
  • Private transportation between destinations
  • Accommodation in Casa Particulars with daily breakfasts
  • 2 lunches
  • Old Havana Walking Tour
  • Lunch at a fantastic Cuban Paladar
  • A tour of Havana in a classic car
  • 1 drink at Hotel Nacional
  • Vinales Township Walk
  • Organic Farm Lunch
  • Farmland guided walk or cycle
  • Mural de la Prehistoria
  • Tobacco Farm and drying house
  • Los Jazmines Look0ut Point
  • Visit to the Havana Rum Museum
  • Visit to the Partagas Cigar Factory (closed on weekends)
  • Callejon de Hammel
  • Finca Vigia OR Museum of the Revolution OR Museum of Fine Arts
  • El Floridita: Taste a famous Cuban Daiquiri at one of Hemingway's favourite haunts
  • Che Guevara Memorial
  • Trinidad Township Walk
  • Visit Casa la Musica for a fantastic evening of Cuban dance and music
  • Salsa lesson (optional)
  • 2 out of the following 3 options
    • Visit the Valley of the Sugar Mills
    • Trek to ZSalto del Caburni
    • Visit Playa Ancon
  • Wim/snorkel at the Bay of Pigs and a visit to the local museum there
  • Cienfuegos City Walk
  • 1 drink at Palacio de Valle
  • Visits and entry to the Che monument and historical sites in Santa Clara


  • Air passage to/from Havana
  • Cuban visa, where required
  • Personal expenditure such as soft/hard beverages, phone calls, internet access, laundry, etc
  • Tipping for guide and driver, and other service providers
  • Optional tours and excursions