Cuba and Hispaniola

To visit Cuba is to step back in time and we invite you to do just that on this exhilarating 24-day tour, which also traverses the ‘next door ’island of Hispaniola from Haiti’s capital Port au Prince to the colonial jewel of Santo Domingo in the Dominican Republic.

There’s no time like the present to visit Cuba, a unique island almost trapped in a time-warp. After more than 50 years of frozen relations with the United States began to thaw, then stalled again, who knows what lies in store for this fascinating island in the future? But one thing is certain: the window of opportunity to visit this fascinating country before it changes, is closing. Unlike many tours to this remarkable destination, we cover the entire island from Pinar del Rio and the enchanting capital, Havana, to Santiago de Cuba at the country’s eastern tip. En route we take in Che Guevara’s adopted hometown, Santa Clara, and the fabulous World Heritage-listed town of Trinidad. From here it’s a short flight to the forefront of adventure travel, the island of Hispaniola shared by Haiti and the Dominican Republic. The adversity of fires and earthquakes has only served to preserve and fuel the remarkable Haitian spirit. As well as an outstanding art scene with voodoo overtones, the country is home to the most astonishing fortress in the world, La Citadelle Laferrière. Built by 20,000 slaves, it makes even Krak des Chevaliers in Syria look insignificant! From Haiti, we cross the land border with the Dominican Republic for a three-night stay in Santo Domingo. The oldest continuously inhabited conurbation in the new world cradles a magnificent gem in her underbelly: Ojos National Park (the three eyes), is a stunning complex of caves and underground crystal-clear blue water lagoons set in lush tropical vegetation. Join us on a remarkable journey and a truly unique Caribbean experience!

Tour Fitness Level: Moderate



  • City tour of Havana in classic 1950s American cars
  • Four-night stay in the fascinating old city of Havana
  • Enjoy dinner at Ernest Hemingway’s favourite restaurant in Havana
  • Visit the home of Grigorio Fuentes, the inspiration for Hemingway’sThe Old Man and the Sea
  • Celebrate Cuban-style with an exclusive salsa party with a local family
  • Take a 4WD tour to Guanayara Reserve, an area rich in flora and fauna
  • Visit the fascinating Che Guevara museum at his adopted city, Santa Clara
  • Ride on a 1920s steam engine through vast sugar plantations
  • Explore the stunning heritage-listed colonial town of Trinidad
  • Enjoy the infectious rhythms of the little-visited city of rum and revolution – Santiago de Cuba
  • Visit the grave of Che Guevara at Santiago de Cuba


  • Soak up the art, spirit and culture of colourful Jacmel in Haiti
  • Experience Port au Prince’s amazing Iron Market
  • Experience the intensity of Haiti’s capital, Port au Prince
  • Ride on horseback to the mountaintop fortress of Citadelle Laferrière at Cap-Haitien
  • Cross one of the world’s most amazing borders between the two very contrasting worlds of Haiti and Dominican Republic
  • 3-night stay at one of the oldest luxurious hotels in the world, Nicholas de Ovando, in Santo Domingo
  • Discover the oldest city in the New World, Santo Doming
  • Visit Los Tres Ojos – the Three Eyes National Park – at Santo Domingo


  • All flights between Australia and Cuba/Hispaniola (including domestic from your preferred capital city)
  • All flights, transportation and transfers within Cuba & Hispaniola
  • All ticketable taxes (may be subject to change)
  • All accommodation (twin-share)
  • All meals as specified
  • Experienced tour leader throughout
  • Expert local guides
  • All entrance fees in specified sightseeing
  • All visas and courier fees
  • All tips and gratuities

Please note that whilst every effort will be made to adhere to the above pricing, currency fluctuations beyond our control can affect final tour costs. A booking form is to be completed by all passengers, and a non-refundable deposit of AUD $2,000 paid at the time of booking. All escorted tours are based on a minimum group size of 10 people travelling.


03/11/2023 Sydney – Los Angeles – Mexico City – Havana (D)

Check in at your chosen airport for the domestic flight to Sydney. Connect with the international flight to Mexico City via Los Angeles. Crossing the International Date Line, we arrive in Mexico City on the same day.

Depart Sydney Qantas QF 11, 11.50

Arrive Los Angeles 06.35

Depart Los Angeles Aero Mexico AM 631, 09.15

Arrive Mexico City 14.50

Depart Mexico City CU 153, 16.30

Arrive Havana 19.00

After completing Cuban customs and immigration formalities we transfer to our hotel.

Hotel Plaza


03/11/2023 Havana (BLD)

This morning we begin to explore this fascinating city with a tour of old Havana (Habana Vieja). We visit Plaza de Armas and the cathedral before taking in the handicraft markets and enjoying a stroll through the narrow, cobbled streets of the old city. After lunch at the Morro Fortress we tour the new part of the city in 1950s American open-topped cars, visiting the Plaza de la Revolucion and the university.

04/11/2023 Havana – Pinar del Rio – Havana (BLD)

No visit to Cuba would be complete without an excursion to the ‘tail’ of the island, which is in the shape of a shark. This region, Pinar del Rio, is the westernmost province and contains some spectacular scenery. The beautiful Vinales Valley is the finest tobacco-growing area in the world, and, after lunch, we visit a cigar factory and meet the workers before returning to Havana for dinner.

05/11/2023 Havana (BLD)

Today we head out of central Havana to the delightful fishing village of Cojimar, a ‘pilgrimage’ for fans of Ernest Hemingway. While living here in the 1940s and ‘50s, the great author wrote The Old Man and the Sea – a simple but profound story that was awarded the Pulitzer Prize for Fiction in 1953, and saw Hemingway receive the Nobel Prize in Literature a year later. After lunch we return to Havana for some leisure time before dinner.

06/11/2023 Havana – Bay of Pigs – Cienfuegos (BLD)

After breakfast we leave Havana for Cienfuegos via the Bay of Pigs – a large isolated inlet on Cuba’s southern coast. It was here that the ill-fated Bay of Pigs invasion was launched shortly before midnight on 16 April 1961. A group of some 1,500 Cuban exiles, trained and financed by the CIA, came ashore at the Bay of Pigs in an attempt to overthrow Fidel Castro and his revolution. This afternoon the story of the failed operation unfolds and later we continue on to Cienfuegos.

Hotel La Union


07/11/2023 Cienfuegos – Trinidad (BLD)

Known locally as Perla del Sur (Pearl of the South), Cienfuegos traverses a wonderful natural bay and is one of Cuba’s glittering gems. Architecturally, this UNESCO city is one of the most interesting and eclectic of all Caribbean settlements and its sense of pervading tranquility contributes to its considerable allure. After lunch we travel through vast sugar cane plantations and mountainous countryside of the Sierra del Escambray, where sheer-walled limestone cliffs are covered in magnificent bougainvillea. Finally we reach Trinidad, the jewel of Cuba’s colonial cities. Fantastically preserved, this charming town is a national monument with no modern buildings, few cars and old cobbled streets.

Iberostar Grand Hotel


08/11/2023 Trinidad (BLD)

This morning we take a tour of this fabulous town, visiting the main square and the markets. The afternoon is at leisure.

09/11/2023 Trinidad (BLD)

Located between the Escambray Mountains and the Caribbean Sea, the Valle de los Ingeios, this beautiful region was the heart of the Cuban sugar industry. Trinidad’s fortunes were made from sugar and slaves and this valley is littered with the ruins of long abandoned sugar mills. While Cuba still harvests fields of sugar cane, most production has long since moved away from this region. We also visit the Manaca-Iznaga tower where there are magnificent panoramic views across the rural landscape.

10/11/2023 Trinidad – Santa Clara – Camaguey (BLD)

After breakfast we leave Trinidad and drive to the national park of Topes de Collantes. We transfer to 4WD vehicles and drive into the Guanayara Reserve, an area rich in flora and fauna. A local guide takes us on a fascinating walk through the forest where we may be lucky and see the exquisite Cuban hummingbird. Continuing through the mountains, we reach Santa Clara, the adopted city of the great revolutionary, Che Guevara. This was the site of one of the most important battles of the revolution and an impressive mausoleum houses Guevara’s remains. After a tour of the city we head south to Camaguey.

Hotel Gran (or similar)


11/11/2023 Camaguey – Santiago de Cuba (BLD)

This morning we enjoy a walking tour through the warren of delightful winding alleys and hidden plazas of Camaguey. After lunch we continue our journey south to one of the most beautiful cities in the Caribbean, Santiago de Cuba. Due to its remote location, few travellers visit this irresistible cosmopolitan city. Known as the home of rum and revolution, Santiago is the second-largest city on the island. It has a rich racial mix, producing some of the most exciting architecture, music and art in the Caribbean.

Hotel Melia


12/11/2023 Santiago de Cuba (BLD)

In the morning we explore both the old quarter and the new part of this lovely city, visiting delightful plazas, parks, the Moncada Museum and the magnificent Morro Castle on the cliffs overlooking Santiago Bay. This afternoon we visit El Cobre, the most important shrine for Cubans and most famous church in the country, which is lodged in the foothills of the Sierra Maestra near the old copper mines that give it its name. Pilgrims from all over Cuba come here to pay their respects and ask for protection.

13/11/2023 Santiago de Cuba (BLD)

After breakfast we leave Santiago for the extraordinary Parque Baconao. The UNESCO Biosphere Reserve is an important haven for a whole ecosystem. Within this nature reserve is an astonishing park of life-sized dinosaur sculptures and the mountain of Gran Peidra. From the summit of Gran Piedra there is an all-round view over the Parque Nacional de Baconao from the Sierra Maestra down to the Carribean sea. Baconao’s biodiversity is nothing short of remarkable and there are more than 1800 endemic species of flora – from craning royal palms to prickly cliffside cacti. Fauna includes many types of endangered bats and spiders.

14/11/2023 Santiago de Cuba – Port au Prince (Haiti) (BLD)

After breakfast we transfer to the airport for our short flight to Port au Prince.

Depart Santiago Sunrise Airlines H1 2125, 10.15

Arrive Port au Prince 11.30

Landing in Haiti for the first time redefines what adventure travel really is. As the site of the world’s only successful slave rebellion, the music, art and culture that encompass it, make Haiti entirely unique, fascinating and compelling. In many ways people and events such as ‘Baby Doc’ in 1985 and Hurricane Matthew which hit in October 2016 have helped to preserve the soul of this beautiful country. After completing customs and immigration formalities we transfer across the mountains to Jacmel, a port town on the south coast of Haiti.

Hotel Cyadier Plage


15/11/2023 Jacmel (BLD)

Jacmel, Haiti’s fourth-largest city with a population of 40,000, has long been known as the capital of Haiti’s culture. Founded in 1698, the French city Jacmel was the centre of coffee and sugar production and was booming until 1896 when a great fire destroyed a large part of the city. But the city rebuilt quickly with cast-iron-furnished buildings that later came to influence the iconic architecture of the French Quarter in New Orleans. Today the architecture of these elegant ‘gingerbread’ townhouses attracts travellers from all over the world. Jacmel is also known for its vibrant arts and craft scene, including nearly 200 papier-mâché artisans, as well as a school of painting and a music and film school that is recognized among the best in Haiti.

16/11/2023 Jacmel – Port au Prince (BLD)

This morning we visit the famous Bassin Bleu, 12 kilometres from the city centre. Here a series of three cobalt-blue pools are linked by waterfalls that make stunning rock pools deep into the mountain. After lunch we continue to Port au Prince.

Kinam Hotel

Port au Prince

17/11/2023 Port au Prince (BLD)

The Haitian capital is situated on a magnificent bay at the apex of the Gulf of Gonaïves, and is protected from the open sea by the island of La Gonâve. The city was laid out in a grid pattern in 1749 by the French. Despite earthquakes, civil strife and fires, the spirit of the city survives and flourishes. The streets are still lined with vendors and up-beat music vibrates beneath the pavements. Today we explore this irrepressible metropolis that became the inspiration for Graeme Green’s novel, ‘The Comedians’.

18/11/2023 Port au Prince – Cap-Hatien (BLD)

This morning we start to head west along the coast before turning inland and north towards Cap-Hatien. Passing through rocky mountain passes we arrive at Haiti’s second largest city by mid-afternoon. Also referred to as ‘Le Cap’, the city was founded in 1670 by the French and was renowned as the ‘Paris of the Antilles’. It served as capital of the colony until 1770 and was the scene of infamous slave uprisings in 1791.

Hotel du Roi Christophe

Cap Haitian

19/11/2023 Cap Hatien (BLD)

Today we visit the Citadelle Laferrière, a mountaintop fortress, located on the top of Bonnet a L’Eveque Mountain. Depicted on local currency, stamps and postcards, this amazing structure has become the symbol of Haiti’s power and independence. It was built at the beginning of the 19th century by Henri Christophe, one of the leaders of Haiti’s slave revolution and self-proclaimed king. Referred to by locals as the Eighth Wonder of the World, the Citadelle was nominated as a UNESCO World Heritage Site in 1982. This massive stone construction is the largest fortress in the Americas. The site has the most comprehensive collection of artillery, cannons and cannon balls from the era anywhere in the world today. The Citadelle was built in 1804 by 20,000 Haitian slaves after defeating Napoleon’s army and consequently establishing the first black republic. This astonishingly huge structure was created by war and for war, but the French attack never materialised, and this amazing fortress has survived almost unchanged. The scale and the setting of this fortress is simply the embodiment of unlimited human imagination.

20/11/2023 Cap Haitian – Santo Domingo (BLD)

This morning we leave Haiti for the Dominican Republic crossing the Dajabon-Ouanaminthe border and arriving in the capital, Santo Domingo, in the afternoon. Hodelpa Nicolas de Ovanda
Santo Domingo

21/11/2023 Santo Domingo (BLD)

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World. The city is also the seat of the oldest Roman Catholic archbishopric in the Americas. The city was founded in 1496 by Bartholomew Columbus, brother of Christopher Columbus, as the capital of the first Spanish colony in the New World. This is a city that boasts an almost unbelievable cultural legacy while maintaining a vibrant atmosphere and a carefree Caribbean vibe. A plethora of cultures, neighbourhoods, parks, cobblestone streets and museums, it is easy to forget that this is the Caribbean. Indeed, as we explore the city we find a living museum in the heart of the West Indies.

22/11/2023 Santo Domingo (BLD)

Today we travel just beyond the city limits to the incredible natural wonder of Los Tres Ojos National Park (the three eyes), a stunning complex of caves, crystal-clear blue water lagoons and lush tropical vegetation. The park gets its name from the lagoons (eyes), that were formed thousands of years ago, when seismic activity caused the roof of the underground limestone caves to collapse. The resulting sinkholes were subsequently filled with water, fed by an underground river. The varying depths of the lagoons, coupled with the rays of sunlight that dart in from above, create a kaleidoscope of blue and green tones. The caves’ awe-inspiring vistas led the native Taíno population to consider this a holy site, and as such has since been preserved in its wild state. Visiting Los Tres Ojos is akin to stepping into a lost world, hidden beneath the metropolis of Santo Domingo.

23/11/2023 Santo Domingo – Miami – Los Angeles (B)

This morning we depart Santo Domingo on our flight to Los Angeles.

Depart Santo Domingo American Airlines AA 161, 07.30

Arrive Los Angeles 16.30

On arrival in Los Angeles we transfer to our hotel.

Crowne Plaza Los Angeles Airport

Los Angeles

24/11/2023 Los Angeles (B)

After breakfast we embark on a tour of some of the notable sights of Los Angeles including Hollywood Boulevard and the famous ‘Walk of Fame’. After a relaxing day in the ‘City of Angels’ we transfer to the airport for our flight back to Australia.

Depart Los Angeles QF 12, 22.25

25/11//2023 In flight

As we head back towards Australia we cross the International Date Line.

26/11/2023 Arrive Sydney 08.25

On arrival in Sydney we transfer to the domestic terminal for the flight to our chosen Australian city.