Pirates of the Caribbean

If contrasts are the measure of success on any adventure, ‘Pirates of the Caribbean’ will not be overshadowed by any of Travel Directors other worldwide offerings. This remarkable 30-day tour will reveal the very soul of the Caribbean in an exhilarating and enthralling traverse that takes us to eight diverse nations.

This epic journey, that charts the course of Christopher Columbus and ruthless pirates, starts in little visited Nicaragua. This is a country that has emerged from a sinister past to become the focal point of eco and pioneer tourism in Central America. Possessing fairy tale colonial towns, lakes and volcanoes, it also has the largest area of primary rainforest north of the Amazon. The tour then moves onto Jamaica, the Caribbean proper. The ‘birthplace of reggae’ is a treasure trove of natural jewels wrapped up in haunted mansions, a rich culture and a captivating African vibe. Traversing the playground of the pirates in a chartered boat, we arrive in Santiago de Cuba – a remote location on Cuba’s eastern tip which ensures a dearth of tourists. This is the irresistible birthplace of rum and revolution revealed in an exotic racial cocktail. From here it’s a short flight to the forefront of adventure travel, the island of Dominica, shared by Haiti and the Dominican Republic. Fires and earthquakes have 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 in the early 1800s. From Haiti, we cross the land border with the Dominican Republic for a three-night stay in Santo Domingo. The oldest continuously inhabited settlement in the new world is also home to the magnificent Ojos National Park – a stunning complex of caves and underground crystal-clear blue water lagoons set in lush tropical vegetation. An overnight ferry takes us to Puerto Rico in the commonwealth of the United States. A rich and diverse island, this is where salsa and the Atlantic meet the West Indies. We then fly to ‘little England’ in the Caribbean, Barbados, before heading to the capital of Trinidad and Tobago – Port of Spain – for the spectacular finale to our momentous adventure. Here we witness one of the greatest parties on earth – the two day extravaganza that is the Trinidad Carnival. Thousands of masqueraders flood the streets throughout both islands in bold, colourful costumes, dancing through the parade routes to the exhilarating sounds of soca, steelpan and calypso music. ‘Pirates of the Caribbean’ is an exhilarating adventure in true Travel Directors’ style, and a canvas for painting indelible memories!

Tour Fitness Level: Active



  • 5-night stay at Nicaragua’s colonial masterpiece, Granada: our base for exploration of the volcanoes and lagoons
  • Visit the ‘oasis of peace’ in the middle of Lake Nicaragua
  • See the river of molten lava inside the rim of the Masaya Volcano


  • Take a bamboo raft ride in Jamaica’s interior along the Rio Grande
  • See the birth place of Bob Marley at Nine Mile village
  • See Rose Hall haunted house in Montego Bay
  • 2-night stay in Falmouth, the best preserved Georgian town in the Caribbean


  • Cruise into the remote eastern tip of Cuba
  • Spend 2 days exploring Santiago de Cuba, home of rum and revolution
  • Visit Cuba’s time capsule, Cayo Granma


  • Soak up the art, spirit and culture of colourful Haiti
  • Ride on horseback to the mountaintop fortress of Citadelle Laferrière at Cap Haitien

Dominican Republic

  • Discover the oldest city in the New World, Santo Domingo
  • Visit Los Tres Ojos – the Three Eyes National Park – at Santo Domingo

Puerto Rico

  • Cross on the beautiful overnight ferry from Dominican Republic to Puerto Rico
  • See the seamless intermingling of old and new in the wonderful city of San Juan


  • Circumnavigate ‘little England’ in the Caribbean, Barbados

Trinidad & Tobago

  • See the colourful spectacle of the Scarlet Ibis nesting grounds in the marshes of Trinidad
  • Expore Tobago, home of the Swiss Family Robinson
  • Soak up the vibrant and colourful atmosphere of the world’s greatest party, The Trinidad Carnival


  • All flights between Australia and Nicaragua/Trinidad and Australia (inc domestic from your preferred capital city)
  • All accommodation (twin-share)
  • All ticketable air taxes (may be subject to change)
  • All transfers
  • All boat travel within the Caribbean
  • All ground transportation
  • All meals as specified
  • Travel Directors’ 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 costs. A booking form is to be completed by all passengers, and a non-refundable deposit of AUD $3,000 per person paid at the time of booking. All escorted tours are based on a minimum group size of 10 people travelling.


07/02/2019 Sydney – Houston – Managua (D)

Depart from your chosen capital city to connect with the flight from Sydney.

Depart Sydney UA 100, 11.50

Arrive Houston 10.30

Depart Houston UA 1421, 14.51

Arrive Managua 18.05

Nicaragua’s landscape of lakes and volcanoes, lush rainforests and deserted beaches is a nature lover’s paradise. With 76 protected areas covering more than 20% of its landmass, it makes its neighbour, Costa Rica, look almost ordinary. Indeed, the country contains the largest area of primary rainforest north of the Amazon and is home to 7% of the world’s biodiversity, including many endangered species such as howler, white-faced and spider monkeys. Jaguars and crocodiles are plentiful, as are a multitude of birds, butterflies and orchids. Moreover, the negative image of this captivating country is totally undeserved. Peaceful for sixteen years, with three successive democratically elected governments, it is now one of the safest countries in Central America. In 2016, Nicaragua recorded a 20% growth in tourism and this is now the country’s largest industry.

Hotel Estrada


08/02/2019 Granada (BLD)

Perched on the shores of Lake Nicaragua, Granada is a vision of colonial beauty as pastel hues compete with each other amidst baroque and Moorish architecture. Flowers and palms rise over ochre-coloured roof tiles against a breathtaking backdrop of lake shores and volcanoes. It is no wonder that Granada has been a source of inspiration for countless numbers of artists, writers and poets. Yet Granada’s beauty defies a turbulent past, which dates back to the 16th century. Its strategic location on the shore of Lake Nicaragua made it a prime spot for conquistadors and pirates. As an important port for Spanish transport of silver and gold, the city became a target for the English, Dutch and French and was plundered by pirates on numerous occasions. Captain Morgan himself once paid a visit to the city. Today we explore Granada on foot and find out why the laid-back Nicaraguans are regarded as the happiest people in the world.

09/02/2019 Granada – Ometepe Island – Granada (BLD)

Today we travel by road and ferry to Isla Ometepe which is isolated from the rest of Nicaragua by the Cocibolca, or Lake of Nicaragua, referred to as the ‘Oasis of Peace’. The island is a mesmerising place, and full of stunning natural attractions. It is composed of two volcanoes which are joined by a thin, flat isthmus that shape Ometepe like an hour glass. The two volcanoes are visible from everywhere and are a powerful and dominate the landscape. The volcanic ash makes the soil extremely fertile and the land yields abundant crops. In recent years many farms have turned over to sustainable farming practices, and restaurants on the island serve their own, self-grown fruit and vegetables. The island is without doubt one of Nicaragua’s most intriguing destinations.

10/02/2019 Granada – Apoyo Lagoon – Granada (BLD)

When Apoyo Volcano erupted, about 23,000 years ago, it left a huge 7 km-wide crater that gradually filled with water. Today this lake, which is surrounded by the old crater wall, still has active fumaroles at the western shore of the lagoon, which suggests that the volcano is far from dormant. After breakfast we set out to explore the lagoon and surrounding area.

11/02/2019 Granada – Masaya – Granada (BLD)

The Masaya Volcano National Park comprises an area of 54 km² and includes two volcanoes and five craters. The volcanoes have erupted several times and were feared by both the indigenous people and their Spanish conquerors. The Spanish baptised the active volcano ‘La Boca del Infierno’ or ‘The Mouth of Hell’. In the 16th century they planted a cross, ‘La Cruz de Bobadilla’ (named after Father Francisco Bobadilla), on the crater lip in order to exorcise the Devil. What makes Masaya Volcano extraordinary is its accessibility, because almost no walking is required to get there. As evening falls magnificent green parakeets fly in to roost, making a colourful display. These birds have somehow become adapted to the sulphuric fumes expelled from the volcano and live inside the crater itself. We reach the summit by 4WD as darkness descends to witness the unique event of lava flowing from the bottom of the crater. This lava forms a river of magma that glows in the dark and illuminates the interior of the volcano.

12/02/2019 Managua – Kingston (Jamaica) (BD)

Depart Managua CM 710 07.28

Arrive Panama 10.03

Depart Panama CM 418, 11.52

Arrive Kingston 13.49

Known as the ‘birthplace of reggae’, Jamaica boasts a treasure trove of natural jewels and a captivating African vibe. Golden beaches, emerald mountains, turquoise seas, cascades, coral reefs, rainforests, rivers, and mineral springs are just some of these gems. On arrival we start to explore the Jamaican capital, visiting the superb botanical gardens and the former Kingston home of Bob Marley. The king of Reggae lived and recorded here from 1975 until his death in 1981. Today the house is both a tourist attraction and shrine and has been preserved exactly as it was in Marley’s day.

Jamaica Pegasus Hotel


13/02/2019 Kingston – Rio Grande – Falmouth (BLD)

This morning we depart Kingston across the Blue Mountains for the town of Port Antonio and beyond to the Rio Grande. We board bamboo rafts which were once used to transport produce, especially bananas from the interior to the coast. The famous 1950’s actor, Errol Flynn, popularised bamboo rafting for fun – as well as the island itself with his exuberant parties. We float through a lush river valley where villagers spear fish and children play on the banks: this is rural Jamaica at its most authentic and captivating. After we disembark, we continue to nearby Port Antonio. Exuding the relaxed charm of a sleepy fishing village Port Antonio is distinctly less commercial than other resort towns on the island. After lunch we continue along the north coast, where Christopher Columbus landed, to the town of Falmouth, some 35 kilometres from Montego Bay.

Mangos Hotel


14/02/2019 Falmouth – Montego Bay – Falmouth (BLD)

Surrounded by sugar estates and cattle land, Falmouth is one of the Caribbean’s best-preserved Georgian towns. Once a leading port, the town has excellent examples of 19th-century Georgian architecture including a faithful restoration of the courthouse. The Greenwood Great House is also a magnificent drawcard. Built in 1790 by Richard Barrett, a relative of poet Elizabeth Barrett Browning, the Great House is now a museum with period furniture and a rare collection of musical instruments and Wedgwood china. After exploring Falmouth, we continue to Montego Bay. On arrival at the bay we visit one of the great houses in the Caribbean. Built in 1770, Rose Hall is a restored plantation house with beautiful ocean views. The legend surrounding Rose Hall and its infamous owner, Annee Palmer, also known as ‘The White Witch of Rose Hall’, is one that has fascinated generations of island natives and visitors alike. It is a story with all the elements of an engaging novel: a beautiful heroine, unrequited love, black magic and revenge – all set in a gracious old plantation tucked amid the green hills of Jamaica.

15/02/2019 Falmouth – Nine Mile – Falmouth (BLD)

Today we head into Jamaica’s beautiful mountainous interior passing through Brown’s Town before arriving at the small village of Nine Mile. This remote village in the hills of St Ann is the birth and resting place of Bob Marley. Soon after we arrive we enter the Marley family home. Almost all of the home is as it was when Marley was growing up. The message in Bob Marley’s music has influenced many generations from all over the world and despite his death, the legend of Bob Marley lives on in the lyrics in his songs.

16/02/2019 Ocho Rios – Santiago de Cuba (BLD)

After breakfast we head back along the north coast to Ocho Rios where we board our charter boat for Santiago de Cuba, one of the most beautiful cities in the Caribbean, 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


17/02/2019 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.

18/02/2019 Santiago de Cuba – Cayo Granma – Santiago de Cuba (BLD)

Today we visit Cayo Granma, a small island in the natural harbour of Santiago de Cuba. Almost a fantasy island inhabited by fishermen and rarely visited by foreigners, Cayo Granma has withstood the intrusions of modernity.

19/02/2019 Santiago de Cuba – Port au Prince (Haiti) (BLD)

This morning is at leisure in Santiago de Cuba. After lunch we transfer to the airport for our flight to Port au Prince.

Depart Santiago Cubana de Aviacion CU 2125, 15.15

Arrive Port au Prince 17.50

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 like ‘Baby Doc’ in 1985 and events such as Hurricane Matthew which struck in October 2016,demonstrate how the the soul of this beautiful country has remained intact despite huge adversity.

Marriott Hotel

Port au Prince

20/02/2019 Port au Prince (BLD)

Port-au-Prince, capital of Haiti 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’.

21/02/2019 Port au Prince – Cap-Haitien (BLD)

This morning we start to head west along the coast before turning inland and north towards Cap-Haitien. 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 Haitien

22/02/2019 Cap-Haitien (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 in the beginning of the 19th century by Henri Christophe, one of the leaders of Haiti’s slave revolution and self-proclaimed king. The Citadelle is referred to by locals as the Eighth Wonder of the World and in 1982 it was nominated as a UNESCO World Heritage Site. 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.

23/02/2019 Cap-Haitien – 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

24/02/2019 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 diversity 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.

25/02/2019 Santo Domingo (BLD)

Today we travel just beyond the city limits to an 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 it has 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.

26/02/2019 Santo Domingo – San Juan (Puerto Rico) (BL)

This morning we further explore Santo Domingo and in the evening, we board our comfortable ferry for the overnight journey to San Juan, Puerto Rico.

Depart Santo Domingo Ferries Del Caribe, 19.00

27/02/2019 Arrive San Juan 08.00 (BLD)

After centuries of Spanish rule, Puerto Rico became a territory of the United States in 1898 and has been largely self-governing since the mid-20th century. A diverse and magnificent conurbation, the Puerto Rican capital of San Juan ties together the historic and the modern. In this rich cultural gem, rainbow-coloured colonial buildings and art districts sit side by side with smart boutiques and Spanish forts. The old city streets alone, narrow and gridded, are cobbled with ballast from Spanish galleons! This unique jewel is where salsa and the Atlantic meet the West Indies.

Hotel El Convento

San Juan

28/02/2019 San Juan (BD)

This morning we visit the home of Ponce de Leon, which is one of the earliest structures in the old city. La Casa Blanca was both its earliest fortress and home to its earliest ruling family. Ponce de Leon was the man who created his legacy in the search for the mythical Fountain of Youth. Before he took off on his chase for immortality he built this home, and his family lived here for 200 years. Today, the home is a wonderful trip back through the ages, and one of the cultural highlights of Old San Juan.

San Juan – Bridgetown (Barbados)

Depart San Juan 3S 251, 13.40

Arrive Bridgetown 18.40

On our arrival in Bridgetown, we transfer to our hotel.

Courtyard by Marriott


01/03/2019 Bridgetown (BLD)

The easternmost Caribbean island, Barbados is only 34 kilometres long and 20 kilometres wide with a sandy coastline of 97 kilometres. With 11 parishes, this is ‘little England’ in the Caribbean. In fact, no other European nation ever controlled the island and English is the only official language. Here, afternoon tea is still observed, even on the beaches. After breakfast we explore Bridgetown visiting the National Heroes Square and the parliament museum which showcases the island’s proud democratic heritage. In the afternoon we circumnavigate the entire island stopping at Shark Hole and the quiet and beautiful Miami beach.

02/03/2019 Bridgetown – Port of Spain (Trinidad) (BLD)

Depart Bridgetown BW 456, 09.35

Arrive Port of Spain 10.15

Trinidad and Tobago were discovered in 1498 by Christopher Columbus, who claimed the islands for Spain. Three hundred years later, in 1798, the British seized the territory and immediately abolished slavery. To make up for the resulting labour shortage, the British encouraged immigration from Portugal, France, Germany, China and India, and in the early 1900s, the country invited thousands of black immigrants from the Caribbean, Venezuela and Colombia. Today Trinidad is the most developed nation in the Caribbean and the island is a cultural melting pot renowned for its pulsating beat of steel drums and calypso music. Today we make a full tour of the capital and explore the myriad of influences as we stroll through the botanical gardens, Independence Square and the Brian Lara Promenade. Driving east, we see houses surrounded by fragments of coloured cloth fluttering on long bamboo poles. These Hindu prayer flags are put up for major occasions like births, graduations and weddings. At times it is possible to forget that we are on a Caribbean island, as we see people harvesting sugar cane with machetes and water buffalo slowly ploughing their way through teak forests and rice paddies – more reminiscent of India.

Radisson Hotel

Port of Spain

03/03/2019 Port of Spain – Tobago – Port of Spain (BLD)

Tobago is the beautiful little sister island of Trinidad, located only 30km from Venezuela and 250km to the south of Barbados. It is renowned for its white sand beaches, idyllic bays, crystal clear waters, unspoiled coral reefs, unique undersea world, waving palms and tropical rainforest. We spend the day exploring the 41km wide island as we delve into small villages framed by mountains, cocoa plantations and forests before returning to Trinidad in the late afternoon.

04/03/2019 Port of Spain (BLD)

Known as ‘the biggest street party on earth’, Trinidad’s Carnival is officially celebrated on the Monday and Tuesday before Ash Wednesday every year. The Carnival festivities start just after Christmas and continue through to Ash Wednesday. For half a century from 1783 the French developed their Carnival, which was noted to be a season of lively and elegant festivities extending from Christmas to Ash Wednesday. These festivities consisted of dinners, balls, concerts and hunting parties. The Africans started to participate in the festivities from 1833 after the Emancipation Bill was passed. In early celebration of the festival by the masses, activities were held over the three days preceding Ash Wednesday. However, in the face of over 60 years of criticism from the upper class about the low standard of Carnival and strong feelings expressed about the desecration of the Sabbath, in 1943 Carnival on the street was restricted to the Monday and Tuesday. Today opens with J’Ouvert at 4am, when revellers parade through the streets immersed in paint, grease and mud until sunrise.

05/03/2019 Port of Spain (BLD)

Today is Carnival Tuesday and thousands of masqueraders flood the streets throughout both islands in bold, colourful costumes, dancing through the parade routes to the exhilarating sounds of soca, steelpan and calypso music. Each band has its own historical, mythological or tropical concept with various sections depicting aspects of the main theme.

06/03/2019 Port of Spain – Miami/Houston – Sydney (B)

Depart Port of Spain AA 2282, 09.00

Arrive Miami 11.56

Depart Miami AA 4476, 14.15

Arrive Houston 15.59

Depart Houston UA 101, 20.30

07/03/2019 In Flight

Crossing the International Dateline


Arrive Sydney 07.00

On arrival in Sydney, we connect with the flight to our chosen Australian city.