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



  • 4-night stay at Nicaragua’s colonial masterpiece, Granada: our base for exploration of the volcanoes and lagoons
  • Overnight stay at beautiful Ometepe Island, the ‘Oasis of Peace’
  • 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 La Gran Piedra formed by a volcanic rupture millions of years ago


  • 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

  • See the seamless intermingling of old and new in the wonderful city of San Juan
  • Visit the home of  Ponce de Leon, a cultural highlight 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.


06/02/2019 Sydney – Houston

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

Depart Sydney United Airlines UA 100, 11.50

Arrive Houston 10.30

On arrival in Houston transfer to the hotel.

Ramada by Wyndham

Houston International Airport

7/02/2019 Houston – Managua (BD)

After breakfast transfer to the airport for the flight to Managua.

Depart Houston United Airlines UA 1032,  09.50

Arrive Panama 14.55

Depart Panama Copa Airlines CM 712, 1831

Arrive Managua 19.14

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. On arrival in Managua we drive 40kms to our hotel in Granada.

Hotel Plaza Colon


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 – 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.

10/02/2019 Granada – Ometepe Island  (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.

Villa Paraiso

Ometepe Island

11/02/2019 Ometepe Island – Granada (BLD)

After breakfast we depart for Granada and on our arrival we board a boat to explore Lake Managua as we cruise between a maze of islands.

Hotel Plaza Colon


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

Depart Managua Taca TA 396,  10.20

Arrive Miami 13.52

Depart Miami American Airlines AA1082,  18.25

Arrive Kingston 20.12

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.

Knutsford Court Hotel


13/02/2019 Kingston – Dunn’s River Falls – Falmouth (BLD)

Today we leave Kingston and 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.  After lunch in Ocho Rios, we visit Dunn’s River Falls. It can be described as a living and growing phenomenon as it continuously regenerates itself from deposits of travertine rock. This is a result of precipitation of calcium carbonate from the river, as it flows over the falls. The small dome-shaped cataracts are usually associated with thermal spring activity found in limestone caves. This, combined with its location near to the sea, gives Dunn’s River the distinction of being the only one of its kind in the Caribbean.

Melia Braca Village


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

This morning we board bamboo rafts which were once used to transport produce, especially bananas from the interior to the coast. The famous 1950s 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. After disembarking from our rafts we continue through vast sugar plantations to the parish of Montego Bay and Rose Hall Great House. 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 – Kingston – Santiago de Cuba (BD)

Depart Kingston Aerogaviota KG 6085,  14.10

Arrive Santiago de Cuba 16.10

After breakfast we head to Kingston airport for our flight to Santiago de Cuba, one of the most beautiful cities in the Caribbean, Due to its remote location, few travelers 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


16/02/2019 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. During our tour of the city we also visit the astonishing cemetery of Ifigenia, where Jose Marti is buried alongside Fidel Castro. Today Cubans from all over the island lay flowers and break down in tears as they kiss the simple stone of Fidel.

17/02/2019 Santiago de Cuba – La Gran Piedra – Santiago de Cuba (BLD)

Today we head out of Santiago de Cuba to Baconao Park, were we visit a fascinating museum of old Cuban cars. We then switch to smaller vehicles as we start to drive through a micro climate with unique flora consisting of many varieties of ferns, orchids, maestrense pines, cypresses and a variety of fruit-bearing trees which include peach. At 1,225 metres above sea level we reach La Gran Piedra (the grand stone). Formed from a volcanic rupture, La Gran Piedra is an enormous rock situated on the summit of a mountain and some scientists believe that it was formed by the impact of a meteorite that fell to the earth millions of years ago.

18/02/2019 Santiago de Cuba – Port au Prince – Jacmel (BLD)

Depart Santiago Sunrise Airways S6 301,  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 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. On our arrival in the capital, we head through the mountains to Jacmel town on the southern coast of Haiti. Situated on a hillside overlooking palm-fringed Jacmel Bay, the town flourished under the French as a port for the shipments of sugar, coffee, and cotton. Today it is a commercial centre for such products as bananas, cacao, and coffee.

Cyvadier Hotel


19/02/2019 Jacmel – Port au Prince (BLD)

This morning we start to unravel Jacmel’s charm as we walk through the old town centre which is littered with mansions and merchants’ warehouses that are graced by  wrought-iron balconies, peeling facades and wonderful urban mosaics. After lunch we drive to Port-au-Prince.

Kinam Hotel

Port au Prince

20/02/2019 Port au Prince (BLD)

The Haitian 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


22/02/2019 Cap-Haitien – Citadelle Laferriere – 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) (BLD)

This morning we transfer to the airport for our flight to Puerto Rico.

Depart Santo Domingo Jetblue Airways B6 1638,  08.25

Arrive San Juan 09.28

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. ! This unique jewel is where salsa and the Atlantic meet the West Indies. 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.

Hotel El Convento

San Juan

27/02/2019 San Juan (BLD)

Today we enjoy a full day excursion to the north eastern corner of Puerto Rico famous for its natural springs, waterfalls and caves.

28/02/2019 San Juan (BD)

This morning is at leisure before we transfer to the airport for our flight to Barbados.

Depart San Juan Liat Airlines LI 563, 14.35

Arrive Antigua 16.00

Depart Antigua Liat Airlines LI 523, 1700

Arrive Bridgetown 19.05

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

Hotel Radisson


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.

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

After breakfast we circumnavigate the entire island of Barbados stopping at Speightstown on the gentle west coast. We then cross to the surfer’s paradise of the Caribbean, the rugged east coast. Late afternoon we arrive at Grantley Adams airport for our flight to Trinidad.

Depart Bridgetown Caribbean Airlines BW 449,  19.15

Arrive Port of Spain 20.15

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.

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 – Sydney (B)

Early this morning we transfer to the airport for our homeward journey.

07/03/2019 Arrive Australia

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