49 days in Caribbean Itinerary

49 days in Caribbean Itinerary

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Route & dates

49 days in Caribbean Itinerary

Start: Cluj-Napoca, Romania
Fly:  23​h 45​min
1
Nassau, Bahamas
— 3 nights
Fly:  4​h 30​min
2
Havana, Cuba
— 4 nights
Drive:  3​h
3
Cienfuegos, Cuba
— 2 nights
Drive:  1​h 30​min
4
Trinidad, Cuba
— 2 nights
Drive:  9​h
5
Santiago de Cuba, Cuba
— 2 nights
+2
train + taxi + Fly:  6​h 45​min
6
Montego Bay, Jamaica
— 4 nights
Fly:  7​h 15​min
7
Santo Domingo, Dominican Republic
— 4 nights
Fly:  2​h 45​min
8
San Juan, Puerto Rico
— 4 nights
Fly:  5​h
9
Roseau, Dominica
— 4 nights
Fly:  4​h 45​min
10
Bridgetown, Barbados
— 4 nights
Fly:  3​h 45​min
11
Port of Spain, Trinidad and Tobago
— 4 nights
Fly:  5​h 15​min
12
Willemstad, Curacao
— 4 nights
bus + Fly:  1​h 45​min
13
Oranjestad, Aruba
— 4 nights
Fly:  25​h
End: Cluj-Napoca, Romania


Learn more about your trip

3
nights
Nassau, Bahamas

Nassau ©
On a trip to Nassau you can immerse yourself in a dynamic city atmosphere or spend your days lazing on the soft golden sands.
You've added Parliament Square, Fort Fincastle, Ardastra Gardens, Zoo and Conservation Center, and other attractions to your itinerary. Next up on the itinerary: enjoy the sand and surf at Cable Beach, try to win big at Atlantis Casino, steep yourself in history at Queen's Staircase, and take an in-depth tour of Pirates of Nassau Museum.

To see photos, where to stay, other places to visit, and other tourist information, use the Nassau day trip planning tool .

Cluj-Napoca, Romania to Nassau is an approximately 24-hour flight. Traveling from Cluj-Napoca to Nassau, you'll gain 7 hours due to the time zone difference. Traveling from Cluj-Napoca in August, expect nights in Nassau to be warmer, around 30°C, while days are a bit warmer, around 38°C. Wrap up your sightseeing on the 8th (Thu) to allow time to travel to Havana.

Things to do in Nassau

Parks Zoos & Aquariums Theme Parks

Side Trip

Paradise Island
Highlights from your plan
Marine Habitat at Atlantis ©
Marine Habitat at Atlantis
Cable Beach ©
Cable Beach
Aquaventure ©
Aquaventure

4
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Your day-by-day itinerary now includes Palacio De Los Capitanes Generales as well as Calle Obispo. There's much more to do: make a trip to El Malecon, get engrossed in the history at Museum of the Revolution (Museo de la Revolucion), explore the different monuments and memorials at Christopher Columbus Cemetery (Cemetario de Colon), and steep yourself in history at Old Square (Plaza Vieja).

For photos, where to stay, reviews, and tourist information, use the Havana trip builder website .

Traveling by flight from Nassau to Havana takes 4.5 hours. Traveling from Nassau in August, expect little chillier with lows of 26°C in Havana. Finish your sightseeing early on the 12th (Mon) to allow enough time to drive to Cienfuegos.

Things to do in Havana

Historic Sites Museums Neighborhoods
Highlights from your plan
Old Havana ©
Old Havana
El Malecon ©
El Malecon
Plaza de la Catedral ©
Plaza de la Catedral

2
nights
Cienfuegos, Cuba

Cienfuegos ©
The city of Cienfuegos sits in a scenic natural bay, attracting visitors from across the country and further afield since its establishment in the early 19th century.
Your day-by-day itinerary now includes Jagua Castle, Che Guevara Mausoleum, Teatro La Caridad, and other attractions you added. On the 13th (Tue), admire the sheer force of El Nicho Waterfalls, walk around Parque Leoncio Vidal, then make a trip to Teatro La Caridad, and finally appreciate the history behind Che Guevara Mausoleum. On your second day here, walk around Cueva de los Peces, admire the striking features of Palacio de Valle, and then step into the grandiose world of Jagua Castle.

Inspirock's itinerary builder makes planning a Cienfuegos trip simple and quick.

Drive from Havana to Cienfuegos in 3 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 39°C in August, and nighttime lows around 28°C. Finish up your sightseeing early on the 14th (Wed) so you can go by car to Trinidad.

Things to do in Cienfuegos

Parks Historic Sites Nature

Side Trips

Santa Clara, Cueva de los Peces
Highlights from your plan
El Nicho Waterfalls ©
El Nicho Waterfalls
Che Guevara Mausoleum ©
Che Guevara Mausoleum
Jagua Castle ©
Jagua Castle

2
nights
Trinidad, Cuba

Trinidad ©
Built on sugar and seemingly preserved in molasses, the town of Trinidad attracts visitors with its well-aged 19th century architecture and rustic charm, showcasing the sounds, scents, and sights of days gone by.
On the 15th (Thu), admire the sheer force of Salto del Caburni, then tour the pleasant surroundings at Ancon Beach, then examine the collection at Romance Museum, and finally look for all kinds of wild species at Valle de los Ingenios.

Planning Trinidad trip won't be overwheling when you use's Insprock itinerary maker.

You can drive from Cienfuegos to Trinidad in 1.5 hours. Other options are to take a bus; or take a shuttle. In August, plan for daily highs up to 39°C, and evening lows to 28°C. On the 16th (Fri), you'll travel to Santiago de Cuba.

Things to do in Trinidad

Parks Historic Sites Wildlife
Highlights from your plan
Valle de los Ingenios ©
Valle de los Ingenios
Ancon Beach ©
Ancon Beach
Romance Museum ©
Romance Museum

2
nights
Santiago de Cuba, Cuba

Santiago de Cuba ©
Santiago de Cuba has taken almost as much influence from Haiti and the Dominican Republic as it has from Havana, distilling a concoction of cultures to create a city with a distinct identity.
On the 17th (Sat), walk around Cespedes Park, get engrossed in the history at Casa de Diego Velazquez, steep yourself in history at Moncada Barracks, then don't miss a visit to Antonio Maceo Revolution Square, and finally stroll the grounds of Cementerio Santa Ifigenia. Get ready for a full day of sightseeing on the 18th (Sun): explore the historical opulence of Castillo de San Pedro de la Roca and then take a memorable drive along La Gran Piedra (The Big Rock).

To see traveler tips, reviews, maps, and tourist information, you can read our Santiago de Cuba road trip planning website .

Drive from Trinidad to Santiago de Cuba in 9 hours. Alternatively, you can do a combination of bus and train; or take a bus. Expect a daytime high around 37°C in August, and nighttime lows around 28°C. Finish your sightseeing early on the 18th (Sun) to allow enough time to travel to Montego Bay.

Things to do in Santiago de Cuba

Historic Sites Scenic Drive Outdoors
Highlights from your plan
Cementerio Santa Ifigenia ©
Cementerio Santa Ifigenia
Casa de Diego Velazquez ©
Casa de Diego Velazquez
Castillo de San Pedro de la Roca ©
Castillo de San Pedro de la Roca

4
nights
Montego Bay, Jamaica

Montego Bay ©
The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Your day-by-day itinerary now includes YS Falls, Greenwood Great House, Negril Cliffs, and other attractions you added. You'll find plenty of places to visit near Montego Bay: Original Mayfield Falls Jamaica (in Pennycooke) and Seven Mile Beach (in Negril). There's more to do: steep yourself in history at Rose Hall Great House and enjoy the sand and surf at Doctor's Cave Beach.

For maps, where to stay, photos, and tourist information, use the Montego Bay journey planner.

Getting from Santiago de Cuba to Montego Bay by combination of train and flight takes about 7 hours. Other options: do a combination of flight and bus. In August, daily temperatures in Montego Bay can reach 39°C, while at night they dip to 29°C. On the 22nd (Thu), wrap the sightseeing up by early afternoon so you can travel to Santo Domingo.

Things to do in Montego Bay

Parks Nature Beaches

Side Trips

Negril, YS Falls, Original Mayfield Falls Jamaica, Green Grotto Caves
Highlights from your plan
Green Grotto Caves ©
Green Grotto Caves
Seven Mile Beach ©
Seven Mile Beach
YS Falls ©
YS Falls

4
nights
Santo Domingo, Dominican Republic

Santo Domingo
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Your day-by-day itinerary now includes National Palace, Mercado Modelo and Calle de Las Damas. The adventure continues: make a trip to Zona Colonial, contemplate the long history of Parque Colon, explore the ancient world of Monasterio de San Francisco, and explore the wealth of natural beauty at National Botanical Garden.

Plan my Santo Domingo trip by asking Inpirock to come up with tips and suggestions.

Traveling by flight from Montego Bay to Santo Domingo takes 7.5 hours. You'll lose 1 hour traveling from Montego Bay to Santo Domingo due to the time zone difference. Wrap up your sightseeing by early afternoon on the 27th (Tue) to allow time for travel to San Juan.

Things to do in Santo Domingo

Historic Sites Nature Parks
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial

4
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Your day-by-day itinerary now includes Bioluminescent Bay, Parque Nacional de las Cavernas del Rio Camuy and Calle del Cristo. Take a break from San Juan with a short trip to El Yunque Rain Forest in El Yunque National Forest, about 1h 10 min away. The adventure continues: steep yourself in history at Old San Juan, appreciate the extensive heritage of Sitio Histórico de San Juan, and enjoy the sand and surf at Condado Beach.

For other places to visit, traveler tips, and other tourist information, you can read our San Juan trip maker app .

You can fly from Santo Domingo to San Juan in 3 hours. Alternatively, you can do a combination of shuttle and flight; or ride a ferry. August in San Juan sees daily highs of 37°C and lows of 30°C at night. Finish your sightseeing early on the 31st (Sat) to allow enough time to travel to Roseau.

Things to do in San Juan

Parks Nature Historic Sites

Side Trips

Bioluminescent Bay, El Yunque Rain Forest, Parque Nacional de las Cavernas del Rio Camuy
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Condado Beach ©
Condado Beach

4
nights
Roseau, Dominica

Roseau ©
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
You've added The Carib Territory, Valley of Desolation, Victoria Falls, and other attractions to your itinerary. Go for a jaunt from Roseau to Morne Trois Pitons National Park to see Emerald Pool Nature Trail about 40 minutes away. It doesn't end there: admire the sheer force of Trafalgar Falls and hike along Titou Gorge.

To see traveler tips, other places to visit, and other tourist information, use the Roseau road trip planning tool .

You can fly from San Juan to Roseau in 5 hours. Finish up your sightseeing early on the 4th (Wed) so you can travel to Bridgetown.

Things to do in Roseau

Parks Nature Wildlife

Side Trips

Morne Trois Pitons National Park, Victoria Falls, Scott's Head Pinnacles, The Carib Territory
Highlights from your plan
Trafalgar Falls ©
Trafalgar Falls
Boiling Lake ©
Boiling Lake
Emerald Pool Nature Trail ©
Emerald Pool Nature Trail

4
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Your list of things to see and do now includes Crane Beach, Bathsheba Beach, Dover Beach, and other attractions. The adventure continues: enjoy the sand and surf at Carlisle Bay, take a leisurely stroll along South Coast Boardwalk, and brush up on your knowledge of spirits at Mount Gay Visitor Centre.

Plan a Bridgetown trip in moments using our itinerary builder.

Traveling by flight from Roseau to Bridgetown takes 5 hours. Alternatively, you can do a combination of ferry and flight. Expect a daytime high around 36°C in September, and nighttime lows around 30°C. Wrap up your sightseeing on the 8th (Sun) early enough to travel to Port of Spain.

Things to do in Bridgetown

Parks Beaches Outdoors

Side Trips

Saint Joseph Parish, Saint Philip Parish, Saint George Parish, Dover Beach, South Coast Boardwalk
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Bottom Bay ©
Bottom Bay
Andromeda Botanic Gardens ©
Andromeda Botanic Gardens

4
nights
Port of Spain, Trinidad and Tobago

Port of Spain ©
Port of Spain, the country's capital, sits between the sea and a scenic green mountain range, and acts as a gateway for eclectic adventures on land and sea.
Your day-by-day itinerary now includes National Museum and Art Gallery as well as La Brea Pitch Lake. There's much more to do: identify plant and animal life at Asa Wright Nature Centre, walk around Queen's Park Savannah, admire the natural beauty at Royal Botanic Gardens, and take in the history at Mount St. Benedict Monastery.

To find other places to visit, traveler tips, and more tourist information, refer to the Port of Spain trip site .

Traveling by flight from Bridgetown to Port of Spain takes 4 hours. In September, plan for daily highs up to 39°C, and evening lows to 28°C. On the 12th (Thu), wrap the sightseeing up by early afternoon so you can travel to Willemstad.

Things to do in Port of Spain

Parks Wildlife Beaches

Side Trip

Trinidad
Highlights from your plan
Asa Wright Nature Centre ©
Asa Wright Nature Centre
Queen's Park Savannah ©
Queen's Park Savannah
Maracas Beach
Maracas Beach

4
nights
Willemstad, Curacao

Willemstad ©
Willemstad is the capital city of Curaçao, an island in the southern Caribbean Sea that forms a constituent country of the Kingdom of the Netherlands. Your list of things to see and do now includes Mikve Israel-Emanuel Synagogue, Riffort Village, Shete Boka Park, and other attractions. There's much more to do: snap pictures at Queen Emma Pontoon Bridge, relax in the rural setting at The Aloe Vera Plantation, Home of Curaloe, and explore the activities along Kleine Knip.

Quickly create a custom-made itinerary for Willemstad using our trip planner.

Traveling by flight from Port of Spain to Willemstad takes 5.5 hours. Traveling from Port of Spain in September, Willemstad is a bit warmer at night with lows of 32°C. Cap off your sightseeing on the 16th (Mon) early enough to travel to Oranjestad.

Things to do in Willemstad

Parks Nature Beaches

Side Trips

Cas Abao Beach, Mount Christoffel
Highlights from your plan
Shete Boka Park ©
Shete Boka Park
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Cas Abao Beach ©
Cas Abao Beach

4
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
You've added Donkey Sanctuary Aruba, Aruba Ostrich Farm, Ayo and Casibari Rock Formations, and other attractions to your itinerary. Spend the 20th (Fri) exploring nature at Arikok National Park. The adventure continues: enjoy the sand and surf at Eagle Beach, visit a coastal fixture at California Lighthouse, and stroll through Palm Beach.

To see traveler tips, ratings, where to stay, and more tourist information, read Oranjestad vacation planner.

Do a combination of bus and flight from Willemstad to Oranjestad in 2 hours. September in Oranjestad sees daily highs of 39°C and lows of 32°C at night. Finish up your sightseeing early on the 20th (Fri) so you can travel back home.

Things to do in Oranjestad

Parks Beaches Nature

Side Trips

Santa Cruz, Palm - Eagle Beach, Noord, Ayo and Casibari Rock Formations
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Arikok National Park ©
Arikok National Park

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