54 days in Caribbean Itinerary

54 days in Caribbean Itinerary

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Route & dates

54 days in Caribbean Itinerary

Start: Cluj-Napoca, Romania
Fly:  17​h 15​min
1
Oranjestad, Aruba
— 3 nights
Fly + bus:  2​h
2
Willemstad, Curacao
— 5 nights
Fly + bus:  5​h 30​min
3
Port of Spain, Trinidad and Tobago
— 4 nights
Fly:  4​h
4
Bridgetown, Barbados
— 4 nights
Fly:  4​h
5
Soufriere, St. Lucia
— 4 nights
Fly:  6​h 30​min
6
Road Town, British Virgin Islands
— 2 nights
taxi + Fly:  1​h
7
St. Croix, U.S. Virgin Islands
— 3 nights
Fly:  1​h
8
Charlotte Amalie, U.S. Virgin Islands
— 2 nights
Fly + taxi:  30​min
9
Virgin Gorda, British Virgin Islands
— 2 nights
Fly:  2​h 30​min
10
San Juan, Puerto Rico
— 3 nights
Fly:  3​h
11
Santo Domingo, Dominican Republic
— 5 nights
Fly + bus:  9​h
12
Ocho Rios, Jamaica
— 1 day
bus:  1​h 30​min
13
Montego Bay, Jamaica
— 3 nights
Fly:  5​h 30​min
14
Havana, Cuba
— 2 nights
Drive:  4​h 30​min
15
Trinidad, Cuba
— 3 nights
+3
bus + train + taxi + Fly:  10​h 30​min
16
Nassau, Bahamas
— 4 nights
Fly:  18​h
End: Cluj-Napoca, Romania

3
nights
Oranjestad, Aruba

Oranjestad ©
When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
Your day-by-day itinerary now includes Ayo and Casibari Rock Formations, Boca Catalina and Natural Pool. There's much more to do: enjoy the sand and surf at Eagle Beach, look for all kinds of wild species at The Butterfly Farm, steep yourself in history at Bushiribana Gold Mill Ruins, and tour the pleasant surroundings at Palm Beach.

To find ratings, reviews, traveler tips, and tourist information, use the Oranjestad itinerary planner .

Cluj-Napoca, Romania to Oranjestad is an approximately 17.5-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. You'll gain 6 hours traveling from Cluj-Napoca to Oranjestad due to the time zone difference. When traveling from Cluj-Napoca in September, plan for a bit warmer days in Oranjestad, with highs around 39°C, while nights are warmer with lows around 32°C. Finish your sightseeing early on the 5th (Thu) so you can travel to Willemstad.

Things to do in Oranjestad

Parks Outdoors Beaches

Side Trips

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

5
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 day-by-day itinerary now includes Playa Porto Marie, Shete Boka Park, Blue Bay Beach, and other attractions you added. Next up on the itinerary: take in the views from Queen Emma Pontoon Bridge and tour the pleasant surroundings at Cas Abao Beach.

Plan a trip to Willemstad easily and quickly by telling Inspirock to suggest an itinerary.

Do a combination of flight and bus from Oranjestad to Willemstad in 2 hours. In September, plan for daily highs up to 38°C, and evening lows to 32°C. Finish your sightseeing early on the 10th (Tue) to allow enough time to travel to Port of Spain.

Things to do in Willemstad

Parks Outdoors Beaches

Side Trip

Curacao
Highlights from your plan
Cas Abao Beach ©
Cas Abao Beach
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Playa Porto Marie ©
Playa Porto Marie

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 La Brea Pitch Lake, San Fernando Hill and Queen's Hall. The adventure continues: identify plant and animal life at Asa Wright Nature Centre, explore the world behind art at National Museum and Art Gallery, take in the architecture and atmosphere at Mount St. Benedict Monastery, and contemplate the waterfront views at Caroni Swamp.

For photos, traveler tips, reviews, and tourist information, read our Port of Spain journey planner .

You can fly from Willemstad to Port of Spain in 5.5 hours. Traveling from Willemstad in September, Port of Spain is a bit cooler at night with lows of 28°C. Wrap up your sightseeing on the 14th (Sat) early enough to travel to Bridgetown.

Things to do in Port of Spain

Parks Wildlife Nature

Side Trips

Trinidad, San Fernando Hill
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
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Your day-by-day itinerary now includes Atlantis Submarines Barbados, Bathsheba Beach, Orchid World & Tropical Flower Garden, and other attractions you added. Take a break from Bridgetown with a short trip to Bottom Bay in Saint Philip Parish, about 38 minutes away. There's still lots to do: admire the natural beauty at Hunte's Gardens, enjoy the sand and surf at Dover Beach, tour the pleasant surroundings at Carlisle Bay, and sample the fine beverages at Mount Gay Visitor Centre.

To see where to stay, maps, traveler tips, and other tourist information, read our Bridgetown trip planner .

Fly from Port of Spain to Bridgetown in 4 hours. Expect slightly colder weather when traveling from Port of Spain in September: highs in Bridgetown hover around 36°C, while lows dip to 30°C. Finish up your sightseeing early on the 18th (Wed) so you can travel to Soufriere.

Things to do in Bridgetown

Parks Outdoors Beaches

Side Trips

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

4
nights
Soufriere, St. Lucia

Soufriere ©
Home to some of Saint Lucia's landmark buildings and natural features, Soufriere provides travelers with an engaging and direct route into the center of island life.
Your list of things to see and do now includes Marigot Bay, Rodney Bay, La Soufriere Drive-In Volcano, and other attractions. Next up on the itinerary: explore the wealth of natural beauty at Pigeon Island National Park, admire the natural beauty at Diamond Falls Botanical Gardens, hike along Tet Paul Nature Trail, and take your sightseeing to a higher altitude at Gros Piton.

For where to stay, other places to visit, traveler tips, and other tourist information, go to the Soufriere vacation planner.

You can fly from Bridgetown to Soufriere in 4 hours. September in Soufriere sees daily highs of 36°C and lows of 30°C at night. Wrap up your sightseeing on the 22nd (Sun) to allow time to travel to Road Town.

Things to do in Soufriere

Parks Nature Trails

Side Trips

St. Lucia, Rodney Bay
Highlights from your plan
Diamond Falls Botanical Gardens ©
Diamond Falls Botanical Gardens
Pigeon Island National Park ©
Pigeon Island National Park
Rodney Bay ©
Rodney Bay

2
nights
Road Town, British Virgin Islands

Road Town ©
Road Town, located on Tortola, is the capital of the British Virgin Islands. On the 23rd (Mon), identify plant and animal life at Dolphin Discovery Tortola, explore the gorgeous colors at Smuggler's Cove, and then explore the wealth of natural beauty at Sage Mountain National Park. Keep things going the next day: contemplate the long history of Callwood Distillery, kick back and relax at Cane Garden Bay, and then kick back and relax at Brewers Bay.

To see reviews, where to stay, other places to visit, and tourist information, refer to the Road Town online travel route planner .

Getting from Soufriere to Road Town by flight takes about 6.5 hours. September in Road Town sees daily highs of 37°C and lows of 31°C at night. Finish your sightseeing early on the 24th (Tue) to allow enough time to travel to St. Croix.

Things to do in Road Town

Parks Nature Outdoors

Side Trip

Tortola
Highlights from your plan
Cane Garden Bay ©
Cane Garden Bay
Sage Mountain National Park ©
Sage Mountain National Park
Smuggler's Cove ©
Smuggler's Cove

3
nights
St. Croix, U.S. Virgin Islands

St. Croix ©
The largest of the U.S.
Your day-by-day itinerary now includes Salt River Bay National Historical Park and Ecological Preserve, St. George Village Botanical Garden and Carambola Tide Pools. There's lots more to do: explore the gorgeous colors at Buck Island Reef National Monument, take in the waterfront at Frederiksted Pier, appreciate the history behind Point Udall, and stroll through Rhythms at Rainbow Beach.

To see ratings, reviews, more things to do, and more tourist information, read our St. Croix online attractions planner .

Getting from Road Town to St. Croix by combination of taxi and flight takes about an hour. Other options: do a combination of ferry and flight; or ride a ferry. Expect a daytime high around 37°C in September, and nighttime lows around 29°C. Cap off your sightseeing on the 27th (Fri) early enough to travel to Charlotte Amalie.

Things to do in St. Croix

Parks Historic Sites Outdoors
Highlights from your plan
Buck Island Reef National Monument ©
Fort Christiansvaern ©
Fort Christiansvaern
Point Udall ©
Point Udall

2
nights
Charlotte Amalie, U.S. Virgin Islands

Charlotte Amalie ©
One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Your day-by-day itinerary now includes Annaberg Sugar Plantation, 99 Steps and Drake's Seat. On the 28th (Sat), steep yourself in history at Annaberg Sugar Plantation and then kick back and relax at Trunk Bay. Get ready for a full day of sightseeing on the next day: kick back and relax at Magens Bay, take in the dramatic natural features at Drake's Seat, and then don't miss a visit to 99 Steps.

To find where to stay, more things to do, other places to visit, and more tourist information, refer to the Charlotte Amalie online attractions planner .

Traveling by flight from St. Croix to Charlotte Amalie takes an hour. Alternatively, you can ride a ferry. In September, daily temperatures in Charlotte Amalie can reach 37°C, while at night they dip to 30°C. Finish your sightseeing early on the 29th (Sun) to allow enough time to travel to Virgin Gorda.

Things to do in Charlotte Amalie

Parks Outdoors Beaches

Side Trips

Virgin Islands National Park, Drake's Seat, Magens Bay
Highlights from your plan
Trunk Bay ©
Trunk Bay
Magens Bay ©
Magens Bay
Annaberg Sugar Plantation ©
Annaberg Sugar Plantation

2
nights
Virgin Gorda, British Virgin Islands

Virgin Gorda ©
Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.
Start off your visit on the 30th (Mon): explore the striking landscape of Devil's Bay National Park and then contemplate the waterfront views at Savannah Bay. Get ready for a full day of sightseeing on the next day: discover the riches below the earth's surface at Copper Mine Point, then take in the dramatic natural features at The Baths, and then stroll through Spring Bay.

To find more things to do, traveler tips, ratings, and more tourist information, go to the Virgin Gorda trip planner.

Virgin Gorda is very close to Charlotte Amalie. September in Virgin Gorda sees daily highs of 37°C and lows of 31°C at night. Finish your sightseeing early on the 1st (Tue) to allow enough time to travel to San Juan.

Things to do in Virgin Gorda

Parks Nature Outdoors
Highlights from your plan
Spring Bay ©
Spring Bay
The Baths ©
The Baths
Devil's Bay National Park ©
Devil's Bay National Park

3
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
You've added Fortin de San Geronimo del Boqueron, Catedral Metropolitana Basilica de San Juan Bautista, Museo de Arte de Puerto Rico, and other attractions to your itinerary. 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. There's more to do: get to know the fascinating history of Old San Juan and steep yourself in history at Sitio Histórico de San Juan.

To plan San Juan vacation without wasting time, ask Inspirock to design an itinerary.

You can fly from Virgin Gorda to San Juan in 2.5 hours. Alternatively, you can do a combination of ferry and flight. In October in San Juan, expect temperatures between 38°C during the day and 30°C at night. Finish up your sightseeing early on the 4th (Fri) so you can travel to Santo Domingo.

Things to do in San Juan

Historic Sites Nature Wildlife

Side Trip

El Yunque Rain Forest
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

5
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 Mercado Modelo, Parque Colon, National Pantheon (Pantheon Nacional), and other attractions you added. There's much more to do: contemplate the long history of Alcazar de Colon, see the interesting displays at Museum of the Royal Houses, get up close and personal with brilliant marine life at National Aquarium, and take in the spiritual surroundings of Catedral Primada de America.

To see photos, maps, more things to do, and more tourist information, read our Santo Domingo attractions planning website .

Traveling by flight from San Juan to Santo Domingo takes 3 hours. Alternatively, you can do a combination of flight and shuttle; or ride a ferry. Wrap up your sightseeing on the 9th (Wed) early enough to travel to Ocho Rios.

Things to do in Santo Domingo

Parks Historic Sites Nature
Highlights from your plan
The 3 Eyes National Park ©
The 3 Eyes National Park
Alcazar de Colon ©
Alcazar de Colon
Zona Colonial ©
Zona Colonial

1
day
Ocho Rios, Jamaica

Ocho Rios ©
A trip to Ocho Rios, the tourist hub of Saint Ann Parish, offers travelers a staggering amount of activities and cultural attractions.
Fern Gully has been added to your itinerary. Kick off your visit on the 10th (Thu): admire the sheer force of Dunn's River Falls and Park, stroll around Konoko Falls, and then hike along Fern Gully.

To see more things to do, other places to visit, reviews, and other tourist information, read our Ocho Rios travel route planning app .

You can do a combination of flight and bus from Santo Domingo to Ocho Rios in 9 hours. The time zone difference moving from Atlantic Standard Time to Eastern Standard Time is minus 1 hour. In October in Ocho Rios, expect temperatures between 38°C during the day and 30°C at night. Finish your sightseeing early on the 10th (Thu) so you can take a bus to Montego Bay.

Things to do in Ocho Rios

Parks Nature Trails
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Fern Gully ©
Fern Gully
Konoko Falls ©
Konoko Falls

3
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, Negril Cliffs and Bloody Bay. Step out of Montego Bay to go to Pennycooke and see Original Mayfield Falls Jamaica, which is approximately 1h 20 min away. There's still lots to do: contemplate the long history of Rose Hall Great House, contemplate the waterfront views at Martha Brae Rafting Village, and kick back and relax at Doctor's Cave Beach.

For reviews, traveler tips, and tourist information, refer to the Montego Bay trip itinerary planner .

Take a bus from Ocho Rios to Montego Bay in 1.5 hours. Alternatively, you can drive. In October, plan for daily highs up to 38°C, and evening lows to 28°C. Finish your sightseeing early on the 13th (Sun) to allow enough time to travel to Havana.

Things to do in Montego Bay

Parks Nature Outdoors

Side Trips

Negril, YS Falls, Original Mayfield Falls Jamaica
Highlights from your plan
Doctor's Cave Beach ©
Doctor's Cave Beach
YS Falls ©
YS Falls
Original Mayfield Falls Jamaica
Original Mayfield Falls Jamaica

2
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Havana is known for historic sites, museums, nightlife, beaches, and classes. Your plan includes some of its best attractions: get to know the fascinating history of El Malecon, contemplate the long history of Castillo de la Real Fuerza, don't miss a visit to Plaza de la Catedral, and get engrossed in the history at Museum of the Revolution (Museo de la Revolucion).

To find ratings, reviews, traveler tips, and more tourist information, read our Havana travel itinerary planner .

Traveling by flight from Montego Bay to Havana takes 5.5 hours. Traveling from Montego Bay in October, expect a bit cooler with lows of 24°C in Havana. Finish up your sightseeing early on the 16th (Wed) so you can go by car to Trinidad.

Things to do in Havana

Historic Sites Museums
Highlights from your plan
Old Havana ©
Old Havana
Malecón of Havana ©
Malecón of Havana
Plaza de la Catedral ©
Plaza de la Catedral

3
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.
Kick off your visit on the 17th (Thu): pause for some photo ops at Che Guevara Mausoleum, kick back and relax at Ancon Beach, and then explore and take pictures at Valle de los Ingenios. On the next day, take in the dramatic scenery at Salto del Caburni, then take in the dramatic scenery at El Nicho Waterfalls, and then make a trip to Plaza Mayor.

To find traveler tips, other places to visit, reviews, and tourist information, you can read our Trinidad trip itinerary maker app .

Getting from Havana to Trinidad by car takes about 4.5 hours. Other options: take a shuttle; or take a bus. October in Trinidad sees daily highs of 36°C and lows of 26°C at night. You will leave for Nassau on the 19th (Sat).

Things to do in Trinidad

Parks Nature Historic Sites

Side Trips

Che Guevara Mausoleum, El Nicho Waterfalls
Highlights from your plan
Ancon Beach ©
Ancon Beach
Plaza Mayor ©
Plaza Mayor
Che Guevara Mausoleum ©
Che Guevara Mausoleum

4
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.
Your day-by-day itinerary now includes Clifton Heritage National Park, Versailles Gardens and French Cloister and Ardastra Gardens, Zoo and Conservation Center. Next up on the itinerary: kick back and relax at Cable Beach, try to win big at Atlantis Casino, observe the fascinating underwater world at Marine Habitat at Atlantis, and don't miss a visit to The Cloisters Nassau.

To see ratings, traveler tips, reviews, and tourist information, read our Nassau day trip site .

Traveling by combination of bus, train, and flight from Trinidad to Nassau takes 10.5 hours. October in Nassau sees daily highs of 36°C and lows of 28°C at night. Wrap up your sightseeing by early afternoon on the 23rd (Wed) to allow enough time to travel back home.

Things to do in Nassau

Parks Zoos & Aquariums Nature

Side Trip

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

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