37 days in Caribbean Itinerary

37 days in Caribbean Itinerary

Created using Inspirock Caribbean planner

Plan created by another user.Make it yours

Route & dates

Start: Cluj-Napoca, Romania
Fly:  18 h
1
Bridgetown, Barbados
— 3 nights
Fly:  4 h
2
Port of Spain, Trinidad and Tobago
— 2 nights
Fly:  4 h 30 min
3
Roseau, Dominica
— 3 nights
Fly:  5 h
4
San Juan, Puerto Rico
— 3 nights
Fly:  3 h
5
Santo Domingo, Dominican Republic
— 3 nights
Fly:  2 h 15 min
6
Noord, Aruba
— 1 night
Fly:  2 h
7
Willemstad, Curacao
— 2 nights
Fly:  2 h
8
Oranjestad, Aruba
— 3 nights
Fly:  7 h
9
Montego Bay, Jamaica
— 2 nights
Fly:  7 h 30 min
10
Santiago de Cuba, Cuba
— 1 day
Drive:  9 h
11
Trinidad, Cuba
— 1 day
Drive:  1 h 30 min
12
Cienfuegos, Cuba
— 2 nights
Drive:  3 h
13
Havana, Cuba
— 3 nights
Fly:  2 h
14
Nassau, Bahamas
— 5 nights
Fly:  18 h
End: Cluj-Napoca, Romania

3
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Your day-by-day itinerary now includes Barbados Museum & Historical Society, Flower Forest, Parliament Buildings, and other attractions you added. There's lots more to do: Head underground at Harrison's Cave., sample the fine beverages at Mount Gay Visitor Centre, and admire the natural beauty at Welchman Hall Gully.

To find other places to visit, reviews, where to stay, and tourist information, read our Bridgetown road trip site.

Cluj-Napoca, Romania to Bridgetown is an approximately 18-hour flight. The time zone changes from Eastern European Standard Time to Atlantic Standard Time, which is usually a -6 hour difference. Traveling from Cluj-Napoca in July, expect much hotter with lows of 30°C in Bridgetown. Finish your sightseeing early on the 4th (Sat) so you can travel to Port of Spain.

Things to do in Bridgetown

Parks Historic Sites Nature

Side Trips

Saint Thomas Parish, Saint George Parish, Bathsheba, George Washington House, Sunbury Plantation House
Find places to stay Jul 1 — 4:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Andromeda Botanic Gardens ©
Andromeda Botanic Gardens

2
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 Mount St. Benedict Monastery as well as Caroni Swamp. On the 5th (Sun), take in nature's colorful creations at Royal Botanic Gardens, stroll through Asa Wright Nature Centre, and then stroll around Queen's Park Savannah. On the next day, learn about wildlife with up-close encounters at Emperor Valley Zoo, thencontemplate the waterfront views at Caroni Swamp, and then take in the architecture and atmosphere at Mount St. Benedict Monastery.

To see more things to do, ratings, reviews, and other tourist information, read our Port of Spain travel planner.

Traveling by flight from Bridgetown to Port of Spain takes 4 hours. In July in Port of Spain, expect temperatures between 38°C during the day and 28°C at night. Cap off your sightseeing on the 6th (Mon) early enough to travel to Roseau.

Things to do in Port of Spain

Parks Wildlife Nature

Side Trip

Trinidad
Find places to stay Jul 4 — 6:
Highlights from your plan
Asa Wright Nature Centre ©
Asa Wright Nature Centre
Queen's Park Savannah ©
Queen's Park Savannah
Mount St. Benedict Monastery ©
Mount St. Benedict Monastery

3
nights
Roseau, Dominica

Roseau ©
The capital city, Roseau maintains a small scale, but possesses a convincing Caribbean charm in its architecture, cuisine, and culture.
Your list of things to see and do now includes Fort Shirley, Papillote Tropical Gardens, Champagne Beach, and other attractions. Next up on the itinerary: admire the sheer force of Trafalgar Falls and take in nature's colorful creations at Dominica Botanic Gardens.

To see more things to do, reviews, photos, and other tourist information, you can read our Roseau online vacation planner.

Getting from Port of Spain to Roseau by flight takes about 7 hours. Cap off your sightseeing on the 9th (Thu) early enough to travel to San Juan.

Things to do in Roseau

Parks Nature Outdoors

Side Trips

Morne Trois Pitons National Park, Fort Shirley
Find places to stay Jul 6 — 9:
Highlights from your plan
Boiling Lake ©
Boiling Lake
Trafalgar Falls ©
Trafalgar Falls
Valley of Desolation ©
Valley of Desolation

3
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 Luquillo Beach, Condado Beach and Parque Nacional de las Cavernas del Rio Camuy. Go for a jaunt from San Juan to El Yunque National Forest to see El Yunque Rain Forest about 1h 10 min away. And it doesn't end there: steep yourself in history at Old San Juan, take in the architecture and atmosphere at Catedral Metropolitana Basilica de San Juan Bautista, and appreciate the extensive heritage of Sitio Histórico de San Juan.

To see maps, reviews, and other tourist information, read San Juan trip itinerary maker.

Traveling by flight from Roseau to San Juan takes 5 hours. In July, daily temperatures in San Juan can reach 37°C, while at night they dip to 30°C. Wrap up your sightseeing on the 12th (Sun) to allow time to travel to Santo Domingo.

Things to do in San Juan

Parks Nature Beaches

Side Trips

El Yunque Rain Forest, Luquillo Beach, Parque Nacional de las Cavernas del Rio Camuy
Find places to stay Jul 9 — 12:
Highlights from your plan
El Yunque Rain Forest ©
El Yunque Rain Forest
Old San Juan ©
Old San Juan
Luquillo Beach ©
Luquillo Beach

3
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 list of things to see and do now includes National Pantheon (Pantheon Nacional), Basilica Cathedral of Santa Maria la Menor, Fortaleza Ozama, and other attractions. There's still lots to do: examine the collection at Columbus Lighthouse (Faro A Colon), explore the historical opulence of Alcazar de Colon, make a trip to Zona Colonial, and explore the ancient world of Monasterio de San Francisco.

To find more things to do, traveler tips, where to stay, and tourist information, read Santo Domingo day trip app.

Fly from San Juan to Santo Domingo in 3 hours. Alternatively, you can ride a ferry. Cap off your sightseeing on the 15th (Wed) early enough to travel to Noord.

Things to do in Santo Domingo

Historic Sites Museums Parks
Find places to stay Jul 12 — 15:
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Fortaleza Ozama ©
Fortaleza Ozama
Columbus Lighthouse (Faro A Colon) ©
Columbus Lighthouse (Faro A Colon)

1
night
Noord, Aruba

Noord ©
Noord itineraries allow for cultural exploration and adventure tourism, as the most populous and visited town on the island.
Natural Pool has been added to your itinerary. Start off your visit on the 16th (Thu): take in the architecture and atmosphere at St. Ann's Catholic Church, explore the striking landscape at Natural Pool, stop by Vadavas, thenkick back and relax at Arashi Beach, and finally enjoy the sea views from California Lighthouse.

To find maps, traveler tips, and tourist information, read Noord attractions planner.

You can fly from Santo Domingo to Noord in 5 hours. In July, daily temperatures in Noord can reach 38°C, while at night they dip to 31°C. Wrap up your sightseeing on the 16th (Thu) to allow time to travel to Willemstad.

Things to do in Noord

Parks Beaches Nature

Side Trip

Arashi Beach
Find places to stay Jul 15 — 16:
Highlights from your plan
Arashi Beach ©
Arashi Beach
California Lighthouse ©
California Lighthouse
Natural Pool ©
Natural Pool

2
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 Cas Abao Beach, Mikve Israel-Emanuel Synagogue, Maritime Museum Curacao, and other attractions you added. Start off your visit on the 17th (Fri): take an in-depth tour of Maritime Museum Curacao, examine the collection at Kura Hulanda Museum, thensnap pictures at Queen Emma Pontoon Bridge, thentake a stroll through Riffort Village, and finally take a leisurely stroll along Handelskade. Here are some ideas for day two: Head underground at Hato Caves, examine the collection at Mikve Israel-Emanuel Synagogue, and then enjoy the sand and surf at Cas Abao Beach.

To find ratings, reviews, maps, and more tourist information, read our Willemstad trip maker website.

Traveling by flight from Noord to Willemstad takes 4.5 hours. Expect a daytime high around 38°C in July, and nighttime lows around 30°C. Wrap up your sightseeing on the 18th (Sat) early enough to travel to Oranjestad.

Things to do in Willemstad

Parks Beaches Museums

Side Trip

Cas Abao Beach
Find places to stay Jul 16 — 18:
Highlights from your plan
Cas Abao Beach ©
Cas Abao Beach
Queen Emma Pontoon Bridge ©
Queen Emma Pontoon Bridge
Handelskade ©
Handelskade

3
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 National Archaeological Museum Aruba, Wilhelmina Park, Ayo and Casibari Rock Formations, and other attractions to your itinerary. Change things up with a short trip to Baby Beach in San Nicolas (about 32 minutes away). And it doesn't end there: enjoy the sand and surf at Eagle Beach, tour the pleasant surroundings at Palm Beach, visit a coastal fixture at California Lighthouse, and steep yourself in history at Bushiribana Gold Mill Ruins.

To see reviews, photos, more things to do, and other tourist information, you can read our Oranjestad tour itinerary planning tool.

You can fly from Willemstad to Oranjestad in 4.5 hours. In July, daytime highs in Oranjestad are 38°C, while nighttime lows are 31°C. Finish your sightseeing early on the 21st (Tue) so you can travel to Montego Bay.

Things to do in Oranjestad

Parks Nature Beaches

Side Trips

Palm - Eagle Beach, Baby Beach, Ayo and Casibari Rock Formations, Arikok National Park, California Lighthouse
Find places to stay Jul 18 — 21:
Highlights from your plan
Eagle Beach ©
Eagle Beach
Palm Beach ©
Palm Beach
Arikok National Park ©
Arikok National Park

2
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 list of things to see and do now includes Green Grotto Caves, Martha Brae Rafting Village, Dunn's River Falls and Park, and other attractions. There's more to do: steep yourself in history at Rose Hall Great House and kick back and relax at Doctor's Cave Beach.

To see where to stay, photos, and more tourist information, refer to the Montego Bay online driving holiday planner.

You can fly from Oranjestad to Montego Bay in 9.5 hours. You'll gain 1 hour traveling from Oranjestad to Montego Bay due to the time zone difference. In July, daily temperatures in Montego Bay can reach 39°C, while at night they dip to 29°C. Finish up your sightseeing early on the 24th (Fri) so you can travel to Santiago de Cuba.

Things to do in Montego Bay

Parks Nature Beaches

Side Trips

Negril, Green Grotto Caves, Dunn's River Falls and Park, YS Falls
Find places to stay Jul 21 — 24:
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Seven Mile Beach ©
Seven Mile Beach
YS Falls ©
YS Falls

1
day
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.
Kick off your visit on the 25th (Sat): take an in-depth tour of Casa de Diego Velazquez, step into the grandiose world of Castillo de San Pedro de la Roca, stroll around Cespedes Park, thenexplore the different monuments and memorials at Cementerio Santa Ifigenia, thenmake a trip to Antonio Maceo Revolution Square, and finally steep yourself in history at Moncada Barracks.

To see traveler tips, photos, and more tourist information, refer to the Santiago de Cuba online road trip planner.

Getting from Montego Bay to Santiago de Cuba by flight takes about 8 hours. Expect a daytime high around 36°C in July, and nighttime lows around 28°C. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Trinidad.

Things to do in Santiago de Cuba

Historic Sites Parks Museums
Find places to stay Jul 24 — 25:
Highlights from your plan
Moncada Barracks ©
Moncada Barracks
Cementerio Santa Ifigenia ©
Cementerio Santa Ifigenia
Casa de Diego Velazquez ©
Casa de Diego Velazquez

1
day
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.
Your day-by-day itinerary now includes Salto del Caburni as well as Museo de Historia Municipal. Kick off your visit on the 26th (Sun): see the interesting displays at Museo de Historia Municipal, examine the collection at Romance Museum, thendon't miss a visit to Plaza Mayor, thensteep yourself in history at Valle de los Ingenios, and finally admire the sheer force of Salto del Caburni.

For ratings, photos, where to stay, and tourist information, read Trinidad road trip planner.

Drive from Santiago de Cuba to Trinidad in 9 hours. Alternatively, you can do a combination of train and bus; or take a bus. In July in Trinidad, expect temperatures between 39°C during the day and 28°C at night. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Cienfuegos.

Things to do in Trinidad

Parks Wildlife Museums
Find places to stay Jul 25 — 26:
Highlights from your plan
Valle de los Ingenios ©
Valle de los Ingenios
Plaza Mayor ©
Plaza Mayor
Museo de Historia Municipal ©
Museo de Historia Municipal

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 as well as Jardin Botanico de Cienfuegos. Start off your visit on the 27th (Mon): take a stroll through Punta Gorda, admire the landmark architecture of Palacio de Valle, thendon't miss a visit to Parque Jose Marti, and finally admire the sheer force of El Nicho Waterfalls. On the 28th (Tue), you'll have a packed day of sightseeing: pause for some photo ops at Che Guevara Mausoleum, appreciate the history behind Monumento a la Toma del Tren Blindado, thenexplore the historical opulence of Jagua Castle, and finally admire the natural beauty at Jardin Botanico de Cienfuegos.

For ratings, traveler tips, more things to do, and tourist information, read Cienfuegos trip tool.

Traveling by car from Trinidad to Cienfuegos takes 1.5 hours. Alternatively, you can take a shuttle; or take a bus. In July, daytime highs in Cienfuegos are 39°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 28th (Tue) to allow time to drive to Havana.

Things to do in Cienfuegos

Parks Historic Sites Nature

Side Trip

Santa Clara
Find places to stay Jul 26 — 28:
Highlights from your plan
El Nicho Waterfalls ©
El Nicho Waterfalls
Che Guevara Mausoleum ©
Che Guevara Mausoleum
Parque Jose Marti ©
Parque Jose Marti

3
nights
Havana, Cuba

Havana ©
Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
You've added Plaza de San Francisco, Church and Convent of St. Francis of Asisi, Central Park, and other attractions to your itinerary. And it doesn't end there: get to know the fascinating history of Malecón of Havana, take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), make a trip to Plaza de Armas, and admire the landmark architecture of Havana Cathedral.

To find reviews, photos, traveler tips, and other tourist information, go to the Havana trip itinerary site.

Drive from Cienfuegos to Havana in 3 hours. Alternatively, you can take a shuttle; or take a bus. In July, daily temperatures in Havana can reach 38°C, while at night they dip to 26°C. Wrap up your sightseeing on the 31st (Fri) early enough to travel to Nassau.

Things to do in Havana

Historic Sites Museums Parks
Find places to stay Jul 28 — 31:
Highlights from your plan
Malecón of Havana ©
Malecón of Havana
Fortaleza de San Carlos de la Cabana ©
Fortaleza de San Carlos de la Cabana

5
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 The National Art Gallery of The Bahamas, Christ Church Cathedral, Clifton Heritage National Park, and other attractions to your itinerary. Next up on the itinerary: enjoy the sand and surf at Cable Beach, contemplate the long history of Queen's Staircase, try your luck at Atlantis Casino, and browse the eclectic array of goods at Straw Market.

For traveler tips, photos, more things to do, and more tourist information, use the Nassau online route planner.

Traveling by flight from Havana to Nassau takes 4.5 hours. Traveling from Havana in July, Nassau is a bit warmer at night with lows of 30°C. Wrap up your sightseeing on the 5th (Wed) early enough to travel back home.

Things to do in Nassau

Parks Beaches Outdoors

Side Trip

Paradise Island
Find places to stay Jul 31 — Aug 5:
Highlights from your plan
Cable Beach ©
Cable Beach
Marine Habitat at Atlantis ©
Marine Habitat at Atlantis
Cabbage Beach ©
Cabbage Beach

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