19 days in Caribbean Itinerary

19 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

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Route & dates

19 days in Caribbean Itinerary

Start: Mumbai, India
Fly:  25​h
1
Havana, Cuba
— 2 nights
Fly:  5​h 30​min
2
Montego Bay, Jamaica
— 3 nights
Fly:  7​h
3
Cap-Haitien, Haiti
— 2 nights
Drive:  5​h 30​min
4
Santo Domingo, Dominican Republic
— 2 nights
Fly:  3​h
5
San Juan, Puerto Rico
— 1 night
Fly:  10​h
6
Bridgetown, Barbados
— 2 nights
Fly:  4​h
7
Port of Spain, Trinidad and Tobago
— 3 nights
Fly:  26​h
End: Mumbai, India

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.
Kick off your visit on the 25th (Wed): make a trip to Old Havana, make a trip to Plaza de la Catedral, and then get to know the fascinating history of El Malecon. On the next day, appreciate the history behind Neptune Statue, don't miss a visit to El Capitolio, then don't miss a visit to Plaza de Armas, and finally don't miss a visit to Old Square (Plaza Vieja).

To find other places to visit, where to stay, reviews, and other tourist information, read our Havana route planning app .

Mumbai, India to Havana is an approximately 25-hour flight. You can also do a combination of flight and train. The time zone changes from India Standard Time to Cuba Standard Time, which is usually a -10 hour difference. In September in Havana, expect temperatures between 36°C during the day and 26°C at night. Wrap up your sightseeing on the 26th (Thu) to allow time to travel to Montego Bay.

Things to do in Havana

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

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.
On the 27th (Fri), steep yourself in history at Rose Hall Great House, then steep yourself in history at The Cage, and then enjoy the sand and surf at Seven Mile Beach. Get ready for a full day of sightseeing on the next day: admire the sheer force of Original Mayfield Falls Jamaica and then tour the pleasant surroundings at Doctor's Cave Beach.

To see other places to visit, where to stay, maps, and other tourist information, you can read our Montego Bay visit planner.

Fly from Havana to Montego Bay in 5.5 hours. In September in Montego Bay, expect temperatures between 38°C during the day and 29°C at night. You will have some time to spend on the 29th (Sun) before leaving for Cap-Haitien.

Things to do in Montego Bay

Parks Beaches Outdoors

Side Trips

Original Mayfield Falls Jamaica, Seven Mile Beach
Highlights from your plan
Seven Mile Beach ©
Seven Mile Beach
Rose Hall Great House ©
Rose Hall Great House
Original Mayfield Falls Jamaica
Original Mayfield Falls Jamaica

2
nights
Cap-Haitien, Haiti

Cap-Haitien ©
Haiti's second city, Cap-Haitien offers an atmosphere at odds with what you'll find in the capital.
Kick off your visit on the 30th (Mon): pause for some serene contemplation at Cathedrale Notre Dame de Cap Haitien, explore the historical opulence of Sans Souci Palace, then make a trip to Citadelle Laferrière, and finally contemplate the long history of National History Park - Citadel, Sans Souci, Ramiers. On the 1st (Tue), you'll have a packed day of sightseeing: appreciate the history behind Heros de Vertieres and then contemplate in the serene atmosphere at Cathedrale de Milot.

To see reviews, photos, maps, and other tourist information, read our Cap-Haitien holiday planning website .

You can fly from Montego Bay to Cap-Haitien in 7 hours. In September, daytime highs in Cap-Haitien are 36°C, while nighttime lows are 31°C. Wrap up your sightseeing by early afternoon on the 1st (Tue) to allow time for the car ride to Santo Domingo.

Things to do in Cap-Haitien

Historic Sites

Side Trips

Milot, National History Park - Citadel, Sans Souci, Ramiers
Highlights from your plan
Citadelle Laferrière ©
Citadelle Laferrière
Sans Souci Palace ©
Sans Souci Palace

2
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.
On the 2nd (Wed), steep yourself in history at Fortaleza Ozama and then make a trip to Zona Colonial. On the next day, appreciate the history behind Columbus Lighthouse (Faro A Colon), steep yourself in history at Palacio Consistorial, then contemplate in the serene atmosphere at Catedral Primada de America, then explore the historical opulence of Alcazar de Colon, and finally get up close and personal with brilliant marine life at National Aquarium.

Plan my day in Santo Domingo using traveler tips and tourist information provided by Inspirock.

Getting from Cap-Haitien to Santo Domingo by car takes about 5.5 hours. Other options: take a bus; or do a combination of bus and flight. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Wrap up your sightseeing on the 3rd (Thu) early enough to travel to San Juan.

Things to do in Santo Domingo

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

1
night
San Juan, Puerto Rico

Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Kick off your visit on the 4th (Fri): skim along the rocks with a canyoning and rapelling tour.

For traveler tips, reviews, more things to do, and more tourist information, read San Juan route builder app .

Traveling by flight from Santo Domingo to San Juan takes 3 hours. Alternatively, you can do a combination of shuttle and flight; or ride a ferry. Expect a daytime high around 38°C in October, and nighttime lows around 30°C. Wrap up your sightseeing by early afternoon on the 4th (Fri) to allow time for travel to Bridgetown.

Things to do in San Juan

Outdoors Tours
Highlights from your plan
Canyoning & Rappelling Tours

2
nights
Bridgetown, Barbados

Bridgetown ©
Bridgetown is the capital and largest city of Barbados. Get out of town with these interesting Bridgetown side-trips: Saint Philip Parish (Bottom Bay & Sunbury Plantation House). There's still lots to do: take in nature's colorful creations at Hunte's Gardens, sample the fine beverages at Mount Gay Visitor Centre, see the interesting displays at Barbados Concorde Experience, and stroll through Carlisle Bay.

To see reviews, where to stay, traveler tips, and tourist information, you can read our Bridgetown trip builder website .

Fly from San Juan to Bridgetown in 10 hours. Alternatively, you can do a combination of car and flight. In October, daily temperatures in Bridgetown can reach 36°C, while at night they dip to 29°C. Wrap up your sightseeing by early afternoon on the 7th (Mon) to allow time for travel to Port of Spain.

Things to do in Bridgetown

Outdoors Parks Beaches

Side Trips

Saint Philip Parish, South Coast Boardwalk, Hunte's Gardens, Dover Beach, Barbados Concorde Experience
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Bottom Bay ©
Bottom Bay
Mount Gay Visitor Centre ©
Mount Gay Visitor Centre

3
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.
Take a break from Port of Spain with a short trip to Yerette in Maracas Bay, about 30 minutes away. There's still lots to do: walk around Queen's Park Savannah, enjoy the sand and surf at Maracas Beach, meet the residents at Emperor Valley Zoo, and explore the activities along Caroni Swamp.

Plan my day in Port of Spain using traveler tips and tourist information provided by Inspirock.

You can fly from Bridgetown to Port of Spain in 4 hours. In October in Port of Spain, expect temperatures between 38°C during the day and 28°C at night. On the 10th (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Port of Spain

Parks Wildlife Beaches

Side Trip

Yerette
Highlights from your plan
Queen's Park Savannah ©
Queen's Park Savannah
Maracas Beach
Maracas Beach
Emperor Valley Zoo ©
Emperor Valley Zoo

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