22 days in Caribbean Itinerary

22 days in Caribbean Itinerary

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Route & dates

22 days in Caribbean Itinerary

Start: Belize City, Belize
Fly:  10​h 15​min
1
Kingston, Jamaica
— 3 nights
Fly:  6​h 30​min
2
Havana, Cuba
— 5 nights
Fly:  3​h
3
Santo Domingo, Dominican Republic
— 4 nights
Fly:  3​h
4
San Juan, Puerto Rico
— 4 nights
Fly:  8​h
5
Port of Spain, Trinidad and Tobago
— 1 night
Fly:  23​h 30​min
End: Cluj-Napoca, Romania

3
nights
Kingston, Jamaica

Kingston ©
The country's capital, Kingston offers all the excitement of a lively and storied city, while also housing the services and facilities travelers need to get around and see the rest of the island.
Your day-by-day itinerary now includes Blue Mountains, James Bond Beach and Blue Hole. Step out of Kingston to go to Ocho Rios and see Dunn's River Falls and Park, which is approximately 1h 25 min away. There's lots more to do: explore the galleries of Bob Marley Museum, go for a stroll along the water at Port Royal, walk around Emancipation Park, and pause for some photo ops at Devon House.

To see traveler tips, other places to visit, maps, and other tourist information, go to the Kingston sightseeing planner.

Belize City, Belize to Kingston is an approximately 10.5-hour flight. Traveling from Belize City to Kingston, you'll lose 1 hour due to the time zone difference. In September, daily temperatures in Kingston can reach 38°C, while at night they dip to 30°C. You'll set off for Havana on the 5th (Thu).

Things to do in Kingston

Parks Nature Historic Sites

Side Trip

Ocho Rios
Highlights from your plan
Dunn's River Falls and Park ©
Dunn's River Falls and Park
Blue Mountains ©
Blue Mountains
Bob Marley Museum ©
Bob Marley Museum

5
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 Museu Nacional de Belas Artes de Cuba, Plaza de San Francisco, Calle Obispo, and other attractions to your itinerary. There's lots more to do: get to know the fascinating history of El Malecon, don't miss a visit to Old Havana, contemplate the long history of El Morro, and take an in-depth tour of Museum of the Revolution (Museo de la Revolucion).

To find photos, where to stay, maps, and tourist information, read Havana online day trip planner .

Traveling by flight from Kingston to Havana takes 6.5 hours. Plan for a bit cooler nights when traveling from Kingston in September since evenings lows in Havana dip to 26°C. Wrap up your sightseeing on the 10th (Tue) to allow time to travel to Santo Domingo.

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

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 list of things to see and do now includes Mercado Modelo, Parque Colon, Bellapart Museum (Museo Bellapart), and other attractions. There's lots more to do: don't miss a visit to Zona Colonial, browse the exhibits of Columbus Lighthouse (Faro A Colon), steep yourself in history at Fortaleza Ozama, and observe the fascinating underwater world at National Aquarium.

For traveler tips, where to stay, photos, and more tourist information, go to the Santo Domingo vacation planner .

Traveling by flight from Havana to Santo Domingo takes 3 hours. The time zone changes from Cuba Standard Time to Atlantic Standard Time, which is usually a 1 hour difference. Finish your sightseeing early on the 14th (Sat) to allow enough time to travel to San Juan.

Things to do in Santo Domingo

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

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, Calle del Cristo, Catedral Metropolitana Basilica de San Juan Bautista, and other attractions you added. 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: wander the streets of Old San Juan, get to know the fascinating history of Sitio Histórico de San Juan, kick back and relax at Condado Beach, and admire the masterpieces at Museo de Las Americas.

To find other places to visit, photos, ratings, and more tourist information, you can read our San Juan sightseeing planner.

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 September, and nighttime lows around 30°C. Cap off your sightseeing on the 18th (Wed) early enough to travel to Port of Spain.

Things to do in San Juan

Parks Nature Historic Sites

Side Trips

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

1
night
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 Las Cuevas Beach as well as Asa Wright Nature Centre. Start off your visit on the 19th (Thu): look for all kinds of wild species at Asa Wright Nature Centre, walk around Queen's Park Savannah, and then contemplate the waterfront views at Caroni Swamp. Get ready for a full day of sightseeing on the next day: enjoy the sand and surf at Las Cuevas Beach, take in nature's colorful creations at Royal Botanic Gardens, and then kick back and relax at Maracas Beach.

For where to stay, reviews, and other tourist information, you can read our Port of Spain road trip planning app .

Getting from San Juan to Port of Spain by flight takes about 8 hours. In September, daily temperatures in Port of Spain can reach 39°C, while at night they dip to 28°C. Wrap up your sightseeing on the 20th (Fri) to allow time to travel back home.

Things to do in Port of Spain

Parks Wildlife Beaches

Side Trip

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

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