14 days in Caribbean Itinerary

14 days in Caribbean Itinerary

Created using Inspirock Caribbean attractions planner

Make it your trip
Fly
1
Bridgetown, Barbados
— 1 night
Fly to Beef Island, Ferry to Cruz Bay
2
Cruz Bay, U.S. Virgin Islands
— 3 nights
Ferry to Red Hook, St Thomas, Fly to Santo Domingo
3
Santo Domingo, Dominican Republic
— 2 nights
Fly
4
Havana, Cuba
— 3 nights
Drive
5
Cayo Guillermo, Cuba
— 1 night
Drive
6
Trinidad, Cuba
— 1 night
Bus
7
Cayo Largo, Cuba
— 1 night
Fly

S M T W T F S
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Bridgetown, Barbados

— 1 night
Bridgetown is the capital and largest city of Barbados. Kick off your visit on the 4th (Sun): Head underground at Harrison's Cave. and then tour the pleasant surroundings at Dover Beach. On the next day, discover the deep blue sea with a scuba or snorkeling tour and then enjoy the sand and surf at Carlisle Bay.

To see reviews, traveler tips, other places to visit, and other tourist information, read our Bridgetown online tour itinerary planner.

Vienna, Austria to Bridgetown is an approximately 15-hour flight. Traveling from Vienna to Bridgetown, you'll gain 5 hours due to the time zone difference. Plan for much hotter temperatures traveling from Vienna in April, with highs in Bridgetown at 35°C and lows at 28°C. Wrap up your sightseeing on the 5th (Mon) early enough to travel to Cruz Bay.

Things to do in Bridgetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Cruz Bay, U.S. Virgin Islands

— 3 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Discover out-of-the-way places like Caneel Bay Beach and Bamboo Studio. Your itinerary includes some good beach time at Magens Bay and Cinnamon Bay Beach. Take a break from Cruz Bay with a short trip to Lindqvist Beach in Smith Bay, about 42 minutes away. The adventure continues: stroll through Trunk Bay Beach, enjoy the sand and surf at Maho Bay Beach, and contemplate the long history of Annaberg Sugar Plantation.

To see maps, photos, other places to visit, and other tourist information, read our Cruz Bay tour planner.

Traveling by combination of flight and ferry from Bridgetown to Cruz Bay takes 7.5 hours. April in Cruz Bay sees daily highs of 34°C and lows of 28°C at night. Finish up your sightseeing early on the 8th (Thu) so you can travel to Santo Domingo.

Things to do in Cruz Bay

Beaches · Outdoors · Parks · Historic Sites

Side Trips

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Kick off your visit on the 9th (Fri): steep yourself in history at Fortaleza Ozama, explore the historical opulence of Alcazar de Colon, then take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, and finally appreciate the extensive heritage of Calle Las Damas. Here are some ideas for day two: pause for some photo ops at Columbus Lighthouse (Faro A Colon) and then make a trip to Zona Colonial.

To see more things to do, photos, and other tourist information, refer to the Santo Domingo trip planner.

Traveling by combination of ferry and flight from Cruz Bay to Santo Domingo takes 6.5 hours. Cap off your sightseeing on the 10th (Sat) early enough to travel to Havana.

Things to do in Santo Domingo

Historic Sites · Museums

Havana, Cuba

— 3 nights

Rome of the Caribbean

Cuba's capital and major commercial center, Havana manages to be very old and very modern at the same time.
Popular historic sites such as Malecón of Havana and El Morro are in your itinerary. Your cultural itinerary includes sights like Old Square (Plaza Vieja) and Fortaleza de San Carlos de la Cabana. There's lots more to do: appreciate the extensive heritage of Old Havana, take in the spiritual surroundings of Havana Cathedral, take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), and contemplate the long history of Castillo de la Real Fuerza.

To see other places to visit, more things to do, photos, and other tourist information, read Havana trip itinerary builder app.

You can fly from Santo Domingo to Havana in 5.5 hours. The time zone difference moving from Atlantic Standard Time to Cuba Standard Time is minus 1 hour. April in Havana sees daily highs of 36°C and lows of 22°C at night. Finish your sightseeing early on the 13th (Tue) so you can drive to Cayo Guillermo.

Things to do in Havana

Historic Sites · Museums · Neighborhoods

Cayo Guillermo, Cuba

— 1 night
A kay of the Jardines del Rey archipelago, Cayo Guillermo has become a popular international tourist destination, buoyed by the construction of luxury all inclusive resorts that dot the paradisal island.
On the 14th (Wed), step off the mainland to explore Cayo Media Luna, then enjoy the sand and surf at Playa Pilar, and then enjoy the sand and surf at Cayo Guillermo.

To find ratings, where to stay, other places to visit, and other tourist information, go to the Cayo Guillermo trip planning app.

You can drive from Havana to Cayo Guillermo in 7 hours. Other options are to do a combination of bus and car; or do a combination of train and taxi. Traveling from Havana in April, Cayo Guillermo is somewhat warmer at night with lows of 26°C. Finish up your sightseeing early on the 14th (Wed) so you can go by car to Trinidad.

Things to do in Cayo Guillermo

Parks · Beaches · Outdoors · Nature

Trinidad, Cuba

— 1 night
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.
Start off your visit on the 15th (Thu): view the masterpieces at YuditVidalFaife, stroll through Ancon Beach, see the interesting displays at Museo de Historia Municipal, then make a trip to Plaza Mayor, and finally see the interesting displays at Romance Museum.

For photos, traveler tips, other places to visit, and tourist information, you can read our Trinidad trip tool.

You can drive from Cayo Guillermo to Trinidad in 4.5 hours. Another option is to take a bus. In April in Trinidad, expect temperatures between 36°C during the day and 24°C at night. Finish up your sightseeing early on the 15th (Thu) so you can catch the bus to Cayo Largo.

Things to do in Trinidad

Museums · Beaches · Outdoors · Parks

Cayo Largo, Cuba

— 1 night
The stress of modern life feels a million miles away when you holiday on Cayo Largo, a small and unspoiled resort island off the coast of Cuba.
On the 16th (Fri), enjoy the sand and surf at Playa Blanca Beach, then kick back and relax at Sirena Beach, and then enjoy the sand and surf at Punta Mal Tiempo.

To see maps, more things to do, where to stay, and tourist information, read our Cayo Largo trip planner.

Take a bus from Trinidad to Cayo Largo in 4.5 hours. In April, plan for daily highs up to 34°C, and evening lows to 25°C. Wrap up your sightseeing on the 16th (Fri) to allow time to travel back home.

Things to do in Cayo Largo

Beaches · Outdoors · Parks