25 days in Caribbean Itinerary

25 days in Caribbean Itinerary

Created using Inspirock Caribbean tour itinerary planner

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1
Havana, Cuba
— 4 nights
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2
Providenciales, Turks and Caicos
— 2 nights
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3
Santo Domingo, Dominican Republic
— 2 nights
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4
Willemstad, Curacao
— 2 nights
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5
Bridgetown, Barbados
— 2 nights
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6
Fort-de-France, Martinique
— 2 nights
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7
St. John's, Antigua and Barbuda
— 2 nights
Fly to St Maarten, Ferry to Anguilla
8
Shoal Bay Village, Anguilla
— 2 nights
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9
Culebra, Puerto Rico
— 2 nights
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10
Punta Cana, Dominican Republic
— 3 nights
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Havana, Cuba

— 4 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.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: appreciate the extensive heritage of Malecón of Havana, get the lay of the land with Walking tours, wander the streets of Christopher Columbus Cemetery (Cemetario de Colon), and don't miss a visit to Paseo del Prado.

To find more things to do, photos, reviews, and tourist information, read Havana travel planner.

Jakarta, Indonesia to Havana is an approximately 31-hour flight. The time zone difference moving from Western Indonesia Time to Cuba Standard Time is minus 12 hours. Plan for slightly colder temperatures traveling from Jakarta in January, with highs in Havana at 30°C and lows at 19°C. Finish up your sightseeing early on the 11th (Mon) so you can travel to Providenciales.

Things to do in Havana

Historic Sites · Museums · Tours · Neighborhoods

Providenciales, Turks and Caicos

— 2 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
On the 12th (Tue), tee off at Provo Golf Club, stroll through Grace Bay Beach, and then indulge in some personalized pampering at Glow Fitness TCI. On the 13th (Wed), you'll have a packed day of sightseeing: contemplate the long history of Cheshire Hall Plantation and then enjoy the sand and surf at Taylor Bay Beach.

To find more things to do, photos, traveler tips, and more tourist information, refer to the Providenciales trip planner.

Traveling by flight from Havana to Providenciales takes 7.5 hours. Traveling from Havana in January, you can expect nighttime temperatures to be somewhat warmer in Providenciales, with lows of 27°C. Finish your sightseeing early on the 13th (Wed) so you can travel to Santo Domingo.

Things to do in Providenciales

Outdoors · Beaches · Parks · Golf

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 14th (Thu): examine the collection at Museo De Las Casas Reales, steep yourself in history at Alcazar de Colon, then take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, and finally explore the ancient world of Monasterio de San Francisco. On your second day here, pause for some photo ops at Columbus Lighthouse (Faro A Colon) and then don't miss a visit to Zona Colonial.

To see other places to visit, traveler tips, and more tourist information, go to the Santo Domingo trip itinerary site.

Traveling by flight from Providenciales to Santo Domingo takes 4.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Wrap up your sightseeing on the 15th (Fri) early enough to travel to Willemstad.

Things to do in Santo Domingo

Museums · Historic Sites

Willemstad, Curacao

— 2 nights
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. On the 16th (Sat), admire the masterpieces at Kura Hulanda Museum, enjoy the sand and surf at Blue Bay Beach, and then see some colorful creatures with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the next day: take a leisurely stroll along Handelskade, then snap pictures at Queen Emma Pontoon Bridge, and then see the interesting displays at Mikve Israel-Emanuel Synagogue.

To see ratings, maps, more things to do, and other tourist information, you can read our Willemstad online trip builder.

You can fly from Santo Domingo to Willemstad in 4.5 hours. In January, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing on the 17th (Sun) to allow time to travel to Bridgetown.

Things to do in Willemstad

Outdoors · Beaches · Museums · Parks

Bridgetown, Barbados

— 2 nights
Bridgetown is the capital and largest city of Barbados. On the 18th (Mon), take in nature's colorful creations at Welchman Hall Gully, explore the fascinating underground world of Harrison's Cave., take in nature's colorful creations at Hunte's Gardens, then contemplate the waterfront views at Foul Bay, and finally kick back and relax at Bottom Bay. Keep things going the next day: get a new perspective on things with Boat Tours & Water Sports, take in panoramic vistas at Gun Hill Signal Station, then steep yourself in history at Andromeda Botanic Gardens, and finally enjoy the sand and surf at Soup Bowl.

To find more things to do, maps, and tourist information, go to the Bridgetown online route maker.

Traveling by flight from Willemstad to Bridgetown takes 8 hours. In January, daily temperatures in Bridgetown can reach 34°C, while at night they dip to 27°C. Cap off your sightseeing on the 19th (Tue) early enough to travel to Fort-de-France.

Things to do in Bridgetown

Parks · Outdoors · Beaches · Nature

Side Trips

Fort-de-France, Martinique

— 2 nights
The political capital of Martinique, Fort-de-France has a thriving commercial center and a number of historic sites.
On the 20th (Wed), take in the spiritual surroundings of St. Louis Cathedral, admire the landmark architecture of Schoelcher Library, appreciate the history behind Espace Camille Darsiere, then take in nature's colorful creations at Jardin de Balata, and finally take your sightseeing to a higher altitude at Pitons du Carbet. Keep things going the next day: steep yourself in history at Habitation Clement, take an in-depth tour of La Savane des Esclaves, and then take a memorable tour with An Dlo.

To see reviews, photos, maps, and more tourist information, refer to the Fort-de-France trip planner.

Traveling by flight from Bridgetown to Fort-de-France takes 4.5 hours. January in Fort-de-France sees daily highs of 34°C and lows of 26°C at night. Finish up your sightseeing early on the 21st (Thu) so you can travel to St. John's.

Things to do in Fort-de-France

Parks · Historic Sites · Nature · Tours

Side Trips

St. John's, Antigua and Barbuda

— 2 nights
The capital and largest city of Antigua and Barbuda, St John's represents the commercial and touristic center of the twin-island country.
Kick off your visit on the 22nd (Fri): explore the striking landscape of Nelson's Dockyard. Keep things going the next day: kick back and relax at Hawksbill Bay, then take a leisurely stroll along Heritage Quay, and then contemplate the waterfront views at Dickenson Bay.

For more things to do, traveler tips, photos, and other tourist information, read our St. John's online trip itinerary planner.

Getting from Fort-de-France to St. John's by flight takes about 5.5 hours. In January, daily temperatures in St. John's can reach 32°C, while at night they dip to 26°C. Finish up your sightseeing early on the 23rd (Sat) so you can travel to Shoal Bay Village.

Things to do in St. John's

Parks · Nature · Beaches · Outdoors

Side Trips

Shoal Bay Village, Anguilla

— 2 nights
On the 24th (Sun), enjoy the sand and surf at Shoal Bay, step off the mainland to explore Sandy Island, and then enjoy the sand and surf at Meads Bay. On the 25th (Mon), you'll have a packed day of sightseeing: explore the activities along Maundays Bay, shop like a local with Limin' Boutique, and then kick back and relax at Rendezvous Bay Beach.

For traveler tips, other places to visit, reviews, and more tourist information, refer to the Shoal Bay Village visit planner.

Traveling by combination of flight and ferry from St. John's to Shoal Bay Village takes 4.5 hours. Expect a daytime high around 33°C in January, and nighttime lows around 26°C. Wrap up your sightseeing on the 25th (Mon) to allow time to travel to Culebra.

Things to do in Shoal Bay Village

Parks · Beaches · Outdoors · Nature

Side Trips

Culebra, Puerto Rico

— 2 nights

Little Island

With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Kick off your visit on the 26th (Tue): tour the pleasant surroundings at Zoni Beach, then step off the mainland to explore Culebrita Island, and then enjoy the sea views from Culebrita Lighthouse. Here are some ideas for day two: kick back and relax at Flamenco Beach.

For ratings, traveler tips, where to stay, and tourist information, use the Culebra trip itinerary builder app.

Traveling by flight from Shoal Bay Village to Culebra takes 6.5 hours. January in Culebra sees daily highs of 34°C and lows of 26°C at night. Wrap up your sightseeing on the 27th (Wed) to allow time to travel to Punta Cana.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature

Punta Cana, Dominican Republic

— 3 nights
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Kick off your visit on the 28th (Thu): tee off at Punta Espada Golf Course and then see some colorful creatures with Aqua Track Private Day Trips. Get ready for a full day of sightseeing on the 29th (Fri): relax and rejuvenate at Ocean Adventures Punta Cana, then enjoy the sand and surf at Bavaro Beach, and then stop by HARRISON'S Fine Caribbean Jewelers.

To find traveler tips, more things to do, and more tourist information, use the Punta Cana online tour builder.

Traveling by flight from Culebra to Punta Cana takes 6.5 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, shuttle, and bus. In January, daily temperatures in Punta Cana can reach 33°C, while at night they dip to 25°C. Wrap up your sightseeing on the 30th (Sat) early enough to travel back home.

Things to do in Punta Cana

Outdoors · Beaches · Parks · Golf