16 days in Caribbean Itinerary

16 days in Caribbean Itinerary

Created using Inspirock Caribbean holiday planner

Make it your trip
Fly
1
Havana, Cuba
— 3 nights
Fly
2
Providenciales, Turks and Caicos
— 1 night
Fly
3
Santo Domingo, Dominican Republic
— 1 night
Fly
4
San Juan, Puerto Rico
— 3 nights
Fly
5
Culebra, Puerto Rico
— 2 nights
Fly
6
Virgin Gorda, British Virgin Islands
— 1 night
Ferry to Beef Island, Fly to Antigua
7
English Harbour, Antigua and Barbuda
— 1 night
Fly
8
Bridgetown, Barbados
— 2 nights
Fly

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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.
Havana is known for historic sites, nightlife, and museums. Your plan includes some of its best attractions: make a trip to Malecón of Havana, take an in-depth tour of Museum of the Revolution (Museo de la Revolucion), take a stroll through Christopher Columbus Cemetery (Cemetario de Colon), and appreciate the extensive heritage of Old Havana.

To find maps, traveler tips, other places to visit, and other tourist information, refer to the Havana driving holiday planner.

Tel Aviv, Israel to Havana is an approximately 19.5-hour flight. The time zone difference moving from Israel Standard Time (IST) to Cuba Standard Time (CST) is minus 7 hours. Prepare for a bit warmer weather when traveling from Tel Aviv in January: high temperatures in Havana hover around 79°F and lows are around 62°F. Finish your sightseeing early on the 6th (Wed) to allow enough time to travel to Providenciales.

Things to do in Havana

Historic Sites · Museums · Neighborhoods

Providenciales, Turks and Caicos

— 1 night
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Start off your visit on the 7th (Thu): play a few rounds at Provo Golf Club, then tour the pleasant surroundings at Grace Bay Beach, and then indulge in some personalized pampering at Glow Fitness TCI.

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

You can fly from Havana to Providenciales in 7.5 hours. Traveling from Havana in January, plan for a bit warmer nights in Providenciales, with lows around 74°F. Wrap up your sightseeing on the 7th (Thu) early enough to travel to Santo Domingo.

Things to do in Providenciales

Outdoors · Beaches · Parks · Golf

Santo Domingo, Dominican Republic

— 1 night
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Start off your visit on the 8th (Fri): contemplate the long history of Fortaleza Ozama, then pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor, then explore the historical opulence of Alcazar de Colon, and finally pause for some photo ops at Columbus Lighthouse (Faro A Colon).

To see more things to do, reviews, traveler tips, and more tourist information, refer to the Santo Domingo journey planning website.

You can fly from Providenciales to Santo Domingo in 4.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. Cap off your sightseeing on the 8th (Fri) early enough to travel to San Juan.

Things to do in Santo Domingo

Historic Sites · Museums

San Juan, Puerto Rico

— 3 nights

Walled City

Founded by the Spanish in 1521, San Juan is the oldest city under U.S. jurisdiction and one of the oldest in the Americas.
Step out of San Juan to go to El Yunque National Forest and see El Yunque Rain Forest, which is approximately 1h 10 min away. And it doesn't end there: get to know the fascinating history of Old San Juan, make a trip to Calle del Cristo, contemplate the long history of Sitio Histórico de San Juan, and take in the architecture and atmosphere at Catedral Basilica Menor de San Juan Bautista.

For maps, reviews, ratings, and other tourist information, use the San Juan trip builder tool.

You can fly from Santo Domingo to San Juan in 3 hours. Alternatively, you can ride a ferry. Expect a daytime high around 84°F in January, and nighttime lows around 73°F. Wrap up your sightseeing on the 11th (Mon) early enough to travel to Culebra.

Things to do in San Juan

Parks · Wildlife · Nature · Historic Sites

Side Trip

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 12th (Tue): enjoy the sand and surf at Flamenco Beach. On the 13th (Wed), you'll have a packed day of sightseeing: stroll through Playa Punta Soldado Beach, enjoy the sand and surf at Zoni Beach, and then head off the coast to Culebrita.

For traveler tips, ratings, other places to visit, and tourist information, refer to the Culebra road trip planner.

You can fly from San Juan to Culebra in 2 hours. Alternatively, you can do a combination of car and ferry; or do a combination of shuttle and ferry. In January in Culebra, expect temperatures between 84°F during the day and 73°F at night. Cap off your sightseeing on the 13th (Wed) early enough to travel to Virgin Gorda.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature

Virgin Gorda, British Virgin Islands

— 1 night
Thankfully lacking some of the commercialism of other islands nearby, Virgin Gorda offers a relaxing place to holiday, and maintains a feeling of intimacy despite its reputation as an exclusive destination.
Start off your visit on the 14th (Thu): tour the pleasant surroundings at Spring Bay and then tour the pleasant surroundings at The Baths.

For maps, traveler tips, photos, and other tourist information, you can read our Virgin Gorda road trip website.

Fly from Culebra to Virgin Gorda in 5.5 hours. Expect a daytime high around 84°F in January, and nighttime lows around 75°F. Finish up your sightseeing early on the 14th (Thu) so you can travel to English Harbour.

Things to do in Virgin Gorda

Beaches · Outdoors · Parks · Nature

English Harbour, Antigua and Barbuda

— 1 night
Start off your visit on the 15th (Fri): explore the striking landscape of Nelson's Dockyard.

To find traveler tips, photos, and more tourist information, read our English Harbour online trip itinerary maker.

Do a combination of ferry and flight from Virgin Gorda to English Harbour in 6.5 hours. In January, plan for daily highs up to 82°F, and evening lows to 73°F. Finish your sightseeing early on the 15th (Fri) so you can travel to Bridgetown.

Things to do in English Harbour

Parks · Nature
Highlights from your trip

Bridgetown, Barbados

— 2 nights
Bridgetown is the capital and largest city of Barbados. Start off your visit on the 16th (Sat): contemplate the long history of Andromeda Botanic Gardens, take in nature's colorful creations at Hunte's Gardens, take in nature's colorful creations at Welchman Hall Gully, then Head underground at Harrison's Cave., and finally delve into the lush surroundings at Flower Forest. Here are some ideas for day two: examine the collection at Sunbury Plantation House, then enjoy the sand and surf at Bottom Bay, then contemplate the waterfront views at Foul Bay, and finally get a new perspective on things with Boat Tours & Water Sports.

To find ratings, more things to do, traveler tips, and more tourist information, refer to the Bridgetown trip site.

You can fly from English Harbour to Bridgetown in 6 hours. January in Bridgetown sees daily highs of 84°F and lows of 74°F at night. Finish up your sightseeing early on the 17th (Sun) so you can travel back home.

Things to do in Bridgetown

Parks · Nature · Outdoors · Tours

Side Trips