16 days in Caribbean Itinerary

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 11th (Fri): visit Iglesias de San Francisco de Paula and then make a trip to Plaza de Armas. Get ready for a full day of sightseeing on the next day: make a trip to Old Havana, make a trip to Old Square (Plaza Vieja), then make a trip to Plaza de la Catedral, and finally admire the landmark architecture of Havana Cathedral.

For reviews, where to stay, ratings, and other tourist information, you can read our Havana route planning site.

Halifax, Canada to Havana is an approximately 10-hour flight. The time zone difference moving from Atlantic Standard Time to Cuba Standard Time is minus 1 hour. Plan for much warmer temperatures traveling from Halifax in February, with highs in Havana at 32°C and lows at 19°C. Finish your sightseeing early on the 13th (Sun) to allow enough time to travel to Santo Domingo.

Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.

On the 14th (Mon), explore the ancient world of Monasterio de San Francisco and then don't miss a visit to Zona Colonial. Here are some ideas for day two: appreciate the history behind Columbus Lighthouse (Faro A Colon), contemplate the long history of Alcazar de Colon, then take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor, and finally contemplate the long history of Fortaleza Ozama.

To find ratings, other places to visit, more things to do, and tourist information, read our Santo Domingo road trip planning website.

Fly from Havana to Santo Domingo in 5.5 hours. You'll lose 1 hour traveling from Havana to Santo Domingo due to the time zone difference. Finish your sightseeing early on the 15th (Tue) to allow enough time to travel to Isla de Vieques.

For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.

On the 16th (Wed), stroll through Media Luna Beach, take in the waterfront at Mosquito Pier, and then tour the pleasant surroundings at Vieques National Wildlife Refuge. Keep things going the next day: take a leisurely stroll along Malecon and then enjoy the sand and surf at Sun Bay Beach.

For maps, photos, traveler tips, and more tourist information, use the Isla de Vieques holiday site.

You can fly from Santo Domingo to Isla de Vieques in 5.5 hours. Another option is to do a combination of ferry and taxi. In February, plan for daily highs up to 33°C, and evening lows to 26°C. Finish up your sightseeing early on the 17th (Thu) so you can travel to Culebra.

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 18th (Fri): enjoy the sand and surf at Playa Punta Soldado Beach and then kick back and relax at Flamenco Beach. Get ready for a full day of sightseeing on the next day: enjoy the sea views from Culebrita Lighthouse, then head off the coast to Culebrita Island, and then enjoy the sand and surf at Zoni Beach.

For where to stay, reviews, other places to visit, and other tourist information, you can read our Culebra trip itinerary maker.

Traveling by combination of car and flight from Isla de Vieques to Culebra takes 4 hours. Alternatively, you can ride a ferry. In February, plan for daily highs up to 34°C, and evening lows to 26°C. On the 20th (Sun), wrap the sightseeing up by early afternoon so you can travel to Bridgetown.

Bridgetown is the capital and largest city of Barbados. Kick off your visit on the 21st (Mon): take in panoramic vistas at Gun Hill Signal Station, then explore the activities along Foul Bay, then tour the pleasant surroundings at Bottom Bay, and finally get interesting insight from Tours. On the 22nd (Tue), you'll have a packed day of sightseeing: admire the natural beauty at Welchman Hall Gully, explore the fascinating underground world of Harrison's Cave., admire the natural beauty at Hunte's Gardens, then steep yourself in history at Andromeda Botanic Gardens, and finally see the interesting displays at Sunbury Plantation House.

To find traveler tips, reviews, ratings, and other tourist information, you can read our Bridgetown trip itinerary planning site.

Fly from Culebra to Bridgetown in 10.5 hours. February in Bridgetown sees daily highs of 34°C and lows of 27°C at night. Finish up your sightseeing early on the 22nd (Tue) so you can travel to English Harbour.

Start off your visit on the 23rd (Wed): explore the wealth of natural beauty at Nelson's Dockyard. Get ready for a full day of sightseeing on the next day: take some stellar pictures from Shirley Heights and then contemplate the waterfront views at Dickenson Bay.

For other places to visit, where to stay, and other tourist information, read our English Harbour holiday planning site.

Traveling by flight from Bridgetown to English Harbour takes 6 hours. In February, daily temperatures in English Harbour can reach 32°C, while at night they dip to 26°C. Finish your sightseeing early on the 24th (Thu) so you can travel to Providenciales.

The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.

Kick off your visit on the 25th (Fri): indulge in some personalized pampering at Glow Fitness TCI, then play a few rounds at Provo Golf Club, and then enjoy the sand and surf at Grace Bay Beach.

To see where to stay, reviews, photos, and other tourist information, you can read our Providenciales online trip builder.

Traveling by flight from English Harbour to Providenciales takes 6 hours. Traveling from English Harbour to Providenciales, you'll gain 1 hour due to the time zone difference. In February, plan for daily highs up to 32°C, and evening lows to 27°C. You will have some time to spend on the 26th (Sat) before leaving for home.