19 days in Caribbean Itinerary

19 days in Caribbean Itinerary

Created using Inspirock itinerary planner

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1
Havana, Cuba
— 2 nights
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2
Palm - Eagle Beach, Aruba
— 2 nights
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3
Simpson Bay, St. Maarten-St. Martin
— 2 nights
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4
Culebra, Puerto Rico
— 2 nights
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5
Santo Domingo, Dominican Republic
— 2 nights
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6
Providenciales, Turks and Caicos
— 2 nights
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7
Montego Bay, Jamaica
— 2 nights
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Havana, Cuba

— 2 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: get to know the fascinating history of Malecón of Havana, make a trip to Plaza de la Catedral, and steep yourself in history at Fortaleza de San Carlos de la Cabana.

To find ratings, maps, where to stay, and other tourist information, you can read our Havana trip itinerary planning tool.

Toronto, Canada to Havana is an approximately 7-hour flight. Traveling from Toronto in April, expect Havana to be warmer, temps between 36°C and 22°C. Wrap up your sightseeing on the 13th (Tue) to allow time to travel to Palm - Eagle Beach.

Things to do in Havana

Historic Sites
Find places to stay Apr 11 — 13:

Palm - Eagle Beach, Aruba

— 2 nights
A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
When in Palm - Eagle Beach, make a side trip to see Baby Beach in San Nicolas, approximately San Nicolas away. There's lots more to do: tour the pleasant surroundings at Eagle Beach, get a new perspective on things with Boat Tours & Water Sports, enjoy the sea views from California Lighthouse, and steep yourself in history at Bushiribana Gold Mill Ruins.

To see other places to visit, photos, traveler tips, and other tourist information, you can read our Palm - Eagle Beach driving holiday planner.

Fly from Havana to Palm - Eagle Beach in 8.5 hours. Traveling from Havana to Palm - Eagle Beach, you'll lose 1 hour due to the time zone difference. Traveling from Havana in April, plan for a bit warmer nights in Palm - Eagle Beach, with lows around 30°C. Finish your sightseeing early on the 16th (Fri) so you can travel to Simpson Bay.

Things to do in Palm - Eagle Beach

Outdoors · Parks · Beaches · Wildlife

Side Trips

Find places to stay Apr 13 — 16:

Simpson Bay, St. Maarten-St. Martin

— 2 nights
Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 17th (Sat), kick back and relax at Kim Sha Beach, tour the pleasant surroundings at Paradise Peak, and then enjoy the sand and surf at Orient Bay Beach. Keep things going the next day: look for gifts at Le Grande Marche, then take a tour by water with Boat Tours & Water Sports, then contemplate the waterfront views at Mullet Bay Beach, and finally enjoy the sand and surf at Maho Beach.

To find where to stay, traveler tips, other places to visit, and tourist information, read our Simpson Bay online driving holiday planner.

Getting from Palm - Eagle Beach to Simpson Bay by flight takes about 7 hours. Traveling from Palm - Eagle Beach in April, expect nights in Simpson Bay to be about the same, around 28°C, while days are a bit cooler, around 34°C. Wrap up your sightseeing on the 19th (Mon) early enough to fly to Culebra.

Things to do in Simpson Bay

Outdoors · Parks · Beaches · Nature

Side Trips

Find places to stay Apr 16 — 19:

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.
Culebra is known for beaches, wildlife, and nature. Your plan includes some of its best attractions: enjoy the sand and surf at Flamenco Beach, take a tour by water with Boat Tours & Water Sports, stroll through Playa Punta Soldado Beach, and step off the mainland to explore Culebrita.

To see photos, ratings, traveler tips, and tourist information, read our Culebra visit planner.

You can fly from Simpson Bay to Culebra in 5.5 hours. In April, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing by early afternoon on the 21st (Wed) to allow enough time to travel to Santo Domingo.

Things to do in Culebra

Parks · Outdoors · Beaches · Nature
Find places to stay Apr 19 — 21:

Santo Domingo, Dominican Republic

— 2 nights
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
On the 22nd (Thu), see the interesting displays at Columbus Lighthouse (Faro A Colon) and then make a trip to Zona Colonial. On the 23rd (Fri), you'll have a packed day of sightseeing: 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 get to know the fascinating history of Calle Las Damas.

To find maps, other places to visit, traveler tips, and tourist information, refer to the Santo Domingo itinerary builder site.

Getting from Culebra to Santo Domingo by flight takes about 6 hours. Other options: do a combination of ferry and taxi. Finish your sightseeing early on the 23rd (Fri) to allow enough time to travel to Providenciales.

Things to do in Santo Domingo

Historic Sites · Museums
Find places to stay Apr 21 — 23:

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.
Kick off your visit on the 24th (Sat): stroll through Half Moon Bay, step off the mainland to explore Little Water Cay, and then tee off at Provo Golf Club. Keep things going the next day: kick back and relax at Grace Bay Beach and then take in the dramatic natural features at Smith's Reef.

Ask Inspirock to suggest an itinerary and make planning a trip to Providenciales fast, fun, and easy.

Getting from Santo Domingo to Providenciales by flight takes about 4.5 hours. You'll gain 1 hour traveling from Santo Domingo to Providenciales due to the time zone difference. In April, plan for daily highs up to 34°C, and evening lows to 28°C. Wrap up your sightseeing on the 25th (Sun) early enough to travel to Montego Bay.

Things to do in Providenciales

Parks · Outdoors · Beaches · Nature

Side Trip

Find places to stay Apr 23 — 25:

Montego Bay, Jamaica

— 2 nights
The second largest city in Jamaica, Montego Bay boasts an international airport and a major cruise-line terminal, so it regularly receives a big influx of visitors to the island.
Go for a jaunt from Montego Bay to Ocho Rios to see Blue Hole about 1h 55 min away. Spend the 26th (Mon) wandering through the wild on a nature and wildlife tour. There's still lots to do: stroll through Doctor's Cave Beach, steep yourself in history at Rose Hall Great House, make a trip to Hip Strip, and take an exotic tour of Rastasafari Experience.

For reviews, traveler tips, more things to do, and other tourist information, read our Montego Bay trip itinerary planning app.

Getting from Providenciales to Montego Bay by flight takes about 9.5 hours. In April, plan for daily highs up to 37°C, and evening lows to 28°C. Finish up your sightseeing early on the 28th (Wed) so you can travel back home.

Things to do in Montego Bay

Outdoors · Tours · Wildlife · Parks

Side Trip

Find places to stay Apr 25 — 28:

Jamaica travel guide

4.1
Waterfalls · Beaches · Nightlife
The third most populous English-speaking country in the Americas, Jamaica remains a member of the Commonwealth of Nations, with the British monarch its official head of state. Jamaica tourism thrives thanks to the island nation's reputation for natural beauty, outstanding cuisine, and lively music scene. The country's landscape is as diverse as its population, its tropical climate supporting varied ecosystems that include everything from savannahs to rugged mountain slopes. For most visitors, a holiday in Jamaica is a largely outdoor affair, with hiking, fishing, golfing, camping, snorkeling, horseback riding, and kite surfing among the most popular things to do.