27 days in Caribbean Itinerary

27 days in Caribbean Itinerary

Created using Inspirock Caribbean travel route planner

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1
Punta Cana, Dominican Republic
— 3 nights
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2
San Juan, Puerto Rico
— 3 nights
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3
Culebra, Puerto Rico
— 2 nights
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4
Simpson Bay, St. Maarten-St. Martin
— 3 nights
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5
Bridgetown, Barbados
— 2 nights
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6
Willemstad, Curacao
— 2 nights
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7
Palm - Eagle Beach, Aruba
— 2 nights
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8
Santo Domingo, Dominican Republic
— 2 nights
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9
Providenciales, Turks and Caicos
— 3 nights
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10
Havana, Cuba
— 3 nights
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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.
Step out of Punta Cana to go to La Romana and see Altos de Chavon, which is approximately 1h 20 min away. There's still lots to do: enjoy the sand and surf at Bavaro Beach, examine the collection at Aromas Museum, tee off at Punta Espada Golf Course, and make a trip to Jesus Maestro Parish.

To find where to stay, maps, reviews, and more tourist information, refer to the Punta Cana tour planner.

Jeddah, Saudi Arabia to Punta Cana is an approximately 19-hour flight. The time zone difference moving from Arabian Standard Time to Atlantic Standard Time is minus 7 hours. Expect little chillier temperatures when traveling from Jeddah in May; daily highs in Punta Cana reach 35°C and lows reach 28°C. Wrap up your sightseeing on the 4th (Tue) early enough to travel to San Juan.

Things to do in Punta Cana

Outdoors · Theme Parks · Beaches · Parks

Side Trip

Find places to stay May 1 — 4:

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. There's lots more to do: get to know the fascinating history of Old San Juan, indulge in some culinary diversions at a local gastronomic tour, pause for some serene contemplation at Catedral Basilica Menor de San Juan Bautista, and contemplate the long history of Sitio Histórico de San Juan.

Find out how to plan San Juan trip without stress by asking Inspirock to help create an itinerary.

You can fly from Punta Cana to San Juan in 2.5 hours. Another option is to do a combination of bus and ferry. In May, plan for daily highs up to 36°C, and evening lows to 28°C. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel to Culebra.

Things to do in San Juan

Parks · Wildlife · Nature · Historic Sites

Side Trip

Find places to stay May 4 — 7:

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 8th (Sat): enjoy the sand and surf at Flamenco Beach. On the 9th (Sun), you'll have a packed day of sightseeing: stroll through Playa Punta Soldado Beach, then take a tour by water with Boat Tours & Water Sports, and then step off the mainland to explore Culebrita Island.

To see traveler tips, other places to visit, ratings, and other tourist information, use the Culebra travel itinerary planner.

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 May, plan for daily highs up to 36°C, and evening lows to 29°C. Finish your sightseeing early on the 9th (Sun) to allow enough time to fly to Simpson Bay.

Things to do in Culebra

Outdoors · Parks · Beaches · Tours
Find places to stay May 7 — 9:

Simpson Bay, St. Maarten-St. Martin

— 3 nights
Simpson Bay offers luxury resort living and good access to the main areas of the island.
Simpson Bay is known for wildlife, nightlife, and casinos. Your plan includes some of its best attractions: stroll through Maho Beach, try your luck at Casino Royale, see some colorful creatures with a scuba or snorkeling tour, and contemplate the waterfront views at Mullet Bay Beach.

For reviews, where to stay, photos, and tourist information, you can read our Simpson Bay trip maker website.

Traveling by flight from Culebra to Simpson Bay takes 5.5 hours. In May, plan for daily highs up to 34°C, and evening lows to 29°C. Cap off your sightseeing on the 12th (Wed) early enough to travel to Bridgetown.

Things to do in Simpson Bay

Outdoors · Parks · Beaches · Casinos

Side Trips

Find places to stay May 9 — 12:

Bridgetown, Barbados

— 2 nights
Bridgetown is the capital and largest city of Barbados. Start off your visit on the 13th (Thu): admire the natural beauty at Welchman Hall Gully, explore the fascinating underground world of Harrison's Cave., take in nature's colorful creations at Hunte's Gardens, then take in panoramic vistas at Gun Hill Signal Station, and finally take a tour by water with Boat Tours & Water Sports. On the 14th (Fri), you'll have a packed day of sightseeing: see the interesting displays at Sunbury Plantation House, enjoy the sand and surf at Bottom Bay, and then admire the natural beauty at Andromeda Botanic Gardens.

To find more things to do, where to stay, photos, and other tourist information, use the Bridgetown trip itinerary maker website.

You can fly from Simpson Bay to Bridgetown in 7.5 hours. In May, daily temperatures in Bridgetown can reach 35°C, while at night they dip to 29°C. Wrap up your sightseeing on the 14th (Fri) to allow time to travel to Willemstad.

Things to do in Bridgetown

Parks · Outdoors · Tours · Historic Sites

Side Trips

Find places to stay May 12 — 14:

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 15th (Sat), look for gifts at The Goods BV, take in the views from Queen Emma Pontoon Bridge, then take in the waterfront at Handelskade, and finally kick back and relax at Blue Bay Beach. Keep things going the next day: look for all kinds of wild species at Wildlife Areas, then see the interesting displays at Mikve Israel-Emanuel Synagogue, and then enjoy the sand and surf at Mambo Beach.

To see maps, ratings, other places to visit, and more tourist information, read our Willemstad holiday builder.

Fly from Bridgetown to Willemstad in 8 hours. In May, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing on the 16th (Sun) early enough to travel to Palm - Eagle Beach.

Things to do in Willemstad

Outdoors · Beaches · Parks · Wildlife

Side Trip

Find places to stay May 14 — 16:

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.
Kick off your visit on the 17th (Mon): tour the pleasant surroundings at Hadicurari Beach and then tour the pleasant surroundings at Eagle Beach. On the 18th (Tue), you'll have a packed day of sightseeing: tour the pleasant surroundings at Palm Beach and then visit a coastal fixture at California Lighthouse.

To find where to stay, more things to do, traveler tips, and more tourist information, go to the Palm - Eagle Beach day trip planning site.

Traveling by flight from Willemstad to Palm - Eagle Beach takes 4.5 hours. May in Palm - Eagle Beach sees daily highs of 38°C and lows of 31°C at night. Finish up your sightseeing early on the 18th (Tue) so you can travel to Santo Domingo.

Things to do in Palm - Eagle Beach

Beaches · Outdoors · Parks · Historic Sites

Side Trip

Find places to stay May 16 — 18:

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 19th (Wed), pause for some photo ops at Columbus Lighthouse (Faro A Colon) and then don't miss a visit to Zona Colonial. Here are some ideas for day two: admire nature's wide array of creatures at National Aquarium, then steep yourself in history at Fortaleza Ozama, then explore the historical opulence of Alcazar de Colon, and finally pause for some serene contemplation at Basilica Cathedral of Santa Maria la Menor.

To find where to stay, traveler tips, ratings, and other tourist information, read our Santo Domingo visit planner.

You can fly from Palm - Eagle Beach to Santo Domingo in 5 hours. Finish your sightseeing early on the 20th (Thu) to allow enough time to travel to Providenciales.

Things to do in Santo Domingo

Historic Sites · Zoos & Aquariums · Parks · Museums
Find places to stay May 18 — 20:

Providenciales, Turks and Caicos

— 3 nights
The most commercialized part of the Turks and Caicos, Providenciales remains the islands' tourism heaven, boasting many resorts, hotel chains, and condominiums.
Providenciales is known for beaches, wildlife, and nature. Your plan includes some of its best attractions: kick back and relax at Grace Bay Beach, explore the striking landscape at Smith's Reef, contemplate the long history of Cheshire Hall Plantation, and play a few rounds at Provo Golf Club.

Before you visit Providenciales, use our trip planner to discover what you can do and see there.

You can fly from Santo Domingo to Providenciales in 4.5 hours. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. Expect a daytime high around 35°C in May, and nighttime lows around 29°C. Cap off your sightseeing on the 23rd (Sun) early enough to travel to Havana.

Things to do in Providenciales

Outdoors · Parks · Wildlife · Beaches

Side Trip

Find places to stay May 20 — 23:

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: get to know the fascinating history of Malecón of Havana, steep yourself in history at Fortaleza de San Carlos de la Cabana, don't miss a visit to Old Havana, and explore the world behind art at Museu Nacional de Belas Artes de Cuba.

Planning Havana trip won't be overwhelming when you use Inspirock's itinerary maker.

Traveling by flight from Providenciales to Havana takes 7.5 hours. Traveling from Providenciales in May, plan for little chillier nights in Havana, with lows around 24°C. Finish your sightseeing early on the 26th (Wed) so you can travel back home.

Things to do in Havana

Historic Sites · Neighborhoods · Museums
Find places to stay May 23 — 26: