18 days in Caribbean Itinerary

18 days in Caribbean Itinerary

Created using Inspirock Caribbean trip planner

Make it your trip
Drive to Larnaca International Airport, Fly to Punta Cana
1
Punta Cana, Dominican Republic
— 4 nights
Fly
2
Providenciales, Turks and Caicos
— 2 nights
Fly to San Juan, Ferry to Culebra
3
Culebra, Puerto Rico
— 2 nights
Fly to Vieques, Taxi to Isla de Vieques
4
Isla de Vieques, Puerto Rico
— 2 nights
Fly to Charlotte Amalie, Taxi to East End
5
East End, U.S. Virgin Islands
— 2 nights
Taxi to Charlotte Amalie, Fly to Shoal Bay Village
6
Shoal Bay Village, Anguilla
— 2 nights
Ferry
7
Simpson Bay, St. Maarten-St. Martin
— 2 nights
+2
Drive to Princess Juliana International Airport, Fly to Larnaca International Airport, Drive to Ayia Napa

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Punta Cana, Dominican Republic

— 4 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.
Spend a day of island exploring on the 6th (Wed) at Saona Island. There's still lots to do: fulfill a lifelong dream with a swim-with-the-dolphins experience, relax and rejuvenate at Flavio Acuna Spa Natural Center, kick back and relax at Bavaro Beach, and stop by La Perla Dominicana.

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

Ayia Napa, Cyprus to Punta Cana is an approximately 23-hour combination of car and flight. You can also fly. The time zone changes from Eastern European Standard Time (EET) to Atlantic Standard Time (AST), which is usually a -6 hour difference. Prepare for somewhat warmer weather when traveling from Ayia Napa in October: high temperatures in Punta Cana hover around 36°C and lows are around 28°C. Wrap up your sightseeing on the 8th (Fri) to allow time to fly to Providenciales.

Things to do in Punta Cana

Outdoors · Parks · Tours · Nature

Side Trip

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 9th (Sat): head off the coast to Little Water Cay, then stroll through Grace Bay Beach, and then relax and rejuvenate at Glow Fitness TCI. On your second day here, steep yourself in history at Cheshire Hall Plantation and then explore the striking landscape at Smith's Reef.

To find where to stay, maps, reviews, and other tourist information, read Providenciales trip itinerary builder site.

Traveling by flight from Punta Cana to Providenciales takes 5 hours. The time zone difference moving from Atlantic Standard Time (AST) to Eastern Standard Time (EST) is minus 1 hour. In October, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing by early afternoon on the 10th (Sun) to allow enough time to travel to Culebra.

Things to do in Providenciales

Parks · Nature · Wildlife · Beaches

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.
On the 11th (Mon), kick back and relax at Playa Zoni and then head off the coast to Culebrita. On the 12th (Tue), you'll have a packed day of sightseeing: kick back and relax at Flamenco Beach.

To find more things to do, photos, traveler tips, and other tourist information, use the Culebra travel route site.

You can do a combination of flight and ferry from Providenciales to Culebra in 9.5 hours. You'll lose 1 hour traveling from Providenciales to Culebra due to the time zone difference. In October, plan for daily highs up to 36°C, and evening lows to 30°C. Wrap up your sightseeing on the 12th (Tue) to allow time to fly to Isla de Vieques.

Things to do in Culebra

Parks · Beaches · Outdoors · Nature

Isla de Vieques, Puerto Rico

— 2 nights

Isla Nena

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.
Start off your visit on the 13th (Wed): take in the waterfront at Malecon and then tour the pleasant surroundings at Balneario Sun Bay. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Playa La Chiva and then stroll through Playa Caracas.

To find maps, where to stay, reviews, and other tourist information, use the Isla de Vieques online trip maker.

Traveling by combination of flight and taxi from Culebra to Isla de Vieques takes 3.5 hours. Alternatively, you can fly; or ride a ferry. In October, daytime highs in Isla de Vieques are 36°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 14th (Thu) early enough to travel to East End.

Things to do in Isla de Vieques

Parks · Beaches · Outdoors

East End, U.S. Virgin Islands

— 2 nights
St.
On the 15th (Fri), stroll through Trunk Bay Beach and then contemplate the waterfront views at Leinster Bay. Here are some ideas for day two: kick back and relax at Coki Point Beach, admire nature's wide array of creatures at Coral World Ocean Park, and then enjoy the sand and surf at Magens Bay.

To see other places to visit, more things to do, traveler tips, and more tourist information, refer to the East End trip itinerary planning website.

Do a combination of flight and taxi from Isla de Vieques to East End in 5.5 hours. In October, daily temperatures in East End can reach 36°C, while at night they dip to 30°C. Finish your sightseeing early on the 16th (Sat) so you can travel to Shoal Bay Village.

Things to do in East End

Parks · Beaches · Outdoors · Nature

Side Trips

Shoal Bay Village, Anguilla

— 2 nights
On the 17th (Sun), steep yourself in history at Wallblake House, stroll through Little Bay, and then stroll through Shoal Bay. Get ready for a full day of sightseeing on the 18th (Mon): tour the pleasant surroundings at Meads Bay, then explore the activities along Maundays Bay, and then tour the pleasant surroundings at Rendezvous Bay Beach.

For other places to visit, reviews, more things to do, and more tourist information, refer to the Shoal Bay Village route builder site.

Do a combination of taxi and flight from East End to Shoal Bay Village in 5 hours. Alternatively, you can do a combination of taxi, flight, and ferry. October in Shoal Bay Village sees daily highs of 36°C and lows of 28°C at night. Cap off your sightseeing on the 18th (Mon) early enough to catch the ferry to Simpson Bay.

Things to do in Shoal Bay Village

Parks · Beaches · Outdoors · Nature

Side Trips

Simpson Bay, St. Maarten-St. Martin

— 2 nights
Simpson Bay offers luxury resort living and good access to the main areas of the island.
Kick off your visit on the 19th (Tue): get some thrills on the water with a speed boat tour and then kick back and relax at Dawn Beach. Get ready for a full day of sightseeing on the 20th (Wed): stroll through Maho Beach, explore the activities along Mullet Bay Beach, and then try to win big at Casino Royale.

Plan a Simpson Bay trip in moments using our itinerary builder.

You can ride a ferry from Shoal Bay Village to Simpson Bay in 1.5 hours. Another option is to fly. In October, daytime highs in Simpson Bay are 36°C, while nighttime lows are 31°C. Wrap up your sightseeing on the 20th (Wed) to allow time to fly back home.

Things to do in Simpson Bay

Outdoors · Parks · Beaches · Tours

Side Trips