14 days in Caribbean Itinerary

Created using Inspirock Caribbean route planner
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1
Punta Cana, Dominican Republic
— 3 nights
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2
Providenciales, Turks and Caicos
— 2 nights
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3
Palm - Eagle Beach, Aruba
— 3 nights
Fly to St Maarten, Ferry to Shoal Bay Village
4
Shoal Bay Village, Anguilla
— 2 nights
Ferry to Sint Maarten, Fly to Bridgetown
5
Bridgetown, Barbados
— 2 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.
Spend a day of island exploring on the 3rd (Thu) at Saona Island. There's still lots to do: kick back and relax at Bavaro Beach, play a few rounds at Punta Espada Golf Course, explore the activities along Hoyo Azul, and look for gifts at Manuel cigarros.

To see photos, reviews, other places to visit, and other tourist information, use the Punta Cana trip planner.

Chennai, India to Punta Cana is an approximately 26-hour flight. The time zone difference when traveling from Chennai to Punta Cana is minus 9.5 hours. When traveling from Chennai in June, plan for little chillier days and about the same nights in Punta Cana: temperatures range from 36°C by day to 28°C at night. Finish your sightseeing early on the 4th (Fri) so you can fly to Providenciales.
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Find places to stay Jun 1 — 4:

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 5th (Sat): contemplate the long history of Cheshire Hall Plantation, tour the pleasant surroundings at Grace Bay Beach, then head off the coast to Little Water Cay, and finally get reinvigorated at Glow Fitness TCI.

For traveler tips, more things to do, and other tourist information, read Providenciales trip itinerary planning tool.

You can fly from Punta Cana to Providenciales in 5 hours. The time zone difference when traveling from Punta Cana to Providenciales is minus 1 hour. In June, plan for daily highs up to 37°C, and evening lows to 31°C. Wrap up your sightseeing by early afternoon on the 6th (Sun) to allow time for the flight to Palm - Eagle Beach.
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Find places to stay Jun 4 — 6:

Palm - Eagle Beach, Aruba — 3 nights

A long stretch of powdery white sand and aquamarine waters, Palm - Eagle Beach remains one of Aruba's most visited vacation spots.
Take a break from Palm - Eagle Beach with a short trip to Baby Beach in San Nicolas, about 48 minutes away. The adventure continues: stroll through Eagle Beach, enjoy the sea views from California Lighthouse and Sasariwichi Dunes, kick back and relax at Palm Beach, and experience rural life at Aruba Ostrich Farm.

For reviews, traveler tips, more things to do, and more tourist information, use the Palm - Eagle Beach online itinerary planner.

Getting from Providenciales to Palm - Eagle Beach by flight takes about 10.5 hours. The time zone difference moving from Eastern Standard Time (EST) to Atlantic Standard Time (AST) is 1 hour. June in Palm - Eagle Beach sees daily highs of 38°C and lows of 31°C at night. On the 9th (Wed), wrap the sightseeing up by early afternoon so you can travel to Shoal Bay Village.
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Find places to stay Jun 6 — 9:

Shoal Bay Village, Anguilla — 2 nights

Kick off your visit on the 10th (Thu): tour the pleasant surroundings at Meads Bay, explore the activities along Maundays Bay, and then stroll through Rendezvous Bay Beach. Get ready for a full day of sightseeing on the next day: stroll through Shoal Bay and then get a taste of the local shopping with Limin' Boutique.

To see maps, traveler tips, and tourist information, read our Shoal Bay Village holiday builder site.

Do a combination of flight and ferry from Palm - Eagle Beach to Shoal Bay Village in 9.5 hours. Alternatively, you can do a combination of flight, ferry, and taxi. In June, daytime highs in Shoal Bay Village are 36°C, while nighttime lows are 30°C. On the 11th (Fri), wrap the sightseeing up by early afternoon so you can travel to Bridgetown.
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Find places to stay Jun 9 — 11:

Bridgetown, Barbados — 2 nights

Bridgetown is the capital and largest city of Barbados. Kick off your visit on the 12th (Sat): examine the collection at Sunbury Plantation House, enjoy the sand and surf at Bottom Bay, then steep yourself in history at Andromeda Botanic Gardens, then take in nature's colorful creations at Hunte's Gardens, and finally Head underground at Harrison's Cave..

For where to stay, maps, and other tourist information, go to the Bridgetown day trip tool.

You can do a combination of ferry and flight from Shoal Bay Village to Bridgetown in 8.5 hours. Alternatively, you can do a combination of taxi, ferry, and flight; or fly. In June, daytime highs in Bridgetown are 35°C, while nighttime lows are 30°C. Wrap up your sightseeing by early afternoon on the 13th (Sun) to allow enough time to fly back home.
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Find places to stay Jun 11 — 13: