16 days in Caribbean Itinerary

Created using Inspirock Caribbean trip itinerary planner
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Fly
1
Punta Cana, Dominican Republic
— 3 nights
Fly to Beef Island, Ferry to Cruz Bay
2
Cruz Bay, U.S. Virgin Islands
— 3 nights
Ferry to Red Hook, St Thomas, Taxi to Charlotte Amalie
3
Charlotte Amalie, U.S. Virgin Islands
— 1 night
Fly to Anguilla, Ferry to Simpson Bay
4
Simpson Bay, St. Maarten-St. Martin
— 2 nights
Fly
5
Bridgetown, Barbados
— 4 nights
Fly
6
Oranjestad, Aruba
— 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.
You'll get in some beach time at Bavaro Beach and Juanillo Beach. You'll explore the less-touristy side of things at Hoyo Azul and Ocean Adventures Punta Cana. Venture out of the city with trips to Bayahibe (Nature & Wildlife Tours & Speed Boats Tours). There's more to do: stop by HARRISON'S Fine Caribbean Jewelers.

To see where to stay, photos, traveler tips, and other tourist information, go to the Punta Cana attractions planner.

Portland, USA to Punta Cana is an approximately 13.5-hour flight. The time zone difference moving from Pacific Standard Time (PST) to Atlantic Standard Time (AST) is 4 hours. Traveling from Portland in May, you will find days in Punta Cana are a bit warmer (86°F), and nights are warmer (75°F). Cap off your sightseeing on the 3rd (Sat) early enough to travel to Cruz Bay.
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Cruz Bay, U.S. Virgin Islands — 3 nights

Love City

The gateway to the island of Saint John, Cruz Bay represents the island's largest town, port, and commercial center.
Escape the urban bustle at Trunk Bay Beach and Maho Bay Beach. You'll explore the less-touristy side of things at Kayaking & Canoeing and Salt Pond Bay. And it doesn't end there: kick back and relax at Hawksnest Beach, stroll through Cinnamon Bay Beach, examine the collection at Cinnamon Bay Archeology Museum & Lab, and look for gifts at Bamboo Studio.

To find maps, ratings, reviews, and tourist information, read Cruz Bay trip planner.

You can do a combination of flight and ferry from Punta Cana to Cruz Bay in 6 hours. In June, daytime highs in Cruz Bay are 89°F, while nighttime lows are 79°F. Cap off your sightseeing on the 6th (Tue) early enough to travel to Charlotte Amalie.
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Charlotte Amalie, U.S. Virgin Islands — 1 night

Duty-free Capital of the World

One of the most visited cruise ship destinations in the Caribbean, the town of Charlotte Amalie is known around the world for its duty-free jewelry, perfume, and liquor shops.
Kick off your visit on the 7th (Wed): kick back and relax at Magens Bay and then surround yourself with nature on The VI Cat.

To see other places to visit, maps, and other tourist information, read Charlotte Amalie day trip website.

Do a combination of ferry and taxi from Cruz Bay to Charlotte Amalie in 1.5 hours. Alternatively, you can ride a ferry. June in Charlotte Amalie sees daily highs of 89°F and lows of 79°F at night. Finish up your sightseeing early on the 7th (Wed) so you can travel to Simpson Bay.
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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 8th (Thu): contemplate the waterfront views at Mullet Bay Beach, then stroll through Maho Beach, then examine the collection at Yoda Guy Movie Exhibit, and finally see some colorful creatures with a scuba or snorkeling tour. Here are some ideas for day two: stop by Joe's Jewelry and then get a dose of the wild on a nature and wildlife tour.

To see ratings and more tourist information, read Simpson Bay trip maker app.

You can do a combination of flight and ferry from Charlotte Amalie to Simpson Bay in 4 hours. Other options are to do a combination of flight and ferry; or fly. In June, daytime highs in Simpson Bay are 86°F, while nighttime lows are 79°F. Wrap up your sightseeing on the 9th (Fri) early enough to fly to Bridgetown.
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Bridgetown, Barbados — 4 nights

Bridgetown is the capital and largest city of Barbados. You'll explore the less-touristy side of things at Carlisle Bay and Bathsheba Beach. Get some cultural insight at Scuba & Snorkeling and Andromeda Botanic Gardens. You'll find plenty of places to visit near Bridgetown: Bottom Bay (in Saint Philip Parish) and Crane Beach (in Union Hall). There's much more to do: enjoy the sand and surf at Dover Beach, take in nature's colorful creations at Hunte's Gardens, Head underground at Harrison's Cave., and sample the fine beverages at Mount Gay Visitor Centre.

For maps, photos, and tourist information, use the Bridgetown trip itinerary maker.

Traveling by flight from Simpson Bay to Bridgetown takes 7.5 hours. In June, daytime highs in Bridgetown are 86°F, while nighttime lows are 78°F. Wrap up your sightseeing by early afternoon on the 13th (Tue) to allow enough time to fly to Oranjestad.
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Oranjestad, Aruba — 2 nights

When vacationing on Aruba, don't miss taking a tour of Oranjestad, the capital of the small Caribbean island.
On the 14th (Wed), take in the dramatic natural features at Natural Pool, then see the vivid underwater world at Baby Beach, and then enjoy the sand and surf at Arashi Beach.

To see reviews and tourist information, you can read our Oranjestad online day trip planner.

Traveling by flight from Bridgetown to Oranjestad takes 9.5 hours. Expect a daytime high around 90°F in June, and nighttime lows around 80°F. Wrap up your sightseeing by early afternoon on the 15th (Thu) to allow enough time to fly back home.
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Find places to stay Jun 13 — 15:
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