60 days in Caribbean Itinerary

Created using Klarna Trips Caribbean vacation planner
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1
George Town, Cayman Islands
— 6 nights
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2
Oranjestad, Aruba
— 6 nights
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3
Willemstad, Curacao
— 5 nights
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4
Bridgetown, Barbados
— 7 nights
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5
Simpson Bay, St. Maarten-St. Martin
— 4 nights
Fly to Beef Island, Ferry to East End
6
East End, U.S. Virgin Islands
— 4 nights
Ferry
7
Cruz Bay, U.S. Virgin Islands
— 7 nights
Ferry to Red Hook, St Thomas, Fly to Isla de Vieques
8
Isla de Vieques, Puerto Rico
— 5 nights
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9
Punta Cana, Dominican Republic
— 7 nights
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10
Providenciales, Turks and Caicos
— 8 nights
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George Town, Cayman Islands — 6 nights

Bring the kids along to Scuba & Snorkeling and Smith's Barcadere. Get in touch with nature at Starfish Point and Spotts Beach.

To find reviews, more things to do, where to stay, and other tourist information, go to the George Town tour itinerary planner.

Austin, USA to George Town is an approximately 8.5-hour flight. Traveling from Austin to George Town, you'll lose 1 hour due to the time zone difference. Expect a bit cooler weather when traveling from Austin in June: highs in George Town hover around 88°F, while lows dip to 79°F. Wrap up your sightseeing by early afternoon on the 17th (Sat) to allow time for the flight to Oranjestad.
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Oranjestad, Aruba — 6 nights

Take a break from the city and head to Eagle Beach and Palm Beach. Bring the kids along to Baby Beach and JADS Dive Center. There's still lots to do: stroll through Boca Cataavlina, see Off-Road Tours, enjoy the sand and surf at Malmok Beach, and view the masterpieces at Purely Aruban Artwork.

To find traveler tips, where to stay, reviews, and tourist information, you can read our Oranjestad trip builder website.

You can fly from George Town to Oranjestad in 9.5 hours. You'll lose 1 hour traveling from George Town to Oranjestad due to the time zone difference. June in Oranjestad sees daily highs of 90°F and lows of 80°F at night. Finish your sightseeing early on the 23rd (Fri) to allow enough time to fly to Willemstad.
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Willemstad, Curacao — 5 nights

You'll explore the less-touristy side of things at Kleine Knip and Playa Lagun. Get a sense of the local culture at Punda and Kura Hulanda Museum. Step out of Willemstad to go to Sabana Westpunt and see Playa Piskado/Playa Grandi, which is approximately 56 minutes away. Spend the 26th (Mon) exploring nature at Shete Boka Park.

To find where to stay, ratings, traveler tips, and other tourist information, you can read our Willemstad online travel route builder.

Fly from Oranjestad to Willemstad in 4 hours. In June, daily temperatures in Willemstad can reach 89°F, while at night they dip to 80°F. Finish your sightseeing early on the 28th (Wed) to allow enough time to fly to Bridgetown.
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Bridgetown, Barbados — 7 nights

Take a break from the city and head to Carlisle Bay and Nature & Wildlife Tours. Your itinerary includes some good beach time at Paynes Bay Beach and Bathsheba Beach. You'll find plenty of places to visit near Bridgetown: Harrismith Beach (in Bottom Bay), Bottom Bay (in Saint Philip Parish) and Crane Beach (in Union Hall).

To see where to stay, maps, ratings, and tourist information, you can read our Bridgetown trip itinerary website.

Traveling by flight from Willemstad to Bridgetown takes 7 hours. In June, daily temperatures in Bridgetown can reach 86°F, while at night they dip to 78°F. Wrap up your sightseeing on the 5th (Wed) early enough to fly to Simpson Bay.
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Simpson Bay, St. Maarten-St. Martin — 4 nights

You'll enjoy a bit of beach vacationing at Little Bay Beach and Great Bay Beach. Family-friendly places like Nature & Wildlife Tours and Cupecoy Bay Beach will thrill your kids. There's still lots to do: see some colorful creatures with a scuba or snorkeling tour, see the interesting displays at Yoda Guy Movie Exhibit, tour the pleasant surroundings at Baie Rouge, and head off the coast to Pinel Island.

To see other places to visit, reviews, maps, and more tourist information, read Simpson Bay trip itinerary website.

Fly from Bridgetown to Simpson Bay in 7.5 hours. In July in Simpson Bay, expect temperatures between 87°F during the day and 79°F at night. Finish your sightseeing early on the 9th (Sun) so you can travel to East End.
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East End, U.S. Virgin Islands — 4 nights

Bring the kids along to Magens Bay and Sapphire Beach. Relax by the water at Lindqvist Beach and Secret Harbour. There's lots more to do: discover the deep blue sea with a scuba or snorkeling tour, meet the residents at Coral World Ocean Park, look for gifts at House of Rajah Jewelers, and kick back and relax at Coki Point Beach.

To see reviews, ratings, photos, and more tourist information, use the East End trip planning site.

Traveling by combination of flight and ferry from Simpson Bay to East End takes 5 hours. Alternatively, you can do a combination of flight and taxi; or do a combination of ferry, flight, and taxi. In July, daytime highs in East End are 90°F, while nighttime lows are 80°F. Wrap up your sightseeing on the 13th (Thu) to allow time to ride a ferry to Cruz Bay.
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Cruz Bay, U.S. Virgin Islands — 7 nights

Love City

Family-friendly places like Trunk Bay Beach and Kayaking & Canoeing will thrill your kids. Your cultural itinerary includes sights like Annaberg Sugar Plantation and Cinnamon Bay Archeology Museum & Lab. Change things up with a short trip to Hansen Bay Beach in East End (about 36 minutes away). There's lots more to do: explore the activities along Hawksnest Beach, kick back and relax at Maho Bay Beach, stroll through Cinnamon Bay Beach, and get interesting insight from Tours.

For maps, traveler tips, ratings, and other tourist information, go to the Cruz Bay journey builder tool.

Traveling by ferry from East End to Cruz Bay takes an hour. In July, plan for daily highs up to 90°F, and evening lows to 80°F. Wrap up your sightseeing on the 20th (Thu) to allow time to travel to Isla de Vieques.
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Isla de Vieques, Puerto Rico — 5 nights

Isla Nena

We've included these beaches for you: Playa Caracas and Playa Navio. Eschew the tourist crowds and head to Balneario Sun Bay and Playa Pata Prieta. There's lots more to do: enjoy the sand and surf at Playa La Chiva, see some colorful creatures with a scuba or snorkeling tour, and tour the pleasant surroundings at Playa Media Luna.

To find more things to do, maps, and other tourist information, go to the Isla de Vieques visit planning site.

You can do a combination of ferry and flight from Cruz Bay to Isla de Vieques in 5.5 hours. Expect a daytime high around 88°F in July, and nighttime lows around 79°F. Cap off your sightseeing on the 25th (Tue) early enough to catch the flight to Punta Cana.
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Punta Cana, Dominican Republic — 7 nights

You'll get in some beach time at Juanillo Beach and Bavaro Beach. You'll explore the less-touristy side of things at Scuba & Snorkeling and Reserva Ecologica Ojos Indigenas. Change things up with these side-trips from Punta Cana: Bayahibe (Nature & Wildlife Tours & Horseback Riding Tours). And it doesn't end there: get interesting insight from Tours, tour the pleasant surroundings at Macao Beach, examine the collection at Aromas Museum, and relax and rejuvenate at Ocean Adventures Punta Cana.

To see other places to visit, more things to do, photos, and tourist information, go to the Punta Cana trip itinerary builder tool.

Fly from Isla de Vieques to Punta Cana in 6 hours. Alternatively, you can do a combination of ferry, taxi, and bus; or do a combination of ferry, taxi, and shuttle. In July, plan for daily highs up to 88°F, and evening lows to 77°F. Cap off your sightseeing on the 1st (Tue) early enough to catch the flight to Providenciales.
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Providenciales, Turks and Caicos — 8 nights

Eschew the tourist crowds and head to Scuba & Snorkeling and Chalk Sound. Get in touch with nature at Grace Bay Beach and Half Moon Bay. Next up on the itinerary: enjoy the sand and surf at Long Bay Beach, make a trip to Leeward Beach, stroll through Coral Gardens Reef, and explore the gorgeous colors at Smith's Reef.

To see reviews, traveler tips, ratings, and other tourist information, read our Providenciales trip planner.

You can fly from Punta Cana to Providenciales in 5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Punta Cana to Providenciales. Expect a daytime high around 90°F in August, and nighttime lows around 81°F. On the 9th (Wed), wrap the sightseeing up by early afternoon so you can fly back home.
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