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Beach Day

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A couple of born-and-bred New Yorkers fell in love with St. John and its year-round swimming nine years ago; they have sold their bungalow on Long Island and plan to start a bed and breakfast on the tropical island.

Caribbean Life

Working Less and Living More on St. John

A scuba-loving couple moves from Houston, Texas, to Honduras after falling in love with Utila after their first visit; they're excited to make the island their permanent home and their price range gives them many options.

Diving Into Utila

A couple that fell in love with Vieques, Puerto Rico, 30 years ago is ready to buy a home of their own on the island; they hope to find a home with plenty of space to entertain family and friends when they come to visit.

Keeping Vieques a Family Tradition

A New York City lawyer is ready to move back to the US Virgin Islands to be closer to her family and friends; when a career opportunity on St. Thomas presents itself, it's one she simply cannot turn down.

St. Thomas Bound

A family is ready to trade in the monotony of their day-to-day life in northern Virginia for the rich Caribbean culture of Aruba; Dad and the kids remain stateside while mom looks for the perfect home for her family to start a new chapter.

Starting Over in Aruba

Two kids with extremely busy parents in Inner Harbor, Baltimore, hope a change of scenery will inspire Mom and Dad to be more adventurous; the family wants to find a house with amazing beach views and rental potential on Vieques in Puerto Rico.

Stepping Out of the Comfort Zone on Vieques

A couple of island renters are ready to become island homeowners on St. John, US Virgin Islands; they love boating, scuba diving and snorkeling, so they feel that planting roots on the island will benefit their water sport company.

Owning the Dream in St. John

A couple has lived their whole lives in Minnesota but are ready for a warmer climate; after visiting the Caribbean several times, they found Roatan and knew it was the right fit.

Finding Warmer Weather on Roatan

After meeting in Grand Cayman, a pair of accountants are ready to find a place to settle down together; they both love living in the Caribbean, and a new job has given them the option of moving to St. Croix, US Virgin Islands.

St. Croix is the Bee's Knees

After returning to the U.S. for a job offer, a California family realizes Aruba is where they are meant to be; they decide to move back and settle down permanently on the island.

Replanting Roots on Aruba

A couple is ready to escape their stressful commutes in California and fulfill their dream of moving to St. John; they hope to find a home with the potential to generate a rental income.

Renting St. John

A California couple is tired of busy city life and wants a fresh start in the Caribbean with a home on the water; they've spent three years searching for the perfect location and finally discovered Roatan, a small island in Honduras.

Jumping Feet First Into Roatan

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S11 E3 | Jumping Feet First Into Roatan