Season 5

Steve and Sue have worked for the same company for decades, with Sue working long overnight shifts that take a toll on her. Now the couple is ready to take on a new lifestyle in sunny St. Thomas. The couple wants a condo with an ocean view, amenities like a pool, and great outdoor space to finally enjoy the good life they're worked so hard to achieve. They've enlisted agent Karen Korsgren to help them find the perfect place close to the beach.

Atlanta-based Nicole and Michael are tired of spending their life sitting in traffic and want more time together in the sun and sand. Luckily, they have the flexibility to move their two home-run businesses to Placencia, Belize and fulfill their dream of a healthier outdoor lifestyle. With real estate broker Charmaine Voss, Michael and Nicole search for a home where they can find the perfect work-life balance.

Jerry and Michael have spent the majority of their lives in the Midwest and have had it with the brutal winters. The distance to the ocean and limited months of warm weather have been a struggle since they love to sail. They've dreamed of pursuing this passion on St. Thomas by opening up a charter sailing business. Now ready to start a new life in the Caribbean, they're working with real estate agent Kerstin McConnell to find their oceanfront condo.

Neil, Amber, and their son Ian have been living in Siesta Key, Florida and feel it's become too populated and expensive. While traveling, they discovered Vieques, Puerto Rico and fell in love with the unpopulated beaches and the outdoor lifestyle. Neil and Amber are excited to raise their son on a bilingual island and live a more relaxing lifestyle. With the help of real estate agent Gustavo Marin, they hope to find their new Caribbean home.

Brian and Mary have worked their whole lives through the snowy winters in Maryland to save enough to resettle on Ambergris Caye in Belize. Now ready to make the move, they're excited to work with real estate broker Daniel Hartin to find a new home on the ocean--ideally one that comes with a small business that will enable them to share their new island lifestyle with visitors.

Jen has spent her life enduring the cold winters of Pittsburgh. Now that her two sons are grown and out of the house, she's ready to uproot her life and move to a warmer climate. After traveling to Vieques with a friend, she fell in love with the friendly people and beautiful scenery. She's decided to start over by finding a new job and a new house in this tropical paradise. With her best friend Jill and broker Lin Wetherby, Jen will have lots of help finding her dream in Puerto Rico.

Eunice met Carlos in the Dominican Republic on a vacation and the two fell in love. Carlos followed Eunice back to Boston and after 20 years of living in the cold, it's time to bring Eunice back to his Caribbean homeland. The move is an exciting one since Carlos is a chef and is planning on opening a restaurant. With the help of agent Alma Arellano, Carlos and Eunice hope to find their tropical home.

With three daughters on the verge of adulthood, Minnesota parents Norm and Tami are finding it difficult to keep their family together. They and the girls have a love for the water and sunshine and hate long winters, so Norm and Tami know that a move to Placencia, Belize is just what the family needs. With the help of their oldest daughter, Mackenzie, and broker Boris Mannsfeld, they hope to find an oceanfront home that the girls will come back to for years to come.

Kenny and Morgan just got married after spending two years dating long-distance. Both avid surfers, they fell in love with Puerto Rico when they vacationed there. After eloping recently, they'll be moving in together for the first time when they find their new house in Aguada. Broker Miggie Hernandez will guide the young couple as they search for a place close to the beach so they can spend their days surfing.

Maruf and Sonal's three kids are off to college and they're contemplating a move to St. Maarten. Both have worked very hard and are finally ready to buy a piece of property on the beach with room for their entire extended family to visit and enjoy. Arun Jagtiani of Island Real Estate is there to help them every step of the way as they criss-cross the Dutch side of the island in search of their dream home.

Andrew and Kelly are constantly busy making over the homes of clients in their New Jersey-based business. Now, they want to escape to St. John and find their dream home, a fixer-upper they can make their very own. Eric Bauman of USVI Sotheby's International Realty helps the couple search the lush green hillsides of St. John to find a home with enough land to expand, enough room for guests, and beautiful views.

When Jeff and Stephen met a decade ago they bonded over their hatred of Canadian winters. The couple quickly began researching locations with great weather and no hurricanes and discovered Aruba. They were sold as soon as they stepped off the plane. Real estate agent Brad Croes is on hand to help Stephen and Jeff find the perfect home on Aruba with both room for guests and a pool.

Karin is a native New Yorker and a successful writer who can work from anywhere in the world. So when she came to Las Terrenas for a dance festival, she knew she wanted to leave the rat race behind for the most beautiful spot in the Dominican Republic. Her son Dylan has made the trip south to help her choose the perfect condo with open living, a pool, and an extra bedroom for guests. With the help of broker Jesus Iturralde, Karin knows she'll find the perfect place to dance the night away.

When they first visited St. Thomas on a cruise many years ago, Kenny and Sheila noticed the U.S. courthouse on the island and Kenny, a public defender, realized he could move his family to a tropical paradise and keep his job. With a large blended family of four kids, plus Sheila's parents, the couple needs to find a house big enough for everyone, plus room for a pool and a gorgeous view. St. Thomas native Kerstin McConnell is up to the challenge of finding them the perfect home within their budget.