May 3, 2020
A newlywed couple are on the hunt for a different home on Anguilla; they love the view from their current house, but they want something more updated that offers privacy and the potential to expand their family.


We follow families as they leave the mainland behind and head to the Caribbean to live on island time. Join their search for an affordable slice of heaven, touring gorgeous homes on white sandy beaches. You don't have be rich to live in paradise!
Browse every episode and jump into details.
May 3, 2020
A newlywed couple are on the hunt for a different home on Anguilla; they love the view from their current house, but they want something more updated that offers privacy and the potential to expand their family.
Aug 9, 2020
A couple plans to practise law on the island of St. Croix and looks for a home with a yard for their puppies. They also want at least two bedrooms and a private casita to provide rental income, along with a beautiful scenic view.
Aug 9, 2020
A father and son are leaving the snow in Canada behind for the sunny island of St. Maarten; they're looking for a studio or one-bedroom condo that offers scenic views, a swimming pool and is located near the action close to town.
Aug 16, 2020
A Texas couple wants to live a stress-free life on the quiet island of St. John; he'd prefer a stand-alone home so their dog, Barley, has room to run around, but she loves the idea of a condo where the maintenance is taken care of.
Aug 16, 2020
A real estate agent from California is fulfilling her dream by moving to Honduras; finding a home on beautiful West Bay Beach is her top priority, but she knows the market in that area is very competitive.
Aug 23, 2020
A Wisconsin couple is looking for their forever home down in sunny Roatan. They'd like to find a place with 3 bedrooms for the kids to come visit, and they both agree a scenic view is non-negotiable.
Aug 23, 2020
After getting engaged on St. Croix, a Texas couple are making the island their new home; they would love the unit to be move-in ready, but with a wedding to pay for, they don't want to spend over $250,000 and would like a condo with ocean views.
Aug 30, 2020
A couple from Arizona is escaping the dry desert to live full-time on the beautiful island of Roatan. He can't wait to work from their new home, while she plans to start a mermaid school on the island.
Aug 30, 2020
A young student from California is looking to purchase a home in Aruba that she can also rent out. Her mum is helping her with the purchase, and they're looking for a two bed house, close to town and beaches, ideally with a pool.
Sep 13, 2020
A couple from Rhode Island are ready to move to Vieques; their kids are grown and they're ready to set sail for adventures as they begin a new chapter; she wants a home with a view, but his concern is finding something that also has rental potential.
Sep 20, 2020
A father and son look for a condo on St. Thomas with at least two bedrooms and enough space for both of them to unwind; they're willing to compromise for a place that's move-in ready but would like to find a water view and pool.
Sep 20, 2020
After always focusing on their jobs and children, a couple look to have fun together on Aruba in a home with a pool and a view; as a general contractor, he wants to leave his tools behind, but she finds a project to be done in every property.
Sep 27, 2020
An adventurous couple relocates to St. Croix to open a small bed and breakfast. Since he's a chef, he wants an updated kitchen, and she is looking for a water view to enjoy a more relaxed lifestyle.
Sep 27, 2020
A couple from Massachusetts wants to be able to enjoy boating 365 days a year on Utila. She's hoping to find a large home with room for their five kids, while he's focused on finding a waterfront property.
Quick answers about this season's release timeline and episode lineup.
Caribbean Life Season 20 premiered on May 3, 2020.
Caribbean Life Season 20 has 14 episodes.
The season opens with Season 20 Episode 1, "Cooking Up a New Chapter on Anguilla". It aired on May 3, 2020.
Go to Season 20 Episode 1