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- Season 1 2014-01-01
- Season 2 2015-01-01
- Season 3 2015-03-01
- Season 4 2016-01-01
- Season 5 2016-02-21
- Season 6 2016-09-11
- Season 7 2017-01-01
- Season 8 2017-03-05
- Season 9 2017-07-16
- Season 10 2017-09-03
- Season 11 2018-04-08
- Season 12 2018-07-15
- Season 13 2018-09-02
- Season 14 2018-10-21
- Season 15 2019-01-01
- Season 16 2019-03-24
- Season 17 2019-05-19
- Season 18 2019-10-20
- Season 19 2020-02-12
- Season 20 2020-05-03
Season 20 Episode
- Season 5 Soaring Above St. Thomas
- Season 5 A Change of Pace in Placencia
- Season 5 Setting Sail for St. Thomas
- Season 5 Swapping Florida For Vieques
- Season 5 A New Beginning In Belize
- Season 5 Starting Over In Vieques
- Season 5 Back to the Dominican Republic
- Season 5 A Family That Moves Together
- Season 5 New Adventures In Puerto Rico
- Season 5 Unwinding In St. Maarten
- Season 5 Branching Out In St. John
- Season 5 Ride Like The Wind On Aruba
- Season 5 New Chapter In The DR
- Season 5 Family Time On St. Thomas
Caribbean Life - Season 5 Episode 3 Setting Sail for St. Thomas
8.00 21 minutes 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.
