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| Episode | Episode Name | Air Date | | 1 | On the Hunt For Waterfront on St. Thomas | Sun May 19, 2019 | | 2 | Off the Beaten Path in St. Croix | Sun Sep 08, 2019 | | 3 | Relocating to Paradise | Sun Sep 08, 2019 | | 4 | Newlyweds in St. Croix | Sun Nov 17, 2019 | | 5 | Father and Son Bonding in Las Terrenas | Sun Nov 17, 2019 | | 6 | Dreaming Big on St. John | Sun Nov 24, 2019 | | 7 | Starting Fresh on Roatan | Sun Nov 24, 2019 | | 8 | From Maine to Puerto Rico | Sun Dec 01, 2019 | | 9 | Falling in Love With St. Croix | Sun Dec 01, 2019 | | 10 | Blowing Out of Chicago; Sunrise and Sunset on St. John | Sun Jun 07, 2020 | | 11 | Looking for the Water Trifecta | Sun Aug 02, 2020 | | 12 | From Atlanta to Vieques | Sun May 03, 2020 | | 13 | Blowing out of Chicago | Sun May 10, 2020 | | 14 | From Canada to Roatan | Sun May 10, 2020 |
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