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!
| Title | Air Date | Duration | ||
|---|---|---|---|---|
| Season 1 | Episode 1 | A family from St. Louis looks for their dream home on St. Croix | 2014-01-01 | 30 min |
| Season 1 | Episode 2 | Settling Down in St. Croix | 2014-01-01 | 30 min |
| Season 1 | Episode 3 | A Couple Moves from Cold Connecticut to Sunny Sint Maarten | 2014-03-30 | 30 min |
| Season 1 | Episode 4 | So Long Vermont, Hola Vieques | 2014-03-30 | 30 min |
| Season 1 | Episode 5 | From New York City to Puerto Rico | 2014-04-06 | 30 min |
| Season 1 | Episode 6 | Two DJs Feel the Beat in Sunny Sint Maartin | 2014-04-06 | 30 min |
| Season 1 | Episode 7 | From Chicago to Puerto Rico | 2014-04-13 | 30 min |
| Season 1 | Episode 8 | To the Dominican Republic | 2014-04-13 | 30 min |
| Season 1 | Episode 9 | Minnesota to the Dominican Republic | 2014-04-20 | 30 min |
| Season 1 | Episode 10 | From Minnesota to Vieques | 2014-04-20 | 30 min |
| Season 1 | Episode 11 | From Alberta to St. Lucia | 2014-04-27 | 30 min |
| Season 1 | Episode 12 | Turks and Caicos, Hurrah! | 2014-05-04 | 30 min |
| Season 1 | Episode 13 | Moving out of Nebraska, for island life of Turks and Caicos | 2014-05-11 | 30 min |
| Season 1 | Episode 14 | From freezing Canada to the dream of a lifetime in Turks and Caicos | 2014-05-11 | 30 min |
| Season 2 | Episode 1 | Calming Down on St. Croix | 2015-01-01 | 30 min |
| Season 2 | Episode 2 | Following Our Hearts to Honduras | 2015-01-01 | 30 min |
| Season 2 | Episode 3 | Leaving West Virginia for St. Croix | 2015-01-04 | 30 min |
| Season 2 | Episode 4 | Starting a New Business in Panama | 2015-01-04 | 30 min |
| Season 2 | Episode 5 | Getting Real in Bocas del Toro | 2015-01-11 | 30 min |
| Season 2 | Episode 6 | Trading Snow for Sun in Puerto Rico | 2015-01-11 | 30 min |
| Season 2 | Episode 7 | Starting a Family in Puerto Rico | 2015-01-18 | 30 min |
| Season 2 | Episode 8 | Living the Caribbean Life on St. Croix | 2015-01-18 | 30 min |
| Season 2 | Episode 9 | Living the Dream Life in Honduras | 2015-01-25 | 30 min |
| Season 2 | Episode 10 | A Pennsylvania family moves to Puerto Rico for culture, Sun and Local Cuisine | 2015-01-25 | 30 min |
| Season 2 | Episode 11 | A New Job and a New Life in Puerto Rico | 2015-02-08 | 30 min |
| Season 2 | Episode 12 | Goodbye, Canada. Hello, Honduras! | 2015-02-08 | 30 min |
| Season 2 | Episode 13 | Picture-Perfect in St. Croix | 2015-02-15 | 30 min |
| Season 2 | Episode 14 | Falling in Love with Bocas del Toro | 2015-02-15 | 30 min |
| Season 3 | Episode 1 | Taking a Chance on the Caymans | 2015-03-01 | 30 min |
| Season 3 | Episode 2 | Getting Back to My Roots on Barbados | 2015-03-01 | 30 min |
| Season 3 | Episode 3 | Homecoming on the Caymans | 2015-03-08 | 30 min |
| Season 3 | Episode 4 | Trading Texas for St. Thomas | 2015-03-08 | 30 min |
| Season 3 | Episode 5 | Living the Dream in the Dominican Republic | 2015-03-15 | 30 min |
| Season 3 | Episode 6 | Finding My Bliss on Barbados | 2015-03-15 | 30 min |
| Season 3 | Episode 7 | Building a Business in Cozumel | 2015-03-22 | 30 min |
| Season 3 | Episode 8 | Finding a Forever Home in St. John | 2015-03-22 | 30 min |
| Season 3 | Episode 9 | Seeking Success in the Dominican Republic | 2015-03-29 | 30 min |
| Season 3 | Episode 10 | Returning to My Roots on St. Maarten | 2015-03-29 | 30 min |
| Season 3 | Episode 11 | Staying Put in Playa Del Carmen | 2015-04-05 | 30 min |
| Season 3 | Episode 12 | A couple leaves the hustle of NYC to be their own bosses of a restaurant on St. John | 2015-04-05 | 30 min |
| Season 3 | Episode 13 | Following Our Dreams to Cozumel | 2015-04-12 | 30 min |
| Season 3 | Episode 14 | Shooting the Breeze in the Dominican Republic | 2015-04-12 | 30 min |
| Season 4 | Episode 1 | Trading Country Roads for Ocean Views | 2016-01-01 | 30 min |
| Season 4 | Episode 2 | Taking the Plunge in Jamaica | 2016-01-01 | 30 min |
| Season 4 | Episode 3 | Branching Out in the Bahamas | 2016-01-03 | 30 min |
| Season 4 | Episode 4 | Boating Around Bocas del Toro | 2016-01-03 | 30 min |
| Season 4 | Episode 5 | Bringing It All Back Home to the Caymans | 2016-01-10 | 30 min |
| Season 4 | Episode 6 | Finding My Passion in Utila | 2016-01-10 | 30 min |
| Season 4 | Episode 7 | Starting Over in Utila | 2016-01-17 | 30 min |
| Season 4 | Episode 8 | Seeking Sunnier Skies in St. Croix | 2016-01-17 | 30 min |
| Season 4 | Episode 9 | Opening Up in Bocas del Toro | 2016-01-24 | 30 min |
| Season 4 | Episode 10 | A Grand Home on Grand Cayman | 2016-01-24 | 30 min |
| Season 4 | Episode 11 | Buying in the Bahamas | 2016-01-31 | 30 min |
| Season 4 | Episode 12 | Desperately Seeking Sea Views in St. Croix | 2016-01-31 | 30 min |
| Season 4 | Episode 13 | A New Life in Negril | 2016-02-14 | 30 min |
| Season 4 | Episode 14 | A New Career on St. Croix | 2016-02-14 | 30 min |
| Season 5 | Episode 1 | A Change of Pace in Belize | 2016-02-21 | 30 min |
| Season 5 | Episode 2 | Starting Again in St. Thomas | 2016-02-21 | 30 min |
| Season 5 | Episode 3 | Setting Sail for St. Thomas | 2016-03-06 | 30 min |
| Season 5 | Episode 4 | Swapping Florida for Vieques | 2016-03-06 | 30 min |
| Season 5 | Episode 5 | A New Beginning in Belize | 2016-03-13 | 30 min |
| Season 5 | Episode 6 | Starting Over in Vieques | 2016-03-13 | 30 min |
| Season 5 | Episode 7 | Back to the Dominican Republic | 2016-03-20 | 30 min |
| Season 5 | Episode 8 | Big Move to Belize | 2016-03-20 | 30 min |
| Season 5 | Episode 9 | Newlywed Adventures in Aguada | 2016-03-27 | 30 min |
| Season 5 | Episode 10 | Find Paradise on St. Maarten | 2016-03-27 | 30 min |
| Season 5 | Episode 11 | Branching Out in St. John | 2016-04-03 | 30 min |
| Season 5 | Episode 12 | Ready to Entertain on Aruba | 2016-04-03 | 30 min |
| Season 5 | Episode 13 | Dancing in the Dominican Republic | 2016-04-10 | 30 min |
| Season 5 | Episode 14 | Family Time on St. Thomas | 2016-04-10 | 30 min |
| Season 6 | Episode 1 | Boating Life on St. Maarten | 2016-09-11 | 30 min |
| Season 6 | Episode 2 | Landing on St. Croix | 2016-09-11 | 30 min |
| Season 6 | Episode 3 | A Laid-Back Life on St. John | 2016-09-18 | 30 min |
| Season 6 | Episode 4 | Southern Charm on St. Croix | 2016-09-18 | 30 min |
| Season 6 | Episode 5 | Dreams Come True in Jamaica | 2016-09-25 | 30 min |
| Season 6 | Episode 6 | A New Business on St. John | 2016-09-25 | 30 min |
| Season 6 | Episode 7 | Living the St. Maarten Dream | 2016-10-02 | 30 min |
| Season 6 | Episode 8 | Changing Gears in Jamaica | 2016-10-02 | 30 min |
| Season 6 | Episode 9 | Finding Peace on Vieques | 2016-10-09 | 30 min |
| Season 6 | Episode 10 | Curing the Blues in Curacao | 2016-10-09 | 30 min |
| Season 6 | Episode 11 | Double the Fun on St. Croix | 2016-10-16 | 30 min |
| Season 6 | Episode 12 | Treasured Time in Roatan | 2016-10-16 | 30 min |
| Season 6 | Episode 13 | A Fruitful Life in Vieques | 2016-10-23 | 30 min |
| Season 6 | Episode 14 | A Curacao State of Mind | 2016-10-23 | 30 min |
| Season 7 | Episode 1 | Escaping to the Bahamas | 2017-01-01 | 30 min |
| Season 7 | Episode 2 | Texas BBQ on St. John | 2017-01-01 | 30 min |
| Season 7 | Episode 3 | A Dominican Dream Come True | 2017-01-08 | 30 min |
| Season 7 | Episode 4 | Homegrown Living on Utila | 2017-01-08 | 30 min |
| Season 7 | Episode 5 | New Beginnings in the Bahamas | 2017-01-15 | 30 min |
| Season 7 | Episode 6 | Monkeying Around on Roatan | 2017-01-15 | 30 min |
| Season 7 | Episode 7 | Slowing Down on Utila | 2017-01-22 | 30 min |
| Season 7 | Episode 8 | Beachfront on St. Thomas | 2017-01-22 | 30 min |
| Season 7 | Episode 9 | Raising a Family on Bonaire | 2017-01-29 | 30 min |
| Season 7 | Episode 10 | Starting Over on St. Thomas | 2017-01-29 | 30 min |
| Season 7 | Episode 11 | New Adventures in the DR | 2017-02-12 | 30 min |
| Season 7 | Episode 12 | New Experiences in the Bahamas | 2017-02-12 | 30 min |
| Season 7 | Episode 13 | Lessons Learned in Las Terrenas | 2017-02-19 | 30 min |
| Season 7 | Episode 14 | Diving Into Bonaire | 2017-02-19 | 30 min |
| Season 8 | Episode 1 | Dominican Dream Home | 2017-03-05 | 30 min |
| Season 8 | Episode 2 | Finding Zen in Nevis | 2017-03-05 | 30 min |
| Season 8 | Episode 3 | A New Business on Roatan | 2017-03-12 | 30 min |
| Season 8 | Episode 4 | Harmonizing in Providenciales | 2017-03-12 | 30 min |
| Season 8 | Episode 5 | Raising a Family on St. Croix | 2017-03-19 | 30 min |
| Season 8 | Episode 6 | Paradise in Bocas del Toro | 2017-03-19 | 30 min |
| Season 8 | Episode 7 | From the Farm to Nevis | 2017-03-26 | 30 min |
| Season 8 | Episode 8 | Diving Into a Simple Life on Roatan | 2017-03-26 | 30 min |
| Season 8 | Episode 9 | All That Jazz on St. Croix | 2017-04-02 | 30 min |
| Season 8 | Episode 10 | Melting the Stress Away in Utila | 2017-04-02 | 30 min |
| Season 8 | Episode 11 | Finding Peace in Las Terrenas | 2017-04-09 | 30 min |
| Season 8 | Episode 12 | Relaxing in Turks and Caicos | 2017-04-09 | 30 min |
| Season 8 | Episode 13 | Family Time on St. Croix | 2017-04-16 | 30 min |
| Season 8 | Episode 14 | A New Adventure in Panama | 2017-04-16 | 30 min |
| Season 9 | Episode 1 | Raising Two Boys on St. Croix | 2017-07-16 | 30 min |
| Season 9 | Episode 2 | Cowabunga Bocas | 2017-07-16 | 30 min |
| Season 9 | Episode 3 | Unwinding in Elbow Cay | 2017-07-23 | 30 min |
| Season 9 | Episode 4 | Finding a Fixer-Upper in the Dominican Republic | 2017-07-23 | 30 min |
| Season 9 | Episode 5 | NYC Days to Puerto Rico Nights | 2017-07-30 | 30 min |
| Season 9 | Episode 6 | Looking for Adventure in the Dominican Republic | 2017-07-30 | 30 min |
| Season 9 | Episode 7 | Trading Winter for Summer | 2017-08-06 | 30 min |
| Season 9 | Episode 8 | Rhode Island Family Looks to Ditch Winter Jackets for Scuba Gear in Bonaire | 2017-08-06 | 30 min |
| Season 9 | Episode 9 | Healthy Living on St. Croix | 2017-08-13 | 30 min |
| Season 9 | Episode 10 | Snowy Boston to Sunny Vieques | 2017-08-13 | 30 min |
| Season 9 | Episode 11 | Boating in Treasure Cay | 2017-08-20 | 30 min |
| Season 9 | Episode 12 | Quality of Life in Puerto Rico | 2017-08-20 | 30 min |
| Season 9 | Episode 13 | No Regrets on Bonaire | 2017-08-27 | 30 min |
| Season 9 | Episode 14 | A New Life in St. Croix | 2017-08-27 | 30 min |
| Season 10 | Episode 1 | New York City to Grand Cayman | 2017-09-03 | 30 min |
| Season 10 | Episode 2 | A New Chapter in Puerto Rico | 2017-09-03 | 30 min |
| Season 10 | Episode 3 | Empty Nesters Go Back Home | 2018-01-01 | 30 min |
| Season 10 | Episode 4 | Diving Into Roatan | 2018-01-01 | 30 min |
| Season 10 | Episode 5 | Taking Care of Business in Grand Cayman | 2018-02-25 | 30 min |
| Season 10 | Episode 6 | Seeking Seclusion on Roatan | 2018-02-25 | 30 min |
| Season 10 | Episode 7 | Starting Over in the Dominican Republic | 2018-03-11 | 30 min |
| Season 10 | Episode 8 | Finding Peace on St. John | 2018-03-11 | 30 min |
| Season 10 | Episode 9 | A New Job on St. Croix | 2018-03-18 | 30 min |
| Season 10 | Episode 10 | Elbow Room in Cabo Rojo | 2018-03-18 | 30 min |
| Season 10 | Episode 11 | All About the Kids in the Dominican Republic | 2018-03-25 | 30 min |
| Season 10 | Episode 12 | Fulfilling a Dream on St. John | 2018-03-25 | 30 min |
| Season 10 | Episode 13 | From Busy L.A. to Tranquil St. Thomas | 2018-04-01 | 30 min |
| Season 10 | Episode 14 | Returning Home to Puerto Rico | 2018-04-01 | 30 min |
| Season 11 | Episode 1 | St. John Nature Retreat | 2018-04-08 | 30 min |
| Season 11 | Episode 2 | Falling in Love with Aruba | 2018-04-08 | 30 min |
| Season 11 | Episode 3 | Jumping Feet First into Roatan | 2018-04-15 | 30 min |
| Season 11 | Episode 4 | Renting St. John | 2018-04-15 | 30 min |
| Season 11 | Episode 5 | Replanting Roots on Aruba | 2018-04-22 | 30 min |
| Season 11 | Episode 6 | St. Croix is the Bee's Knees | 2018-04-22 | 30 min |
| Season 11 | Episode 7 | Finding Warmer Weather on Roatan | 2018-04-29 | 30 min |
| Season 11 | Episode 8 | Owning the Dream in St. John | 2018-04-29 | 30 min |
| Season 11 | Episode 9 | Stepping Out of the Comfort Zone on Vieques | 2018-05-06 | 30 min |
| Season 11 | Episode 10 | Starting Over in Aruba | 2018-05-06 | 30 min |
| Season 11 | Episode 11 | St. Thomas Bound | 2018-05-13 | 30 min |
| Season 11 | Episode 12 | Keeping Vieques a Family Tradition | 2018-05-13 | 30 min |
| Season 11 | Episode 13 | Diving into Utila | 2018-05-20 | 30 min |
| Season 11 | Episode 14 | Working Less and Living More on St. John | 2018-05-20 | 30 min |
| Season 12 | Episode 1 | Grand Adventure on Grand Cayman | 2018-07-15 | 30 min |
| Season 12 | Episode 2 | Adios Miami, Hola Caribbean | 2018-07-15 | 30 min |
| Season 12 | Episode 3 | Finding Roatan by Accident | 2018-07-22 | 30 min |
| Season 12 | Episode 4 | Living the Dream in Bonaire | 2018-07-22 | 30 min |
| Season 12 | Episode 5 | California Flair in Panama | 2018-07-29 | 30 min |
| Season 12 | Episode 6 | Making a Deal in Utila | 2018-07-29 | 30 min |
| Season 12 | Episode 7 | Finding the Cay to Happiness on Utila | 2018-08-05 | 30 min |
| Season 12 | Episode 8 | Diving Into Bonaire | 2018-08-05 | 30 min |
| Season 12 | Episode 9 | Soaking in the Dominican Sun | 2018-08-12 | 30 min |
| Season 12 | Episode 10 | Working Hard While Hardly Working on Utila | 2018-08-12 | 30 min |
| Season 12 | Episode 11 | Going Coco Loco in Bocas | 2018-08-19 | 30 min |
| Season 12 | Episode 12 | Designing a New Life on Grand Cayman | 2018-08-19 | 30 min |
| Season 12 | Episode 13 | A Healthy Plan in Roatan | 2018-08-26 | 30 min |
| Season 12 | Episode 14 | Flying High in Cabarete | 2018-08-26 | 30 min |
| Season 13 | Episode 1 | Exploring New Terrain on Aruba | 2018-09-02 | 30 min |
| Season 13 | Episode 2 | Trading Scrubs for Wet Suits | 2018-09-02 | 30 min |
| Season 13 | Episode 3 | A Family Adventure | 2018-09-09 | 30 min |
| Season 13 | Episode 4 | A New Chapter in the Dominican Republic | 2018-09-09 | 30 min |
| Season 13 | Episode 5 | Return to Island Living in the Dominican Republic | 2018-09-16 | 30 min |
| Season 13 | Episode 6 | Island Dream in Bocas del Toro, Panama | 2018-09-16 | 30 min |
| Season 13 | Episode 7 | Tackling a Roatan Fixer-upper | 2018-09-23 | 30 min |
| Season 13 | Episode 8 | Positive Vibes on Turks and Caicos | 2018-09-23 | 30 min |
| Season 13 | Episode 9 | Bocas del Toro or Bust | 2018-09-30 | 30 min |
| Season 13 | Episode 10 | Flipping Over Eleuthera, Bahamas | 2018-09-30 | 30 min |
| Season 13 | Episode 11 | Exploring Reefs on Utila | 2018-10-07 | 30 min |
| Season 13 | Episode 12 | Mother-Daughter Hunt on Turks and Caicos | 2018-10-07 | 30 min |
| Season 13 | Episode 13 | Healthy Life in the Dominican Republic | 2018-10-14 | 30 min |
| Season 13 | Episode 14 | From the Big Apple to Aruba | 2018-10-14 | 30 min |
| Season 14 | Episode 1 | Raising a Family on St. John | 2018-10-21 | 30 min |
| Season 14 | Episode 2 | A Flip Flop Island for Flip Flop People | 2018-10-21 | 30 min |
| Season 14 | Episode 3 | Time to Relax on Roatan | 2018-10-28 | 30 min |
| Season 14 | Episode 4 | Slowing Down on Aruba | 2018-10-28 | 30 min |
| Season 14 | Episode 5 | Island Time, All the Time | 2018-11-04 | 30 min |
| Season 14 | Episode 6 | Taking the Family to Turks and Caicos | 2018-11-04 | 30 min |
| Season 14 | Episode 7 | Breaking a Sweat in Puerto Rico | 2018-11-11 | 30 min |
| Season 14 | Episode 8 | Heading Home to St. Thomas | 2018-11-11 | 30 min |
| Season 14 | Episode 9 | Sun and Serenity on Utila | 2018-11-18 | 30 min |
| Season 14 | Episode 10 | Rediscovering on Barbados | 2018-11-18 | 30 min |
| Season 14 | Episode 11 | Trading New England Cold for St. John Sun | 2018-11-25 | 30 min |
| Season 14 | Episode 12 | Historic Move to San Juan, Puerto Rico | 2018-11-25 | 30 min |
| Season 15 | Episode 1 | New Adventures on Roatan | 2019-01-01 | 30 min |
| Season 15 | Episode 2 | Trading Business Suits for Bathing Suits | 2019-01-01 | 30 min |
| Season 15 | Episode 3 | Reeling in the Good Life | 2019-01-27 | 30 min |
| Season 15 | Episode 4 | Kicking Back on St. Thomas | 2019-01-27 | 30 min |
| Season 15 | Episode 5 | From New York to St. Thomas | 2019-02-10 | 30 min |
| Season 15 | Episode 6 | Banana Pudding in Las Terrenas | 2019-02-10 | 30 min |
| Season 15 | Episode 7 | Working It Out | 2019-02-17 | 30 min |
| Season 15 | Episode 8 | From Pittsburgh to Paradise in Puerto Rico | 2019-02-17 | 30 min |
| Season 15 | Episode 9 | Utila or Bust | 2019-03-03 | 30 min |
| Season 15 | Episode 10 | Jetting All Over Vieques, Puerto Rico | 2019-03-03 | 30 min |
| Season 15 | Episode 11 | Building a New Life on St. Thomas | 2019-03-10 | 30 min |
| Season 15 | Episode 12 | Laid-back Life in Utila, Honduras | 2019-03-10 | 30 min |
| Season 15 | Episode 13 | A Place to Unwind | 2019-03-17 | 30 min |
| Season 15 | Episode 14 | From the Big Apple to the Small Island of Vieques, Puerto Rico | 2019-03-17 | 30 min |
| Season 15 | Episode 15 | The Couple That Bikes Together in St. Croix | 2019-03-24 | 30 min |
| Season 15 | Episode 16 | Back to Barbados | 2019-03-24 | 30 min |
| Season 16 | Episode 1 | Working to Be With Family in Puerto Rico | 2019-03-28 | 30 min |
| Season 16 | Episode 2 | Slowing Down in Anguilla | 2019-03-28 | 30 min |
| Season 16 | Episode 3 | Slimming Down in the Dominican Republic | 2019-03-31 | 30 min |
| Season 16 | Episode 4 | Beachside with a Cocktail | 2019-03-31 | 30 min |
| Season 16 | Episode 5 | Unplugging in Aruba | 2019-04-07 | 30 min |
| Season 16 | Episode 6 | Discovering a New Rhythm in the Dominican Republic | 2019-04-07 | 30 min |
| Season 16 | Episode 7 | Pulling Teeth for the Dominican Republic | 2019-04-14 | 30 min |
| Season 16 | Episode 8 | Feeling Salty on St. Thomas | 2019-04-14 | 30 min |
| Season 16 | Episode 9 | Revving Up for a New Life in Aruba | 2019-04-21 | 30 min |
| Season 16 | Episode 10 | Finding Solace on Roatan, Honduras | 2019-04-21 | 30 min |
| Season 16 | Episode 11 | Swinging Down to St. Maarten | 2019-04-28 | 30 min |
| Season 16 | Episode 12 | Open to New Adventures on Utila | 2019-04-28 | 30 min |
| Season 16 | Episode 13 | Family Time in Puerto Rico | 2019-05-02 | 30 min |
| Season 16 | Episode 14 | To Build or Not to Build in Aruba | 2019-05-02 | 30 min |
| Season 17 | Episode 1 | On the Hunt for Waterfront on St. Thomas | 2019-05-16 | 30 min |
| Season 17 | Episode 2 | Starting Fresh on Roatan | 2019-08-25 | 30 min |
| Season 17 | Episode 3 | Looking for the Water Trifecta | 2019-08-25 | 30 min |
| Season 17 | Episode 4 | From Atlanta to Vieques | 2019-09-01 | 30 min |
| Season 17 | Episode 5 | From Canada to Roatan | 2019-09-01 | 30 min |
| Season 17 | Episode 6 | Off the Beaten Path in St. Croix | 2019-09-08 | 30 min |
| Season 17 | Episode 7 | Relocating to Paradise | 2019-09-08 | 30 min |
| Season 17 | Episode 8 | From Maine to Puerto Rico | 2019-09-15 | 30 min |
| Season 17 | Episode 9 | Falling in Love with St. Croix | 2019-09-15 | 30 min |
| Season 17 | Episode 10 | Newlyweds in St. Croix | 2019-09-22 | 30 min |
| Season 17 | Episode 11 | Father and Son Bonding in Las Terrenas | 2019-09-22 | 30 min |
| Season 17 | Episode 12 | Blowing Out of Chicago | 2019-09-29 | 30 min |
| Season 17 | Episode 13 | Sunrise and Sunset on St. John | 2019-09-29 | 30 min |
| Season 18 | Episode 1 | Cracking a Smile on St. Croix | 2019-10-06 | 30 min |
| Season 18 | Episode 2 | Dreaming Big on St. John | 2019-10-06 | 30 min |
| Season 18 | Episode 3 | Classic Cocktails and New Adventures on the Beaches of Roatan | 2019-10-13 | 30 min |
| Season 18 | Episode 4 | Back Home to the Bahamas | 2019-10-13 | 30 min |
| Season 18 | Episode 5 | Testing New Waters in Sosua, Dominican Republic | 2019-10-20 | 30 min |
| Season 18 | Episode 6 | Living Among the Flora of Bocas del Toro, Panama | 2019-10-20 | 30 min |
| Season 18 | Episode 7 | A Ferry Ride to a Fairyland House on St. Thomas | 2019-10-27 | 30 min |
| Season 18 | Episode 8 | Seeking Room for Nine in Roatan, Honduras | 2019-10-27 | 30 min |
| Season 18 | Episode 9 | A Rendezvous with a View on St. John | 2019-12-14 | 30 min |
| Season 18 | Episode 10 | Taking a Bite out of the Bahamas | 2019-12-14 | 30 min |
| Season 18 | Episode 11 | Growing as a Family on St. Thomas | 2019-12-21 | 30 min |
| Season 18 | Episode 12 | Going Out on a Limb and Getting the Whole Tree in Bocas del Toro, Panama | 2019-12-21 | 30 min |
| Season 18 | Episode 13 | Moving Out of Your Comfort Zone in Roatan, Honduras | 2020-01-11 | 30 min |
| Season 18 | Episode 14 | New Adventures and Coco Locos in Samana, Dominican Republic | 2020-01-11 | 30 min |
| Season 19 | Episode 1 | Embracing the Sunshine in Sosua | 2020-02-12 | 30 min |
| Season 19 | Episode 2 | Beach Views or Bust on St. Croix | 2020-02-12 | 30 min |
| Season 19 | Episode 3 | And Baby Makes Three on St. Thomas | 2020-02-17 | 30 min |
| Season 19 | Episode 4 | All Aboard for a New Life on St. Maarten | 2020-02-17 | 30 min |
| Season 19 | Episode 5 | Strong Opinions and Strong Drinks on St. Maarten | 2020-03-31 | 30 min |
| Season 19 | Episode 6 | Checking in to a Life on St. Croix | 2020-03-31 | 30 min |
| Season 19 | Episode 7 | Bringing Southern Charm to Vieques, Puerto Rico | 2020-04-19 | 30 min |
| Season 19 | Episode 8 | Bringing the Family Home | 2020-04-19 | 30 min |
| Season 19 | Episode 9 | Working Out on the Beaches of Cabarete | 2020-04-26 | 30 min |
| Season 19 | Episode 10 | A New Life on Utila | 2020-04-26 | 30 min |
| Season 19 | Episode 11 | Family Time in the Sun on Vieques | 2020-05-03 | 30 min |
| Season 19 | Episode 12 | Finding a New Rhythm in Punta Cana, Dominican Republic | 2020-05-17 | 30 min |
| Season 19 | Episode 13 | Letting Loose in St. Thomas | 2020-05-17 | 30 min |
| Season 19 | Episode 14 | Paddling Into a New Life on St. Thomas | 2020-05-24 | 30 min |
| Season 20 | Episode 1 | Trading the Rat Race for the Beaches of St. Croix | 2020-08-09 | 30 min |
| Season 20 | Episode 2 | Searching for the Perfect Bachelor Pad on St. Maarten | 2020-08-09 | 30 min |
| Season 20 | Episode 3 | Pulling the Trigger and Ending a Three-Year Search on Roatan | 2020-08-16 | 30 min |
| Season 20 | Episode 4 | Debating Home vs. Condo on St. John | 2020-08-16 | 30 min |
| Season 20 | Episode 5 | Walking Down the Aisle and into A New Home on St. Croix | 2020-08-23 | 30 min |
| Season 20 | Episode 6 | Bringing the Family Home to Roatan | 2020-08-23 | 30 min |
| Season 20 | Episode 7 | Girls Just Want to Have Fun on Aruba | 2020-08-30 | 30 min |
| Season 20 | Episode 8 | Becoming a Mermaid on Roatan | 2020-08-30 | 30 min |
| Season 20 | Episode 9 | Trading Moguls for Water Skis | 2020-09-06 | 30 min |
| Season 20 | Episode 10 | Stepping Out of The Comfort Zone on Vieques | 2020-09-13 | 30 min |
| Season 20 | Episode 11 | Cooking Up a New Chapter on Anguilla | 2020-09-13 | 30 min |
| Season 20 | Episode 12 | Mating for Life Like Ostriches on Aruba | 2020-09-20 | 30 min |
| Season 20 | Episode 13 | A New Family Venture on St. Thomas | 2020-09-20 | 30 min |
| Season 20 | Episode 14 | Cooking Up a Bed and Breakfast on St. Croix | 2020-09-27 | 30 min |
| Season 20 | Episode 15 | Making a Splash on Utila | 2020-09-27 | 30 min |
