Season 1 Season 1
14 ep
1
Dave and Julie - St. Croix
2014-01-01
2
Corinne and Patrick -St. Croix
2014-01-01
3
Margi and Jessi - Vieques
2014-03-30
4
Cliff and Janine - Sint Maarten
2014-03-30
5
Ona and Johnny - Sint Maarten
2014-04-06
6
From NYC to Puerto Rico
2014-04-06
7
David and Laurie - Dominican Republic
2014-04-13
8
Caroline and Omar -San Juan, Puerto Rico
2014-04-13
9
Carl and Janna - Vieques
2014-04-20
10
Karrin and John -Punta Cana
2014-04-20
11
Doris and Don From Alberta to St Lucia
2014-04-27
12
Neela and Jason -Turks and Caicos
2014-04-27
13
David and Jayne -Canada to Turks and Caicos
2014-05-11
14
Heidi and Steve -Turks and Caicos
2014-05-18
Season 2 Season 2
14 ep
1
Buck and Amy
2015-01-01
2
Lloyd and Michelle
2015-01-01
3
John and Janaea
2015-01-04
4
Billy and Deanna
2015-01-04
5
David and Arturo
2015-01-11
6
A Colorado Family Leaves Snowy Fort Collins
2015-01-11
7
Amy and Marc
2015-01-18
8
From the Desert to the Tropics of Isabella
2015-01-18
9
Michael and Tara
2015-01-25
10
Jay and Lavina
2015-01-25
11
Kacie and Casey
2015-02-08
12
JC and Felicia
2015-02-08
13
Matt and Kristy
2015-02-15
14
Scott and Lauren
2015-02-15
Season 3 Season 3
14 ep
1
Natasha and Collin
2015-03-01
2
Brian and Sarah
2015-03-01
3
From Texas to St. Thomas
2015-03-08
4
From California to the Caymans
2015-03-08
5
Bye Ontario, Hello Barbados
2015-03-15
6
Chuck and Alicia
2015-03-15
7
Erik and Samantha
2015-03-22
8
From New Mexico to Cozumel
2015-03-22
9
From D.C. to St. Maarten
2015-03-29
10
Canada to Dominican Republic
2015-03-29
11
Goodbye NYC, hello St. John
2015-04-05
12
Brad and Meredith
2015-04-05
13
Curtis and Eva
2015-04-12
14
Bill and Mary
2015-04-12
Season 4 Season 4
14 ep
1
Newlyweds taking The Plunge In Jamaica
2016-01-01
2
Country Roads to Ocean Views
2016-01-01
3
The Bahamas Beckons a Florida Couple
2016-01-03
4
Boating Around Bocas
2016-01-03
5
Finding Her Passion in Utila
2016-01-10
6
Bringing It All Back Home
2016-01-10
7
A Doctor and Nurse Take the Plunge in St. Croix
2016-01-17
8
Canadian Couple Seek Great Diving in Utila
2016-01-17
9
A Grand Home on Grand Cayman
2016-01-24
10
Opening Up in Bocas del Toro
2016-01-24
11
Desperately Seeking Sea Views
2016-01-31
12
Buying in the Bahamas
2016-01-31
13
A New Career On St. Croix
2016-02-14
14
A New Life In Negril
2016-02-14
Season 5 Season 5
14 ep
1
Soaring Above St. Thomas
2016-02-21
2
A Change of Pace in Placencia
2016-02-21
3
Setting Sail for St. Thomas
2016-03-06
4
Swapping Florida For Vieques
2016-03-06
5
A New Beginning In Belize
2016-03-13
6
Starting Over In Vieques
2016-03-13
7
Back to the Dominican Republic
2016-03-20
8
A Family That Moves Together
2016-03-20
9
New Adventures In Puerto Rico
2016-03-27
10
Unwinding In St. Maarten
2016-03-27
11
Branching Out In St. John
2016-04-03
12
Ride Like The Wind On Aruba
2016-04-03
13
New Chapter In The DR
2016-04-10
14
Family Time On St. Thomas
2016-04-10
Season 6 Season 6
14 ep
1
Boating Life On St. Maarten
2016-09-11
2
Landing on St. Croix
2016-09-11
3
A Laid-back life on St. John
2016-09-18
4
Southern Charm in St. Croix
2016-09-18
5
Dreams Come True in Jamaica
2016-09-25
6
A New Business On St. John
2016-09-25
7
St. Louis to St. Maarten
2016-10-02
8
Changing Gears in Jamaica
2016-10-02
9
Finding Peace On Vieques
2016-10-09
10
Curing The Blues In Curacao
2016-10-09
11
Moving Twins to St. Croix
2016-10-16
12
Treasured Time in Roatan
2016-10-16
13
Fruitful in Vieques
2016-10-23
14
A Curacao State Of Mind
2016-10-23
Season 7 Season 7
14 ep
1
A California Girl Escapes the City for the Bahamas
2017-01-01
2
Bringing the Best of Texas to the Virgin Islands
2017-01-01
3
A Dream Come True in the Dominican Republic
2017-01-08
4
Homegrown Living on Utila
2017-01-08
5
Monkeying Around on Roatan
2017-01-15
6
New Beginnings in the Bahamas
2017-01-15
7
Beachfront on St. Thomas
2017-01-22
8
Slowing Down on Utila
2017-01-22
9
Colorado Mom and Daughter Start New Life on St. Thomas
2017-01-29
10
Raising a Family on Bonaire
2017-01-29
11
Ditching the Desert for an Oceanfront Oasis
2017-02-12
12
New Adventures in the DR
2017-02-12
13
Diving Into Bonaire
2017-02-19
14
Lessons Learned in Las Terrenas
2017-02-19
Season 8 Season 8
14 ep
1
Room for Family in the D.R.
2017-03-05
2
Finding Zen in Nevis
2017-03-05
3
A New Business on Roatan
2017-03-12
4
Harmonizing in Providenciales
2017-03-12
5
Raising a Family on St Croix
2017-03-19
6
Paradise in Bocas Del Toro
2017-03-19
7
From the Farm to Nevis
2017-03-26
8
Diving Into A Simple Life On Roatan
2017-03-26
9
All That Jazz on St Croix
2017-04-02
10
Melting the Stress Away in Utila
2017-04-02
11
Peace in Las Terrenas
2017-04-09
12
Relaxing in Turks and Caicos
2017-04-09
13
Family Time on St Croix
2017-04-16
14
Beginning a New Adventure in Bocas Del Toro
2017-04-16
Season 9 Season 9
14 ep
1
Raising Two Boys on St. Croix
2017-07-16
2
Cowabunga Bocas
2017-07-16
3
Unwinding in Elbow Cay
2017-07-23
4
Finding a Fixer-Upper in the Dominican Republic
2017-07-23
5
NYC Days to Puerto Rico Nights
2017-07-30
6
Looking for Adventure in the Dominican Republic
2017-07-30
7
Trading Winter for Summer
2017-08-06
8
Rhode Island Family Looks to Ditch Winter Jackets
2017-08-06
9
Healthy Living on St. Croix
2017-08-13
10
Snowy Boston to Sunny Vieques
2017-08-13
11
Boating in Treasure Cay
2017-08-20
12
Quality of Life in Puerto Rico
2017-08-20
13
No Regrets on Bonaire
2017-08-27
14
A New Life in St. Croix
2017-08-27
Season 10 Season 10
14 ep
1
New York City to Grand Cayman
2017-09-03
2
A New Chapter in Puerto Rico
2017-09-03
3
Empty Nesters Go Back Home
2018-01-01
4
Diving Into Roatan
2018-01-01
5
Taking Care of Business in Grand Cayman
2018-02-25
6
Seeking Seclusion on Roatan
2018-02-25
7
Fresh Start in the Dominican Republic
2018-03-11
8
Finding Peace on St. John
2018-03-11
9
A New Job on St. Croix
2018-03-18
10
Elbow Room in Cabo Rojo
2018-03-18
11
All About the Kids in the Dominican Republic
2018-03-25
12
Fulfilling a Dream on St. John
2018-03-25
13
From Busy L.A. to Tranquil St. Thomas
2018-04-01
14
Returning Home to Puerto Rico
2018-04-01
Season 11 Season 11
14 ep
1
St John Nature Retreat
2018-04-08
2
Falling in Love With Aruba
2018-04-08
3
Jumping Feet First Into Roatan
2018-04-15
4
Renting St. John
2018-04-15
5
Replanting Roots on Aruba
2018-04-22
6
St Croix is the Bee's Knees
2018-04-22
7
Finding Warmer Weather on Roatan
2018-04-29
8
Owning the Dream in St John
2018-04-29
9
Stepping Out of the Comfort Zone on Vieques
2018-05-06
10
Starting Over in Aruba
2018-05-06
11
St Thomas Bound
2018-05-13
12
Keeping Vieques a Family Tradition
2018-05-13
13
Diving Into Utila
2018-05-20
14
Working Less and Living More on St. John
2018-05-20
Season 12 Season 12
14 ep
1
Adventure On Grand Cayman
2018-07-15
2
Adios Miami, Hola Caribbean
2018-07-15
3
Finding Roatan by Accident
2018-07-22
4
Living the Dream in Bonaire
2018-07-22
5
Replanting Roots on Aruba
2018-07-29
6
Making a Deal in Utila
2018-07-29
7
Finding the Cay to Happiness on Utila
2018-08-05
8
Diving Into Bonaire
2018-08-05
9
Soaking in the Dominican Sun
2018-08-12
10
Business And Leisure On Utila
2018-08-12
11
Going Coco Loco in Bocas
2018-08-19
12
A Stylish Life On Grand Cayman
2018-08-19
13
A Healthy Plan in Roatan
2018-08-26
14
Flying High in Cabarete
2018-08-26
Season 13 Season 13
14 ep
1
Exploring New Terrain on Aruba
2018-09-02
2
Trading Scrubs for Wet Suits
2018-09-02
3
A Family Adventure
2018-09-09
4
A New Chapter in the Dominican Republic
2018-09-09
5
Return To Island Living In The Dominican Republic
2018-09-16
6
Island Dream In Bocas Del Toro
2018-09-16
7
Tackling a Roatan Fixer-Upper
2018-09-23
8
Positive Vibes
2018-09-23
9
Bocas Del Toro or Bust
2018-09-30
10
Flipping Over Eleuthera
2018-09-30
11
Exploring Reefs on Utila
2018-10-07
12
Mother-Daughter Hunt
2018-10-07
13
Healthy Life In The Dominican
2018-10-14
14
From the Big Apple to Aruba
2018-10-14
Season 14 Season 14
14 ep
1
Raising a Family on St. John
2018-10-21
2
A Flip Flop Island for Flip Flop People
2018-10-21
3
Time to Relax on Roatan
2018-10-28
4
Slowing Down on Aruba
2018-10-28
5
Island Time, All the Time
2018-11-04
6
Taking the Family to Turks and Caicos
2018-11-04
7
Breaking a Sweat in Puerto Rico
2018-11-11
8
Heading Home to St. Thomas
2018-11-11
9
Sun and Serenity on Utila
2018-11-18
10
Rediscovering on Barbados
2018-11-25
11
Trading Cold For St. John Sun
2018-11-25
12
Historic Move to San Juan, Puerto Rico
2018-11-25
13
Building a New Life on St. Thomas
2019-03-10
14
Back to Barbados
2019-03-24
Season 15 Season 15
14 ep
1
New Adventures on Roatan
2019-01-01
2
Trading Business Suits for Bathing Suits
2019-01-01
3
Reeling in the Good Life
2019-01-27
4
Kicking Back on St. Thomas
2019-01-27
5
From New York to St. Thomas
2019-02-10
6
Banana Pudding in Las Terrenas
2019-02-10
7
Working It Out
2019-02-17
8
From Pittsburgh to Paradise in Puerto Rico
2019-02-17
9
Utila or Bust
2019-03-03
10
Jetting All Over Vieques, Puerto Rico
2019-03-03
11
Laid-Back Life in Utila, Honduras
2019-03-10
12
A Place to Unwind
2019-03-17
13
From the Big Apple to the Small Island of Vieques
2019-03-17
14
The Couple That Bikes Together in St. Croix
2019-03-24
Season 16 Season 16
14 ep
1
Working to Be With Family in Puerto Rico
2019-03-24
2
Slowing Down in Anguilla
2019-03-24
3
Slimming Down in the Dominican Republic
2019-03-31
4
Beachside With a Cocktail
2019-03-31
5
Unplugging in Aruba
2019-04-07
6
Discovering a New Rhythm in the Dominican Republic
2019-04-07
7
Pulling Teeth for the Dominican Republic
2019-04-14
8
Feeling Salty on St. Thomas
2019-04-14
9
Revving Up for a New Life in Aruba
2019-04-21
10
Finding Solace On Roatan Honduras
2019-04-21
11
Swinging Down to St. Maarten
2019-04-28
12
Open to New Adventures on Utila
2019-04-28
13
Family Time in Puerto Rico
2019-05-05
14
To Build or Not to Build in Aruba
2019-05-05
Season 17 Season 17
14 ep
1
On the Hunt for Waterfront on St. Thomas
2019-05-19
2
Off the Beaten Path in St. Croix
2019-09-08
3
Relocating to Paradise
2019-09-08
4
Newlyweds in St. Croix
2019-11-17
5
Father and Son Bonding in Las Terrenas
2019-11-17
6
Dreaming Big on St. John
2019-11-24
7
Starting Fresh on Roatan
2019-11-24
8
From Maine to Puerto Rico
2019-12-01
9
Falling in Love With St. Croix
2019-12-01
10
Blowing Out of Chicago; Sunrise and Sunset on St. John
2020-06-07
11
Looking for the Water Trifecta
2020-08-02
12
From Atlanta to Vieques
2020-05-03
13
Blowing out of Chicago
2020-05-10
14
From Canada to Roatan
2020-05-10
Season 18 Season 18
14 ep
1
Testing New Waters in Sosua, Dominican Republic
2019-10-20
2
Living Among the Flora of Bocas del Toro, Panama
2019-10-20
3
Classic Cocktails and New Adventures on the Beaches of Roatan
2019-12-08
4
Back Home to The Bahamas
2019-12-08
5
A Rendezvous With a View on St. John
2019-12-15
6
Taking a Bite out of the Bahamas
2019-12-15
7
Growing as a Family on St. Thomas
2019-12-22
8
Going Out on a Limb and Getting the Whole Tree in Bocas del Toro, Panama
2019-12-22
9
Moving Out of Your Comfort Zone in Roatan, Honduras
2020-01-12
10
New Adventures and Coco Locos in Samana, Dominican Republic
2020-01-12
11
Cracking a Smile on St. Croix
2020-03-22
12
Room for 9 in Roatan, Honduras
2020-03-22
13
Finding a New Rhythm in Punta Cana, Dominican Republic
2020-05-17
14
Fairyland House on St. Thomas
2020-05-24
Season 19 Season 19
14 ep
1
Embracing the Sunshine in Sosua
2020-02-12
2
Beach Views or Bust on St. Croix
2020-02-12
3
And Baby Makes Three on St. Thomas
2020-02-18
4
All Aboard for a New Life on St. Maarten
2020-02-18
5
Strong Opinions and Strong Drinks on St. Maarten
2020-03-29
6
Checking in to a Life on St. Croix
2020-03-29
7
Bringing Southern Charm to Vieques, Puerto Rico
2020-04-19
8
Bringing the Family Home
2020-04-19
9
Working Out on the Beaches of Cabarete
2020-04-26
10
A New Life on Utila
2020-04-26
11
Family Time in the Sun on Vieques
2020-05-03
12
Letting Loose in St. Thomas
2020-05-17
13
Paddling Into a New Life on St. Thomas
2020-05-24
14
delete
2020-05-24
Season 20 season 20
14 ep
1
Cooking Up a New Chapter on Anguilla
2020-05-03
2
Trading the Rat Race for the Beaches of St. Croix
2020-08-09
3
Searching for the Perfect Bachelor Pad on St. Maarten
2020-08-09
4
Debating Home vs Condo on St. John
2020-08-16
5
Pulling the Trigger and Ending a Three-Year Search on Roatan
2020-08-16
6
Bringing the Family Home to Roatan
2020-08-23
7
Walking Down the Aisle and Into a New Home on St. Croix
2020-08-23
8
Becoming a Mermaid on Roatan
2020-08-30
9
Girls Just Want to Have Fun on Aruba
2020-08-30
10
Stepping Out of the Comfort Zone on Vieques
2020-09-13
11
A New Family Venture on St. Thomas
2020-09-20
12
Mating for Life Like Ostriches on Aruba
2020-09-20
13
Cooking Up a Bed and Breakfast on St. Croix
2020-09-27
14
Making a Splash on Utila
2020-09-27