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S05E03: Setting Sail for St. Thomas

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.

Genres:

Air Date:

Mar 06, 2016

Casts:

Caribbean Life

Dave and Julie - St. Croix

Corinne and Patrick -St. Croix

Margi and Jessi - Vieques

Cliff and Janine - Sint Maarten

Ona and Johnny - Sint Maarten

From NYC to Puerto Rico

David and Laurie - Dominican Republic

Caroline and Omar -San Juan, Puerto Rico

Carl and Janna - Vieques

Karrin and John -Punta Cana

Doris and Don From Alberta to St Lucia

Neela and Jason -Turks and Caicos

David and Jayne -Canada to Turks and Caicos

Heidi and Steve -Turks and Caicos

Lloyd and Michelle

John and Janaea

Billy and Deanna

David and Arturo

A Colorado Family Leaves Snowy Fort Collins

From the Desert to the Tropics of Isabella

Michael and Tara

Kacie and Casey

Matt and Kristy

Scott and Lauren

Natasha and Collin

Brian and Sarah

From Texas to St. Thomas

From California to the Caymans

Bye Ontario, Hello Barbados

Chuck and Alicia

Erik and Samantha

From New Mexico to Cozumel

From D.C. to St. Maarten

Canada to Dominican Republic

Goodbye NYC, hello St. John

Brad and Meredith

Newlyweds taking The Plunge In Jamaica

Country Roads to Ocean Views

The Bahamas Beckons a Florida Couple

Boating Around Bocas

Finding Her Passion in Utila

Bringing It All Back Home

A Doctor and Nurse Take the Plunge in St. Croix

Canadian Couple Seek Great Diving in Utila

A Grand Home on Grand Cayman

Opening Up in Bocas del Toro

Desperately Seeking Sea Views

Buying in the Bahamas

A New Career On St. Croix

A New Life In Negril

Soaring Above St. Thomas

A Change of Pace in Placencia

Setting Sail for St. Thomas

Swapping Florida For Vieques

A New Beginning In Belize

Starting Over In Vieques

Back to the Dominican Republic

A Family That Moves Together

New Adventures In Puerto Rico

Unwinding In St. Maarten

Branching Out In St. John

Ride Like The Wind On Aruba

New Chapter In The DR

Family Time On St. Thomas

Boating Life On St. Maarten

Landing on St. Croix

A Laid-back life on St. John

Southern Charm in St. Croix

Dreams Come True in Jamaica

A New Business On St. John

St. Louis to St. Maarten

Changing Gears in Jamaica

Finding Peace On Vieques

Curing The Blues In Curacao

Moving Twins to St. Croix

Treasured Time in Roatan

Fruitful in Vieques

A Curacao State Of Mind

A California Girl Escapes the City for the Bahamas

Bringing the Best of Texas to the Virgin Islands

A Dream Come True in the Dominican Republic

Homegrown Living on Utila

Monkeying Around on Roatan

New Beginnings in the Bahamas

Beachfront on St. Thomas

Slowing Down on Utila

Colorado Mom and Daughter Start New Life on St. Thomas

Raising a Family on Bonaire

Ditching the Desert for an Oceanfront Oasis

New Adventures in the DR

Diving Into Bonaire

Lessons Learned in Las Terrenas

Room for Family in the D.R.

Finding Zen in Nevis

A New Business on Roatan

Harmonizing in Providenciales

Raising a Family on St Croix

Paradise in Bocas Del Toro

From the Farm to Nevis

Diving Into A Simple Life On Roatan

All That Jazz on St Croix

Melting the Stress Away in Utila

Peace in Las Terrenas

Relaxing in Turks and Caicos

Family Time on St Croix

Beginning a New Adventure in Bocas Del Toro

Raising Two Boys on St. Croix

Cowabunga Bocas

Unwinding in Elbow Cay

Finding a Fixer-Upper in the Dominican Republic

NYC Days to Puerto Rico Nights

Looking for Adventure in the Dominican Republic

Trading Winter for Summer

Rhode Island Family Looks to Ditch Winter Jackets

Healthy Living on St. Croix

Snowy Boston to Sunny Vieques

Boating in Treasure Cay

Quality of Life in Puerto Rico

No Regrets on Bonaire

A New Life in St. Croix

New York City to Grand Cayman

A New Chapter in Puerto Rico

Empty Nesters Go Back Home

Diving Into Roatan

Taking Care of Business in Grand Cayman

Seeking Seclusion on Roatan

Fresh Start in the Dominican Republic

Finding Peace on St. John

A New Job on St. Croix

Elbow Room in Cabo Rojo

All About the Kids in the Dominican Republic

Fulfilling a Dream on St. John

From Busy L.A. to Tranquil St. Thomas

Returning Home to Puerto Rico

St John Nature Retreat

Falling in Love With Aruba

Jumping Feet First Into Roatan

Renting St. John

Replanting Roots on Aruba

St Croix is the Bee's Knees

Finding Warmer Weather on Roatan

Owning the Dream in St John

Stepping Out of the Comfort Zone on Vieques

Starting Over in Aruba

St Thomas Bound

Keeping Vieques a Family Tradition

Diving Into Utila

Working Less and Living More on St. John

Adventure On Grand Cayman

Adios Miami, Hola Caribbean

Finding Roatan by Accident

Living the Dream in Bonaire

Replanting Roots on Aruba

Making a Deal in Utila

Finding the Cay to Happiness on Utila

Diving Into Bonaire

Soaking in the Dominican Sun

Business And Leisure On Utila

Going Coco Loco in Bocas

A Stylish Life On Grand Cayman

A Healthy Plan in Roatan

Flying High in Cabarete

Exploring New Terrain on Aruba

Trading Scrubs for Wet Suits

A Family Adventure

A New Chapter in the Dominican Republic

Return To Island Living In The Dominican Republic

Island Dream In Bocas Del Toro

Tackling a Roatan Fixer-Upper

Bocas Del Toro or Bust

Flipping Over Eleuthera

Exploring Reefs on Utila

Mother-Daughter Hunt

Healthy Life In The Dominican

From the Big Apple to Aruba

Raising a Family on St. John

A Flip Flop Island for Flip Flop People

Time to Relax on Roatan

Slowing Down on Aruba

Island Time, All the Time

Taking the Family to Turks and Caicos

Breaking a Sweat in Puerto Rico

Heading Home to St. Thomas

Sun and Serenity on Utila

Rediscovering on Barbados

Trading Cold For St. John Sun

Historic Move to San Juan, Puerto Rico

Building a New Life on St. Thomas

Back to Barbados

New Adventures on Roatan

Trading Business Suits for Bathing Suits

Reeling in the Good Life

Kicking Back on St. Thomas

From New York to St. Thomas

Banana Pudding in Las Terrenas

From Pittsburgh to Paradise in Puerto Rico

Jetting All Over Vieques, Puerto Rico

Laid-Back Life in Utila, Honduras

A Place to Unwind

From the Big Apple to the Small Island of Vieques

The Couple That Bikes Together in St. Croix

Working to Be With Family in Puerto Rico

Slowing Down in Anguilla

Slimming Down in the Dominican Republic

Beachside With a Cocktail

Unplugging in Aruba

Discovering a New Rhythm in the Dominican Republic

Pulling Teeth for the Dominican Republic

Feeling Salty on St. Thomas

Revving Up for a New Life in Aruba

Finding Solace On Roatan Honduras

Swinging Down to St. Maarten

Open to New Adventures on Utila

Family Time in Puerto Rico

To Build or Not to Build in Aruba

On the Hunt for Waterfront on St. Thomas

Off the Beaten Path in St. Croix

Relocating to Paradise

Newlyweds in St. Croix

Father and Son Bonding in Las Terrenas

Dreaming Big on St. John

Starting Fresh on Roatan

From Maine to Puerto Rico

Falling in Love With St. Croix

Blowing Out of Chicago; Sunrise and Sunset on St. John

Looking for the Water Trifecta

From Atlanta to Vieques

Blowing out of Chicago

From Canada to Roatan

Testing New Waters in Sosua, Dominican Republic

Living Among the Flora of Bocas del Toro, Panama

Classic Cocktails and New Adventures on the Beaches of Roatan

Back Home to The Bahamas

A Rendezvous With a View on St. John

Taking a Bite out of the Bahamas

Growing as a Family on St. Thomas

Going Out on a Limb and Getting the Whole Tree in Bocas del Toro, Panama

Moving Out of Your Comfort Zone in Roatan, Honduras

New Adventures and Coco Locos in Samana, Dominican Republic

Cracking a Smile on St. Croix

Room for 9 in Roatan, Honduras

Finding a New Rhythm in Punta Cana, Dominican Republic

Fairyland House on St. Thomas

Embracing the Sunshine in Sosua

Beach Views or Bust on St. Croix

And Baby Makes Three on St. Thomas

All Aboard for a New Life on St. Maarten

Strong Opinions and Strong Drinks on St. Maarten

Checking in to a Life on St. Croix

Bringing Southern Charm to Vieques, Puerto Rico

Bringing the Family Home

Working Out on the Beaches of Cabarete

A New Life on Utila

Family Time in the Sun on Vieques

Letting Loose in St. Thomas

Paddling Into a New Life on St. Thomas

Cooking Up a New Chapter on Anguilla

Trading the Rat Race for the Beaches of St. Croix

Searching for the Perfect Bachelor Pad on St. Maarten

Debating Home vs Condo on St. John

Pulling the Trigger and Ending a Three-Year Search on Roatan

Bringing the Family Home to Roatan

Walking Down the Aisle and Into a New Home on St. Croix

Becoming a Mermaid on Roatan

Girls Just Want to Have Fun on Aruba

Stepping Out of the Comfort Zone on Vieques

A New Family Venture on St. Thomas

Mating for Life Like Ostriches on Aruba

Cooking Up a Bed and Breakfast on St. Croix

Making a Splash on Utila

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