Matt and Tom are an adventurous young couple hailing from Chicago, Illinois.

Pablo and Michelle are a newly engaged couple with a romantic story. On their first date Pablo took Michelle on a romantic helicopter ride around Los Angeles and it was love at first flight! The couple now resides in vibrant town of Homestead, FL, near South Beach. Although Pablo has enjoyed the Keys since he was a child, they became even more special to him with Michelle in his life. The Keys are a part of their love story. What started as a yearly romantic getaway blossomed into island visits that they'd plan as much as possible.

Eric proposed to Shontae only two weeks into their relationship sixteen years ago..

Tracey grew up in Maine and visited Mount Desert Island all through her childhood. She introduced JC, her husband, to the island and he immediately loved it. JC and Tracey moved to Bethel, Maine a few years ago before getting married. Now parents to a three-year-old son, they've decided to fulfill a lifelong dream and make Mt. Desert Island their home permanently.

John and Megan married on Mount Desert Island seven years ago and Megan grew up going to the island with her family. They met in Richmond, VA, where they have both lived for most of their lives. In Richmond, they live on a very hip, urban street with a vibrant social atmosphere. Even though they've enjoyed living there, they're ready and looking forward to finding a home in a quieter, quaint, more scenic and natural location close to parks and the ocean. Mount Desert Island was a clear choice for them since it's their favorite vacation spot. While tourism is huge on the Island, it still maintains a small town feel, almost indicative of another era entirely.

Nantucket is special for Jason and Courtney: it's where they first met, and now they're getting married on the island this summer. While Jason has lived on Nantucket for the past 10 years, Courtney has only visited--but after meeting him she quickly fell in love with both Jason and the island and decided to join him there

Rob and Suzanne live right outside Boston and lead very busy lives. Being busy professionals with demanding jobs doesn't leave much time for relaxation. They've been going to Martha's Vineyard for over ten years and each year they have fallen in love with the island more and more. Now, they've decided to make the island their permanent home and are hunting for a house with historic charm where they can leave the stress of their former lives behind.

For years Frederick and Carina have been in search of the perfect place to call home and raise their three kids. They've tested the waters of Boston, Houston and even Miami. In the end, they realized what they really wanted was a life outside a city. They had vacationed in Key Largo many years before, loved it and wondered if it be possible to actually make a place like that their home.

Stephen and Beth lead a hectic lifestyle in Cincinnati, Ohio. Stephen is CFO of a company and Beth is a busy stay-at-home mom raising their 14 year-old daughter, Maya. They live in a sub-division where every house looks the same, 600 miles from the sea, surrounded by fast food chains, and have to drive four miles if they want to buy a pint of milk. Beth first visited Key West when she was growing up and immediately fell in love with it. She went back a few years ago with her husband who also quickly felt at home on the island. Now, with Stephen able to work remotely, they're ready to make their favorite vacation destination their permanent home…they just need to find the perfect house.

Josh Goffin and Stephanie Clabaugh are two peas in a pod. They refer to themselves as water babies, having been born and raised within a 5-minute drive of the Puget Sound. They could never live anywhere far away from water.

Chris and Laura both grew up in the Midwest and met in Iowa. Chris does consulting work for dental offices and travels a lot--up to 38 times a year-- while Laura is a writer who works from home while they raise their 5-year-old daughter and 3 year-old son. When the opportunity arose for Chris to relocate for work and not travel as much, they were given the choice of New York City, Salt Lake City, or the San Juan Islands. The Pacific Northwest island location was their pick right off the bat. They immediately fell in love with it and everything it had to offer.

Nesward and his wife Jackie lived in Alaska years ago for his job as a rescue swimmer with the Coast Guard. Now, three daughters later, the family has been living in Nesward's native Hawaii with his parents. Life is good, but they never stopped missing Alaska.

David, a Coast Guard Rescue Swimmer, and his wife Ashley, a stay-at-home mom of a 5- and 2- year old, have lived in Hawaii since they married in 2007. Now, the Coast Guard is transferring them from Hawaii to David's first choice assignment: Kodiak Island, Alaska.