Hosts Phil and Sarah compete to persuade our young at heart, soon to be empty nester couple Tim and Angela and their sixteen- year old twin girls Daisy and Dorothy and twenty- year old son Louie in their decision whether to live in the Upper Beaches of Toronto or in lakeside, small town feel, Oakville. Our couple seeks to re-visit the social life they had before having kids, attending stand up comedy nights. They wrestle with the hassle of a commute, wanting access to a garden and nature trails as well as access to a High School with a great arts program for their kids. Will Tim and Angela choose the eclectic Upper Beaches, “Toronto’s Favourite Lakeside Community”? Or, will they choose quaint Oakville for its fine dining, beachside pubs, great schools, and historic 19th Century buildings?