Theodore Tugboat, an icon of the Halifax Harbour for the last 21 years, is about to embark on a new journey to Hamilton, Ont.

The smiling tugboat with the red baseball cap left Halifax on Thursday and will travel more than 1,200 miles, stopping in 15 ports, before reaching his final destination in July.

Theodore was owned by Halifax company Ambassatours for the last several years but was recently sold to an Ontario marine firm Breakwater Investments.

"Theodore is going to make his way up to Hamilton, he will travel throughout the lakes this summer," says Breakwater CEO Blair McKeil. "We know how important he is to the Maritimes."

But McKeil says Theodore's long-term mission over the next three to five years is to share with all Canadians how great the Maritimes are.

"Really sharing with everyone in our country the importance of water, our connectedness to water, that's what connects all of us," says McKeil.

"That's what striving him to do what he's doing, as a special iconic Canadian."

For many, his departure is bittersweet.