Trip Flip: Throwing Axes and Zoobombing Pictures

It's the tale of three cities ... three cities with the same name that is. Bert heads to Portland, TN, to surprise one lucky couple with the trip of a lifetime to Portland, OR, and Portland, ME.

Host Bert Kreischer and Brandon and Sue West prepare to go rappelling in the Cascade Mountains just outside of Portland, OR.

Bert jumps from a 30-foot-tall waterfall while canyoneering in the Cascade Mountains.

After everyone makes the jump, Bert, Sue and Brandon get ready for their next Oregon adventure.

Bert, Sue and Brandon prepare to bomb a hill in Portland, OR. The term “bombing a hill” refers to the act of riding down a hill without carving or turning.

Bert, Sue and Brandon join a group of hipsters to bomb the hill in Portland, OR.

Built in 1857, Seguin Island Lighthouse is Maine's tallest and second oldest lighthouse -- located roughly 3 miles from the mouth of the Kennebec River.

Brandon, Sue, Bert and commercial fishermen prepare to go lobster fishing in Casco Bay off the coast of Portland, ME.

Sue and Brandon smile for the camera with their lobster bait while aboard their commercial lobster boat.

Sue and Brandon help move lobster traps from one side of the boat to the other while Bert looks on amusingly.

A close-up look at one of the lobsters Bert and his travelers caught in Casco Bay.

Brandon, Sue and Bert bring their fresh lobsters to E.A.T. Lobster to be cooked for dinner.

Sue, Bert and Brandon get a lesson on kite scudding while on Pine Point Beach in Scarborough, ME.

Bert tries his hand at kite scudding on Pine Point Beach.