Caleb Porter #3, Timbers vs. Sounders, 10.13.13

BEAVERTON, Ore. – The Portland Timbers depart Thursday on what will be their longest road trip of the season and surely the longest two-game trip that any MLS team will make in 2014.

First, Portland will head to Boston ahead of Saturday’s game with the New England Revolution (4:30 pm ET, KPTV). After that match, they will hop aboard a plane chartered for the approximately 2,500-mile flight bound for Georgetown, Guyana, on the northern coast of South America for a CONCACAF Champions League matchup Tuesday against Alpha United (5 pm PT, FOX Soccer Plus).

The Timbers will then turn around and head 4,700 miles back to Portland for the always-massive Cascadia showdown with the Seattle Sounders on Aug. 24 at Providence Park (2pm PT, ESPN2).

It all begs the question: With the Timbers trying to claw their way above the red line in the brutally competitive Western Conference while also juggling their inaugural foray into the Champions League, how do they balance this travel itinerary?

“I think the real key is having a plan for what we’re going to do in Guyana,” Timbers head coach Caleb Porter said following Wednesday’s training session at the team facility.

Porter said the Timbers will travel nearly the entire roster – 28 players – to New England. After Saturday’s game, he will decide on 18 to travel to Guyana while sending 10 players back to the Rose City to train for three days with assistant coach Sean McAuley in preparation for Seattle.

Porter said that should alleviate some of the burden, unlike a similar three-game stretch in late May and early June that saw the entire group travel to New York, then to Chivas USA before heading back to Portland for a Cascadia matchup against the Vancouver Whitecaps, all in the span of a week.

“It’s the toughest [road trip] from the standpoint of distance,” Porter said of the Massachusetts-Guyana-Portland swing. “But I would say the tougher trip, honestly – because we won’t travel everybody to both places, Boston and Guyana – the tougher trip was probably New York to Chivas and then back to Portland. So we’ve managed a similar trip, three games in eight days, multiple travel, so I would say that’s tougher. But this is not easy.”

Porter said he has a “pretty good idea” of who will make the trip to Guyana but that there are three or four decisions still to make based on performance and health coming out of the Revolution game.

“We’re going to play to win all three, and we feel like to do that – we want to have a good chance to win the league games – we have to rotate in that Champions League game,” Porter said. “We have a deep enough squad where we feel we can get the result by doing that.”

Dan Itel covers the Timbers for