On a recent Wednesday morning, regional high school athletics director Mark McCarthy was attempting to predict the weather. There was a cross-country meet and a soccer match scheduled for later in the day, but there was also rain in the forecast. Mr. McCarthy had already been on the phone with the athletic directors of Barnstable and Dennis-Yarmouth, whose teams were scheduled to come to the Vineyard.

Barnstable decided to make the trip in spite of the rainy prediction. Dennis-Yarmouth did not, but it wasn’t because they didn’t want to get wet. They were concerned that the wind would pick up, the boats would stop running, and their athletes would get stuck on the Island.

Sports travel for an island school is a unique beast, one that takes what is already a complicated endeavor — ensuring that hundreds of student athletes and their coaches get from Point A to Point B and back safely — and throws in a seven-mile wide obstacle in the form of the Vineyard Sound.

In the fall, more than 40 per cent of the student body plays a sport — about 280 athletes in total. There are fewer sports in the winter, with only about 150 students on a team. Participation numbers rise again in the spring to about 250 students. This year, enrollment at the regional high school was 686.

Regional high school has fleet of three buses and two Priuses on the other side. — Ivy Ashe

On any given week during the school year, there are between seven and 10 trips off-Island for the sports teams, Mr. McCarthy said.

In fiscal year 2015, the high school was allocated 260 off-Island trips at a budget of $97,805.

“The majority of that is sports,” said school business administrator Amy Tierney. “There are probably 20 field trips per year, and the other 240 are sports runs.”

The Vineyard signs a contract each year with the Steamship Authority to provide boat travel for its teams as well as paying for the travel for teams in the Eastern Athletic Conference — Somerset Berkley, Coyle Cassidy, Bishop Feehan and Bishop Stang. Schools that are not in the EAC pay for their own boat fares.

The Steamship contract was $60,000 last fiscal year, and comprises the bulk of the high school’s transportation budget. Steamship Authority treasurer Robert Davis said the cost represents a rate discount of approximately 50 per cent. In the coming weeks, he said, the school and the Steamship will begin working together to set the total for next year’s contract, which is based on the number of travel vouchers used the previous year.

Even for schools that are nearby, travel is complicated. In Falmouth, the closest school to the Vineyard, students get early dismissal and are bussed to Woods Hole. It’s a lengthy process even though the Vineyard “feels like it’s just down the street,” Falmouth athletic director Kathleen Burke said.

“It’s a great experience for most kids,” Ms. Burke said. “Most kids just look forward to the opportunity.”

Falmouth High School, a division one school with a student body of more than 1,100, has a transportation budget of about $100,000 per year.

On Nantucket, the high school and middle school share a budget for sports-related transportation. That budget ranges from $170,000 to $175,000 per year, athletic director Chris Maury said. The Nantucket high school student body hovers around 450 students each year, and about 70 per cent of students play at least one sport.

“From our perspective, both boat lines, the Steamship and the Hy-Line, are terrific to us,” Mr. Maury said. The Hy-Line’s high speed boat, which makes the 30-mile crossing in an hour, “saves us,” he said.

Though some schools refuse to play on the Vineyard or Nantucket because of the boats, other opponents “absolutely love it,” Mr. Maury said. It’s the novelty that draws them in. Early dismissals, presumably, also help.

When Vineyard athletes travel for sports, nearly all are dismissed at lunchtime so they can make the 1:15 p.m. boat. Mr. McCarthy makes bus requests for getting students from the high school to the boat one week in advance. During the fall and spring, however, when there are two ports open on the Island, there can be more complications. Boats scheduled to leave from Oak Bluffs often end up going out of Vineyard Haven on the day of sail because of weather conditions.

“So now I’ve got to get the kids to Vineyard Haven,” Mr. McCarthy said. “And the kids who drive to the boat, their cars are in Oak Bluffs, but the boat comes back to Vineyard Haven.”

Springtime is the most complicated season for travel scheduling, not only because there are more teams, but because the sports are more affected by the weather.

“With tennis, you’re not going to be able to play even if it gets a little wet,” Mr. McCarthy said. Rescheduling is frequent and Mr. McCarthy is in constant communication with school transportation director Jimmy Flynn as well as with Ken Wass, who coordinates bus travel on “the other side.”

There is a fleet of three buses parked in the Palmer lot, along with two Priuses, which the golf team recently used to travel to the state championships. The fleet serves the whole Island, and will expand to five buses soon.

The longest travel days for the Vineyard and for Nantucket are usually when the schools play each other. The only time there is a direct boat from the Vineyard is during years when the Island Cup football game is played on Nantucket, and the football booster club charters a ferry. For every other contest, teams go from the Vineyard to Woods Hole, then are driven to Hyannis, and then take the fast ferry.

“It’s basically a 12-hour day,” Mr. McCarthy said.

Of course, if the weather is bad there won’t be any travel at all. Sometimes Mr. McCarthy will cancel a game only to have the sun come out later in the day. But he’s never seen an opposing team stranded on the Vineyard during his tenure, in spite of Dennis-Yarmouth’s worries

“Knock on wood,” Mr. McCarthy said.

Vineyard teams have been caught on the mainland, but only as a result of missing the last boat. Sometimes, it’s a game that was delayed because referees were late. Other times, it’s a weather postponement that extends the competition. If the team misses the last boat, they’ll take the Patriot boat home.

“You can’t do this job without constant communication,” Mr. McCarthy said. “You don’t want to leave anybody at the dock.”