Pine Islanders paddle all the major rivers in Maine and several of its lakes in either canoes or kayaks. At least two trips a year are rowing trips on which boys row double-banked in Pine Island's custom-designed wooden rowboats. Like hiking trips, water trips vary greatly in length and difficulty so that boys of all ages can enjoy them.
A typical summer includes the following canoe, kayak and rowing trips, among others:
Indian Pond - three-day canoe trip from Moosehead Lake to Indian Pond for beginning paddlers.
Oak Island - two-day, one-night introduction to camping. Campers take the War Yacht on Great Pond to neighboring Oak Island.
ONG-BAK - O.A.R. Navigators Going Backward Along the Kennebec - a trip from Waterville to Bath Iron Works for advanced rowers.
West Branch - four-day canoe trip on the West Branch of the Penobscot River. For intermediate paddlers.
Senior Canoe - six-day trip on the Allagash Wilderness Waterway, from the Churchill dam at the head of the Allagash River to Allagash Village. For advanced paddlers.
Kennessassabackscot - Campers paddle the Kennebec to Swan Island, then navigate the Sasanoa, Back, and Sheepscot Rivers to Wiscasset. Three-day trip for beginning paddlers.
Great Pond Rowing Trip - An exploration of Great Pond in rowboats. For beginning and intermediate rowers.
Chip Lakes - four-day trip in canoes on the Chiputneticook Lakes, the headwaters of the Saint Croix River. For intermediate paddlers.
CLIK - Chip Lakes In Kayaks - four-day trip on Chiputneticook Lakes. For intermediate kayakers.
St. Croix - four-day canoeing adventure on St. Croix River from Vanceboro to the Kellyland dam. For intermediate to advanced paddlers.
Clauson's - This 3-day trip does not include the Clauson River nor is it named after Claussen pickles. Several years ago, Pine Island alum Thomas Clauson and his father, alum and board member Henry Clauson, paddled the Kennebago River and determined it to be a great trip for campers. Over the past few summers it has proven to be just that, with beginner to intermediate paddlers gaining tripping experience and catching salmon, brook trout, and bass along the way.
I.P.I.K. - Indian Pond in Kayaks - a 3-day trip for beginner to intermediate paddlers. Campers spend one day kayaking down the west outlet of the Kennebec River and two days paddling on Indian Pond.
St. Johnson - 3-day kayak trip on the St. John River. Three of Pine Island's most experienced trip leaders, Walker McDonald, Noah Brodsky, and Pope Johnson, scouted this trip in the spring of 2019 and reported back that the river is beautiful and filled with moose.