Sailing

Maine Day Sail’s two-masted schooner Timberwind, was originally built in 1931 as Portland Pilot, and having never sailed outside of Maine, now calls Belfast home. Maine Day Sail offers 2-, 4-, and 6-hour day trips, as well as sunset cruises that last about two hours. Guests can expect midday trips to have lighter breezes and warmer temperatures, while afternoon trips are typically characterized by stronger winds and more exciting sailing conditions.

Maine Sailing Adventures’ gaff-rigged cutter, Frances, was built by her captain and launched in 2003 on Casco Bay. With exceptionally wide decks and cushioned seating, Frances is made to carry passengers in comfort. Berthed at the Maine State Pier in Portland, her schedule includes wine sails, sunset sails with live acoustic music, and farm share delivery sails as the boat brings produce from the Cultivating Community CSA to customers on Peaks Island.

Paddle Boarding/Kayaking

National Park Sea Kayak Tours, located in Bar Harbor, gives visitors the opportunity to tour the more remote, western side of Acadia National Park. A registered guide accompanies all trips and decides which is the safest route based on wind, sea, and weather conditions. Depending on the route, kayakers can expect to paddle up to six-and-a-half miles on a half-day trip. Large passenger vans provide easy and comfortable transportation to kayaking destinations.

Portland Paddle is the one-stop shop for kayak and paddle boarding in Maine’s largest city. It offers day trips, guided overnight trips, and self-guided trips for more experienced kayakers. For those looking to try something new, there is also the unique experience of stand-up paddleboard yoga. No previous experience is necessary, but first timers are more prone to getting wet, so appropriate attire is necessary.

Surfing

Aquaholics Surf Shop, headquartered in Kennebunk’s lower village, has been offering surfing lessons since 2002. Instruction is available for all levels and instructors are CPR certified. Lessons include theory and practice, and typically last for an hour and a half. Participants can expect to build confidence, increase endurance, and feel rejuvenated after spending some one-on-one time with the ocean on a surfboard. And because first-timers are sure to spend more time in the water than on the board, a wetsuit is a good idea.

Canoeing

Northwoods Outfitters offers guided and nonguided canoeing experiences on Moosehead Lake from its location in Greenville. This quieter way to explore Maine’s largest lake offers an opportunity to see wildlife, including nesting bald eagles, loons, deer, black bears, and moose feeding from the shallows. More adventurous and experienced paddlers can sign up for guided trips on the Allagash River, which take 4-7 days with a moderate level of difficulty.

Maine Path & Paddle Guides, based in Windham, makes safe and fun wilderness experiences available to a wide range of ages and abilities. Its summer schedule includes day and half-day paddles in greater Portland, flat-water lake canoe camping trips focusing on recreation and relaxation, and multiday, more rigorous trips in Maine’s North Woods. Maine Path & Paddle Guides operates year-round, with trips and activities scheduled in every season.