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Mid-Day Sail

  • Most Popular!
Private Charter Up to 12 people

Explore Kennebunkport from the water as you soak up the sun and ocean air. On this sailing trip, you experience Pineapple hospitality and take in local points of interest.

Kennebunk River Sailing Adventure

Trips depart from the Nonantum Resort in Kennebunkport.

Every day is different on the water, and we sail the best route for the conditions and the day. A “normal” trip travels out of the Kennebunk River and then East along the Kennebunkport coast, past the summer cottages along Ocean Avenue and Walker’s Point, home of George and the late Barbara Bush. If we can make it all the way to Goat Island Lighthouse in Cape Porpoise Harbor, we have covered quite a distance before our return to Kennebunkport.

Keep a lookout for potential marine life sightings as your friendly captain and other entertaining crew members points out sights of interest and share fun facts about sailing, water activities, and the area as we safely navigate these waters. Keep a lookout for some marine life and wildlife, like seals and birds, too! Our Kennebunkport cruises are family-friendly and we can’t wait to welcome you aboard The Pineapple Ketch!

We find that the winds and seas tend to be lighter earlier in the morning and build as the day progresses, so choose a time that fits your sailing style. Complimentary soda and water are provided, but we encourage you to bring whatever snack or beverage you would like to enjoy on your trip.

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