Pineapple Ketch Sailboat, Kennebunkport

All aboard…

Your adventure starts when you arrive at the gorgeous Nonantum Resort

and head down to their docks towards the amazing 1976 Pineapple Ketch sailboat.

The captain and crew will welcome you with big smiles as you settle in. They are full of information about the boat, the town, and do their best making everyone comfortable.

Our Sail…

Your trip may be different from mine because they let the weather and wind determine their route for the day. Our boat, which only had 8 other guests on it and 2 captains, headed out onto the ocean and hugged the Kennebunk coastline for a bit. The wind was really blasting, which made for an exciting ride with big waves and water splashing up at us. My kids would have loved this trip!

We followed Ocean Avenue with their huge summer homes and sailed past Walker’s Point, the compound of the Bush family.

We also went by St. Anne’s Church, one of my favorite churches on the east coast. Just look at how amazing it is. (If you’re in town, you should make this church one of your stops. The outdoor chapel is stunning.)

Back to the Kennebunk River

I am so glad I did this trip in autumn, as the foliage was stunning as it burst into vibrant colors and it serves as a beautiful backdrop for your sail.

There are so many lobster boats moored here.

We enjoyed the panoramic view of the Nonantum Resort.

Then we headed towards the marinas.

We even saw an adorable little seal that kept peeking up at us.

We went all the way to the bridge before turning back. It was neat seeing the bridge from this perspective.

How long is the sail?

Mine was a 2-hour sail, but I didn’t want it to end!

How much does it cost?

It was $45 per person

What other trips do they do?

Sunset Cruise: 2 Hours – $55 Per Person

Enjoy a sunset sail as daylight fades on another beautiful day in Kennebunkport. Your captain and crew guide you along Maine’s coastline, as you explore the landscape, homes, and resorts.

1-Hour Cruise: $35 per person: Looking for a quick, convenient way to see Kennenbunkport? Try our one-hour, affordable sailing trip, complete with all the top sites & nature you want to see.

Private Charters: Starts at $450: Didn’t sail yourself to Kennebunkport? Take advantage of the best way to see the Southern Maine Coast, from one hour to all day! Accommodates up to 12 passengers.