Sail Portland Maine

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1 Portland Sq
Portland, ME 04101
+1 (207) 200-6650
https://sailportlandmaine.com
Two-hour and private charter sailing excursions. Enjoy spectacular views and stunning sunsets aboard the Friendship Sloop Eleanor Hawkes. Bring your favorite beverages and snacks and relax and let the wind blow your stress away.

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Reviews

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4.522 reviews
Beth Ellen R.
9/15/2025

Perfect ride out to Diamond and back. Nice rose served while on board with great crew. I would definitely do it again!

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Karis O.
6/10/2025

Took a private charter with Captain Ian and Chris to Great Diamond Island. We did the "Flappy Hour" experience that Crown Jewel offers, which resulted in complimentary rose for all the guests on...

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Zachary C.
7/29/2024

Cancelled my tour a few hours before sailing on a sunny 85 degree day. Unfortunate, as the boat looked beautiful.

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Lisa B.
10/13/2023

Took a ride with Captain Ian and Nick on our last night in Maine. What an amazing and fun sunset cruise it was. My hubs and I were the only two on the Calista Ann so it was like a private charter....

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Rebekka B.
6/11/2023

We had Nick and Captain Ian take us on a lovey afternoon (3:30-5:30pm) tour around the islands. We hung out and listened to music, brought our own snacks and wine and seltzers and had the best...

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