Sail Portland Maine

01/01/2026

As the sunsets on 2025 Huckleberry and I look forward my 8th season his 6th season!! 🐶🤷🏼‍♂️ 2026 is already shaping up with some promising charters already in the books. So if you know a date call us, go online, email me and we will get you locked in for a 2026 cruise with Huckleberry, the best “surprise” for anyone getting onboard. And don’t forget as always our always popular Flappy Hour cruises will resume Memorial Day weekend.

09/03/2025

*FALL SPECIAL*

From now until the end of October, all charters, up to 12 people will be $500. Send this to your friend who’s been dying to get on the water this season, and join me for a sail on Casco Bay.

08/11/2025

My guy huckleberry is rocking our swag. For purchase only on the boat 🛥️

Book a charter and get one for yourself

06/03/2025

Happy Pride Month to everyone! All are welcome, always.

Love
Ian and Huckleberry 🐶

05/29/2025

Last night I had the absolute pleasure of cooking for a team from who were such fantastic guests. One of them paid me such a compliment “your halibut was cooked better and tasted better” than a certain expensive restaurant near the marina that shall not be named. I even had their crème fraiche onboard randomly for the potatoes. Here’s to a summer of beautiful sunsets and good food and people. 👨‍🍳🐶🍰

05/23/2025

Looking for last-minute Memorial Day plans? Book a private charter for you and your 11 best friends for an iconic sunset trip off the Portland, ME coast.

Book through our website, link in bio 🇺🇸

08/31/2024

We have had many proposals this year and in previous seasons, but this was Calista Ann’s first wedding. The flowers were provided by and the ring bearer Huckleberry, as always, was a crowd favorite 🐶

07/12/2024

06/17/2024

A huge THANK YOU to everyone who helped make our first Adoptable Dog Cruise a success! 🐶⛵️

Last week was such a special experience, getting to take fellow dog-lovers and our special guest “Momma” out on the water for a beautiful sunset sail, and guess what…

MOMMA HAS OFFICIALLY BEEN ADOPTED!!!!! 🎉🎉🎉🎉

She was such a sweet and well-behaved pup on the cruise and we’re so happy to hear she’s found her forever family!!!!

Special thanks to:

for partnering with us for this unique series!
 for joining us on board and helping capture content from our beautiful day!
for helping us organize and promote this unique “Positive Impact” campaign!

Remember, we still have a few more Adoptable Dog Cruises happening this summer!

Tickets are almost sold out on all cruises, so be sure to snag yours now at our link in bio 🎟️

06/12/2024

Have you gotten a chance to be part of the cutest cruise ever? 🐶⁠
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There are only TWO cruises left for our Adoptable Dog Cruise series, with ⁠
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We’ll be sailing with a crew of furry friends who are on a mission to steal your hearts and find their forever homes. ⁠
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Don’t let this opportunity go—book now and be a part of something truly special!⁠
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05/24/2024

Love living somewhere that when the sun and heat come out to play the whole gang gets excited. and are ready to give you the greatest Flappy Hour of your summer. Select weekdays and Sundays all summer long. Go to the website for details.

05/02/2024

It’s time to book your spot for our upcoming Adoptable Dog Cruises, in collaboration with the incredible team at !⁠
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Starting this May and running through August, we’re inviting you to join us aboard our cruises for a cause where not only will you soak in the beauty of the Maine coast but also share precious moments with some of the most charming four-legged crew from The Animal Refuge League of Greater Portland.⁠
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This is more than just a cruise—it’s a chance to make a difference in the lives of these lovable pups while enjoying a memorable day out at sea. ⁠
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Plus, with 20% of cruise sales donated to the Animal Refuge League, your adventure becomes a spark for change! ⁠
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It’s a BIG help for us if you’re able to book your spot early so we know how many to expect! All dates are available for booking on our website, so secure your spot now through the link in our bio!⁠
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