At Sail Portland Maine, our goal is to provide you with the best trip possible on the water. Your enjoyment is of the utmost importance to us, so trust that we will do everything in our power to make your Maine sail trip a memory you’ll talk about for years to come.

Want to hear from experience? Below are some of our 5-star reviews from happy guests!


above deck on the eleanor hawkes
Photo by Cody Henderson

Cody Henderson
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“We had a blast on our morning sail! The weather was perfect along with the beer and mimosas we brought with us. Ian was an excellent captain and showed us all a great time on his beautiful sailboat. I highly recommend sailing with Sail Portland Maine.”



aboard the eleanor hawkes
Photo by Eva Zealy

Eva Zealy
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“Book this now! The experience, atmosphere, boat and scenery is just amazing! The captain is wonderful entertainment and so personable, he really cares about the people he takes around! The boat is not crammed with people and makes you feel like you’re getting a private sailing tour- you can bring your own drinks and you might be lucky enough to have huckleberry as your co-captain! It was amazing we will definitely be back to sail again! The boat is beautiful and clean!”


sunset above deck
Photo by Sean Jones

Sean Jones
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“Just incredible. Worth every penny. Ian has a very professional and relaxing vibe. He is filled with local knowledge and great recommendations.”




sunset sail on casco bay
Photo by Katie Wolitarsky

Katie Wolitarsky
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“Our group of 6 women had a memorable, 2-hour private sail on Casco Bay with Captain Ian on a Saturday evening in June! Ian was super accommodating when we were figuring out dates and times, and we were able to bring wine, cheese and snacks along for the sail. The group is all from out of town and had the most memorable evening aboard the Eleanor Hawkes – seeing the beautiful Portland coastline from another perspective! We had SO much fun, that we decided to extend the sail by another hour – which Ian was so kind to let us do! I speak for everyone in the group that we would highly recommend Ian and Sail Portland Maine!”


sailing aboard the eleanor hawkes
Photo by Emily Smith

Emily Smith
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“Hands down, the BEST thing to-do in Portland, Maine!! Captain Ian sailed us around Casco Bay for 2 hours while we sipped on our BYOBs. He was very knowledgeable about the boat, the bay and Portland. Find time to enjoy the excursion with Sail Portland Maine, you won’t regret it.”



sunny day in the harbor
Photo by Emma Adams

Emma Adams
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“The big schooners are great but they get crowded. This boat and captain make for a much more comfortable and personal experience. You really feel like you’re sailing and the boat is GORGEOUS…I felt like a Kennedy! And you get to see and learn about Portland and the surrounding towns and islands from the coolest perspective, the gorgeous Maine sea. Bring your favorites bevvies and snacks aboard and have the best few hours of your whole trip (or if you live here, the best few hours of your summer!).”


eleanor hawkes at sea
Photo by Alan Platner

Alan Platner
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“You are having another great day in Portland and you’re thinking “I need to get on the water!” You are also thinking “I am so sick of all of these crowds!” Well Sail Portland Maine is hear to give you the intimate and private adventure you are looking for. Sail on a beautiful friendship sloop and take in the sights with just the people you came to enjoy Portland with anyways.”


bug light lighthouse in casco bay
Photo by Chip Dickens

Chip Dickens
“We had a great time out on the water with Ian on the Eleanor Hawkes. Wonderful afternoon cruise. Capt Ian demonstrated his mastery over the channels, wind and barely escaping a looming storm (light drizzle). Highly Recommend!”



couple enjoying a sunny sail
Photo by Jon Ashley

Jon Ashley
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“My wife and I had a glorious morning sail with Ian and another family. Ian is professional, friendly, and has excellent local knowledge and recommendations.”




rose sailAleia Daniel
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“On my trip to Portland, ME all I wanted to do was sail……And Sail Portland (and Ian) did not disappoint!!!! It was the perfect afternoon and Ian was knowledgeable and hilarious. Highlight of our vacation! If you are on the fence about sailing- don’t be! Book a trip with Sail Portland! And its BYOB- what else could you ask for?!?”


sailing the casco bayMatt Robbertz
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“Ian is an excellent host and runs a fantastic trip. There’s a reason he has such stellar reviews. More like a whole handful of reasons. Great guy, small tour size, beautiful boat, and simple logistics. Highly recommended.”


boat tours portland maine | private sailing chartersAshley Medeiros
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“We had the best time on our 2 hour morning cruise with Sail Portland! Pleasant conversation and mimosas were flowing accompanied by the beautiful Maine coastline as a backdrop. Did I mention that this cruise was BYOB?! Stock up on your favorite local treats and bring them aboard! Captain Ian and his first mate, Keith, were seasoned professionals and had a lot of helpful tips to getting the most out of your visit to Portland. I’d certainly cruise with Sail Portland again and can’t wait to return to Portland!”


cropped sunsetGene Ary
“Amazing experience. The Eleanor Hawkes is a beautiful sailing vessel. Captain Ian is knowledgeable of the local history and very welcoming. Truly enjoyed the sunset sail!”


boat tours portland maine | bachelor party portland maineKaitlynn Ford
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“I can’t tell you how wonderful this experience was. I 100% recommend you book a Maine sail trip and if you do it has to be with this small business. Ian is the owner and the captain of Sail Portland Maine. He answers calls, curates food and beverage from other local small businesses, is a great conversationalist, and a fantastic sailor. There are other sailing experiences in Portland and I can tell you the large boats will cram you in like sardines and the experience is just not personal. If that’s for you, go for it. But if you want a peaceful, intimate experience you’ve got to go with Sail Portland Maine with captain Ian!”


captain ian at helm | sail portland maineMelissa Cifuentes
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“It is my families first time visiting Portland, Maine and we needed something fun to do. We found this boat online and the morning of our trip, it was gloomy. Regardless of the weather, it was still enjoyable. Captain Ian was quick to respond and gave us directions when we called him. He is a great conversationalist, very knowledgeable, and kind. We had a great time and it felt like we were in the boat with a long time friend. I would highly recommend- especially those who are afraid of boat rides- this boat doesn’t have many bumps & is smooth sailing. Would love to come again on another visit. Can’t say enough good things, don’t look anywhere else for a fun outdoors activity!”


chartered cruise | family vacation portland maine | sail portland maineDan Clifton
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“Had an awesome time sailing with Ian. He was very accommodating with our toddler and the whole ride was very intimate since there were only 8 people on the boat. Captain Ian was very helpful with recommendations and it made for a beautiful morning on the water. Highly recommend this over the schooners packed with 40+ people. We were able to sit comfortably with plenty of space to stretch out. Be sure to bring snacks and drinks. Thanks again Ian for a great experience.”


harbor sail portland maineChristopher Jacobs
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“Wow, just wow. Captain Ian and Sail Portland Maine was fantastic! I’m not a sailboat person because I get sea sick very easily. However, my fiancée really wanted to go, and after the encouraging persuasion from her and reassurance from Captain Ian, we went. He took us out for a 2 hour private charter and it was smooth sailing. He was very attentive and made sure we both were comfortable. We enjoyed the oysters and rosé from local vendors which completed the experience. We were having such a great time and the sunset over Portland was beautiful so we asked if we could stay out for an extra hour, and he obliged. If you want the intimate sailing excursion seeing Portland from Casco Bay, this is it. Don’t look anywhere else, you won’t regret it.”


eleanor hawkes - yelp elite event | sail portland maineErin Conley
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“Most amazing experience you could imagine! Everything was perfect and Ian was very accommodating. Ian provided us with a great amount of knowledge on sailboats, as well as the surroundings we passed. It was great being able to take our own cooler with drinks and snacks! Definitely an experience that we would do again! If you are worried about getting sea sick… DON’T!!! My mom gets extremely motion sick and felt great the entire trip.”