Our Reviews

I’ve been on Ian’s boat a few times now and it’s always an incredible experience! It’s the perfect activity to do with a group of friends or family or for a networking event! Ian is the sweetest guy, his boat is beautiful and his pup Huckleberry is adorable! Recently went with my best girl friends and it was so much fun!!! 12/10 recommend!

My little family took a tour out on the Calista Ann early July and had a wonderful experience! Ian and Chris showed us a great time out on the water. Relaxed environment and easy going! I would definitely recommend this tour! And Huckleberry the dog was a nice addition to the crew.

Our group of 9 ladies had the BEST time with Ian and Andrea! We had a slight delay due to weather and both were so helpful and friendly while we waited out the storm. Once the storm past we had a beautiful double rainbow, then went off on our adventure. We had d a lovely time cruising, seeing the sunset, and some seals!!! Ian and Andrea were so friendly and made our experience that much better. Plus Ian has the cutest, and most well behaved dog. We were able to bring on board our own food and drinks. Boat size was great for our group too. Can't recommend this enough!!

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!

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

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!).

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!

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.

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.

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.

My group of a half a dozen close friends visiting Maine from New Jersey took a late Friday morning charter with Ian and Sail Portland Maine and had the most wonderful experience! Ian and his first mate were super knowledgeable in the area, sharing great pieces of information along our chartered route, and quickly made us feel right at home on the vessel. Our group brought our own food, beverages, and music, but Ian was prepared with a speaker should we have left it behind. He was also more than happy to take photos of our group along the various stops throughout the charter, which was super sweet. Highly recommend Sail Portland Maine for any small to mid-sized group charter, would book the outing again in a heartbeat!

Ian is the best! We were visiting for a girls weekend and this was a must do! If you’re looking to do some sightseeing and relax and have a few drinks on the water- he is the guy!! Such a peaceful ride and got to see so many beautiful spots and seals. Huckleberry is the best dog and was so well behaved. Absolutely must do if you’re visiting Portland or want to get out on the water and see some of the lighthouses and beaches. Definitely doing this again when we come back! Recommend for group, couples or families! So relaxing and beautiful way to see Portland. Thank you Ian!

We had the best day out on the water! I went with a couple of friends for a day sail and it was an amazing experience from start to finish. The captain and crew were incredibly accommodating, welcoming, and made us feel right at home on board. They were fantastic tour guides, pointing out sights along the way and sharing fun local insights. The atmosphere was relaxed, fun, and unforgettable. Highly recommend this experience to anyone looking for a perfect mix of adventure and hospitality on the water!

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.

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!

My little family took a tour out on the Calista Ann early July and had a wonderful experience! Ian and Chris showed us a great time out on the water. Relaxed environment and easy going! I would definitely recommend this tour! And Huckleberry the dog was a nice addition to the crew.

"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  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!

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.

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.