Portland Schooner Co.

This was such a great way to spend the afternoon!! You can bring whatever drinks and food you want on board and that was such a nice plus. We brought cups and wine and it was awesome. The captains really get you involved in setting the sails (if you want) and that was a really cool experience. Other than that they just let you vibe, no speaker telling you what you’re looking at. However, they are happy to answer questions and walked around to check in with everyone. Whole crew was so nice and welcoming. Best of all, there is a bathroom on board!! I loved the BYOB element and everyone on board was super nice. We had a blast!

Every vacation I seek to do something out of the ordinary. I have been on Portland Schooner Co. sailboats twice. Each time has been great! The views, narration, ability to somewhat explore the boat, it is a fun, leisurely way to spend an afternoon. I have yet to go during a time where the wind is up as I imagine that would be fun. The captain and their mates are excellent. If you are vacationing near Portland, I would suggest considering a trip. It is scenic, relaxing, and fun. You won't be disappointed!

Had the best experience with this company! I celebrated my college graduation with my goofy family and the staff answered all of our questions (and we asked a lot). I like that there isn’t a script they go off of and it’s not a guided tour…. It’s just open for conversation if you have questions about anything. This is a great way to get out on the water and see the area from a different perspective. It’s BYOB and there’s plenty of room for everyone on the boat!

We thoroughly enjoyed our afternoon sail with Baird, Lucas & Kyle aboard Bagheera. They did a fantastic job as captain and crew and were a pleasure to speak with! It was a wonderful sailing experience and we enjoyed hearing stories from Baird. P.S. Michael, if you are reading this, you should be proud! You did a fantastic job!

Jonathan and Baird were great captains. Very chill. Sailing was relaxing. Perfect weather. Sunset sailing at 6pm. Right on time. Great way to end our day.

If you’ve never been on a sailboat before, this is the perfect place to start. The staff is friendly, welcoming, and does a great job explaining everything like how sailing works to fun facts about Portland. If the wind conditions are favorable, they’ll even let you participate in the sailing process, making the experience even more engaging and memorable.

We had an amazing time on this sunset cruise! The entire experience was smooth, relaxing, and absolutely beautiful from start to finish. The views were breathtaking, and watching the sun dip below the horizon out on the water was unforgettable. The staff truly made the trip even more enjoyable—they were incredibly fun, friendly, and welcoming. You can tell they love what they do. They were also super knowledgeable and happy to answer any questions we had along the way. Highly recommend this cruise if you’re looking for a memorable way to spend an evening. Would definitely do it again!

Captain Greg and crew (Erica) are locals and knowledgeable - the tour doesn’t have a lot of people even when full so it’s nice and intimate. Nice tour at sunset and you can bring your own drinks and snacks to enjoy

My family and I hopped aboard the Wendameen for an afternoon sailing trip, and it was an absolute delight. From the moment we stepped aboard, it was clear how friendly and knowledgeable the crew were. They made all the difference! It was a fantastic and unforgettable way to see the beauty of Casco Bay. Could not recommend more!

Pretty sure I have the correct company. We did the afternoon lighthouse tour. Our captain was "C.J." and she was joined by "Mackenna." This was a wonderful tour. Saw all the lighthouses and seals too. The ladies could not have been nicer. Highly recommended!!!

We sailed the late afternoon on the Vela. Just beaitiful. I'm local so familiar with harbor, but have never been on this kind of sailboat ever before. Lovely friendly professional crew. Fabulous experience.

We did the sunset lighthouse tour - it was amazing! CJ & Leo were our captain & crew and they were super knowledgeable & made it an amazing experience. I definitely recommend if you are gonna be in the Portland area.

Fantastic! This made the evening. Captain CJ, was the best! Great stories, informative info but not too overbearing. I think this is an excellent way to see Casco Bay. Would definitely take this tour again.

We took the sunset cruise on Vela with Captain Kyle. Beautiful views. Definitely recommend the sunset! Very peaceful sail. The guests were invited to help pull up the sails - two of my friends jumped in! We were able to bring drinks and snacks. Captain Kyle was informative and friendly. We were "healing & heeling!" TIP: We went the wrong location originally so be sure to double check where you're going!

This is a great, relaxing sail! You can bring a picnic! We picked up a pizza at Flatbread Pizza which is at the docks and packed some wine. The crew was friendly and the scenery beautiful! We went on the sunset cruise and you need to bring a jacket. The crew did provide some blankets. It gets a little chilly toward the end! The schooner we were on was 100 years old. A great experience!

We really enjoyed our time on the Schooner. It was relaxing and scenic. The crew and the check in host were very friendly and helpful. It's well worth the time.

We booked this schooner trip ahead of our trip and check in was easy. We parked in the paid parking garage nearby which was reasonably priced for the evening. The schooner was beautiful and such a fun experience and we had great wind. The Sailors were friendly and made a point to chat with everyone on the boat to help us feel welcomed and answer our questions. They ask for volunteers to help raise the sails, so be sure to jump on that if you'd like to give it a try. It's BYOB so remember to bring drink-ware and snacks as well.

We had a great tour of Casco Harbor. After helping raise the sails, we got to enjoy the sights. The crew would visit with all of the people on the boat and answer any questions. They were very knowledgeable. The tour was well worth it.

Portland Schooner has 3 vessels that will take you out with other ticket holders. They raise the sails, and I have been on schooner short cruises with other companies where that never happened. This was a 10:30 2 hours cruise on the 100 year old Baghera. It was interesting, fun and relaxing. The heat was already at 90 degrees so it was a welcome relief to be on the water, Casco Bay. I highly recommend a hat, sunglasses, cover up and sunscreen. There is no, I mean no shade. You will be sitting on the deck on close to other patrons. You might want to wear a mask, but not required. We did not have a tour guided sail but a lovely sail. If I were to add an improvement, it would be to add cushions to sit on, as the sitting on the deck for a couple of hours would make it a more pleasant sail. Crew was available and pleasant for questions. For tipping bring cash. I did not and wanted to tip, maybe apple pay or something can be integrated as tipping. Seldom do I have to carry cash these days.

Had an amazing time! Totally worth the money! Sunset sail was so peaceful. I've already recommended it to people and I would go again if I have time during my visit!

Went on a lovely sunset cruise--it was the PERFECT vibe. Staff was knowledgeable and there to chat if we needed, but hands off otherwise. Beautiful sail, very low key and love the very BYOB of it all. Cannot recommend more highly!

We had so much fun! Brenna (we think is her name) did amazing, working so hard and climbing up to put the sail away barefoot in the freezing cold. Would definitely recommend

Took an afternoon sail tour and enjoyed very much. The crew works pretty hard and we appreciated these two taking the time to visit with us and answer questions while they kept the boat moving. Captain did a terrific job also and even had a few dad jokes for the passengers. Lovely, calm waters in the bay and was the highlight of our day, thank you Portland Schooner!

Definitely recommend this boat ride. Crew was great. Even though it rained we had a blast.

We went for a sailboat ride as part of a bachelorette party weekend and had a great time! Bad weather threatened to cancel our trip but they actually were able to call us and schedule us for a few hours sooner. The crew was friendly, knowledgeable and very laid back. They even helped us out with a few photos. Can't recommend this company highly enough! BYOB, snacks, and jackets - it's chilly on the water.

I enjoyed our sailing adventure last week. We had a good group of passengers and the 3 sailing guys were friendly, professional, and knowledgeable about the area. We did the Sunset Sail, which was 2 hours. However, it was a rainy day and no sun. If you go in lousy weather dress warm and bring a rain jacket and maybe a towel to dry off your seat. No beverages or snacks are provided, but you can bring your own. In the beginning, they had a bunch of passengers help with hoisting up the sail, it was fun to interact. You didn't have to if you didn't want to though. 2 hours felt kinda long, especially in the foul weather, but I guess we got what we paid for. On the way in the captain had to radio the captain of a cruise ship to get priority in docking which was right next to the dock. It was interesting to see how the communication worked and the seamanship. I would do this trip again, but pray for better weather. On the other hand, I'm glad it wasn't canceled because of gloomy skies and a sprinkle.

Decided to go for a sail with these guys to celebrate our anniversary. The boat was great, spacious and comfortable. The crew did a fantastic job on the cruise. Fortunately the wind was favorable for a sail out to the Portland Head light and back around by Peaks. The crew were knowledgeable about the area and readily available to answer questions. Great trip!

I've been on two sails with this company and cannot speak highly enough of both! I've had the same Captain on both sails and two different crews. All or knowledgeable, friendly, professional, and delightful to talk to! I give this company my highest recommendation! Hurry there now for a sail before it gets too cold!!

Spend an afternoon sailing around Casco Bay in an almost 100 year old schooner, its thrilling and laid back and interesting all at once. For $55 you get a two hour cruise, and the crew could not have been more welcoming. They were so eager to talk about the boat and answer any questions. I dont know a thing about sailing so to see them work as a well coordinated team was something to behold. If I had any gripe it is that you dont really go anywhere far, I had hoped to get closer to the Portland Head Light lighthouse for some photos from the water, but again, I dont know about boats and currents and stuff like that so I guess there is a good reason for it. I would 100% book another trip with them, it was so great.

Enjoyed a sunset cruise with the BF recently. Absolutely worth it. It's BYOB/snacks. If you've forgotten there are plenty of places to pick something up nearby. The staff, the boat, the sunset.....perfect. I'll be back to enjoy many more. Thank you for a wonderful experience.

We had a great sail with Captain Kate! Brought our own snacks and wine and got to help sail the boat. Perfect Saturday afternoon.

This was a very cool experience that I'm very happy we did! It was quite chilly on our sunset cruise but we dressed accordingly and the crew provided blankets. Everyone was friendly and it was so much fun to view the harbor on a schooner! I've been on numerous sunset crusies but none have been as awesome as this :) Ps. We had a little difficulty finding the place...walk past the ferry ticketing and there will be a small gray shack on the right

Had a lot of fun here on my visit to Portland in September. Reasonably priced tickets ( about $60 per person) and BYOB is a great addition to enjoy the nice views. Saw a couple of lighthouses and surrounding area. It was a bit chilly even though during the day it was fairly warm so bring a sweater just in case. We mostly kept to ourselves, but the employees were very friendly. At the beginning before leaving the dock area, they asked for volunteers to help set the sail, which I participated in and thought was a nice touch and memorable moment. The sunset was the highlight of the sail, pictures could not do it justice. Overall, I would recommend to go here for a cheaper yet nice experience. To put in perspective, some surrounding businesses were charging $200 or more.

Awesome experience while you're visiting Portland. You can byob, so we brought some FoulMouth Brewing beer cans. The couple next to us were on a special date and popped a bottle of champagne. Once you set off, the staff work hard to get the sails up ASAP. Depending on the wind, the captain will use the sails only when they can but have a motor back up. There was only a tiny bit of wind on our trip and it was still amazing. You get to see a different part of the bay and ride on a 100 year old ship!

Excellent experience. The crew was professional, friendly, and clearly very experienced. Will absolutely try another sunset trip.

Didn't have anything booked for Portland and found this via a google search. Booked on Sunday for the following Friday. The day of the cruise someone called to confirm and texted very clear instructions on where they were located. Upon arriving we were greeted by a friendly crew who were very knowledgeable. The sunset cruise was the PERFECT end to a vacation week & the crew were so kind. Once out of the port they chat & get to know you & about your travels. Had the best time talking to other guests & taking photos. Cruise is BYOB and BYO snacks.

We went aboard Timberwind for a mid-day summer sail in celebration of our 30th wedding anniversary and it was PERFECTION!! The crew were very personable and it was a smooth, enjoyable cruise--recommended for all, except maybe toddlers and other "littles" who may not appreciate being surrounded by a million awesome things they perhaps shouldn't touch, climb on, or run across. We look forward to going back in the fall to experience a splashier sail. Special shout-out to deckhand Chuck who answered our many questions on the schooner, Portland Harbor's lighthouses, military forts (FYI, they date back to the War of 1812 and Civil War and the walls are 15-ft. thick!), and more!

I really enjoyed our 2 hour sailing out in the harbor. Helped raise the sail, which we did sail most of the trip. Great, fun, knowledgeable crew. Watched the sunset go down behind the city. Our night was chilly, so bring gloves, warm jacket and a hat. It's not expensive. Don't forget to tip your crew. There was 6 of us on board, yep, that is rare and made it seem very personal.

My friends and I had the best time on this schooner with Remi, Max and the captain! The crew was super friendly and made it an interactive adventure. I would highly recommend going on this boat!

Good sail for tourists and first-timers. However, one of the crew never stopped chattering about herself and her life escapades. Annoying doesn't even describe it. You could hear her from all over the ship. She also did not handle sails well or respond to the captain because she was so busy talking. He actually had to go up on deck to get something done that the crew should have done. Also, the crew begging for tips was in poor taste. The captain made a major comment about "tips being welcome for excellent service" and that was offensive (that's not how tips work). After that announcement to our group, one of the crew stood at the bottom of the disembark with a canvas bucket for people to drop money into as if it was an expectation, so people had to do it whether they wanted to or not, as the whole thing was out in the open for everyone to see. It was the tackiest thing I've ever seen. And to think they do this 4x/day! They must be pulling in some serious cash. I will never take my guests there again.

Communication was exemplary and much appreciated since I was booking rather last minute on a holiday weekend. Didn't want to leave Portland without getting on a sailboat, so after some brief research on available options, I landed on Portland Schooner Company. As mentioned above, very friendly and informative service from start to boat. The ride itself is quite lovely and relaxed. The crew is really there to just steer and do all the stuff required with getting sails up, and other than that, they're ghosts. You can definitely engage with them, but there's no official tour or info provided while at sea. Instead, just enjoy the peacefulness of the bay/port and pal around (or not) with the people you're sharing the experience with. BYOeverything, so stop by a local bakery, winery, brewery, etc. and enjoy the delicious spoils of Portland while on the boat. The definition of smooth sailing!

Cool bucket list experience and a beautiful way to spend a few hours on the water. A soloist traveler or a family, anyone can go. Last minute decision and just went with it. Easily booked online and followed the signs at the port. The crew was comprised of 3 people and were very friendly. There were 26 guest on board. It was a very relaxing experience and recommend it for anyone that hasn't be sailing before. Take sunscreen and water. Safe travels!

You'd be crazy not to book this. No better way to see Portland and get a glimpse of the islands and meet some locals (who even let you help them sail!). I was slightly upset the hunky captain didn't ask my hand in marriage but next time. We drank wine and ate cheese + grapes. The moment it got chilly, everyone working the ship was checking in and offering blankets. It even rained a little and no one was bothered. We had a great time!!!!

This was the most appalling experience I've ever had and would rate zero stars if I could. We sailed on the Bagheera on Saturday 8/24 at 1:00 PM. Approximately 20 minutes prior to the end of the trip, the septic tank overflowed, which caused the drain near where we were sitting to spew out human waste all over our exposed feet and the sandals we were wearing. We were unaware of where the drain led to, or else we would have chosen to sit in another location. The staff noticed the leakage immediately and asked everyone sitting on our side of the boat to move. Actually, the female staff member asked the couple sitting on our side to move, even though we were sitting closer to the spurt. It really felt like we were an afterthought as she barely said anything to us. Although we were situated closest to the drain and I had loudly voiced my displeasure and utter disgust over getting splashed several times, the staff never once addressed us directly about it. Even if they hadn't heard me, they should have asked if we were okay considering we were sitting right in front of the leakage, especially the female employee who noticed the incident first and asked us to move. We also did not use the restroom during our cruise, meaning we were splashed with other people's urine and feces. I could not bring myself to leave a tip after the staff's blatant disregard. After docking, we reported the incident to the woman in the office, who apologized but only offered us water (no soap) to rinse off as consolation. Considering human waste is a biohazard, I feel like we should have been refunded. I would never recommend this callous company to anyone.

Had such a lovely evening aboard the schooner! The crew was a delight and this was a perfect sunset cruise out to see Portland's lighthouses. A few folks had a hard time finding a seat but we got there early to get in line and got to sit right in front. You are allowed to BYOB and snacks so pack something to enjoy! I will do this again when I return to Portland.

We took a 2 hour cruise on the Bagheera. Very friendly crew, knowledgeable about the area. Fun to sail on a wooden windjammer. We did see a seal and an osprey, both fishing!

The focal point of our trip to Portland. A perfect day as the winds were strong. The Captain and crew worked very hard to make our trip enjoyable. Breath-taking views and an educational voyage for sure!

We sailed today and the weather was absolutely perfect, truly picturesque. Unfortunately, the captain really didn't deliver. No commentary, no history, hardly engaged with passengers at all. In fact, he was a bit negative, having started the trip talking about a captain death in Newport and then some complaints about places he'd sailed. Passengers were asking him questions to find out more about Portland, but it was difficult to have fun in this atmosphere. It's clear this captain is a very experienced boatman, with a passion for sailing, but not a passion for customer service.

We had an excellent sail today with captain Shakespeare and his crew! He gave us great information about all of the islands, lighthouses and the scooner. The crew were wonderful and friendly and we had a perfect trip!

Very relaxing boat tour. Worth the money. The girls were knowledgeable and the scenes were amazing

We booked a morning ride on the schooner for 10:30 on a weekday. It was a perfect day for sailing and by all measures was a great ride. The captain and crew were chatting and nice to everyone on the packed boat. The only thing I'd say is i think they market it wrong. I thought they would give us some information on Portland and we'd be able to see more lighthouses. Would definitely be better for couples instead of families.

So beautiful and so much fun! The Wendameen was beautiful and so awesome! Also the crew was amazing! So much fun enjoying a BYOB/Bring your own snacks cruise! Remi, Max, and Captain Russ were great! Also they were full of fun facts and info! Would definitely join them again

Awesome time with the staff at Portland Schooner company for a sunset sail on Casco bay. It was the perfect day for sailing with the wind but kinda chilly on the water. We bundled up and appreciated the blankets they provided for added warm. The boat is well maintained, clean. The staff is friendly and made sure we had a good time on the water. Definitely something to do while in Portland!

A nice 2 hour sail. However, when we booked this trip, we thought it would be a water tour-telling us about Portland, what the lighthouses were called, what the islands were, showing us seals, etc. However, the crew didn't provide any narration, so we were googling things as we passed them. And we never got close enough to the shore to see any seals (seeing seals was a big selling point on their website). It was a very nice boat ride (nice cool breeze, smooth, no engine sailing), but we would've gone with another tour company in order to get some Portland information and see the seals.

Loved the sunset cruise we went on great people including the captain and first mate 10/10 would recommend

We had a great sunset sail on a Sunday evening. We got tickets same day but it may have been easier since it's during Covid and it was a Sunday. They didn't overcrowd the boat - again probably because of Covid. It was NOT an "informative" tour - it was simply a sail enjoying the sights, which was perfect. This ride was just two hours of enjoying the sites. Watching the crew work was amazing - they are a well oiled machine and very organized. The whole ship was just propelled by the sails and we had a great wind the whole ride. You can also take your own drinks and food on for the trip. The crew wore masks the entire ride and had hand sanitizer on board. We would definitely recommend this company and would ride again.

This company is horrendous to deal with it. I went to their website to book the Heart's Desire. It was not clear from their website that we were not booking the private charter. When I contacted them "Karen" said it was our fault. Karen then said we needed to confirm we were coming because they were sold out and would re-sell our tickets but refused to refund our money. Karen was rude and insulting. She said we should take the public sailing trip because we didn't have any money to do anything else because she had our money. Who says that? Karen was awful. The website is poorly designed. Do NOT use this company.