This was easily my favorite thing I did while in Salem!!! This sunset sail was so fun, and the crew was amazing! They knew the history of the boat and were great to chat with. You could walk around and even go below to see some old photos. (They also have a bathroom down below) On this trip they let you help with getting the sails up, it was so fun to hear from them and see how much work it takes. The views were breathtaking and although it was a bit cloudy, the sunset was still gorgeous. We got to see a full moon rise as well! Overall: I came to Salem for witchy stuff but am so thankful I decided to add a sail to my itinerary! read more

Sunset Sail Salem - Sailing Near Me - Salem, Massachusetts

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It was smooth sailing aboard this vessel. The crew members were knowledgeable and fun and friendly. They were so eager to teach us about the boat and sailing. The views were stunning, and the drinks were good. read more

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This was the highlight of a recent Salem and MA trip for my daughter and I. Veronica, Kass, and Captain Zack were engaging and wonderful the views and experience was breathtaking. I highly recommend!!! read more

Had an amazing sunset cruise today with Captain Seth and his crew. Seth is a very experienced captain and very interesting to talk with for great sailing stories. Highly recommend Sunset Sail Salem! read more

We had a fantastic sail on the "When and If". All of the crew were wonderful in terms of making everyone feel welcome and comfortable, with great hospitality, and the scenery on the water off of Salem is absolutely beautiful. Highly recommend if you are looking for a lovely sail on a beautiful classic yacht. read more

A great sailing on an amazing boat. Weather was great, winds and sea were fair. I would definitely recommend sailing this boat and crew if you're looking for a quick adventure out into the ocean and back. read more

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Excellent per usual. Captain Matt and his crew gave us 2 hours of smooth sailing. Unique schooner built for General Patton who planned on sailing around the world in it which unfortunately never happened but that dream is still being worked on by the it's newest owners. There are complimentary cold water and sodas. Plus nice options from their bar. Perfect for couples, singles, families, tourists and locals alike. Great way to celebrate birthdays, Father's and Mother's Days, date nights and days. Great way to meet other locals or those visiting Salem. Highly recommend. read more

Went on the Sunset tour out of Salem, MA. It was such a great experience. The crew was knowledgeable and friendly, the boat offered history and a smooth sail, and the cocktails were easy to drink. Would recommend the tour to anyone looking for something memorable to do in Salem that does not relate to witches. read more

Cold drinks , friendly staff, very knowledgeable about the history of the boat. Overall had a wonderful time for the sunset cruise. read more

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Love the When and If. Great crew, relaxed atmosphere. Always a lovely sail. Even the other passengers who you know you would normally find annoying or obnoxious if you met them on the street are cool on the When and If because the atmosphere is just that laid back. It's the perfect cap to any day read more

Sunset Sail Salem - Looking towards Baker's Island on the Sunset Sail - Sailing Near Me - Salem, Massachusetts

It was a great crew, extremely informative. The ship we sailed on was once General Patton's. The crew talked about sailing and about the ship. The drinks were very good. Highly recommend read more

Sunset Sail Salem - Sailing out of Salem MA - Sailing Near Me - Salem, Massachusetts

Perfect sail! The crew was amazing. The boat was spotless. It was a fantastic evening! Go!!!

Very pleasant although a little narritive towards the end would have been nice. we sailed but did see the sunset cruise all swarll exept a liitle more convo would have been nice from the crews. read more

What an amazing experience! So much history with the sailboat and a wonderful Captain and Crew! I recently moved to Northshore and I was looking for an outing to do with my 3 Girlfiends when they came up to visit me- this was perfect we had a beautiful day and learned so much about the area and it was so much fun! I will definitely do it again! Thanks! read more

Captain Seth and his crew were a pleasure to be with! Everyone was more than happy to share their expertise of sailing a beautiful and vintage boat! Thank you crew! read more

Beautiful sail. Awesome crew! Would definitely do it over again. They offered refreshments and I even got to steer!

Our 23 wedding anniversary and we sailed on the " When and If". The sunset sail was so tranquil and romantic a perfect addition to our stay in Salem. Captain Dylan and his crew were incredibly attentive and absolute joy to be with. A fromage tray was provided for their guests and I had a lovely glass of wine and the evening was set for bliss. Thank you so much for the perfect romantic getaway with great people and staff! There is so much history to this schooner and the Captain could tell us a variety of stories about the surrounding islands and the story of the schooner itself. A true pleasure to be with this crew!! read more

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Wonderful sailing adventure. Captain and crew made us feel right a home. We had a perfect night, great views, and relaxing voyage. My family and I would wholeheartedly recommend this Sunset Sail Salem experience. read more

We did a morning sail. Seth and his crew were awesome and the boat is just gorgeous. I highly recommend this cruise

Absolutely gorgeous boat, friendly and knowledgeable crew, beautiful views, great drinks.... all around great time! Highly recommend!

We had a great time on the sunset tour! It was absolutely beautiful and our captain Eric was great- even providing blankets if we got chilly after the sunset. The boat was spacious including access to a cooler with water / soft drinks and even a bathroom if needed. read more

Sunset Sail Salem - Sunset from boat - Sailing Near Me - Salem, Massachusetts

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We sailed on the When and If at sunset. We had clear skies and it was beautiful. The crew was so nice and made sure everyone was taken care of. It was so fun and relaxing and the boat is nice. I would definitely sail with them again. One of the favorite things we did on our vacation. I would highly recommend. read more

My friends and I ended up getting a surprise boat for our friend for her birthday. This ended up being the best option! The captain was soooo friendly educated us on all the areas we sailed to and he let the people on board assist with getting the sails up and steer. We were also allowed to bring our own food and drinks on board which we loved. There is also a bathroom on board, which we really liked it. We loved the boat so much, we would definitely do it again! read more

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A group of five of us had the great pleasure of sailing the When and If on Friday evening. The ship is stunningly beautiful, well kept and comfortably accommodated our group plus another larger group. The crew did an excellent job of giving everyone information on the ship's storied history as well as necessary logistical and safety information regarding the vessel. We were fortunate to have a particularly windy evening, so we were able to experience the ship under full sail and admire the skill and professionalism of the crew. After having visited Salem a myriad of times over the past twenty five years, I would say this is the best activity I've experienced there. Would definitely recommend for all ages. Bring a jacket because it does get cold on the open water. read more

Just went on the sunset sail this past weekend and it was a great, two hour boat trip! I would highly recommend. On the boat they also had a drink menu with cocktails, wine, and beer. The crew was very friendly and accommodating! It was the highlight of our trip to Salem! I would definitely recommend going on this tour. read more

Sunset Sail Salem - Sailing Near Me - Salem, Massachusetts

Eric is a great captain and the area is best seen by sailboat. This was an awesome experience - and we had a beautiful sunset! read more

Sunset Sail Salem - Sailing Near Me - Salem, Massachusetts

Such a great experience! Captain Eric was so knowledgeable of not only the waters, but any questions we asked about the surrounding areas. He provides blankets if it gets too cold and also drinks, which is a great touch. I will recommend him to anyone who comes this way and will go back out on the boat with him when I'm back here! Thanks again, Eric! read more

Sunset Sail Salem - Sailing Near Me - Salem, Massachusetts

Captain Eric was fantastic! He was very prompt with his responses and made it easy to schedule our sail. Eric was extremely friendly and knowledgeable about the surrounding areas. We were able to bring our own food and beverages on board which was fantastic and Eric even let us help steer the boat! I would definitely recommend booking a trip with Captain Eric! read more

Really nice boat. Couldn't really move around on the boat and the staff could have been more professional. This particular group onboard just seemed "over it" and not particularly good or gracious hosts, especially given their heavy emphasis on tipping well. Sub-par experience when we had high expectations. read more

Had a great time with my family. I was looking for something different to do fairly local. We brought our kids which I was initially nervous about but Eric made it so exciting and fun for them. I highly recommend the sunset tour. Although it costs a little more, the experience is truly priceless. It's also conveniently located near great dining for before or after. read more

Extremely satisfied it was fairly cold but all in all was a great trip the guide was very helpful in pointing things out sites to see an extremely knowledgeable of the waters read more

This was my first sailing experience and it was absolutely amazing! Eric is a great captain; extremely professional, friendly and knowledgeable! read more

Sean and the crew were awesome hosts! They made sure we all had a good time and felt safe. One of the highlights from our Salem trip!

Absolutely delightful trip! The crew was friendly, inviting and willing to answer any questions about the history of the boat. I thoroughly enjoyed the trip and watching the crew bring the sails up and down as needed! Thank you! read more

Eric was fantastic and the sailboat was perfect for an evening cruise into Salem Sound. Eric is extremely knowledgeable, fun, personable, and provides a fantastic experience with beautiful scenery. This is a great way to see another side of Salem and view the islands off of the Salem coast. read more

Sunset Sail Salem - Great views. - Sailing Near Me - Salem, Massachusetts

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This was one of the best decisions we made as we were trying to decide what to do next in Salem. We came upon Captain Eric on the wharf and immediately we were all drawn to him. His warmth, knowledge and love for what he did came through immediately. We shared sailing stories and learned so much about not only his beautiful boat but also how he got the sailing bug. This is what he was meant to do. We learned how to steer the boat, what to look for in the sails and feel of the boat. If you want to just enjoy the ride, great you will, but if you want a little more than that you'll get that too. All that and the views are incredible. Thanks so much Eric for a wonderful adventure! read more