Eastwind Schooner — Local services in Boothbay Harbor

I was really looking forward to our sunset sail aboard the Applejack Schooner as a fun night out with a good friend, but unfortunately, the poor customer service we received before boarding left a lasting negative impression.

Our sail was scheduled to depart at 6:30 PM, with a check-in listed at 6:00 PM. At 6:15, we received a call asking where we were. I told the woman on the phone that we were a few minutes walking distance according to Apple Maps, but that we were unfamiliar with the area. Rather than offering helpful directions, she was impatient and dismissive, saying she needed “more than that” and offering condescending comparisons such as checking in early for flights or movie theaters and that we should have been there at 6 PM. It was then where I asked if the boat was scheduled to depart for 6:30 to ensure we were not confused with the departure time, and she confirmed that was the case. Now hurrying, we meet at Pier 6 where the directions told us to go, and couldn’t immediately see signage for Boothbay Sailing. With this, I called back to get the same woman on the phone. She responded with such a hostile demeanor and frustration towards me. I tried to explain that it was a misunderstanding and that we didn’t realize we had to be there by 6 PM, but the tone remained unnecessarily harsh and unprofessional.

We eventually found our way to the dock, only to be met with more passive aggressiveness and rudeness. She immediately let us know she “knew who we were” and told us multiple times we were the last to board, as if to shame us. I expressed confusion about the treatment we were receiving, and she accused me—repeatedly—of having a “bad attitude.” I attempted to keep the conversation respectful but was met with more hostility. It was deeply uncomfortable and not how any paying customer, or anyone for that matter, should be treated.

The sailing itself was pleasant, and the rest of the crew was fine, but the initial interaction literally soured the entirety of our sailing experience. A bit of patience and professionalism could have made all the difference, especially when dealing with us visitors who were unfamiliar with the area and were PAYING for the experience. Sadly, I cannot recommend Boothbay Sailing based on...

If you’re ever lucky enough to find yourself sailing out of Boothbay, do yourself a favor and ask for Captains Josh and Marrison. These two aren’t just skilled sailors—they’re storytellers, teachers, and entertainers wrapped into one unforgettable crew.

From the moment we stepped on board, Josh’s confidence and calm demeanor set the tone for a safe, smooth, and exciting journey. Marrison brought the kind of warm, infectious energy that made every passenger feel like an old friend. Together, they created an atmosphere that was equal parts relaxed and exhilarating.

The scenery was stunning—Boothbay is a gem—but it was their deep knowledge of the coastline, tides, and local lore that elevated the whole experience. Whether trimming sails or pointing out harbor seals, they were always engaged, attentive, and clearly passionate about what they do.

We laughed, learned, and soaked in the sea breeze with two of the best captains in the game. Five stars doesn’t feel like enough. Thank you, Josh and Marrison—you’ve officially ruined us for any other sailing...

What an incredible and perfect sail. My new wife and I chose to charter the Eastwind for a private sail to get married during the Boothbay Harbor Windjammer Festival. And it couldn't have been more perfect. They had a kind, lovely crew aboard that day that went above and beyond to make sure our experience was great. Helping hoist the sales, then going for an awesome sail out around Squirrel Island and back, letting us know when some opportune moments would be to do our quick ceremony, and having champagne ready for it. It quite literally could not have been any better. We had 13 of us aboard and that worked great. It gave us plenty of room for people to walk around and enjoy the ship. We almost used the Applejack, but they convinced us it would be a bit cramped with a full boat, since that one maxes out at 14. The Eastwind that can carry around 30 people, was definitely the better choice. Thank you so much Captain Josh and first Mate Christina for safely taking us out for a great sail! and Mike for working out the...