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    Rockport Charters

    5.0 (1 review)
    Closed 6:00 am - 6:00 pm

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    Maine Windjammer Cruises - Schooner Grace Bailey

    Maine Windjammer Cruises

    (6 reviews)

    Dear Ray & Ann Williamson - Windjammer "Swift" Owner,…read more Thank you, thank you, for giving us the respite so desperately needed!! Your amazing & beautiful boat and perfectly crafted cruise shifted us entirely away from the habitual stressors of our lives. The beauty of the Maine coastline and being taken care of by your amazing crew (our Captain Hans, Deck-hand Miles, and Chef Levin), who were all hardworking, talented and a pleasure to spend time with. They Worked hard all day long, clearly knew what they were doing, shared the load, while enjoying every moment. As we watched their skills in action keeping your fabulous Windjammer upwind from our comfortable deck chairs, we delighted in the fresh sea breezes, and enjoyed the delicious and creative menu, which was unexpectedly luxurious. Thank you again for the gift of our time on Windjammer Swift! Chris & family sailed Camden Maine 7/2/25 - 7/5/25

    My wife chose this trip because it was our 10 year wedding anniversary. I was not going to let…read moremyself get excited; because I have always loved the idea of sailing and yet have never been and did not want to get my hopes up. My only trepidation was having to put up with other people who had no sense of humor. So, Sunday we arrived just an hour before check-in and upon arrival the nice lady at the front desk was probably far more cheerful than I would be at that hour. But I loved it! We brought our small amount of gear on board and was shown our rooms after a brief lesson by the Captain. Our room and beds were small and by no means should you expect one of these rooms to be of cruise like quality, because you should not want to spend your days in your cabin and that is the point! We slept pretty well that first night before we set sail and all of our stuff fit neatly in our cabin with room to stand and change. The ship was probably around 140 years old and was maybe 100 feet in length, with large wood masts heavy sails and you can hear the very slight creaking in the wood all around the boat as it rocked with the ocean. I was totally in love with her already. That night I met a few of the crew and passengers on deck while we kind of introduced ourselves in a non formal fashion which made me more at ease and since I clicked with everyone that I had met, I knew that I was going to have a great time. The next morning they served some Mexican omelette type thing which was cooked on a wood stove down in the galley, which I thought was cool as hell. Now, this omelette set the tone for how the rest of the meals were going to be MOST EXCELLENT! We were invited to help raise sails once we were pushed off out of port and like a kid in a toy store, I did. There was a small complement of crew and passengers, 14 maybe in total, so it was a lot less crowded than it could be. During that time I met the rest of the passengers and crew I did not meet the night before. I went down into the galley to thank the cook that made that fantastic breakfast and ended up chopping garlic. We sailed what seemed like forever and not long enough. Our first stop was Stoningham where we dropped anchor and ate a wonderful dinner, lunch was good too, and also it had garlic. Now when my wife had mentioned that it was a working boat, I thought to myself, GREAT IT WORKS, who knew? LOL, well I ended up doing all kinds of work, not because I was forced or it was mandatory, but because it was something you wanted to do. Once we got back, we hauled anchor again and set sail for another island, which had no one on it and we went ashore and walked it beautiful sandy beaches. I think that night we had lobster cooked over a fire. The next day we raised anchor and set sail to Rockport where after another wonderful dinner we sat and listened to one of the Captains poems that he wrote and was published, he read other things that he liked and we all sat there and listened as we drank our beers and relaxed the night away. The next day we sailed back to Camden and after playing a few jokes on Captain Ray, it was time to go home. I think that I speak for pretty much everyone on board when I say we wanted to stay and everything we had seen and done all over again. I just want to say thank you to Captain Christopher, Dillon, Dawson, Sara, and Collin. I will remember this to be the best anniversary trip ever. Even better than that cruise ship we took for our honeymoon. Oh and speaking of cruise ships, I found out from other ships crews that the Chamber of Commerce has been catering to the large cruise ships which is taking away business to this unique to Maine Schooner sailing. I questioned the crew I was on board with but they just shook their heads without a response. It is too bad if it's true because it was such an amazing experience that I feel that everyone should have a chance to enjoy. Thank you for the most beautiful and memorable experience, Douglass and Dorothy

    Rockport Charters - boating - Updated May 2026

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