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Calendar Islands Sailing Company

South Portland, ME, USA
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Calendar Islands Sailing Company
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Lennox wrote a review Aug 2020
1 contribution
When planning a bachelorette party for a dear friend, I needed a daytime activity that was intimate, seamless, and memorable. Our private charter with Calendar Islands Sailing Co. met and exceeded these high expectations. Leading up to our booking, Sandra (the owner) was responsive, cheerful, and answered all of my questions. I felt like I was conferring with a friend. On the day of our sail, she left us in the trusted hands of her crew, two experienced and able seamen who made us feel safe and well-attended. The boat, the Nichte Ha, is very sleek and stylish, and has everything you need, down to a Bluetooth speaker. Even if you’re in Portland for just one day, this is a MUST DO activity. I couldn’t recommend this highly enough.
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Date of experience: August 2020
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jollygreenjoe wrote a review Sep 2019
Atlanta, Georgia24 contributions6 helpful votes
Semi-private 2hr sailing tour (they only take up to six persons and its a 60’ yacht!) Crew was very easy going and made for a relaxing and very memorable experience. Plan ahead to bring your own snacks and wine (they have stemware, cups, etc) and you’ll have an amazing experience.
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Date of experience: September 2019
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CorZ wrote a review Sep 2019
2 contributions1 helpful vote
4 girlfriends and I did this for two hours Labor Day weekend. We had the most amazing time and the sail boat, crew, and calendar island sailing staff absolutely surpassed all expectations we had. First, I will say the woman who runs this operation is an absolute angel. We had several changes with our booking and each time I called she remembered me and worked with me to accommodate all changes. The sail boat itself was huge and absolutely stunning - we would not believe our eyes once we got on board. Our captain, Nathan, was a true gentlemen and waited on us the whole time we were on board. He gave us glassware, a cheese board, refilled our drinks, and gave us seat cushions and blankets when we got chilly. There is no doubt we will be back! We are already planning another trip to Portland solely so we can do this again. THANK YOU calendar island sailing !
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Date of experience: September 2019
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staceypetro757 wrote a review Aug 2019
3 contributions
The captain and first mate were very nice and informative. We had a great sail! I would definitely sail with them again the next time we're in Portland.
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Date of experience: August 2019
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Samantha B wrote a review Aug 2019
7 contributions
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We are lucky to live so close to Casco Bay and love sailing after work and on weekends. I am from NYC and my fiancé is from Portland and because of family visiting from NYC throughout the summer months, we have been on every cruise or sailing excursion in Casco Bay for years now and wish we knew about Calendar Island SC eons ago. You start out at Fore Points Marina which is absolutely gorgeous and once everyone is in attendance you take a nice jaunt out to the boat. After safety precautions are met, you can relax on any part of the boat. We sat on the stern while some stayed in the cockpit and bow. We were still able to engage in conversation with the crew and rest of the group which lead to great convos. We brought wine and appetizers which made for a perfect trip on the 6pm cruise. The crew on Calendar Island SC made us feel like we made their day. They were jovial, funny, talkative and eager to make our experience the best it could be. From providing glassware for the wine and apps we brought onboard, to offering cushions and bluetooth speakers, we truly had a blast and cannot wait to go out again! It is hands down the best boating experience on Casco Bay! Thank you for an unforgettable night in our hometown!
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Date of experience: August 2019
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