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South Portland

Calendar Islands Sailing Company

South Portland, ME, USA
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Calendar Islands Sailing Company
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Reviews (12)
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All reviews beautiful boat captain nate great sail two hours casco bay glassware nathan grazie sailed crew skiing sailboat portland
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1 - 10 of 12 reviews
Reviewed 3 weeks ago

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...More

Date of experience: September 2019
Thank jollygreenjoe
Reviewed September 7, 2019

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...More

Date of experience: September 2019
1  Thank Shoegirl523
Reviewed August 18, 2019

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.

Date of experience: August 2019
Thank staceypetro757
Reviewed August 14, 2019

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...More

Date of experience: August 2019
Thank Samantha B
Reviewed August 2, 2019

Crew was incredibly friendly. Not overly crowded like other sailing opportunities. Had a great time.

Date of experience: August 2019
Thank Jswiggy
Reviewed July 5, 2019

Very accommodating and friendly! The sail was great!! We had to reschedule to the next day due to weather so we did the morning sail instead of the evening one. Knowledgeable staff. Had a great time!!

Date of experience: June 2019
Thank traveler12Atlanta_GA
Reviewed May 3, 2019

Calendar Island Sailing Company offers one of the best experiences one can enjoy while visiting Portland, Maine. Sail aboard their beautiful Maine built sailboat Nicte Ha on an unforgettable trip around historic Casco Bay. Captain Nate knows this area well and he and his crew...More

Date of experience: September 2018
Thank SSSsaga
Reviewed April 2, 2019

We chartered the boat for the day through Sandra (the Captains mom =)). I wish we were able to do this for the weekend, but by the time I finally had time to make arrangements they had limited availability. I would recommend booking ahead of...More

Date of experience: August 2018
Thank NYCtravel
Reviewed September 19, 2018

If you are thinking about chartering a sailboat while in Portland then this is company for you. I sailed from Portland to Boothbay Harbor and stayed over nigh on the boat and could not have been happier with the boat, Captain Nick, Deck hand Gracie...More

Date of experience: September 2018
Thank greg f
Reviewed August 28, 2017

Sirocco is a beautiful boat and well-suited for sailing in Casco Bay. Captain Nathan and crew are pros and let you do as much or as little as you choose. They know the boat and the water and make sailing easy and relaxing. Make sure...More

Date of experience: August 2017
Thank Susan M
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