I think it would be a wonderful time to go. I've sailed out of NYC in the winter several times and while we had a great time, it was a wee bit nippy and rough . You should have great temps and better seas.
I cruised the Dawn in September and was lucky that I had fairly smooth seas. The temp was in the mid-60's when we left NY but the next day we were in the high 70's and by the time we hit the island we were in the mid-80's.
The seas were smooth for the return trip.
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"There is a great difference between being well traveled and just having been to many places." ~Me
I'm an experienced 'Bermudaphile' only have been going there for the last 30 years or so! My wife and I love the place, and the people are very courteous, polite, and helpful. (hint--if the say 'good morning' they expect a return salutation from you!). The ship is one of the older ones, and will be docking at Dockyards, along with 2-3 other ships. I would highly recommend getting a transportation sheet before hand, as it will tell you how often the ferry's and busses go to Hamilton--I would NOT recommend renting a scooter, as they drive on the LEFT and not the right, and even though you may know how to use a GPS, getting used to the roads can be a bit tricky. The ferry goes to Hamilton goes about every 45 minutes, and is walking distance off of the pier. The bus takes about 45 miinutes to get to Hamilton, and is a easy way to see the island and not worry about transportation. The bus drivers are real ambassadors for the island, and do not be afraid to ask a 'silly' question. I hope this has been a little help from you!