NY to Maine in October?

Apr 23, 2014
54
Irwin 28 Long Island
It is looking like after this summer I am going to be relocating to Portland, Maine. My life is pretty easily packed into a few boxes, but a 28 foot sailboat is another story. I absolutely want it to come with me.

So the question is: If you were in my shoes, how would you transport it up north at that time of the year?

My immediate thought of course was to cruise the coast the whole way up and it would probably take me about a week or so. After a conversation with a 30 year USCG captain though, I am thinking it will be a very dangerous trip. So perhaps I should pay to have a trucking transport service drive it up, no wear and tear on the boat, no miserable sailing in October weather.

I'm considering the advice of the experienced captain I spoke to, but still thought the question was worth posting here. Thoughts?
 
Dec 4, 2008
264
Other people's boats - Milford, CT
I can't see how that trip would be any more dangerous that cruising long island sound.

It would just be a series of day hops from great harbor to harbor. I assume through the cape cod canal, not off shore.

Did the captain have specific dangers to warn about ?
 
Apr 23, 2014
54
Irwin 28 Long Island
Did the captain have specific dangers to warn about ?
That was my thought that I could easily ride the coast hopping from harbor to harbor one day at a time finding somewhere safe to anchor when needed. Absolutely taking the cape cod canal too. No offshoring at all, just coastal cruising the whole way up.

I reached out to that captain who offers delivery service for his advice and the main warning he gave me was the weather at that time of the year on a 28 foot sailboat is risky. Which is a reasonable concern to have.
 
May 21, 2006
321
catalina 25, 30 montauk / manhattan
if decide to go and need a hand, could go for a portion of the trip!
 
Feb 6, 1998
11,701
Canadian Sailcraft 36T Casco Bay, ME
Cruise up in late August and then schedule haul out and winter storage for the boat and head home....

That said October can be some of the most beautiful sailing of the entire year but the Northwest winds can pipe up pretty fast and hard. Not bad if you are staying close to shore but can be rough further out with the fetch. It should not be difficult in October just jump from port to port..
 
Feb 3, 2009
58
Camper Nicholson 39 CC Rockland, Maine
Eugene,

I agree with MaineSail, You should take some vacation time to sail the boat up to Maine in late August or September while the weather is nice. Take your time and enjoy the trip then go back and finish up work and pack the rest of your life away for a proper move.

You can get plenty of info on possible yards to keep your boat in when you decide where you want to live and where you want your boat.

There are plenty of us experienced hands out there who would help on a relaxed passage for a berth and victuals.

Where are you coming from and to where are you going? NYC to Portland in a week is easy if the weather is good.

Cheers

Ansley Sawyer
 
Apr 23, 2014
54
Irwin 28 Long Island
Eugene,

Where are you coming from and to where are you going? NYC to Portland in a week is easy if the weather is good.
Hey Ansley, thanks for the confidence. I am actually on the list for winter dockage at DiMillos in Portland Harbor. I'm sure you know it. Any thoughts?
 
May 10, 2008
392
Catalina 355 Boston
A couple of other things to consider--the days get quite short, so if you want to sail in daylight, your distances per day need to be factored in. It also gets quite cold at night, so make sure you have some heat available. Having said that, it can be fabulous sailing if you get lucky with your weather window. Good luck!
 

Tim R.

.
May 27, 2004
3,626
Caliber 40 Long Range Cruiser Portland, Maine
A couple of thoughts. We sailed from Maine through NY last October staring on the 25th. We have an enclosure so the elements were less of an issue for us but the sailing was nice. You can easily harbor hop in good weather if you do not need to do it all in one hop.

Maine Sails idea is good also.

We live aboard at DiMillos so we will see you when you get there.
 
Apr 23, 2014
54
Irwin 28 Long Island
Hey Tim, I just wrote you a message asking about your experience at DiMillos. I hope you won't mind sharing some stories about the liveaboard life there.
 
Sep 18, 2014
22
Wharram Tiki Belfast ME
Just and observation, October is usually wonderful, but that said, we live about 12 miles inland from Penobscot Bay and have had 15inch of snow on Halloween!