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· Master Mariner
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In my experience, the earlier in October I leave from Newport for the Caribbean, the easier the voyage is. Late October through November is much rougher and once December rolls around well, It's hell on earth, or should I say at sea. Had to clear 2' of snow off the boat before leaving for the Caribbean in January.
Of course, I'm a weather wimp, living in shorts in the tropics pretty much all my adult life.
 

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Hi
Using this older post as a continue the conversation regarding a crossing from Halifax to Bermuda.
Currently in Halifax
boat is a Cape Dory 30 MKII 1987 hull# 3
Fitted with new Viking offshore liferaft
Vesper transponder
Garmin Chartplotter and radar
several tablets with electronic charts plus Bermuda paper charts
EPIRB and personal AIS/GPS beacons
Diesel tank 20 gls
Diesel jugs 4 total 20 gl
Engine Westerbeke 3 cyl well maintained with 2 racors 500 in line with independent connectors to maintain engine running when filters clogged plus a remote vacuum gauge to monitor filters.
Water 40 gl
Jacklines lines from the cockpit to bow,all center installed and extra line from the cockpit to deck around dodger\
autopilot and Monitor windvane
just purchased Iridium go to have communications /weather reports and sign out a routing/weather service when on route
Plus have Garmin InReach explorer II for texting/weather

Me 78 y/o (no comments please)
Have sailed and cruised either short or single hand for the last 40 years
total logged 10000 n/m
last trip 4 years duration from Morro Bay to ST Petersburg via Panama Canal
crew 2 more people aboard with sailing experience
considering a 3rd? the boat is small.
My plan?
leave Halifax to Bermuda first part of October and leave the boat on the hard to return in a couple of months after tropical storms season.
Why? stay positioned for a possible crossing to Europe or whatever considering my age do not longer buy extended warranties or draw long-range plans.
Advice and ideas sought out,I do not take offense if you point out to weakness
of my plans however, there is a limit due to my personality shortcomings.
The idea to sail coastal going south is considered but not sure in the long run is whort it, just finished motor sailing my boat from Morehead City NC and the tought of going back,well not exciting

thank you in advance
David
I'm 77 and thinking of sailing from Toronto to anywhere maybe Jamaica, limited sailing experience plan to do it alone maybe a 30 ft boat
 

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Cooper,

Welcome aboard. I think you have missed the opportunity for this year by quite a large margin. Toronto to anywhere warm is long haul and would need to be planned pretty carefully.

In short you have 3 options, none great.

1- Down the Great Circle Loop - Chicago South on the Mississippi, etc into the Gulf of Mexico. There is a Great Circle organization with lots of online info.
2- Erie Canal past NYC and then down the inter-coastal waterway. Sort of the Great Circle in reverse. Same online resources as above but in reverse order. This is likely your best option.
3- To go down the St Lawrence, around Nova Scotia (but not Cape Breton) then a slow windward slog to the US and eventually down the ICW.

That said, I hear your desire to get someplace warm and tool around on a sailboat. There are many other options. Just fly and buy a boat there.

If I may suggest the Bahamas have good relatively easy sailing conditions. You could buy a boat in the Bahamas or Flordia to Georgia, or anywhere to North Carolina. The ICW is relatively benign but a lot of motoring. The toughest part is the 90-100 miles across the Gulf Stream from Florida to the Bahamas. But if you have time and patience to wait for decent weather this need not be onerous. I like Vero Beach as a staging point but others exist.

We found the Bahamas pleasant. Two major cruising grounds are the Sea of Abaco and Georgetown in the Exumas. We preferred the former. The Family Islands, any of the islands you never heard of, are very friendly and quite safe and peaceful. Not a lot of resources, but close enough to resources to not be a problem.

Many here have far more experience with the Bahamas than I. I strongly suspect you will be warned off Jamaica for many very good reasons.
 
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