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Old 04-09-2012, 16:46   #1
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Leaving Long Island Sound NY for Florida

We are new liveaboards and are planning to leisurely cruise south to Florida for the winter. Typically, when in the fail do cruisers start their journey south? We have a Caliber 40 long range cruiser sailboat. We traveled north in July and had a great experience. We plan to take the ICW back south. Any suggestions would be appreciated.

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Old 04-09-2012, 16:55   #2
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Re: Leaving Long Island Sound NY for Florida

We used to start south from Toronto just after Labour Day. Stay in the Chesapeake till the middle of October. Check your insurance re how far south you can go before the end of October. Many policies have restrictions. It gets cold awful fast so it's wise to get south pretty quickly after October.
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Old 04-09-2012, 17:43   #3
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Re: Leaving Long Island Sound NY for Florida

I'm not as far north as you being near charleston but I wait till the cold fronts get strong enough to carry favorable winds for at least 2 or 3 days at a time. I've done a bunch of intracoastal but much prefer a ride down the coast outside. Georgia is the worst, ran into muck at high tide in middle of channel run 200 mi to make 50 southing etc...
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Old 04-09-2012, 17:48   #4
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Re: Leaving Long Island Sound NY for Florida

In short, Chesapeake in October, get south of Norfolk by Halloween if your insurance lets you.
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Old 04-09-2012, 18:08   #5
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Re: Leaving Long Island Sound NY for Florida

If you want to have some fun, you might think about being in Urbanna, VA on the Rappahannnock River for the Urbanna Oyster Festival 2-3 of November, but I would high tail it away the next day to avoid frost on the cabin deck top. The drop dead date to be south of Chesapeake is December 15. I have seen it ice in at Christmas.

Generally, October 15 is peak snowbird time in lower Chesapeake.

I used to spend Thanksgiving Day in Swansboro, NC and watched a steady stream of snowbirds heading south on the ICW while eating turkey.

I have never done the whole ICW, but I have done from Greenport, NY to Virginia and then parts of NC, SC, GA, and Fl, and am familiar with the weather in VA and NC, and I would think that you would want to leave LI between Labor Day and Oct. 1. How much do you enjoy sailing with frost in the morning? Remember, the later in the season, the less daylight you will have for making miles in the ICW. If you do day sailing only, sun up to sun down, you should be able to make the NYC to Norfolk run in 10 days of hard at it petal to the metal with no time off for good behavior. Once you get to Norfolk, you should be able to relax a little knowing that you are ahead of the ice, and once you go another 5 days to Beaufort, NC, you will have all ice behind you. If you want a push like heck,no fun trip, November 1 is drop dead date to leave. I would recommend leaving by mid September if you want your wife to enjoy the trip. This is all assuming you are doing the ICW. Hope this helps.

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Old 04-09-2012, 18:18   #6
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Re: Leaving Long Island Sound NY for Florida

Here's my ideal itinerary. I've done it numerous times.

Date Schedule
September 1 Head southbound
October 1-31 Cruise Chesapeake Bay
November 1-30 ICW to Florida
November 30 Hurricane season ends
December 1-April 30 Cruise the south
May 1-31 ICW north to Norfolk
June 1 Hurricane season begins
June 1-August 31 Cruise north of Chesapeake Bay
September 1 Start over again!
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Old 04-09-2012, 18:37   #7
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Re: Leaving Long Island Sound NY for Florida

We head south from Long Island Sound as well (the CT side - Essex) usually leaving around October 10th. If we didn't have to work summers, we would definately leave a little earlier & enjoy the Chesapeake. As others have said, the biggest timing issue is your insurance. We can't be south of Cape Hatteras before Nov. 1 - our first year we got carried away, went too far & had to backtrack 20 miles!

Our 2nd year we got smart & called our insurance company around Oct. 20 - there were no hurricanes coming north so they gave us a rider to be south earlier at no additional charge. Our timing also works well to be in Vero Beach for Thanksgiving (usually arriving a week or so earlier). The cruisers put together a great & very friendly Thanksgiving potluck not to be missed!
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Old 04-09-2012, 18:50   #8
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Re: Leaving Long Island Sound NY for Florida

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The cruisers put together a great & very friendly Thanksgiving potluck not to be missed!
There's a big cruisers gathering and potluck Thanksgiving in St. Marys, Georgia, too.
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Old 04-09-2012, 20:11   #9
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Re: Leaving Long Island Sound NY for Florida

Thanks everyone for the valuable information and personal experiences. We are adjusting our plans accordingly. Hope to meet some of you at the Turkey Potluck!

Diane
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Old 06-09-2012, 21:56   #10
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Re: Leaving Long Island Sound NY for Florida

The Thanksgiving at St Mary's Ga. is super.... They really give you great southern hospitality and a good time is always had by all..
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Old 07-09-2012, 05:03   #11
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Re: Leaving Long Island Sound NY for Florida

We tend to travel southbound a little ahead of most and enter Florida around November first. We are currently in New Jersey and we'll likely leave the Chesapeake near October first. Poking about slowly is our style and we avoid making commitments to arrive at any location on a specific date, leaving a wide buffer to make good weather choices.
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Old 07-09-2012, 05:46   #12
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Re: Leaving Long Island Sound NY for Florida

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... we avoid making commitments to arrive at any location on a specific date, leaving a wide buffer to make good weather choices.
I like that part the most, of course.

I found that a lot of folks who are 'usually' down south leave earlier.. their thin blood can't handle those 30 - 40 degree nights.
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Old 07-09-2012, 06:36   #13
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Re: Leaving Long Island Sound NY for Florida

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............I found that a lot of folks who are 'usually' down south leave earlier.. their thin blood can't handle those 30 - 40 degree nights.
I'm sure you're right! Thirty and forty degree nights have been what I have known as winter all my life! I'm quick to acknowledge that I'm a pansy in the cold, but "through me in the briar patch". I miss some of that heat, humidity and that heavy steamed air that rises off the asphalt after just after the 2pm thunderstorm. Summer in Maine had it's moments, but none of them included me in the frigid water. I miss swimming too! Maybe I can get back to Florida before there are any cold nights in the fifties.
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Old 07-09-2012, 07:02   #14
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Re: Leaving Long Island Sound NY for Florida

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Originally Posted by Vasco View Post
We used to start south from Toronto just after Labour Day. Stay in the Chesapeake till the middle of October. Check your insurance re how far south you can go before the end of October. Many policies have restrictions. It gets cold awful fast so it's wise to get south pretty quickly after October.
Just curious which route you take from Toronto to the Chesapeake? Do you come down the Erie or go St. Lawrence?
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Old 07-09-2012, 07:53   #15
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Re: Leaving Long Island Sound NY for Florida

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I'm sure you're right! Thirty and forty degree nights have been what I have known as winter all my life! I'm quick to acknowledge that I'm a pansy in the cold, but "through me in the briar patch". I miss some of that heat, humidity and that heavy steamed air that rises off the asphalt after just after the 2pm thunderstorm. Summer in Maine had it's moments, but none of them included me in the frigid water. I miss swimming too! Maybe I can get back to Florida before there are any cold nights in the fifties.
If you hurry I'm swimming in 80 degree F water here in Long Island Sound area. I usually keep swimming until mid October. But, I actually may be extending it even further this year:
THE BIANKA LOG BLOG: I'M GOING IN!
I have yet to head south for the winter with my boat as my girlfriend continues to drag me along for mid winter and spring crewed catamaran charters. As they say to get along go along. I have lived on board in New York from April to December back in the 90's and found a nice quilt made sleeping nice and toasty when the docks were covered with ice.
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