Offshore sailing from Chesapeake bay to St. Thomas in winter

Dec 3, 2018
22
Hunter 31 Baltimore
Hello all,

I was wondering if anyone had any experience with the offshore jump from Chesapeake Bay(or anywhere on east coast) to the Caribbean during the winter. Planning to go late January/Early February. I would be part of the crew on this trip, not captain. Boat is a 2006 Beneteau 433. Just wondering if anyone has experience with this route during the winter and open to suggestions.

Matt
 
Jun 14, 2010
2,081
Robertson & Caine 2017 Leopard 40 CT
I’ve never done that trip but wouldn’t try it that time of year. Will be watching this thread. Good luck.
 
Mar 21, 2016
20
Hunter MH40 Apollo Beach, FL
Note that all of Don Street’s recommendations say to leave in November. When the Christmas winds pick up in late December it makes it a lot tougher. We went from Marathon, Florida in January 2013 through the Bahamas and waited there until Chris Parker said the winds would be light for several days. Coming from further north you can go East easier before turning south as shown in the article, like we did with the Salty Dawg Rally in November 2013. I wouldn’t make the trip without using Chris Parker for weather and routing advice.
 

SFS

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Aug 18, 2015
2,065
Currently Boatless Okinawa
I echo Phantom154's advice. We used Chris Parker on a delivery from Chesapeake Bay to the Bahamas in mid-November one year. He gave us an accurate window, entry and exit points for the Gulf Stream that were extremely helpful, and updated us throughout the trip.
 

BrentS

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Jan 3, 2020
2
B&B Yachts Princess 26 Chesapeake
As I recall there was a fine window in mid February last year. I did not sail it, but thought about it. At the time it looked like head south east out of the Chesapeake and cross the gulf stream, heading straight for 65W beam reaching with winds mostly less than 20 knots. While the Chesapeake was having freezing conditions, the weather got warmer by the mile once in the ocean. After about 3 days the coats would be put away.

Prior to that it was mostly cold and stormy. Heading off shore out of Beaufort, per Don Street's advice, improves the chances of quickly getting south of the nasty stuff. Once in or east of the gulf stream the temperature can be much more pleasant.
 
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Likes: Will Gilmore
Dec 3, 2018
22
Hunter 31 Baltimore
*Update* We made it, ended up jumping off from Beaufort NC (great little town), weather was very manageable once we got more south and across the gulf stream. Thanks for the advice all

Sailing is the best,

Matt
 
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Likes: Will Gilmore
Oct 19, 2017
7,732
O'Day 19 Littleton, NH
Great read, thanks. I had my best meal ever at the Whale of a Tail restaurant, in St. Thomas. An incredible tuna steak, perfectly rare with a beautiful Béarnaise sauce. The tuna had been caught that day. Sadly, I've heard the restaurant isn't open anymore. :(

-Will (Dragonfly)
 
Oct 22, 2014
20,989
CAL 35 Cruiser #21 moored EVERETT WA
Good for you @Mattcia123 enjoy the islands. Post pictures and give us a bit of a tease. It’s still winter here.
 
Feb 11, 2017
122
former Tartan 30 New London, CT area
Jon Eisberg (RIP) would leave Barnegat Bay in Jan or Feb, posting photos of the icicles on his bow pulpit & lifelines, and head for the Caribbean in his Chance 29. He never made a big deal of it - he just did it. I believe he stayed coastal so he could duck in. Jon is one of the few cruisers I know to make it to the top of Newfoundland! Still miss him..
 
Feb 11, 2017
108
Gulfstar 47 NC
Agree. “RIP”. Jon Eisberg was one of a kind. He could put you “there” with his writings. I still have a file for Bahamas anchorages.
 

DArcy

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Feb 11, 2017
1,690
Islander Freeport 36 Ottawa
I miss Jon's posts. I remember one of his January departures, the hardest part seemed to be getting away from the dock due to low water. The ice and weather didn't seem to bother him much; he just took it all in stride.