Offshore Sailing: Weather Routing to the Caribbean
As ICEBEAR & ISBJORN prepare to depart Annapolis on the Chesapeake Bay, bound for Tortola in the British Virgin Islands, Andy and August brief the passage route and the weather they expect to encounter en route.
August Sandberg is ISBJORN's new skipper going forward.
The 1500-mile passage starts in Annapolis, and both boats will sail down the Bay, where at Norfolk we'll go offshore, aiming for a waypoint about 120 miles south of Bermuda, then we'll hang a right turn and sail due south, bound for the Virgin Islands.
This is one of the toughest passages we do at 59 North - winter has nearly arrived in the northeast, a cold front after cold front will sweet over the region, plus we still have the threat of late season tropical activity. The goal is to depart immediately after a cold front, to get offshore and across the Gulf Stream on northerly winds before the next front rolls through.
The beauty of this trip is that the farther you go, the warmer it gets. After 7-10 days at sea, we'll be firmly in the tradewinds and looking forward to landfall in the tropics!
59° North Sailing
Global offshore sail training and heavy-weather forensics with SV Falken and SV Isbjørn. Join Andy Schell and Mia Karlsson as they manage a professional multi-boat fleet across the South Pacific and North Sea in 2026.
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