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"Nevis Nice"
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On four trips from the Chesapeake to the Virgin Islands or Bermuda, we left a day or so after a frontal passage. In each case, the Gulf stream was docile when we crossed it. Typically on the East Coast, the winds will go light and SE for a day or two after a front blows offshore, then will begin clocking and building from the SW around to the NW as the next front approaches. As the front passes over you, the winds rapidly clock to the N and NE, and are at their maximum strength. The secret is to get across the Gulf Stream before that next front comes through.

In the Fall, once offshore past the Gulf Stream, you'll almost certainly have a strong front pass over you. My experience has been that the seas will build over two or three days with strong northerly winds to 18' to 24', depending on the sustained wind speed. On one trip, we saw 24 footers after the wind had blown 35-40 kts, gusting to 45 kts, for about 60 hours. The good news is that the wave period stretches out the longer the strong wind blows and the bigger the swells get, and if you're headed SE, the swells are on your quarter.

The most uncomfortable conditions can be when the winds are not terribly strong, say 25-35 kts, so that the wind-waves and the pre-existing swells are similar in size, but coming from different directions. That can really cause some weird motions in your boat.
 
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