A good starting point is http://www.bermudatourism.com/pdf/yachts_info.pdf
which has full info on visiting Bermuda by boat.
The Atlantic Pilot Charts can be viewed at http://pollux.nss.nima.mil/pubs/pubs_j_apc....html?rid=10499
Open the December chart and spend some time digesting air/sea temps, % gale frequencies, and note the multiple 25 kt wind arrows. Note the historical tropical storm tracks shown on Dec's chart. Remember that those wind arrows are averages, again note the gale frequenices, and reflect on the fact that vessels which report these details intentionally reroute themselves so as to miss the brunt of a storm; thus, underreporting is a norm and the chart is a more optimistic view of conditions than you are likely to experience.
This would be a great character-building adventure but it would be the result of a poor decision, IMO.