We made the trip last year in June and it was our first time bareboating. I have offshore fishing experience, but my wife and daughters had never been in the open ocean. We had 15 to 20 knot winds and it was relatively comfortable, but anyone who gets even mildly seasick may want to take some medicine prior to this passage. I agree that 25+ would make for an uncomfortable trip. By the way, on a clear day you have visibility to land (back to VG or to Anegada) for most of the trip. Have fun and keep a look out for dolphins.

Also, we rented a car and toured the island. However, we much preferred Cow Wreck to Loblolly. This is important because Cow Wreck is close to the anchorage and Loblolly is much farther away. If you want to tour the island, have fun, but let me warn you that taking the back roads (if you can call them that) from Loblolly to Cow Wreck is an adventure. We had fun, but we will not be doing this again. Straight to Cow Wreck and walks away from Cow Wreck on the deserted beaches for us this year.

Lastly, we ate at Wonky Dog and it was really good. I also hear good things about Potters.

Have fun!
Steve