How early would you leave Cooper Island to sail up to North Sound? Hope to reserve a slip at Bitter end or Leverick for that evening so not going to be racing for a mooring. This will be in May. Expect winds will be running southeast. We will be in a Lagoon 42
Which entrance do you plan on using? Mosquito point entrance 2 hours with the wind ESE. Main entrance add about 45 minutes. I often leave Cooper at 7AM, run people through the baths, dive and lunch stop at the dogs and into the N sound by 3PM.
It's a good fun sail - maybe an hour, hour and a half to the entrance of the sound through the reef between Mosquito and Prickly Pear island. As you say with a slip reserved you will have no time pressure. I would stop at the Dogs for a snorkel or a dive on the way.
Make certain you use the main entrance in if you are on a care boat charter (between Mosquito and Prickly Pear) - many of the charter companies, including ours, TMM, prohibit use of the shortcut between Mosquito and Virgin Gorda.
or go straight to your slip up there and take a taxi down to the Baths in the afternoon and catch Coco Maya for dinner and provision in Spanish town....