Most BVI itineraries are written as a loop. That's the wrong frame. A charter week has a shape to it — the first night is not the fourth night, and the crew you have on Thursday is not the crew you had on Monday.
Here's how we'd sequence it.
Night one: somewhere close
Whatever you do, don't plan a long first leg. You'll clear the base later than you think, someone will still be figuring out the head, and the light goes fast.
The Bight, Norman Island is the standard first stop for a reason — short hop, big protected bay, and the crew gets a swim and a drink without a four-hour beat. It's busy, and that's fine on night one. You want easy, not remote.
Nights two and three: the good stuff
This is where the crew is at peak energy and peak willingness to sail. Spend it.
Cooper Island is the civilized option — good restaurant, decent shelter, and it feels like a place rather than a stop.
The Baths at Virgin Gorda is the one non-negotiable daytime item. Go early. By ten it's a queue, and the whole point is being inside the boulders when the light comes through and there's nobody in the frame.
Anegada if your crew is up for it and your charter company allows it. Flat, low, entirely different from the rest of the BVI, and the lobster is the reason people go back. Check your contract — some operators restrict it.
Night four: Jost
Great Harbour for Foxy's, White Bay for the Soggy Dollar, and be honest with yourself about which one you're actually there for.
Mid-week is the right time for Jost. Early in the trip the crew isn't loose enough; late in the trip they're tired. Day four is the sweet spot, and it's also the night most worth reserving a ball for.
Night five: recover
Somewhere quiet. Little Harbour, Cane Garden Bay, Diamond Cay — anywhere with fewer decisions and an earlier evening. Every good charter has a night where nothing much happens, and it's usually the one people remember most fondly.
Night six: close the loop
Get within striking distance of the base. Nothing ruins a week like a stressful Saturday morning delivery against the wind with a flight to catch. Soper's Hole is the obvious play — you're close, there's a proper marina, and you can hand the boat back without a scramble.
The rule underneath all of this
Front-load the sailing, back-load the ease. Crews arrive wanting adventure and leave wanting comfort, and an itinerary that ignores that produces a mutiny somewhere around day five.
Have a second bay in mind for every single night. The mooring situation makes flexibility a requirement, not a virtue.
The Logbook is where we keep notes from the water. If you've got a trip worth writing up, we want it.