I'm of the opinion that the more options you read about, the more likely you'll find exactly what you want, so I'll provide my approach with your must do list for comparison. I agree with sail445 and tradewinds above regarding the start of the trip to Cooper.
Night 1 - Depending on what time you get away, Deadman's Bay, the Rhone, and Cooper Island for the overnight.
Night 2 - Early start to the Baths, +/- Dogs if inclined, Trellis/Marina Cay overnight
Night 3 - From Trellis area, I would stay on the North side of Tortola, hit Monkey Point for an hour or so and end at JVD for Foxy's, etc. +/- Sandy Spit/Sandy Cay/Bubbly Pool if inclined. (CGB is an option for overnight too and Foxy's the next night)
Night 4 - Crew's choice for me here. Spend some time at White Bay/Sandy Cay/Sandy Spit/Bubbly Pool/Cane Garden Bay/Soper's Hole (ladies want to shop sometimes) or head on to the Indians if you want. Option to stay the night on JVD again/CGB or Norman Island. (Can get water at CGB or West End if needed)
Night 5 - Depending on where you previously stayed and your departure time the next day, I would end at Norman Island or Peter Island as there is not a big difference in distance back to Roadtown, though Peter would be best if you're in a crunch for time.
So, all in all not much different than saill445 above except I would avoid backtracking down the Drake channel for the downwind trip from Trellis and get to the JVD area the 3rd night which gives you a lot of options for that 4th and 5th night for your crew. They may want to relax in White Bay all day that 4th day. You can easily get to the Indians and Caves from JVD and stay in the Bight the last day before heading in the next morning for Roadtown if you want.
Whatever you decide will be fine....I just like the idea of giving my crew different options the last day or so as they may be tired after the first few days of having to get to certain places.
Enjoy the trip!
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