Here's a reply I did for folks doing 14 day charter. The same theory applies.
Leaving Roadtown you can go left or right. With 14 days, i'd put Anegada (with Conch's permission) on your list. This will be the at least a 2-3 day stop. Depending if you want to anchor
or use moorings, be with people or get away from the crowd, will determine your stops. From Road town, i'd stop at Trellis Bay first, grab a mooring, have lunch at the loose mongoose, stroll the beach, dine at the last resort. call for reservations by 4pm, this applies to most restaurants, especially this time of year. From Trellis, I'd head to Virgin Gorda, stopping at the Dogs for a snorkel, or just a pause, to get folks off the boat, in the water. I would pull into Leverick bay, enjoy their pool, do laundry, provision up and ck out North Sound, Vixen Point, Saba, Bitter End. Take a taxi to the Baths, make a day of that. From there, Anegada. Its about 15NM heading 003. Double ck that, as i usually leave from Jost Van Dyke.
THere's a whole website dedicated to Anegada, its approach and what to do there.
Grilled lobster for dinner is offered at most of the restaurants. Take a taxi to loblolly or flash of beauty. this time of year, not sure there will be food at Flash. Take time to explore this island, and do some research. Here's a start: Navigating to Anegada
From Anegada, I'd stop at Marina Cay, across from Trellis bay. Beach fun, food, some shopping. Then, I'd go down the north side of Tortola, stopping in Cane Garden, if the weather permits, on to Jost Van Dyke, Diamond Cay to start. Hike for 10-20 minutes to the bubbler, natures jacuzzi. Work your way to White Bay. Great beach, lots of folks at the Soggy Dollar Bar. I'd leave for West End, Tortola, grab a mooring, and if you could not get into Cane Garden Bay due to weather, rent a car from Jerry's car rental, they'll pick you up, and spend time seeing the beaches, make reservations at banankeet, for best sunset dining and then Pam's delight, for great local food.
From West End, i'd head to Norman Island. Snorkel the caves then head to the beach at Pirates, stopping for lunch on the Willie T. For my last stop, i'd make my way to Cooper Island, directly across from Road town, allowing for an ez run back to Conch.
There's a bunch more/less depending on you.
Shout if i can help