Good choice with CYOA - I've had nothing but positive experience in my two charters with them. Just can't beat the convenience to STT airport, friendly service and great boats.

Captain Jay will have good input but you have excellent advice from BaardJ.

To mix things up a bit, I'll throw out the suggestion of going counter-clockwise:

Day 1: Depart CYOA by 11:00. Clear customs at West End/Sopers Hole (no Ferry traffic to deal with). From there, sail across Sir Francis Drake Channel and spend first night at The Bight at Norman Island (snorkel The Indians and/or The Caves).

Day 2: Sail to Peter or Cooper for night.

Day 3: Start early and head up to Leverick Bay. Take a taxi to The Baths (avoid the competition for a mooring and swim to shore challenge). Arrive for a late lunch at the Top of the Baths, enjoy the Baths (after potential cruise ship traffic) and taxi back to Leverick for Pirate Show and dinner ashore or onboard.

Day 4: Leave Leverick early, snorkel The Dogs, Monkey Point? Sail around East End of Tortola - night at Marina Cay?

Day 5: Beam/broad reach sail to Cane Garden Bay OR Great Harbor, Jost Van Dyke for 5th night.

Day 6: Sail back into USVI using ROAM and spend 6th night at Christmas Cove for Pizza delivered to your boat (or pick up) from the permanently moored/anchored Pizza Pi.

Day 7: Easy 45 minute motor to Charlotte Amalie cruise ship fuel dock and 10 minute motor to CYOA.

Be sure and check Cruise Ship schedule to avoid the crowds at Cane Garden and the Baths (usually gone by 2:30 PM).

Best tip - have a wonderful time and good luck to your son!