My wife and I are just back from our first bareboat charter (monohull) and had an absolutely fantastic time. About two months ago I asked TTOL pretty much the same question that you are asking– and now I feel I can contribute a bit to the conversation!

On the question of clockwise vs anticlockwise – it really is a question of what your sailing experience is and what your objectives are. We sail pretty much exclusively in the south coast of England, so the sailing during our two weeks in early March were pretty much what we usually expect – F3-4 with occasional F5-6. The north side of Tortola is more exposed, so it will be a livelier sail. On the objectives, going clockwise will give you longer sails with more beating early in the week, with the last half of the trip quite relaxed with VERY short, downwind sails between overnights for the second half. Going anticlockwise I think will let you have slightly longer sailing times between stops and the longer downwind sail from Virgin Gorda to JVD will be great. That said – everything is pretty close so you can probably do a figure of eight if you like.

We had a Moorings boat and did not get away until 2:30, so just did a quick sail over to Norman Island and had a nice snorkel of the caves. My two pieces of advice would be to be flexible about your itinerary but get up early (we usually cast off lines at 7:00) and sail to a breakfast stop before heading out to your final anchorage for the night. We were the only people (for a bit) at quite a few popular places (Indians, Baths, Sandy Cay) by doing this.

If I was going to go for a week based on what we learned – I would recommend:
Day 1 - Road Town – Indians – Norman (do the caves that afternoon)
Day 2 – Breakfast at Dead Man Bay – Salt Island – Cooper (definitely snorkel Cistern Point)
Day 3 – Breakfast at Dogs – Leverick Bay – see the Michael Bean show and make sure you meet Nick, he is as great as everyone says
Day 4 - rent a car and head to Baths by 8:00 and drive around the island, Spring Bay, copper mine, Hog Heaven. There is a better view than Hog Heaven that we discovered. Just past (going towards Spanish Town there is a sign to a path to the top of the mountain. It is a 20 minute hike or so, and there is a wooden tower that you can climb and have a full 360 degree view. We parked at an overlook a bit past the hike entrance.
Day 5 – Breakfast at Saba Rock – dinghy around to Eustacia sound for some snorkelling – Sail to Marina Cay – this wasn’t on your list, but was one of our favourite places. Happy Hour show with Stel and Snuggs was a lot of fun.
Day 6 – Breakfast at Monkey Point – sail to JVD. We took a mooring ball in front of Foxy’s Taboo. Highly recommend it. From here you can do the bubbly pool, and Sandy Spit. Taxi over to Great Harbour, visit Foxy’s then hike over to White Bay and do all of that craziness. We met up with Arnd on Zanshin for a sundowner one night here – he has great stories so keep a look out for him – Thanks, Arnd!
Day 7 – Breakfast at Sandy Cay – Sail to Soper’s Hole for a lunch stop (Fish & Lime was great) – then have a great long sail back to Road Town, or Norman if you want to get up early for the return.

We had two weeks so we also did Anegada for 2 nights, which was probably our number 1 stop, so would work it into a 7 day charter, leaving some other places out, but for your first time – I would say give it a pass. We did about 80% of the things I had hoped to do on our trip, so it was a complete success – we have to return to do the other 20%.

Have a great trip. Already planning our return!

p.s. and thanks to everyone on TTOL that gave us so many great ideas and help in our planning.