14:30 is too early, and the scarcity of mooring balls is only at high season in a couple of anchorages.
Your itinerary depends upon what kind of a night anchorage/mooring you are looking for. There are several secluded anchorages which are usually quite empty, but they are out of range or comfortable dinghy-distance from shoreside attractions (namely bars & restaurants). I'll throw out a sample itinerary assuming you will eat & drink ashore:
Day 1 - from Road Town take a short sail across the Sir Francis Drake channel to "The Bight" on Norman Island. This will be a broad reach in almost any conditions, you set your sails and 30-45 minutes later you will be taking them down again in order to motor into the Bight. There are many mooring balls here and I've never seen it 100% full; I always anchor there now as I prefer to spend my $$$ on alcohol and since I'm alone on the boat the $20 doesn't get spread around the boat's passengers that well. If you don't mind anchoring, just get in close to "Pirates" by the concrete docks and anchor in good sand and you won't get in the way of anyone using a mooring ball.
Daytime activities - the "Caves" for snorkelling, reachable by dinghy. "Pirates" has dinner but the bar closes early, and/or visit "Willie T's" for bar-type food and late-night entertainment. Don't moor close to that floating bar unless you are either a heavy sleeper or wish to party till 4am and then have a short dinghy ride to your boat.
Day 2 - head out to grab a daytime mooring at the Pelicans outside of the Bight for snorkelling, or leave early and sail up the Sir Francis Drake channel to “The Baths” off Virgin Gorda. This is usually close enough to the wind that you will have to tack a couple of times and is a good 2 hour sail if not longer. Waves are short and choppy and sometimes uncomfortable but none of it is in unprotected waters. The daytime mooring balls off the Baths fill up quickly. Another option is to take a mooring ball off Virgin Gorda Yacht Harbour and take a $5 taxi to the top of the Baths (best Gazpacho in the Caribbean, in my opinion) and eat lunch at the top and wander down to the water. Take the path starting at the restaurant and avoid the toll booth which I have occasionally seen occupied – I think it opens and charges admission when a cruise ship is in port.
That night you can either take a mooring off VGYH or enter the VGYH marina (about $2 per foot after water/electricity is added to the bill) or take a sail back to Beef Island and take a mooring in Trellis Bay or at Pusser’s Marina Cay. I like to anchor off Marina Cay as it has good holding and you aren’t in the way of mooring balls, but a lot of dinghy traffic goes by there early in the morning and causes a wake.
Dinner is at “The Rock” or perhaps “Chez Bamboo” or the pricey but fine “Giorgio’s” (taxi ride necessary for that one). Or “The Loose Mongoose” in Trellis or Pusser’s on Marina Cay.
Day 3 – Upwind sail to the North Sound. Unless you have a catamaran and feel cocky, don’t cut across between Mosquito Island and Virgin Gorda! On the way you can take a day mooring ball in the Dog Islands for some nice snorkeling (it is usually pretty empty there as well). Once in the sound you have 2 main choices – the Leverick Bay area or the Bitter End. You can also anchor off Prickly Pear across from Leverick and have at most 3 or 4 others in your area but it is just far enough away to make a dinghy unfeasible. I usually anchor between Saba Rock by the Bitter End Resort and Prickly Pear – good holding and my dinghy ride to Saba Rock or the BEYC is shorter than most people who pick up mooring balls. I have never seen the BEYC mooring balls fill up. If possible, pick up a Saba Rock mooring ball as you get free water and a bag of ice the next day and the BEYC mooring balls are now $30 per night. The beach on Prickly Pear is usually empty, but the bar at the beach is usually shut unless a cruise ship shows up. I love to snorkel north of Saba Rock.
Day 4 – if you feel confident about sailing, then Anegada is a worthwhile destination. During the season there are so many boats going to and from Anegada that you don’t have to worry too much about making it through the channel (one of the Sunsail regatta skippers said “it is like a highway”). Follow the directions and study the chart well, since every time I’ve been up there one or more of the buoys has been missing. Anchor or moor as close inshore as you can, my draft is deep and I end up having to anchor waaaay out there and it does get a bit rolly. Onshore there are 2 restaurants who specialize in Lobster dinners and it is wise to reserve early. I usually take a cab to the Loblolly Bay beach and just add it to the dinner charge, but I think the fee is only $5 per person. The beach is impressive and most often empty. Snorkeling is easy inside the breakers and there is a big bar.
Bring lots of OFF. The bar at the Anegada reef hotel has more cans of OFF than shakers of salt & pepper! I always wear long sleeved shirts and long pants and wear a hat when the sun is down.
Day 5 (4 if you skip Anegada) – I recommend doing the big sail (either from Anegada or the North Sound) to either Cane Garden Bay or Jost Van Dyke. Both are going to be pretty much downwind and perhaps a bit rolly with following seas, but it is better than beating upwind on that side! You can choose to thread past Trellis Bay and perhaps stop to snorkel at (can’t remember the island name). The island of “Sandy Cay” is on the way to Great Harbor on JVD or Cane Garden Bay and is a MUST. Easy anchorage on sand just offshore and you have your own paradisical uninhabited island. Take a walk (wear shoes) around the nature path or snorkel the small reef or just sun on the beach! From Sandy Cay you have a short run to Cane Garden Bay which is only mooring balls but has Quito’s and other bars/restaurants on the beach or head into Jost Van Dyke’s Great Harbour and try to anchor there as early as possible. That way by 4-5:30pm you can be onboard sipping your favourite beverage while watching the latecomers try to anchor without coming too close to those already there. If a Sunsail or Mooring regatta comes in at least the professional captains assist in getting everyone sorted out with a minimum of damage.
Onshore on JVD there are a lot of options. White Bay is great with the infamous “Soggy Dollar” bar. I usually dinghy over there from Great Harbour and the beach and bars are usually very active until about 4pm when the US daysailors all tend to head home. Dinner can be at “Foxy’s” or I prefer to try the other places – notably “Corsair’s” where the owner, Vinnie, is a fellow biker and we usually sit there for hours telling tall tales of bikes, booze, women and firearms
I prefer not to patronise Foxy’s for dinner as it is almost like a production line, but when they have music and bands that is the place to be!
Day 6 - If you did JVD on day 5 then Cane Garden Bay is worth it, plus you can take day trips to the surfer area and visit the Bomba Shack or take a ride to the top of the island to see the vista. Or just recover from the hangover using the time-proven Hair of the Dog & lie on the beach cure. If you spent night 5 in Cane Garden Bay then JVD is certainly worth going to. Remember, don’t miss Sandy Cay, it is my favourite place in the BVI.
Alternately you can sail around the west end of Tortola and pick up a morring ball in Soper’s Hole. There are a lot of stores (including the biggest and best selection of provisions in the BVI) plus Pusser’s and several other restaurants and bars for dinner. I haven’t had the best of luck there, so am somewhat prejudiced against Soper’s Hole. I would recommend that you lock your dinghy if you do moor there at night; that is where I had mine stolen and it is pretty much the only place where theft is common.
Day 7 – Head home. This last sail is going to be against the wind and waves but inside the channel. Depending on conditions, time and your energy levels, I think most people will sail downwind to the West End coming from JVD or Cane Garden Bay and then furl./drop sail instead of tacking between Tortola and that little island whose name I cannot remember and then motor the rest of the way to Road Town. I’m normally not in a hurry so will sail, but that adds hours to the trip upwind.