2. What type of certification will I need?
Each charter company is a bit different, but I'd guess that only 10-20% of BVI charterers have your formal qualifications. And less than 5% your practical experience, which the charter companies consider more important. The BVI have no licensing requirements for visiting skippers.
3. Where are the best places to sail to with a 5-day window of opportunity?
With just 5 days, and considering the time needed to check-out and check-in the boat, I'd recommend staying in the BVI the whole time and there are too many locations to list here - a lot depends upon whether you prefer shoreside activities or quieter anchorages.
4. What should I watch out for in terms of governmental problems or encounters with the local citizenry?
No worries. Just say "good morning" or "good afternoon" or "good evening" as a greeting and stay normally polite and you'll have no issues. Crime is relatively low in the BVI, mostly not involving charterers, and the police have no big presence.
5. What would you recommend as the most enjoyable opportunities during the charter?
Too many to list. I'm anchored just off the BVI in the USVI today and am going to go diving, then make a steak for dinner in a secluded anchorage while sipping a fine Rioja. Or I could head into town for dinner ashore. Or I could just be here at anchor and do nothing all day. All of them are enjoyable!
My wife and I have chartered with Sunsail a couple of times in the BVI. Your qualifications should be plenty. I have heard good things about other companies, but we've liked the experience with Sunsail, so we go back. They have very nice shoreside facilities in Road Town--clean showers, storage for any luggage you don't want to take on the boat with you, a couple of nice restaurants, a pool, a bar, etc. They are also, more or less, right across the street from the Riteway supermarket.
As mentioned, what to do depends on what you like. Best advice is probably to talk with the folks you charter the boat from. They will know what's going on currently and will be able to help.
I don't have much to add to the above, except that 5 days is not enough time. 7 days is really the bare minimum and 10 days really preferred.
Only benefit you have is that JetBlue has a red eye out of JFK, so you could leave at 11:59pm the night before your charter starts and actually be on the boat by Noon. And you could leave fairly late the last day too (4pm out of Tortola) - this would at least give you a full noon to noon charter, although Sunsail starts at 6:30, so you may want to check Moorings (same owner as sunsail) or another charter company.
Highly recommend increasing the length of the trip if you can though.
I am the luckiest guy in the world. My wife has just agreed to spend our 25th wedding anniversary aboard a chartered sailboat out of Tortola this January!!...
Since you're going to be celebrating your 25th wedding anniversary, maybe you should tell us what your wife likes to do. You'd get some pretty good, specific advice from this crew. Will you be looking for a really nice restaurant, for example?
I am the luckiest guy in the world. My wife has just agreed to spend our 25th wedding anniversary aboard a chartered sailboat out of Tortola this January!!
I would love some advice on any or all of the following:
1. Which company(ies) are best for chartering a monohull in the 32-28 foot range? Moorings, SunSail, Footloose
2. What type of certification will I need? I have four levels of ASA certification, including coastal navigation, but I never took the bareboat course, since I've been coastal cruising my own 32-footer for 6 years now. No Cert Needed. If you used a toy boat in your bathtub , then your all good.
3. Where are the best places to sail to with a 5-day window of opportunity? Sail clockwise or counter clockwise around Tortola, you just can not screw it up as all the islands are just a few miles away and in clear view.
4. What should I watch out for in terms of governmental problems or encounters with the local citizenry? None as long as you stay in BVI the government and locals are very nice.
5. What would you recommend as the most enjoyable opportunities during the charter? The Bitter End
Any and all advice, insights, info, anecdotes, etc. will be most helpful.
Good point Cotemar made on the anniversary and what the wife likes to do.
I'd highly recommend dinner at Coco Maya on Virgin Gorda. We ate there last July and my wife said if we do nothing else each trip, as long as we eat there each time, she'll be happy.
One thing we love to do is spend 2 nights at Leverick bay and rent a car. We drive to the baths and other locations on Virgin Gorda as well as dinner at Coco Maya. Car rental is 24 hours, so if we arrive on Thursday at 4pm, we get the car and do dinner at Coco Maya that night, then do our island tour Friday and have dinner at the Leverick BBQ Friday night.
Only challenge would be fitting this in to 5 days, but its doable. Any plans you have will leave something out. As Zanshin suggested, visit Traveltalkonline - lots of tips there.
Boat: a pirate at the baltic sea and chartering here and there
Re: Advice on Chartering in Tortola
Congrats, you are gonna have a blast!!!
We just chartered a Leopard 39 for the two of us with Moorings and everything was just perfect, so despite the premium you pay I would still recommend Moorings.
Most has been said already but I would really second the idea to prolong your trip, 5 days is just by far not enough given the beauty of the BVIs.
If you are really stuck to your 5-day window and want to see the highlights but still sail at least a bit (and I assume that these are 5 full sailing days) then I would probably do a counter-clock wise trip as follows:
Day 1: start the morning with a great short sail from Road Harbour to the Indians, which offer great snorkelling and just a perfect lunch spot. You will probably not have enough time to visit the caves or Norman Island itself (which is a pity) so you should leave early afternoon and head to Cooper Island for the night.
Day 2: get up early and head over to the Baths, where you can spend a great morning strolling around the stones, etc. Around lunch time, I would head up north into the North Sound and find a nice mooring in front of Saba Rock rather then Bitter End. Dinner at the waterfront is just fantastic there.
Day 3: For us, Anegada was one of the highlights and depending on the wind, its a quick sail over there. So leave early and you should arrive around or shortly after noon. That leaves enough time to reserve a table for the lobster feast at night and take a car around the islands. The snorkelling at Loblolly Bay is just breath-taking.
Day 4: Sail back to Tortola or rather directly to little JVD for a short stroll to the Bubble Pool. Then sail over to Great Harbour for the night. In the evening, you can dinghy over to white bay with the famous Soggy Dollar Bar. The Beach is nice and after 3-4 painkillers it ain't get better . At night, Foxy's is a famous restaurant at Great Harbour and always great fun.
Day 5: I would definitely make a stop at one of the Sandy's (Sandy Cay is quicker as it got moorings and the swell is usually better to get to the beach safely) and then sail around the west cost of Tortola and head to Peter Islands. We anchored in Dead Men's Bay for the night and this was a great spot for the last night and you are fairly quickly in Road Harbour the next morning.
One thing we love to do is spend 2 nights at Leverick bay and rent a car. We drive to the baths...
In my opinion, a much better way to see The Baths than to try to grab a day mooring. If you go this way, don't forget to bring the form that says you've already paid the Park Service fee. Top of The Baths is a nice place for lunch or dinner, or just a refreshing drink, too.