Jerry, I registered on the forum just to be able to respond to your post. My wife and I love bareboat chartering and we’ve done it in several places in the Caribbean, and a few times in other parts of the world. You will love it. With 3 couples, opt for as much room as you can. If not a catamaran, maybe even 2 monohulls.
BVIs – We were a bit, just a bit, disappointed in the BVIs. It was easy line of sight sailing, but we found it to be rather expensive, and we didn’t feel like it was easy to soak up any local culture. The marinas and anchorages seemed to be attached more to resorts than real towns. One night we did venture out of the marina area to find a lovely little town. We stopped and had a couple of drinks in a “bar” that seemed to be more of a garage attached to this family’s house! Great experience there. We will be giving the BVIs another go.
St. Vincent and the Grenadines – This was a fabulous place. My wife and I actually did some ASA courses on that trip. Just me, my wife, and our instructor. It was great, and the instructor was as much of a guide as anything. The sailing is fairly easy navigation-wise – not as easy as the BVIs, but easy. The islands were different, but wonderful – Bequia, Mustique, Union Island, etc – all very scenic.
St. Martin/St. Maarten – My wife and I did this one on our own, just to see if we could. We did, and it was, again, great. We picked up the boat in St. Maarten, and we sailed down to St. Barts, St. Eustatius, back to St. Barts, then to Anguilla, then back to a few stops in St. M/St.M. The sailing was a little more challenging, as the distances between the islands was greater, but well within our comfort zone.
Guadalupe – I set up this trip for my wife’s 50th birthday. We actually had two boats as we had about 10 people. We were a bit unfortunate with the weather, but we had a really good time. Picked up the boat on the main island, sailed along the south coast, then down to Isle des Saintes, then up along to the west coast to Jacques Cousteau National Park. That was easy sailing.
To change areas of the world completely, BY FAR, our favorite place to charter is Greece, specifically the Dodecanese islands. The Caribbean just can’t compare. We’ve been there twice, the most recent just a few weeks ago. If you can take a few days extra, I would STRONGLY recommend that. It will be the trip of a lifetime. Great sailing, WONDERFUL people. You haven't lived until you've sailed into a port, drank some Retsina, and danced with an old Greek lady!!
If you do go in the Caribbean, you might want to consider doing a course during your trip, either ASA or USSA. You don’t need to, since in the Caribbean, you generally only need to put together a sailing resume to be able to charter. The certificate would help, however, in later charters, especially if you do it in other areas of the world, like Europe.
We’ve always used Sunsail in the Caribbean (except in the Grenadines we used Barefoot Yacht Charters). They’re easy, they’re relatively inexpensive, they provide great service, and you get discounts having chartered with them before. In one anchorage, someone stole our dingy outboard. The next morning, the base manager was at the anchorage with another outboard. However, I think anyone you go with you will like. Ask around about the smaller operations, though.
Sorry for the long post. I’ll be happy to share more info with you if you want.
Fair winds!!
Wink