So, I'll add a couple of details, thoughts, etc. here in response to requests here.
Major Islands/Countries Visited/Sail Path: BVI > Saba > Statia > St Kitts > Nevis > Montserrat > Guadeloupe > Antigua > Barbuda > St Barths > St Martin (Dutch & French) > Anguilla > BVI
Certain islands/places we loved in particular? Well thats hard to say other than a blanket statement that I'm pretty done with the BVIs after 30 years of traveling here (I know, ironic, on this board - it has just changed in many ways that makes it less appealing to me, though we still love Anegada). I don't begrudge those that love the BVIs - its just not the best place for me and my family anymore.
We'd probably say that Guadeloupe, Antigua, Barbuda and Anguilla were particularly awesome and special. But, heck, so was Saba (very challenging getting on and off this island), Statia, and some other places so, we really liked all of the places we visited. I'm a kiteboarder and I particularly enjoy unique and out of the way places, so Barbuda was particularly special for me. With that being said, Guadaloupe is the most diverse with incredible beaches, true rainforest, and ridiculously good food.
Special beaches, restaurants - well, let's just say that there are so many that I can't begin to detail them - we found them everywhere.
As to how we did it - well, that's quite interesting. It took an incredible amount of persistence in the search for a boat in that we had some general parameters that were have to haves (boat type, size range, age, equipment, and importantly, price - I wasn't about to pay full retail for 8 - 12 weeks). We actually looked for boats from the Bahamas all the way down through the Grenandines. Whereever we could find a boat, we were prepared to go. Ultimately, we found a boat in charter (BVI Dream Yachts Charters) and I worked up a unique partnership deal directly with the boat's owner. I think it was a good partnership between him, me, and Dream Yachts. That's all I'll say about that here - I could provide more about this arrangement if someone wanted to contact me directly. (More about my arrangement or about Dream Yachts, or the charter industry in its entirety.)
What I will say is this - planning for this trip took me at least 6 months of steady work. That planning included taking a diesel engine course, updating my navigational skills (even though I've got thousands of miles of offshore experience), going to both Annapolis and Miami sailboat shows for additional meetings, knowledge, etc. And then there was the planning for what we would need that's very different from the many typical weeklong charters we've taken - and the planning for how to pack all of that stuff, and then the actual process of packing all that. Now, that was the real challenge. (And to be clear, my family of 3 each took small backpacks of clothes as carry-ons though we had 7 pieces of checked luggage packed to 50 pounds each with various gear, sporting equipment, etc.) The planning and packing (really, the planning for the packing) required a lot of work.
Just as information, here are just a couple of items that we brought that were particularly important - none of which are necessary for a typical week charter trip:
1. Sunshade "equipment" so that we could rig a sunshade for our catamaran to protect us from the setting set each afternoon. This was brilliant and, unbelievably, it worked well despite never having stepped on the boat before.
2. Yeti cooler. Our cooler was packed with food for the trip down but we never bring food to the BVIs - its just too easy to buy good food there. (The frequent conversations about this always amuse me.) However, having an awesome cooler to keep ice for 4 - 5 days - now that was invaluable.
3. Safety equipment: Harnesses, inflatable PFD's, carabiners, jackline rigging - all necessary and, of course, never on a charter boat.
4. Handheld VHF
5. Delorme Inreach Tracker with 2 way Iridium messaging - awesome piece of equipment at very reasonable price
6. Tools - I brought some, bought some others locally, but didn't have enough - I could have used more. (Next trip I'll make sure to have Carb cleaner with me as I had to take apart and rebuild the carburetor on the dingy on a beach in Antigua when it crapped out. It was a relatively easy hour process on the beach with the help of another boat's liveaboard owner who had cleaner and tools.)
7. Spare Parts - the basics were put on board for me by Dream Yachts in cooperation with the boat's owner: impellers, belts, filters, fluids, etc. (Fortunately, didn't need them, but I was fully prepared with both parts and knowledge in the event I did.)
As for real challenges - we had some though none too serious (in the end). In one situation on Saba the boat got lodged sideways on top of a mooring ball despite our bridle (I don't like mooring balls and use them only when I have no other good option). I've never experienced this before and I had just returned to the boat with my family after dark in 3 - 4 foot choppy swells and 18 knot winds - the boat was pitching and heaving to the seas as it was being hit sideways by both wind and seas - it was dicey as I had to get on the boat and we had no PFDs. In another interesting situation, we'd made a fairly routine 30 mile sail and the mainsail halyard was fully jammed at the top of the mast - when we went to pull the sails down, nothing would drop. (It was a good thing that we weren't sailing at night then and that we didn't need to reef.)
So, I'll leave the commentary at that for now. It was a special trip but required a huge commitment of time. The planning I did made the trip wonderful. I'm "semi retired" so I had that flexibility (in addition to the actual 2 months on the boat). Even though it's nothing like my friends who have sailed aboard for years with multi-week passages, it was an awesome trip that was everything (and more) than we'd hoped it would be. I hope others get to enjoy the same - it can be done!
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