I have sailed aboard the Poly and found the "Windjammer Following" to be good judges of where to stay in the Caribbean. I will not be sailing this year, but, searching for an island or two to visit for about 7-10 days. I very much have the Windjammer "no worries" attitude and am searching for an island with the same. Nothing too expensive but not too remote. Some nightlife would be great but am more interested in great beach shack-type bars and resturants. Snorkeling, hiking, some shopping, sight seeing and relaxing are my activities of choice.
I would love to find someplace quite with a great local crowd and perhaps beach front bungalows or cabins of some sort.
Any suggestions would be greatly appreciated.
I would recommend Tortola in the BVI for exactly what you are looking for. Any number of places to stay, but I would suggest someplace along Cane Garden Bay.
The atmosphere is very much "jammer like". Any number of choices such as Ole Works Inn, Elm, Myetts and on and on. Plus a number of great beach bars and restaurants
including Quitos Gazebo (owned and operated by Quito Rhymer, a reknowned reggae
star). You can find fabulous beaches, and snorkelling in the bays around CGB and can always , by ferry, get to surrounding islands for some of the best beaches and snorkelling anywhere in the world.
May I suggest you look at website bviwelcome.com
It is a fabulous source of information and has a wonderfully responsive message board. A few lines below this posting is a four part review of my trip to the BVI's last spring. We would go back to CGB in a heartbeat.