Sail Pepper - for local flavor

While in St.John, we booked a sunset sail On the 23ft sloop Pepper (link here). Captain Fred and Renee were wonderful hosts. Renee kept the Cruzan rum flowing into our cups as Fred kept a steady hand on the rudder. Initially, the weather threatened to spoil our evening, but by the time we arrived at Maho Bay, the light rain had abated, and winds had died down somewhat.

Fred sailed us out towards Great Thatch Island between Whistling Cay and Mary Point, towards the edge of US / British Territorial boundary. 'The weather started getting rough' but the tiny sloop was not lost. Wave crests that blotted out the view of Great Thatch Island and sent bow spray over the passengers (including Dr Desert Flower's hearing aid! yikes!) began to rock our small craft, when Fred turned us around and back into Francis Bay towards Cinnamon Cay, where Tim and I had tried to snorkel the day before, but had to call it off due to choppy seas. By the second glass of dark rum, my grip on the boat's edge had relaxed. By the third glass, the sun was setting, and I was having a marvelous time. My other cruise-mates had 2 glasses - Tim had to drive the winding mountain roads back to Cruz Bay afterward and the wives are light weights =P

It was Fred and Renee who taught our experienced hosts Tim & Jill the vernacular "St.Trauma" for St.Thomas in 2009 - once you take a careening, poorly maintained, jammed-full-of-tourists van ride from the St.Thomas airport to the Redhook ferry terminal, you'll understand why it's accurately called "St.Trauma". This trip, we learned the traditional jingle about Caneel Bay:
"for the newly wed, and the almost dead. The well fed, and the over-read." There are some suites at the private Caneel Bay resort that go for $12,000 a night - about 40X beyond my price range. I came up with these limerick additions:
"Caneel Bay: for the ridiculously paid who could not otherwise get laid"
"Caneel Bay: for the small member compensating and the chronically constipating"
and
"More money than sense, collagen lips & silicone chests"
We talked about customs & immigration hassles to get to the British Virgin Islands, the best places to see octopus and sea turtles on the island, how more and more yachts are showing up flagged to the Marshal Islands (damn Republicans and their tax loop holes!). It was a very pleasant cruise.

Pepper also has daytime guided snorkeling cruises as well. Check out their website.