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I'm not familiar with your Humane Society but here's how I raised a few hundred dollars and awareness in PA.
First I explained my idea to the SPCA and got their blessing.
I put up an old-fashioned kissing booth and sold kisses from my old beagle. I asked for a dollar but most people gave more. We put pictures of the event in the paper so the business we set up in got free PR, plus newspaper readers could send in their donations (at the very least be reminded that the SPCA exists)
Of course, this event was an excellent excuse to get checks from friends, family, and people I do business with. I say checks because no one writes a check for less than twenty bucks.
This could work there. You have traffic flow- people on vacation already in "spending mode" who are missing their pets at home.
West Indians, who constitute ninety percent of the local population, are unlikely to participate in a kissing booth. The culture here is different from what you're accustomed to in the states, and West Indians are generally reserved with strangers. If you're only attempting to collect money from tourists, you would probably encounter trouble getting a permit for a kissing booth to be located in a high tourist area because it is something West Indians, who grant the permits, would likely frown upon.
Generally speaking, West Indians do not consider dogs "pets" so much a security devices. It is extremely unlikely that any West Indians will want to kiss your, or any other, dog. People who move here from the states are a much smaller pool of people . They will buy Girl Scout cookies or tickets to fundraisers like the Humane Society's annual Doggie Ball, but I don't think kissing your dog will generate much in the way of donations. Local store owners are also unlikely to have the extra space for you and your dog, or the liability insurance should your dog reciprocate a kiss with a bite. If you really want to make a difference in the lives of abused and neglected animals, volunteer your time to your local Humane Society.
While there are many Caribbean natives who do not treat their pets the way some of us like to "pwyle" them, the local humane organizations are quite active with outreach programs aimed at youths and families. These programs have resulted in a bit more respect for animals as sentient beings.
On St. Thomas, visit the Humane Society, http://www.humanesocietyofstthomas.com/, on St. Croix, visit the St. Croix Animal Welfare Center, http://www.cruciancritters.com/; retired horses get a break from VICCTRE (pronounced like "Victory") - http://www.vicctre.com/ and a local citizen runs PAWS: http://www.paws.vi/.
There is also a St. John Animal Care Center. Their annual major fund raiser, Wagapalooza, has some info on the organization on their web site. http://www.wagapalooza.com/about_acc.shtml. You and your kissing pooch will certainly be in good company!
Christi, that's the cutest idea ever! I might steel your idea for the shelter here at home!