Re: 1st time visit
The end of October may bring you rainy weather. You might well consider trip insurance in case of a late season tropical system. You should have no problems avoiding crowds at that time of year. There will be some resturants closed in October. There is a list of resturant closing dates and other info at this website: stjohnspice.com/stjohnrestau...
I would recommend a jeep for the whole stay since you mention your interests are snorkeling and beaches. 99% of all accomodations on StJ are not on the beach as most of the island is National Park land. You will want to drive to a different beach each day. Although this means you will not wake up and walk out onto the beach, it also means that you have about 50 beaches to choose from, very few of these beaches have hotels, residence or other developements on them to spoil the beauty.
I will VTmail you the email address of a person who can arrange excursions of all types, she also arranges to connect people of small groups together to take advantage of trips and excursions that usually require a larger group.
Take a look at my VT StJ page for more information. You can also visit www.seestjohn.com for a great deal of info on beaches, history and other stuff.
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