Get three quotes. Seriously. Don’t go with the first nice guy who shows up. Check if they’re licensed by the Florida Department of Environmental Protection. Ask for references. A bad driller can leave you with a dry hole and a sad bank account.
Also, be clear about what you want. Don’t just say “a well.” Say “a 6-inch diameter, cased, grouted well with a submersible pump and a warranty.” Sounding like you know stuff makes drillers behave better.