23 people? You definitely need to report back and tell us how it went, what worked, what didn’t and so on.
We have used Blue Sky Management for provisioning the villa for the past couple of trips. I find her ordering system to be the easiest and her pricing structure fair and straightforward. I used other companies in the past but like Blue Sky much more. I have heard Starfish will provision but have no experience with them.
http://blueskyconcierge.com/How many houses are you renting? I would let each house worry about and pay for their own food and drinks.
We checked coolers for many trips and if you like doing advance planning, it can be a great time and money saver.
We took meats (steaks, split chicken breasts, sausages, bacon, ham steaks), specialty cheeses and spices for pre-planned meals. I did this for ease of meal planning as well as quality. I am very picky about my meats. That being said, the STJ markets really have come a long way. While I didn’t buy meats, I remember looking at the meats at Starfish and thinking I would buy there next trip.
Snack foods are really pricy on STJ and a lot of people will do a checked bag of snack items like cookies, crackers, cereal and such.
I fill the voids in my suitcase with nuts, coffee and granola bars.
