sailing the Caribbean

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Alright anon I have a question for you regarding lodging and food while sailing the Caribbean.

Backstory: Sailed for the last 2 years as a foredeck hand, and after moving to good old atlanta, I find myself wanting to get back on the water. I'm 90% sure I convinced my old captain and one of my old crewmates to come to the Caribbean with me next year and Sail from Trinidad to Miami. I'm also taking 2 family members and a friend who have no sailing experience (yay! We get to see if they get seasick.)

I've got an estimate on the cost of a 35' monohull bareboat at $1500 per person for 3 weeks, which isn't that bad when you consider the distance that we will be covering. On top of that, we have the custom fees associated with the different islands; no more than $300 per island

What I don't have figured out is how much we should plan for food and lodging. We will be on the boat for an average of 6-8 hours a day (there are a couple 10-12 hour days because of the distance between the islands) so we will be eating 2 meals on the boat.

We absolutely do not need a 4 star hotel, but we can't all sleep on the boat, so we'll need to go ashore for lodging each night. Reserving a whole dorm at a hostel seemed logical, but it appears that the Caribbean had some really high hotel taxes (hostelworld.com $430 for a 6 bed dorm rated at $20 a night per person, it just seems like that's wrong).

So, tl;dr 6 people, food (1 prepared meal at a restaurant and provisions for 2 meals on boat) and lodging budget for various Caribbean islands along the way.