"I have one question from your last statement ''You can cruise very cheaply all over the Caribbean....'', can you define cheaply?"
Ahh, you want to know how many of those angels we can get to dance on the head of that pin, don''t you? <g> An honest answer is ''No'', I really can''t. There have been many threads on this topic on numerous BB''s (and some excellent detailed reporting done by Latitude 38 over some years now) and the answer always seems to be that cruising costs vary widely from one crew to the next and are often directly related to what''s in the wallet. (One corollary seems to be that fancier, more complex boats are sailed by crews who spend more, FWTW). To put this into positive terms, that means you really do have a great amount of control over spending...you just have to exercise it).
IME a careful look at what one CAN spend per month, and a willingness to put a little sweat equity into saving some money, can allow some crews to cruise on $800-1,000 USD/month in the Caribbean, but that excludes expenses back hoome, haul-outs, major repairs, insurance and equipment purchases (all of which are usually paid for before one shoves off). But that answer ignores a lot of pretty relevant variables, such as the material condition of your boat, how good a shopper you are, how full a tool box you carry (self-sufficiency), how simple/complex the boat''s gear is ($$), how well it sails to windward (fuel and engine maintenance = $$) and attitudinal issues, e.g. how much this will be a ''summer vacation'' kind of sabatical cruise vs. the real thing (where the longer you''re out, the more you count pennies) - it''s kinda amazing how much some crews think they are entitled to do/buy/consume and the lifestyle they are entitled to, even as the last few pennies are dribbling out of their pockets.
I know you were looking for hard data and not a philosophy lecture, but here are some data points you might find helpful in general terms:
1. Most island nations charge very little in the way of fees. The Bahamas and DR have both raised them significantly ($150/$300 as I recall, based on boat size, and now close to $100, respectively) but PR
, USVI, St. Martin (French side), Jamaica, Haiti (Ile a Vache'', anyway), Grand Cayman and most of the Bay Is. levied no clearance fees when we visited. Trinidad and BVI''s were quite reasonable, as I recall -$40 USD each or thereabouts. As for the rest, you''ll find everyone weighs the convenience, the attractions, the protection of the harbors, and the cost of a stop, looks at their own imposed sked, and then makes up a somewhat unique itinerary based one what feels right. It is a norm to be able to stop in a protected anchorage or harbor to rest, not go ashore, and then carry on without any clearance formalities or charges.
2. We are talking ''tropical'' here, so there is usually abundant food and, after all, many islanders usually have little money for shopping so a willingness to scout out the local market will pay dependable returns. If the lettuce in the Georgetown, Great Exuma grocery store seems pricey, you''ll buy home grown cabbage and tomatoes from the ladies in the town square and mix up some dynamite cole slaw instead of having a tossed green salad...and that''s about how food purchases go everywhere. If you must have meat, meat, meat, there will be some expensive stops. If chicken and fish tickle the pallet, you''ll spend less. (Chicken in the Caribbean is typically fabulous when compared to the hormone/antibiotic-injected stuff at Publix).
3. Charts & guides can be expensive. OTOH there are LOTS of ''sabatical cruisers'' returning with relatively fresh charts/guides and a plan to sell the boat. Some digging should produce ample choices at reasonable prices without buying old stuff (ALWAYS ask their age). You might perch on www.ssca.org''s Chart Exchange BB and other places like that.
4. We''ve been enjoying an ongoing correspondence with friends who are doing the Thorny Path for the first time. In the last email, Mark described their l-o-n-g one day over-the-island trip from Luperon to DR''s capital city, Santo Domingo. It cost them $100 (a couple), they saw even less than they had time for (the guide was not reputable), and they returned in the dark, exhausted. In his words, it was a ''lesson learned''. When there, we took the local bus over the mountains (incredible scenery, BTW), stayed in a modest little hotel recommended by a local (clean but spartan) and toured in the Old City for 4 days, walked a lot, ate out carefully (easy to do in the DR) and took the luxury bus back (A/C!) and the whole 4-day trip cost us less than $100. I don''t think this was because we''re more clever but rather because we were stretching a budget more than Mark felt they needed to, and we were willing to do our own thing in a way we could afford. (And BTW we had a blast!)
Here''s my hunch: You ask good questions and you are working the ''cost'' issue with apparent care. Those are attributes of someone who can make it work and will stay in control of spending. My hunch is that it''s time to move onto the ''where & when'' and worry just a a bit less about the ''how much''. And I hope you too have a blast!