Begginner sailor, looking for advice on purchasing boat
James, I think you''re overall goal is reasonable, especially if put together in thoughtful segments with a bit more research than you''ve done to date, but I think it would be a lot easier to reverse the route.
First, a few comments about the boat. You''re asking about a fleet of potential boats (27-30 footers, let''s say) all of which are going to be old, in various stages of upkeep (or lack thereof) and alteration by their previous owners, and which therefore defy a general ''yea/nay'' comment. IOW for any given design that''s recommended, you''ll find individual hulls that won''t be at all suitable. (Just so you know...) You''ll also need to carefully order your boat selection priorities (see my suggested list, below) which, in turn, will require a bit of research about boats sailing in big water.
It''s fine to say the waters in which you''ll be sailing are near coastlines, but you omit to mention that those coastlines have few nav aids, no rescue services (at least the USCG is out there...) and are full of current, reinforced Trades during your planned passage season and plenty of convective weather. It''s true that rafts do cross the Florida Straits but most don''t make it, and you should have seen the condition of the 3 crew on the one I found. It''s correct that the runs can be short (tho'' longer in a smaller boat) but the main advantage of a short run, from a safety standpoint, is that you can time your run for decent weather...which means you need a reliable way to obtain wx f''cast info while offshore (don’t expect local radio info to be available) and to use it knowledgeably (another research project!). I guess what I''m saying is that it''s a good thing to be attracted to the adventure inherent in your idea - good on ''ya! - but don''t underestimate the undertaking or enjoy your ignorance too much.
IMO your chosen boat will, assuming it''s generally suitable, have a totally trustworthy rudder (and quadrant/steering system if so equipped – none of this being taken for granted on a 20-30 yr old boat), a somewhat fresh rig (wire and hardware), a reliable engine, at the least a SSB Receiver & laptop (for wxfax and b’cast text f’casts), decent (not tired, not cheap) basic sails, a robust anchor system (at least 2 full anchor/rode combos), and good sun protection.
Assuming a Maimi environs departure, I’d suggest a clockwise route. Enter the Bahamas at Cat Cay, head SE from Nassau and enjoy cruising the Exuma Banks, exit via the Ragged Cays or Crooked Is. Passage, catch your breath at Mathew Town, Great Inagua (boats regularly get pasted there; it’s a lousy anchorage so watch it…), and make for the Windward Passage. At that point, your options all continue down or across the wind – you can choose to clear into Santiago de Cuba (does the Trading with the Enemies Act apply to you?) and begin cruising the Cuban S Coast, or head for Port Antonio’s colonial charm on Jamaica’s N Coast. You could even stop at little Navassa Is. along the way to Jamaica with all the Haitian fisherman, the only Caribbean island I know of run by the U.S. Fish & Wildlife Service (check it out at www.fws.gov). From there on, you’ll continue downwind until you round Cabo de San Antonio at Cuba’s western end to head home. Clearing in/out at Isla Mujeres, Mexico allows you at least a shot at avoiding being prosecuted for visiting Cuba but not a guarantee. (If you think you should be able to visit Cuba like you can visit e.g. China, you might be sure to register for your absentee ballot before leaving…).
The route you suggested is problematic. Exiting Key West for Havana forces you to either file for a zone exclusion with the USCG (putting you into someone’s data base) or violate the law. Also, the easy ride westward with the wind along the Cuban N coast will be the last good news you have on the cruise; from there, all your options are to windward…in a small boat, against prevailing swell, wind wave & current, I might add. Ugh…
A couple of references: Wallace Stone’s Cruising Guide to the Caribbean (30 years old but the routing and wx strategies are timeless and you’ll find it used for only a few bucks; Bruce VanSant’s Passages South (best guide I’ve ever used) for the Bahamas run and general Caribbean weather savvy – paperback and good value; John Lethbridge’s cruising guide of Jamaica, also dated now but not much changes in Jamaica – his wife still sells them; Nigel Calder’s Cruising Guide to Cuba, somewhat the bible…but keep in mind Nigel is a Brit and has been reasonably discouraging about the realities of U.S. citizens visiting Cuba given our current political circumstances.
You’ve combined family ties and a sense for adventure into a great idea; don’t give up on it because it’s harder than you might initially think. After all, it’s easier than sleeping in a pup tent up there in the winter.<g> Let me know if you have any other questions you think I can help you with.