The Aloha 30 is a 'coastal design' good for making passage along close to 'the coast' where if stink weather develops you can 'squirt in' to a port or inlets, etc. for safety, etc.
The 'best' way to make for the caribbean is to go direct to Bermuda and then straight south to the islands ... about a week or more on each 'leg'. A coastal boat isn't strong enough and wasnt built strong enough to handle those unexpected condition that 'can' occur along this 'route'.
Sailing to the Caribbean 'can' be done in a coastal design by the 'thorny path' --- Bahamas --> Turks --> DR --> Puerto Rico ---> BVI ---> then 'south' ... all island hopping but mostly beating straight into the 20kt+ trade winds and adverse currents for days and days on end.
Stowage will be a problem with a 30 ft. boat. Consider that for every 1000 lb. you put on board that an Aloha 30 will 'immerse' by 1" at the waterline ... typical 'cruising loads' will be about one ton+ and thats 2" deeper into the water which will affect 'performance'. Think about being much deeper in the water and beating for days on end into 4-6+ waves on top of large swells and your 30 footer violent 'hobbyhorseing' along because its 'overloaded'. Typically for every 6ft. of waterline increase, you typically 'double' the *internal volume* and carrying capacity. Strongly suggest you consider the longest waterline length boat that you can afford ... and then GO for it.
Sure there are quite a few 30 ft. boats seen in the islands, but usually their decks are overloaded with 'stuff' because of the internal volume is lower, the high deck load is going to affect the 'stability & survivability' when its blowing 'real' stink; plus, where will you stow your needed dinghy as you simply cant tow a dink in the open ocean? ditto, also too any 'liferaft', the obligatory jerry cans, etc. etc. Load up a 30 footer with a wind gen, water maker (you 'can' spend up to $1.00/gallon for water in the 'dry' islands), dinghy, extra anchoring gear, SSB, distance Wifi antenna, etc. etc. and youll wind up 'cluttered' and with not much 'living and sailing' space.
I would suggest seeking the longest waterline length that you can afford, and a boat that is probably a minimum of 32-35ft. waterline length ... and then expect to spend 20% extra for fitting out with all the 'goodies' that make long distance cruising a pleasure. A 'coastal built' boat will do for island hopping ... you just have to wait for the correct 'weather window'.
Strongly suggest you consider the longest waterline length boat that you can afford, allowing an extra 20% of the purchase price for upgrade and refit ... and then GO for it.
How to compare boats:
http://www.image-ination.com/sailcalc.html .... look for 'motion comfort" values for a 'blue water' boat. ditto look for values of 'seakindliness' if you want to sail in the 'deep blue'. These values may be 'artificial' and are based on 'preference', etc. but will give you some idea of what to look for.
Lastly, dont be gullible to the statements that it "makes no difference if the skipper is 'real good and experienced'" .... as many times the skipper 'may' be below and power-puking into the bilge and the boat may have to 'take care of itself'.
If you decide to 'go coastal' get a 'good' coastal boat; if you decided to go the blue water route ... get an 'honest' blue water boat, not a flimsy clorox bottle dockside entertainment center that 'may' come apart in a severe sea state. A 'good' / well founded coastal design is all thats needed for the Carribean Islands.
A 30 footer is going to be 'cramped' and 'deck heavy'.
