My first boat was a 26-foot Westerly Centaur that I purchased for about 10K and happily sailed on the
Great Lakes and several
Bahamas cruises to about 2.5 months. In addition to saving on the boat cost itself,
storage,
maintenance and
insurance were all less expensive. At one point I was paying under $50/month storage and since it wasn't worth much was happy going with liability only
insurance which was something like $250/year. I
sold it 8 years later for 2-3K less than I purchased it for. A great value and no regrets.
There certainly are very capable boats under 30 feet, but I think most of the ones that are inexpensive and good choices for the
Caribbean will be fairly small for two people.
One thing I think you should carefully consider is how important it is for you to be able to take your first boat off shore to the Caribbean. For me, that would make a big difference in what I'm comfortable with. I'd happily use a
Hunter or
Catalina 30 for coastal and
Bahamas sailing for example, but those are not boats I'd personally choose for more extensive cruising.
The
Pacific Seacraft Dana and Flickr are a couple small boats that have great
offshore reputations, but they are rarely found
cheap. The Contessa/Taylor 26, Norsea and Cape Dory 25, and number of folkboats have all proved capable, affordable
offshore boats, but are in my opinion very small. Boats like the Westerly 26-32,
Morgan OI 28 & 30 are options with a bit more room, that can be found at very affordable prices. Although not as built for offshore use, boats like the
Hunter 30,
Catalina 30 and Endavour can be found for 25K or less and to me the extra room they afford over many 26-27 footers is notable. For me, standing
headroom is a very important ergonomic factor in selecting a boat I'll spend any notable time on.
I've owned a 32-foot
Beneteau in the BVIs which has suited me just fine for that location. I just picked up a 30 foot Hunter for Bahamas cruises to 3 months.
Also check into the insurance issues with any boat you are interested in. Boats under 30 feet might be hard to insure for the Caribbean.
The more instruction and experience you can get on other boats before
buying your own, the more you will know about what is important to you.
Hope this helped.