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
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.