Vancouver BC to Southern Islands (probably Cuba) Graduation Trip

[nighttimesailor]

Good time of day to everyone, hope your sailing is going well.

My friend and I are going to be graduating university next summer and we both really wanted to go on an adventure, in particular sail to the southern islands, in particular the islands around Cuba and the Turks and Caicos Islands area. I have some previous sailing experience, with lasers, FJs and a MacGregor 26. But no long-term sailing experience. I have also been reading the forums here, and found a lot of the answers I was looking for (or perhaps Im just too much of a worrywart). In any case, we are considering two options, buying a ready cruiser in the 29'-33' range, and just adding holding/water/fuel tank capacity + some equipment if missing. Or getting a project boat for a smaller price and fixing it up over the year. The budget we were looking at is around 15000 US. I have looked over some sailboat listing websites as well as craigslist, and found that there are some nice Catalinas or NewPorts that are withing our budget/size constraints. But I also read on these forums that these boats are not ideal for an adventure like this.

So to formulate my question:
-What would you say is a better option to buy a ready boat and add some
simple features for a higher price, or get a (possibly bigger) project boat and
finish it?
-According to some of the answers I read, preferred minimum size for such an adventure is 30'+; Would you say a 30' Catalina would be a good way to go?
-Any advice, pointers or suggestions would be highly appreciated, including what literature should I be looking at to plan the route? What would be a good place to look to brush up on all safety protocols etc?


I know there are a lot f questions, and some of them probably seem quite amateur but we are getting ready for our sail, and I want to make sure we encounter as few problems as possible. If you have any suggestions on boats/boat models they would also be highly appreciated

Sincerely,

NightTimeSailor

p.s.
We are planning to sail during daytime only, and avoid nighttime travel as much as possible, does that make our trip a coastal sail?

[Steve1944]

No dumb questions.


By big as you can if you're going to resell.


Sit in the lounge for two or three hours get restless but stay there. That your test trial. Because all things considered, that's what it's like.