You will find plenty of better blogs on this topic by more experienced sailors and better bloggers incl. for instance Cap’n Fatty Goodlander (I am a fan as you can tell…). But here are my 2 cents based on the only boat we bought so far.
- If you want to go cruising on a sailboat in the Carribean, you need something between 37 and 44 feet. We met a few great couples on 37 feet boats who all regretted not going bigger, and likewise, anything above 44 feets becomes quite a bit of work for a couple… There are other considerations (such as price!) and personal preferences, but this is for you to figure out.
- I think many folks struggle with the tradeoff between an older boat privately own or a more recent charter boat. we went down the ex-charter boat route. Folks had warned us that these would be beaten up, but honestly, we could not tell (ours was from 2010 – perhaps older boats could not take the beating as well…). Our next boat could be an older boat privately owned – I will update the post accordingly…
- Budget to make sure you have room for all the upgrades you wish for. You don’t want to be boat-poor when you walk into the chandlery or at happy hour (BTW – I bought most of the upgrades on Ebay, and I found it amazing what you can find from obscure small dealers based in Asia).
- Spend time in Marinas. This is how we figured out which features we liked or not. Also, check blogs from cruisers with similar life situations (we are big fans of windtravelers).
- Try to charter different boats (we discovered really nice boats beyond the Jeanneau’s and Beneteau’s by using smaller charter company)