Wow, wide open question
...and is a little bit difficult to answer without a great deal more information. There's really only one rule:You'll want to find a vessel that matches your needs for the right price.To find out what's available, what each vessel can offer in amenities, tankage, versatility, maintenance, performance, etc., and estimates for used pricing, I highly recommend investing $60 in Practical Sailor's Practical Boat Buying. You can contact them with the link below.http://www.practical-sailor.com/Contact/contact.htmThere are, of course, other boat buying guides; this just happens to be a good value; it gives lots of reviews for just a little money. You can also read owner reviews on dozens of owner's sites. That's also a good place to find out what you want the vessel to do for you, for example, performance vs. giant cabin, very stable vs. a lot faster, and other trade-offs.After finding a few models you're "in love with" try to find them in charter companies or local marinas. If in marinas, you can probably contact the owners for a "test sail" that will only cost you snacks and beverages. Chartering will allow you to really spend a few days digging through the boat, finding all the thru-hulls, assessing the accessability, refridgeration, air conditioning, showers, water pressure, room in the heads, salon, and berths, etc.Your biggest decision will probably be HOW much money to spend. There are many, many boats that can do what you want, you just have to find the "right" one for you. Be patient, have fun, and good luck.