Where to vacation in Thailand?

Sounds about right -- Thailand is a long way to go but things can be very cheap when you get there.  For example -- last summer, I booked round trip tickets from SFO for $1700, but when I was in Thailand for two weeks, I spent less than $700, and that's including airfare between islands, car rental, other transportation, drinks at a couple high end bars, a meal at literally one of the best restaurants in the world, a few nights at a "resort", shopping, and everything else that I would consume on a vacation.  Granted, I did get to stay with friends for a bulk of the trip, though!

If you've never been to Phuket, you should pay it a visit.  It's beautiful.  My parents actually took me there for a family vacation when I was a kid. Another island that I would suggest is Koh Samui.  I almost stayed in Koh Samui last year, but my friend ended up booking a place on the next island over, Koh Phangan.  I did look up Koh Samui spots just in case, though, and there was a really wide range of resorts that you could stay at.  Some were as low as $30 a night, while others, big names like Four Seasons, were around $1000'ish.  I saw some really nice looking ones on the beach for $100'ish and I would personally go with those.  I do not recommend the $30 a night places.

So here's what I actually did the last time I was in Thailand: I flew to Bangkok and road tripped down both coasts, both of which had a lot of beautiful beaches, then I made my way down to Koh Samui and Koh Phangan by flying into Surat Thani and ferrying over.  If you drive down the east coast in Bangkok, you hit Pattaya.

And if you drive down the west, you hit Cha-Am.  Both very well-known and beautiful beach towns.  Maybe you can look into something like this, too.

As for wine, I didn't see many people drinking wine.  One peculiar thing that I noticed, though, was that beer was served either on the rocks, or if it was in a bottle, it would come in a bucket of ice with a straw in the bottle, and you're suppose to sip the beer from the straw in the bottle that's in the bucket of ice :P

Hope you decide to go to Thailand!  Seriously one of my favorite countries :)

I second Koh Samui!

Had a wonderful and very chill experience.  If with the fam, I'd advise minimizing any time in Pattaya.

Surin beach, Phuket, probably the most stunning beach on that coast, nice hotels in the area, family friendly, and has primarily been kept in a very local tradition, inexpensive compared to the rat-race of Patong. One qualifier, I only go to places in low-season to avoid the crowds and expense so I cannot vouch for crowds or otherwise in other seasons