Originally Posted by AustinChief
If you want a cheap but really nice Midwest getaway... I love the Missouri wine country. I convinced my buddy's parents to try it out one year and now they go all the time. What's cool about that is that they used to live near Napa and think that Hermann and the Katy Trail area remind them of all of Napa's early charm before it became popular and douchey. Great trip in the spring but even better in the fall.
If you're big into music there is always Austin for various music festivals. You have SXSW in March, ACL in September. Austin's just a fun town in general.
New Orleans is always fun if you've never been before. Same for Key West. Same for DC.
Late Spring in New York is another great option.
I've never had much desire for visiting NY but I would like to see the WTC site someday. Is NY really a long weekend getaway type trip though?