Kauai. I’ve already been to Maui and the Big Island, and loved them both.
I’ve never seen a MLB game in the home ballparks of the teams im Tampa, Phoenix or Denver. So make it one of those during the baseball season.
Who pays my expenses while I’m there? The cost of the accommodations wold be more than the plane tickets.
As this is imaginary, I don’t know why this rule exists.
Kodiak Island. An ancestor is supposed to be buried there.
Maine, New Hampshire, and/or Vermont. Far enough to take advantage of the free trip. Especially if the trip is this time of year.
Bother! Failed on point 1 
New York. But it has to be when the Yankees are in town. Plus I want a picture of myself extending the middle digit in front of a certain tower.
You don’t get it, do you?
Idle is really going through with this.
ETA: sorry if you weren’t ready to go public with this, IT.
To San Francisco, for Labor Day weekend. My sister, who lives there, is having her baby shower then. I’d love to have someone else buy my plane ticket!
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I’d either go to Columbus, Ohio to visit my sister/family and catch a race or.
I really really really wanna go to this rock festival in Chicago in September.
My dad’s old, Army buddy lives near Wallowa, OR. He’s an interesting dude… owns/maintains a decommissioned fire tower in the wilderness. I read his blog often and would love the opportunity to visit him.
Rather than *paying *for the travel, it’d be great if Idle Thoughts could keep my work and home fires burning while I was away. That’s where the real value is 
Great choice! I am a part-time Hawaii resident (I’m typing this just north of Kona, in Waikoloa, and will be on island until mid-August) and a big fan of all the great ways to spend time here.
Given the 3-day limit, I would probably just fly to another Hawaiian island that I haven’t visited yet, probably Kauai. If I could stay longer I’d go to San Diego. I’ve never been and a good friend is moving there, so I’d wait until she was settled, then visit.
I would go to Idles town and take him out for hot dogs and pop for being so nice to pay for my plane ticket.
Then I would join a jug band and travel the US with my pet goat Kevin the cunt.*
*Warning. Adult words and Kevin acts like a cunt.
I just had a nice vacation with my family and I’m doing some kind of insane work travel this month (American Samoa!), so I’d probably take a ticket to Dallas to meet up with some friends who will be going there for a conference this fall. No real desire to go to Dallas, but would love to hang out with my friends. I might buy my own plane ticket, but obviously free is better.
Given the short duration I’d limit myself to destinations reachable via a direct flight from my airport, and I’d prefer to go somewhere new. My smallish, regional airport only has about a dozen direct flight destinations, including:
Chicago – nope, been plenty of times
Minneapolis – nope, been plenty of times
Detroit – nope, no interest
Washington, DC – been once
Atlanta – would like to go but too big for a short trip
Charlotte – would like to go…this might be best option
Newark – meh
New York – been once but over 20 years ago and would like to go again.
Dallas – would like to go but less desirable than other options.
Denver – been but wouldn’t mind going again.
Salt Lake City – been but not as an adult, about the same level of desirability as Dallas.
Las Vegas – been but wouldn’t mind going again and 3 days is just about perfect.
I have a friend in NYC that I haven’t seen in ages and would love to catch up on things with. So if he’s free, I think that trumps my preference for visiting somewhere I haven’t been. If he’s not free I think I’d go with Charlotte.
I’m not aware of a place called Oceanside, New Jersey. Did you mean Ocean City? Or maybe Seaside? Or the Jersey Shore in general?
To answer the question, I think I would choose Seattle or Chicago. Always wanted to check those places out.
Miami, right now. Keep your return ticket.
Just got back three weeks ago. Great fun.
I would go to Key West, Florida. Maybe jam with Jimmy Buffett.
Hawaii. I’ve been to all 49 of the other states and with just one
to go it looks like I’ll never make it on my own.