Punki: What do you find charming about Sitka? Its architecture? Its people? Its natural surroundings? Ditto on Ketchikan, what aspect makes it interesting?

I like people watching, walking through neighborhoods which have their own distinct character not to be confused with other cities, and taking my time rather than rushing from place to place, trying to check items off a list of places to see. I'd like to find a city with lots of things to do where I could just wing it rather than have to make reservations way in advance. Oh, and if it might help people make suggestions, I very much enjoyed the underground tour in Seattle, that's the kind of thing I want to do whereever I end up going on this voucher.

One thing I'm glad of is that I don't think I can really go wrong, no matter which destination I pick....

Eastbay1K: you're right, the SFO-ANC flight listed in the timetable shows 1 stop, I'm sure it connects through SEA.

How did you end up being a tourist in Alaska over 30 times? Youch. If you said half a dozen times, I'd be envious. But 30 times, I'm not so sure that I should be envious.

With respect to myriads of day and overnight trips available from the south central area, the problem with any of those from my point of view is that it will be very difficult to squeeze excursions in the very short time frame I'm looking at. So I'm looking for advice for a city with interesting stuff to do within the city limits. (Granted in spacious Alaska, I expect there are cities with rather broadly defined municipal limits, but you get the idea, I hope.)

shadow: hitting Mexico just doesn't seem as appealing to me, somehow. I just wouldn't look good on a beach, and I haven't learned any of the interesting water sports like snorkeling, etc.