Corporate:

Hilton Head. Great Golf, beach, warm water, and good scenery. Plus some really great restaurants!

Las Vegas. Great accomodations (Last trip was 3 nights at Monterrey Bay), plus all of the various activities and associated details which will stay in Vegas.

Of course both destinations are better when my wife can come too!

Airline:

Portland, ME. We stayed at the Hilton Garden right by the airport, but the hotel had free tickets downtown. Great bier and lobstah right on the watah. Plus homemade ice cream a block away.

Savannah, GA. Stayed at the Day Inn right downtown a block from River Street. Great night life and plenty to do/eat. The only bad part was the drunken crawl back up the stairs from River Street to the hotel!

Burlington, VT. Stayed near downtown at the Sheraton. Downtown is great. Lots to do both summer and winter and some great pubs/restaurants. Ri'ra (Irish) was one of my favorites (even though it is a chain). Plus it was one of the only overnights where you could get decent food until 4am.