We went in April, at the end of the "low season", before the prices went up quite a bit. We flew out Thursday morning, got our rental car and drove to Dormie Club. Played there Thursday afternoon, then went to our hotel, a 2 BR suite at Residence Inn in Southern Pines, NC. Friday, we played 36 holes. Mid South in the morning, Legacy in the afternoon. Saturday, another 36 hole day. Mid Pines in the morning, Pine Needles in the afternoon. Sunday morning, we packed up, checked out of the hotel and drove to Tobacco Road. After playing there in the morning, we cleaned up and drove to the airport.
Weather note. If you go in April, be prepared for rain. We had rain during all but one round we played, but it only lasted more than a few minutes once. Most times, I didn't even get my umbrella out. Bring a good rain jacket and some rain gloves and you'll be fine.
If memory serves, our package through Tobacco Road Travel cost around $1600/pp. That included the three nights at the hotel and our six rounds of golf. Flight from DFW was around $300, IIRC.
My ranking of the courses is below, based on my memory.
1. Mid Pines -- I loved this place. Pine Needles is right across the street and gets more love, but I enjoyed Mid Pines more. I've never been to the Masters, but if you parachuted me onto this golf course blindfolded, uncovered my eyes and told me it was Augusta, I wouldn't immediately call you a liar.
2. Tobacco Road -- A really unique course. It could be really fun, or really miserable, depending on how you're playing. This was my best scoring round of the trip, so that's probably part of why I loved it.
3. Pine Needles -- When we played there, they were getting ready for the US Senior Women's Open (yes, they have that) a couple of weeks later. So it was set up for a USGA championship....made it play really tough.
4. Mid South -- Another nice NC sandhills golf course, similar to Mid Pines/Pine Needles, just not quite as great.
5. Dormie Club -- Dormie was the most "country" golf course of all that we played. Cool course, good conditions. No frills.
6. Legacy -- Another great course, just not as memorable as the others for me.