15 Year anniversary trip to Kiawah Island. My wife and I aren't real exciting, looking mostly for tour (plantations?) and restuarant favorites in either location.

Don't know how much time you have, but how about a couple of days in each? You could do a couple of nights in Charleston at a B&B and tour the city and a plantation or 2 (highly recommend Middleton Place or Drayton Hall) then you could relax in Kiawah. Kiawah is only about 30 minutes from Charleston so you could just make that your base and drive in a couple of days. The restaurants on Kiawah are not so hot but you can find great dining in Charleston. I don't think you can go wrong either way - that area is one my favorite destinations.

I would highly recommend Charleston over Kiawah. Kiawah is rather dull and although it is nice, you can get teh same atmosphere at any beach resort. Try Charleston for fabulous B&B's, restaurants, shopping, breathtaking views and wonderful history & culture.

Depends on what you are looking for. Charleston is easy to get to from Kiawah if you prefer the laid back, beach scene. If you want the city, restaurants, etc. then stay in town. The plantations are easy to reach from either. For restaurants (in town) I would recommend 82 Queen, Peninsula Grill (in the Planters Inn which I would also recommend) or Carolina's. I would steer clear of Magnolia's. Besides the Planters I would also recommend the Vendue Inn & 2 Meeting street although The Planters does have the best location.

We stayed at the Vendue Inn and Charleston last weekend, we paid $169 and had a FABULOUS room, we had a fire place, marble jacuzzi, and shower and a beautiful room, great location. Also we ate at Tristan which is new on Market and featured in the latest Wine Spectator, it was great but still my favorite is the Peninsula Grill and also Charleston grill, worth the money.

do both! why not. they are both different and have there own things to offer. you need to decide if you want the old city and restaurants tours (charleston) or the more laid back (if possible) beachy Kiawah...try them both.

As far as great eating places are concerned a must for seafood is Hymans in Charleston. Fantastic food but the wait can be long. I visited a few years ago with a friend and loved the whole area.