Here's a couple of quick tips -

Is Fort Sumter already on your itinerary? If not, you can kill two birds with one stone - Charleston harbor ride and historic site.

I haven't seen this tip mentioned but it was a fun day trip for us while we were based in Charleston. Especially nice if you are golf fans. You can take a ride out to Kiawah Island from Charleston and eat at the ocean course club house. The island is private and gated but we made reservations and didn't have any trouble. The Ryder Cup bar in the club house is very posh and sits right on the beach. We went for lunch so it was a little less expensive and we could enjoy the view in the daylight.

I would spend beach time at HH and while in Charleston, do Magnolia Manor (and there's a more authentic but smaller historic house nearby I don't recall the name, but easy to also see on the same day) and see Fort Sumter and walk downtown. Lots of places to eat and people watch. There's not much to actually do in HH, it's just all low key nice. But the lighthouse is fun and it's a great place to bike ride.
There's always the aquarium in Charleston too, I love those anywhere.

Good advice above. We stay at the French Quarter Inn. They have bikes and we bike everywhere. I was there as recently as last April for my DD 30th birthday. I like to look at trip advisor for restaurant reservations and it never lets me down. Hotels as well. I have been to Charleston at least 8 times. But, it's only 3 hours up the road. check out places to stay on the beach. I always wanted to do that but can never seem to find a room. There is a cool bar on the roof top of the Venue Inn. Sunset is a good time. Go to the largest plantation. Can't remember what it is but google it and remember it will take most of the day. They are a bit out outside town. If you have time head to Edisto Island and check out Botany Bay. Hilton head is great if you golf or play tennis. I haven't been to Savannah or HH in years. Enjoy your time in the south!

Is there something specific that you want to see in Savannah? If not, I think you will feel that you drove for two hours to see a less polished version of Charleston.

Since you are coming from Kansas I think you would enjoy more than a day in HH especially if a near ocean or ocean front hotel in your budget. The bike trails, the moss draped oaks, Harbour Town, dolphin tours, etc. I would skip Savannah and add that day to HH.

This post was edited by deee on Mon, Oct 14, 13 at 9:13

A recent issue of Martha Stewart Living noted these places in Charleston to visit/see/dine at. I was in Charleston many years ago, and it was a working trip, so I didn't see a lot more than the office building and 2 restaurants, so I can't vouch for whether these spots are truly not-misses, but our Charleston/Savannah friends might! (Granted, these all might have been "product placement" results through the Chamber of Commerce!)

Restaurants in Charleston:
These for breakfast/lunch:
Wild Flour Pastry
Hominy Grill
Black Tap Coffee
Martha Lou's Kitchen
Xia Bao Biscuit (in a revamped gas station!)
Two Boroughs Larder
Bertha's Kitchen for soul food, fried whitefish
Holy City Brewing

Dinner/drinks:
Husk
Bowens Island Restaurant (10-mile taxi ride from downtown, article says)
The Ordinary/FIG

Exploring:
Planter's Inn
Charleston Farmers Market
Angel Oak Park
Boutiques/galleries along King Street.

You will be able to do all that you listed in Charleston. There are several nearby islands where you can enjoy the beach. Folly, Isle of Palms, Kiawah and Seabrook. We usually stay on Seabrook. Visit the area of Shem Creek on Mt. Pleasant for fresh seafood and seating where you can enjoy the view of the fishing boats coming in. Ft. Sumnter and Ft. Moultrie are nearby. Patriots Point has aircraft carriers, etc.

If I were you - I might not go the added distance of Savannah. It is a nice city and we enjoy going there but if I had limited time, we prefer to spend our time in Charleston. However, if you go to Savannah, it is a nice drive up the coast to Charleston. Also, there is an island - Harbour Island - which is kind of between the two. We have stayed there and made day trips to both locations (within 2 hours to either city). Seabrook, Kiawah and Harbour Islands are much less populated and very lush with foliage and animals (deer, etc.). Fripp Island is another that is very nice. Not your typical beach (which is what we like - we are definitely not Myrtle Beach visitors).

Hilton Head is a nice beach area, lots of restaurants, shopping (does not appeal to me but might to you), GOLF, etc. Lovely area.

One nice thing about these islands is they do not have the high-rises, etc. of some of the more typical SE touristy beaches (such as myrtle). HH even has a limit on how high signs/billboards can be. Love that. We seek the less populated areas to stay - then drive into Charleston.

tina

Naturally, I'm biased towards Hilton Head because I have a place here and have been vacationing here for 20+ years. I don't golf or play tennis, I keep busy with beach time, walking, bike riding, and replying to GW threads. There's also a zip line place, parasailing, dolphin boat tours, and other beachy things so there's plenty to do here.

Even though I highly recommend HHI, I think there are other islands or beach places close by Charleston that would be just as nice and entertaining as HHI. I hear nice things about Kiawah. My impression is tinam61 has visited many of the islands around here and might chime in with advice.

ETA:
Tinam61 was posting at the same time so you did get some advice from her! How funny.

This post was edited by hhireno on Mon, Oct 14, 13 at 11:10

I've never been to Savannah, so I can't speak to that, but we love both Hilton Head and the Charleston area. If you are going to HH for just the beach, you might consider something closer and stay in Charleston the entire time.
Sullivan's Island and Isle of Palms are both maybe 20 minutes from downtown and are lovely areas. Sullivan's is mostly a residential area, but there are a few easy places for lunch - Poe's is casual burger joint. You could easily get to the beach for a nice walk from either place.
We usually stay on Isle of Palms and drive into Charleston, but this time of the year you could do it either way.
We also drove to Kiawah and ate lunch at the Sanctuary. Beautiful hotel, walked down to the beach, nice shops. Kiawah is lovely.
There's a great seafood restaurant in Shem Creek called the Wreck - total dive, but awesome seafood.
It's such a great area - you will have a fabulous time!

Oh HH - you make me laugh. You know me too well (I probably go on and on AND ON about the area LOL). I didn't think about the parasailing, etc. on HH. I think it's a nice place to relax and enjoy the climate! Now I must know, do you zipline????

tina

Yes, I did the zip line last October and really enjoyed it. I would do it again if I had visitors that wanted to do it. I've never done the parasailing but my BFF and her kids do it when they are here in the summer.

I'm not a shopper so today I watched the kids while some of the others went to the outlets just off the island. I didn't even think to mention the outlets in my earlier post so that's an option if Jennifer in Kansas likes to shop.

Two friends went kayaking last week so that's another activity idea.

Deee- I like the idea of combining both the harbor ride and Ft. Sumter. I’ll have to see if the one I was looking at stops by the fort. Golf is not in my blood but DH plays charity tournaments (after which he inevitably says he’s so terrible he’ll never play again but does). I did take a peek at the Ryder Cup bar and it looks amazing. I agree the lunch menu is reasonable and the more I hear about Kiawah Island the more I think it’ll be added to our itinerary. Savannah is only on my list because I thought it was a must-see city. I’ll be in Statesboro for a wedding and figured I would stop by on my way to Charleston or HHI. Between your comment and Tina’s I think I might skip it.

Bumble - A couple of “low key” days are exactly what we’re looking for on this trip. As for the plantations, I can only imagine my husband will be patient enough for one. I’ve seen Magnolia Manor recommended, as well as Middleton. I guess I’ll have to investigate just how long the tours are because I don’t want to spend an entire day there. I certainly won’t visit Drayton Hall - I heard it’s not decorated. Isn’t that part of the fun?

April101 - Wow, the French Quarter Inn looks luxurious. I bet your DD had a great birthday there. I would love to stay there but unfortunately it’s out of my price range. And, yes, I agree that TripAdvisor has been a great resource. I don’t know how I ever traveled without it. And thanks for the Venue Inn tip. For some reason it’s just fun to eat or drink at a rooftop restaurant.

Pammyfay - Thanks for such a great list! I’ve heard of the Hominy Grill and had planned to stop by there. I expect to enjoy my food and not worry about calories but I still don’t think I could order from a place called the Larder. oh, oops, I just realized a larder is a cellar! I was thinking of lard. I’ve saved this list as my grumbling tummy reference.

Tina, I’m so glad you popped in. When I searched GW for Charleston advice you seemed to be the resident expert. Thanks for the tip about Shem Creek. We’ll be eating our share of fresh seafood so it’s nice to go to a reputable area. Last time I was in FL, one of the seafood restaurants I went to was admittedly serving frozen or flown in seafood. Ft. Moultrie and Patriots Point? Now I have too many choices - I think I’ll let DH decide on this one but I suspect my ex-squid will pick Patriots Point. It looks like Harbor Island is near Beaufort, which was a recommended stop for us. I’ll have to check it out and see if that’s more up our alley vs HHI because neither of us are that into golf and I wonder if hotel prices are higher due to that amenity.

Hhireno - Oh, true Outlets?! So tempting. I like to shop but I’ve already blown my budget on this trip. That may not stop me, though. I like to purchase a sweatshirt when I’m in a beachy location. I don it whenever it starts to snow here in KS. Hmm, so you highly recommend HHI? Where to go on the GA/SC coast has turned out more complicated than I thought. It all sounds great. Thanks for the feedback on your lovely island.

Legomom - Sounds like you’ve put in the 2nd vote for staying on one of the islands and driving into Charleston. I must admit it’s nice to wake up to the ocean vs. city life. It wouldn’t bother me a bit to have my morning coffee ocean side and drive into Charleston later. And some of my favorite places have been dives so the Wreck sounds like fun to me.

Thanks so much to everyone.

Now I need to find a good book,
Jennifer

Jennifer,

Thanks for posting, and let us know how your trip goes... I don't go until next spring.

As for a book, try Goodreads. I find great suggestions there.

Just returned from 2 days in Charleston (attended a wedding) & 4 days in Kiawah. We were busy with wedding activities while in Charleston but spent a little time in town. Great restaurants & a fun town to walk around.
The beach at Kiawah is lovely. We had lunch at the Jasmine Porch in the Sanctuary. The "Porch Lunch" is excellent & the "Shrimp & Grits" are yummy! Bring your suits & rent two beach chairs, towels & an umbrella for $35 for the day. You can also rent a bike & ride on the beach or around the island. We didn't have any problem renting beach chairs etc., even though we were not staying at the hotel. During the day, the alligators hang out at the Osprey Clubhouse (one of the 5 golf course clubhouses).
Craving shrimp & grits right now.

I live down here! Plenty to do in Charleston and Savannah, I would skip Hilton Head. So many great restaurants and places to visit. Walk River Street in Savannah and downtown Charleston. Kiawah is the nicest beach area, unless you have time to continue south to Jekyll Island.