Thoughts on Savannah/Tybee Island/Charleston

Charleston is in my top 10 favorite vacation destinations in the US. Lots to do, great ambiance and many excellent restaurants there. Savannah is also nice, like a scaled down version of Charleston. Don't know about the airports; we have always driven. Never been to Tybee Island.

Charleston is the only answer. One of the best cities in the country.

As mentioned in this thread you need a good two days in Savannah. Great History, Beautiful architectural homes, and some great food. My suggestion take one of the trolley tours when your first arrive. Savannah is basically a big grid and the historic squares are the things you want to visit if you like history. We usually stay in a bed and breakfast near one of the squares and just walk around to take it all in. I didn't get specific with places or things to do but just pull up a few youtube videos on what to visit or see in Savannah and you can narrow it down.

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Which is better: fly into Savannah, fly out of Charleston--or vice versa?

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Unless you are wantonly burning cash, fly in and out of one. Rent and return the car at the same. One-way rentals are expensive as are two one-way flights. Or see below:

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Fly in to Greenville is better,

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Or CAE Columbia. You can save some real cash this way. Just be wise as the freeway from Columbia to Charleston is a real speed trap some days.

If you want to visit SAV and CHS, having Columbia as your fly in-out will be a great recommendation.

You can use the search feature to look for past post about Savannah and Charleston. Or, for better results, use google and type Savannah (or Charleston) + Tiger Droppings to find post. Here's one from January 2021 about Savannah.

Tiger droppings Savannah post Jan 2021

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Which is better: fly into Savannah, fly out of Charleston--or vice versa?

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I've never flow into either one but they are only about 2 hours apart. I would think wherever you could get the best deal.

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We like exploring, historical stuff, good restaurants/shopping, relaxing, beaching, etc. Should we add Hilton Head into the mix?

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There are a lot of historical sights and restaurants in both cities. Some of the past TD post will mention them.

Don't take the interstate between the two cities; go through Beaufort, and Bluffton if you want to check out HH. The interstate is faster but not as interesting. You could also detour to Edisto; not a lot there but beach houses and a state park.
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Hilton Head covers a large area, too big to walk everywhere, but there are bike paths in some parts that you might like. It cost $9/vehicle to get into the Sea Pines resort area. Don't know if you have to pay that if you're staying there.