Be sure to make it to Hudson's and walk around back to the seating on the dock, you can sit at the bar or ask for one of the tables further by the water. You can grab lunch or an appy there, then head over to Skull Creek Dockside (Boathouse has turned into a tourist trap with huge wait times) for happy hour/dinner, and if you have little ones there are plenty of jungle gym sets and games to be played in a space shared by both restaurants (again recommend sitting outside) If you're there over a Sunday, I highly recommend going to Hudson's for brunch, the biscuits and gravy are fantastic.
Also a Happy Hour/dinner staple whenever I go is the Hurricane Bar at Black Marlin. Fun little standalone bar that has a lot of live music, and you can order from the Black Marlin menu where the shrimp and grits are out of this world.
If you're looking for an easy spot to get in and out of for a bite, Poseidon is a hot spot that is more modern than the other places mentioned, with a few boutique shops around.
For a romantic night out, I'd recommend Charlie's L'Etoile Verte. It's a nice, quaint spot that is frequented by locals and vacation homeowners, not many tourists. Hand selected (and drawn) menu every day, fabulous wine list, and what looks like a cozy little bar for pre-dinner drinks or a nightcap. With the pandemic, they added a ton of outdoor seating that actually seemed preferable to the indoor seating. Be warned, though, the place is rather small and cramped, so bringing kids or dealing with the kids of others can be a hassle.
And finally, if you want a tried and true tourist experience and are in need of a good steak: Frankie Bones (the one on the island, not Bluffton).
If you're playing golf, I cannot recommend Hilton Head National enough. It's actually off the island in Bluffton, but it is a championship-quality course that has the length of a muni-track and can be had for half of what the Robert Trent Jones or Fazio courses will run you. If you want the feeling of tracing a course through the island and catching glimpses of the ocean without spending to go to those private clubs, either Robbers Row or the Barony Course at Port Royal should be pretty nice this time of year.
EDIT: I forgot about Shelter Cove. That's a cool place to park and walk up and down the harbor, with plenty of restaurants to suit your tastes, but if you're looking for Mexican I recommend San Miguel's. You can get a great view of the cove and their margaritas are top-notch. Other than that, Scott's Fish Market or Bistro 17 probably have more scenic views.
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