Cindala
Here is the link to the online HH dining guide. There are just so many choices for dining options. There are many price points. We have a new places to try list every year.
It is hard to find places on the tiny island at first due to sign restrictions and low lighting and lush foliage. Many places are tucked in little plazas. Best to drive around in the daytime to get your bearings.
You did not say if you prefer casual dining to white tablecloth dining. There are early bird specialsbetween 5-6 for a 3-4 course meal about $15pp at nice places.
CQ's is right next to Harbortown. White Linen tablecloths, stellar service,small portions.
We prefer Stack's for breakfast. In the past we have tried HH Diner or Skillets
Redfish,Frankie Bones( feels like Sinatra will walk in), Aunt Chiladas,Truffles ,Wild Wings,for lunch.
http://www.frankiebonesrestaurant.com
Bonefish opens after 4pm as does Carrabbas.
Like HH Diner ,Stacks has a large menu.
Love Stickey Fingers and it's a must do for us. If you sign up for the club online you will get promo emails and a coupon for a free appetizer or dessert. Use HHI as your local restaurant. http://www.stickyfingersonline.com/...isleinfo.com/favorite_places_&_activities.htm
http://www.hhidining.com
Like everyone has said I would do a dining cruise in a major city. A nice 3hr non dining cruise is on the Schooner Welcome. You can bring white wine aboard and they serve fruit and cheese.
http://www.schooner.net