On Siesta Key proper, there are a wide range of eating options, although most places lean toward the open air funky beach style joint. A short drive over the Stickney Point Road bridge into Sarasota offers everything from fast food to fine dining. I'm not ashamed to admit that one of the favorites was for dad to get into the rental car and make a Wendy's run and bring it back to the pool at the condo.
Here's a rundown of places we enjoyed:
Daiquiri Deck (5250 Ocean Blvd, Siesta Key) -- As the name implies, they feature about every flavor of daiquiri you can think of and they are quite good and reasonably priced. The outdoor deck is on the main drag in Siesta Key and is pretty good location to do a little people watching, sip a watermelon frozen daiquiri, and munch on some fried clams. They'll make virgin versions of the daiquiris for the kids.
Phillipi Creek Oyster Village (5353 S Tamiami Trail, Sarasota) -- Just a short drive away, this creekside restaurant has both indoor and outdoor casual dining and pretty good seafood. We even tried some gator. No, it doesn't taste like chicken - it tastes like gator! Look for the giant great white shark in the parking lot. They claim it came out of the creek but I think that's just to scare the kids so they'll be careful out on the dock!
Turtles on Little Sarasota Bay (8875 Midnight Pass Rd, Siesta Key) -- Located on the south end of Siesta Key, this dressy casual restaurant features seafood and great views out on the deck. The night we went it was very crowded and the only spot on the deck was next to some smokers, so we were forced to dine inside. The fresh grouper was excellent.
Sam Seltzer's Steakhouse (7113 S Tamiami Trail, Sarasota)
-- Within a short distance from each other are Outback, Ruth Chris, and Sam Seltzer's Steakhouses. Every time we drove by, Sam Seltzer's was packed so we decided to check it out. After a long wait (outside on a comfortable porch with ESPN on the TV!), we sat down to a traditional steakhouse meal that was excellent and reasonably priced. Portions were huge - we dined on prime rib sandwiches for another two days!
Shells Seafood Restaurant (7253 S Tamiami Trail, Sarasota) -- This local chain was also packed every night and provides great seafood at reasonable prices in a casual, kid friendly atmosphere. Good chowder, conch fritters, "u peel 'em" shrimp, calamari, and fresh fish which they'll prepare grilled, blackenend, or fried in either six or ten ounce portions.
Coasters at the Southbridge (1500 Stickney Point Rd, Siesta Key) -- Nice location on the water with casual outdoor dining. As we finished our meal, it started to sprinkle. We made it inside just as the downpour hit - I felt sorry for those who were still eating and not as lucky. There are some nice shops adjacent to the restaurant for browsing and walking off your dinner (or for refuge from the rain!).
Olive Garden (4900 S Tamiami Trail, Sarasota) -- I'm not a big fan of Olive Garden, but this one in a typical strip mall location was pretty good.
Carraba's Italian Grill (1940 Stickney Point Rd, Sarasota) -- Just over the bridge from Siesta Key, this is where we really wanted to go for Italian food but it was always so popular and crowded, we wound up at Olive Garden instead.