I typed my previous reply on my phone....and I'm still all thumbs -- literally -- with that.
But I wanted to tell you that you can tailor your Anna Maria Island vacation to your own desires -- ultra casual, smart casual or smart cocktail. At home, we rarely go ultra casual, yet that's what fits our vacation lifestyle. We're in our early 40s and we surprised ourselves with that...and my recommendations are for that type of vacation...which may not be your style.
First, realize that the distance between Holmes and much of Anna Maria is a nice evening stroll...so you have many possibilities (you can also rent bikes for about $40 a week (free delivery and pickup). Additionally, Sarasota (St. Armand's Circle and downtown) is a hop-skip, with lots of waterfront options on the drive in between. Note that there's a Whole Foods in Sarasota, too, so you can fill up your condo with good eats.
Star Fish Company (in Cortez) can be crazy crowded at lunch and dinner (depending on time of year and day), so be prepared to wait. It's not a chore if you expect it going in because there's so much to see. It's all outside dining and there's a tiny bar there to keep you from getting thirsty. It's in a working fishing village and sits among the boats... Note that mosquitos can be hungry at dusk, so you may want to take some repellant in the evenings. Dolphins, birds, customer dogs and Star Fish cats (some with one leg or one eye, but all healthy) are often around. All seem well-behaved, except for the birds -- which can be both bold and stubborn.
The two piers -- Rod and Reel and City -- have distinct personalities. You'll have to see which you like best, but try both. Rod and Reel always has a great sandwich special and we think they do that fish better than their much more expensive neighboring restaurants, both on the island and on the way to Sarasota. Never had a dry piece of fish at Rod and Reel. Paid twice as much for fish and other places in the area and it wasn't as good. That said, Rod and Reel tries to go more upscale (not in what customers wear, but it what they're served) with sauces and other options at night. Pass. Why mess with grilled or blackened perfection? Maybe if you live in Florida, you get bored with the local fresh catch. But when you spend most of your life faced with tilapia (yuk), salmon and fresh-water fish, these gulf fish (and pink shrimp and stone crab) are heaven. Whichever pier you choose, it's hard to beat sipping a beer, watching the sun set...and seeing all the crazy shark, ray and other sea creastures the fishermen are pulling out of the water around you.
The first two times we visited the island, we drove past Duffy's and couldn't see what all the fuss was about. Then, on a rainy day in November, we went inside. I could go years without eating a burger and wouldn't care. (not so for my burger-loving husband). We each got the burger with havarti and jalapenos. In one bite, it was clear how burgers became iconic. So much flavor, and not just from the toppings. Also, it's inexpensive. For a chuckle, look at the menu of another great spot in Holmes -- Eat Here (try the tacos -- yum). Under the burger option on Eat Here's menu, it says something like....turn right and go to Duffy's. That was smart. I've never made it past the burger at Duffy's, but Duffy's has things I haven't ever seen on a menu beyond Greater Cleveland -- braunschweger (sp) sandwiches and navy bean soup.
If you ever get tired of the sun or heat, head for Bortell's in Anna Maria. It's like walking into a friend's huge basement. It's cool and dark and full of pool tables. Many of the younger people working on the island gather here in the evenings.
The liquor store next to Hurricane Hank's (a restaurant/bar owned by the same guy who owns liquor store) in Holmes is small, but well-supllied. It's open Sundays, too. Never ate at Hurricane Hank's but they keep Foster's very, very cold on tap. I think the same people own Martiniville across the street. Nice selection, but steep ($12 and $14) compared with most of the island (not compared to Chicago, though). The main point is -- you can do several bar crawls without hitting the same place twice.