HOLMES BEACH — It’s been a long time since we included Anna Maria Island in our staycation series—14 years, to be exact. Much has changed since then, and most island rats will tell you that the changes haven’t been for the better. That’s probably true, although I’m happy to report that after spending the long Labor Day weekend on Manatee County’s crown jewel destination, it still holds enough of its quaint charm to rival any beach community in Florida.
The one thing I immediately noticed was how few Floridians I ran into. While my previous extended stay was filled mostly with interactions with couples and families from other parts of the state, this trip was notable in that nearly everyone I interacted with was from several states away. Judging by the litany of languages we could hear around us, the international traffic had picked up quite a bit as well.
This seems to be by design. While the Bradenton Area Convention and Visitor Bureau was thrilled to assist us last time out, this time, TBT was told, “We will have to pass on this opportunity as we aim to promote outside of Manatee County to attract in visitors.”
This seemed odd for two reasons. First, we have had a massive influx of out-of-state transplants who relocated to the fast-developing rural hamlets of eastern Manatee over the past few years, all of whom would be ideal candidates for an inaugural staycation. Second, given what all of that development has done in terms of traffic gridlock and its discouraging effects on local beach travel, promoting the fact that you can still drive here from most spots in the county in less time than flying to other destinations, might be a way to help frustrated Manatee County taxpayers consider a new dynamic in terms of our local beaches, especially since skipping the airfare will work to offset the relatively high cost of island vacation rentals.
So, in the spirit of promoting the idea of taking a full-on vacation right in your beautiful paradise of a backyard, we here at TBT pushed forward on our own and got it done.
As most of you know, the island consists of three cities, each with its own distinct flavor. We stayed in Holmes Beach, which is in the middle of the island, both in terms of geography and tempo. Home to the Manatee County’s public beach concession, where you can still get all-you-can-eat pancakes seven days a week (M-F 8-11:00 a.m., S/S 8:00 a.m. to noon) along with a full menu of surprisingly good grub, Holmes Beach also offers some of the best fine dining on the island.
Local treasure Sean Murphy of Beach Bistro fame has expanded his high-end libation laboratory, The Doctor’s Office, into a first-rate bistro. The term “craft cocktail” has become so ubiquitous that it has lost most of its meaning. Suffice it to say, however, that the bar side of the doctor’s practice will impress even the most snobbish of cocktail aficionados.
The Painkiller (Dark Rum, Fresh Pineapple, Fresh Orange, Coconut Milk, Fresh Lime, Grated Nutmeg), the Nightingale (Chamomile-Infused Reposado Tequila, Fresh Lemon, Lavender), and Kiss Kiss Bang Bang (Gin, Muddled Blackberries, Fresh Lemon, St. Germain Elderflower Liquor) are my personal favorites, along with Murphy's take on the Mai Tai. The impressively stocked bar features a well-curated collection of high-end spirits that will prove especially appealing to lovers of rum, bourbon, gin, and rye whiskey.
The addition of the Doctor's Garden (a delightful outdoor space that is also available for weddings and special events) has seen the menu expand considerably since my last visit. Still, my favorite item remains the Big Beef Sammitch—chopped port-braised beef and cabbage on an impossibly fresh brioche roll with port gravy and horseradish cream. This is one of those local delicacies so good that it makes it hard to move around the menu on return visits.
You'll also find a fresh grouper sandwich on par with anything in the region, which is also served on that heavenly brioche roll. Lighter fare includes world-class smoked salmon as well as the Lobstercargots (chunks of Novey lobster baked in a crock with garlic butter) that Bistro regulars would often find themselves munching in their most savory of dreams. Fuller fare like the Doctor's Seafood Stew, Anna Marribbean Grouper (coconut and cashew encrusted Gulf Grouper prettied with red pepper papaya jam and chef's mashed potatoes), or the shrimp and grits are every bit as scrumptious as one would imagine items on a Murphy menu to be.
A new find on this trip was the Chateau Anna Maria. Housed within the Waterline Marina, this romantic little enclave started in upstate New York and now has outposts on Holmes Beach and Siesta Key.
The starter menu's all-stars included baked brie en croute (the perfect accompaniment to their excellent wine list) and grilled little neck clams. The arugula roast beet salad and French onion soup au gratin are standouts among the broths and greens, while duck confit fettucini and the chicken Francese (chicken breast scaloppini, aged parmesan basil egg crust, roasted fingerling potatoes, and house vegetable) wowed us among the main dishes.
If you’re looking for a casual lunch with rustic open-air Key West vibes, be sure to stop by the legendary Skinny’s Place, a hamburger shack directly across from the public beach. There are few burgers like Skinny’s, and if you’re feeling gluttonous after a hot day on the sand, give their Mid-Island Pounder a go while washing it down with an ice-cold Yuengling. Holmes Beach has plenty of other good places to throw down a cold one, many of which have live music (the Ugly Grouper, the Freckled Fin, Decoy Ducks). That said, my hands-down favorite will always be the Anchor Inn, a proper dive bar that serves up ice-cold beers at rock-bottom beach prices.
The City of Anna Maria is the sleepiest and most family-oriented of the three cities. Enjoy the serene beauty of Bean Point, and the bayside beach is an excellent spot for kids to explore sea creatures while digging in the surf. Pine Avenue offers a treasure trove of shops, restaurants, and boutiques.
No trip to the island is complete without a meal at the historic Rod & Reel Pier, and the Waterfront Restaurant & Craft Bar can hold its own with any fine dining experience in the area. Grab some coffee, breakfast/brunch from Ginny’s & Jane E’s, or splurge decadently at the Donut Experiment. Grab lunch at the original Poppo’s Taqueria, where the tortillas are made as you order, and get some ice cream at Two Scoops, across from the City Pier.
Another new find on this trip was also French, the more casual but equally delectable Mademoiselle Paris. When I last visited for our Staycation series, I reviewed a casual breakfast spot in this location that had just been taken over by a French couple who had already reimagined it into something much more. The current owners are also French and have been even more ambitious, filling out a full menu with your favorite French Standards. The restaurant currently offers a full three-course prix fixe special for just $36.90 (two courses are $29.90). I went with Escargot, Beef Burgundy, and crepes Suzette and left a very happy (and full) man.
Anna Maria is not without its own rustic beach bars, including Slim’s Place and Bortell’s Lounge, two longtime favorites of locals. Unfortunately, time did not allow us to grab a meal at the Porch, which I've heard very good things about.
Once an outlaw outpost where rowdy sailors would wet their whistles whenever they came ashore, Bradenton Beach is a little more Disney and much less Duval these days. However, it still holds a tiny bit of that rustic charm, especially at the far end of historic Bridge Street. The Bridgetender offers authentic Florida favorites in a beach casual setting. They don’t take reservations, but you can order from the bar next door or the outside tiki, both of which make good spots to wait for a dining room table if you're so inclined.
Across the street, you’ll find two beachy dive bars that serve as a testament to the Bridge Street of old. It’s hard to score a seat at the cozy Drift Inn, especially if a musician is playing, but try your luck at their outside tiki bar. If you strike out there, move one door down to the Sports Lounge, a well-air-conditioned throwback bar with more seating, ice-cold beer at great prices, and cheerful bartenders that make it even easier to duck the sun while you drain a few cold ones.
Families will enjoy the wide open spaces on Coquina Beach, and nighttime can be spent mini-golfing at the Fish Hole. Swing by the Fudge Factory for some sweets, or grab some outstanding ice cream at Island Scoops.
Several hidden gems are among the fine dining options, including Blue Marlin Seafood, Island Creperie, and Bridge Street Bistro. Unfortunately, scheduling did not allow for the opportunity to get to SALT Bar & Table. However, I’ve heard excellent things about this newer addition to the Bradenton Beach dining scene and am looking forward to trying it soon. For casual fare, check out Oma’s Pizza & Italian (the best pie on the island) and Smoqehouse for an original take on BBQ sandwiches.
Dennis "Mitch" Maley is a novelist, as well as an editor and opinion columnist for The Bradenton Times. In addition to his regular Sunday column, he hosts our weekly podcast and does occasional theater, restaurant, and wine reviews. He is a graduate of Shippensburg University and later served as a Captain in the U.S. Army. Click here for his bio. His novels and short story collection are available here.
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