Anna Maria Island Is a Mother-Daughter Getaway With Old Florida Charm

Come for charming boutiques, mom-and-pop eateries, and a hefty dose of Southern hospitality.

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Anna Maria Island, FL
Photo: Melanie Wynarski / EyeEm / Getty

After a hectic few months, you might want to slow down and unplug with a short getaway—and do it with mom at your side. Our choice to downshift for a few days? Florida's Anna Maria Island is a little slice of Gulf Coast heaven that makes the perfect backdrop for a laid-back, mother-daughter vacation. We packed up the car and set out on our drive from Orlando with the lure of a quiet, coastal weekend leading the way.

The seven-mile stretch of island encompasses three quaint towns: Anna Maria in the north, Bradenton Beach in the south, and Holmes Beach in the middle. We didn't find chain stores, fast-food restaurants, or high-rise hotels. Instead, we enjoyed charming boutiques, mom-and-pop eateries, and lots of local flavors that gave us a taste of old Florida hospitality.

This coastal gem maintains a chill atmosphere. Speed limits top out at 35 mph, flip-flops grace bare feet, and there's a taboo on high-rise buildings and commercialization. Perhaps one of the greatest draws for weary road trippers? The entire island is accessible by the free trolley that runs daily.

How To Get There

Flying into this seaside community is easy. Tampa International Airport is about an hour's drive, while Sarasota-Bradenton International Airport is just 30 minutes away. If you're planning to hit the road and drive south, at least a few miles on I-75 is likely in your future. The highway from Atlanta will drop you almost directly next to Anna Maria Island. Just pack lots of car snacks.

Where To Stay

While plenty of beachfront cottage rentals and small hotels dot the island, we opted for a luxurious stay at the Waterline Villas & Marina in Holmes Beach. The Two Bedroom Villa-Condo units feature a full kitchen and a large, comfy living room. The little touches went a long way. The boat-shaped kitchen table, the glossy wooden staircase wrapped to the first floor, and the turquoise umbrella resting in our suite foyer were friendly reminders that we were officially on island time.

The resort offers plenty of amenities to keep you entertained for those looking to stay close to home. Complimentary bicycles for island cruising, sunset yoga sessions overlooking the marina, local-artist-led watercolor classes, a resort-style pool, and an onsite restaurant make a case for never leaving the property. One morning we found ourselves doing just that as we sat on our porch overlooking the bustling marina, watching charter boats for family fishing trips and eco-tours gear up for the day.

Anna Maria Island, Florida
Tim Graham. Tim Graham / Getty Images

What To Do

Of course, the desire to sit still didn't last long. Our adventures took us to pristine Holmes Beach, where we strolled along the soft, powdery-white sand and watched the sun sink into the Gulf of Mexico. We explored Anna Maria Bayfront Park, which offers stunning views of Tampa Bay and the iconic Sunshine Skyway Bridge. We strolled along historic Pine Avenue, popping into working artist studios like Emerson Quillin's shop, whose whimsical brand of humor hit the mark for us. We tasted grapefruit-spiked oil in Anna Maria Olive Oil Outpost, which beckoned us with flavored oils and freshly baked bread samples. And we explored the town's colorful, creative past at the free Anna Maria Island Historical Society Museum, including hand-woven baskets crafted from palmetto fronds.

In the Historic Bridge Street area (a bustling enclave of boutiques, shops, and restaurants), my mom and I boarded a 90-minute tour courtesy of Paradise Boat Tours. Captain Mike and his first mate Erin charmed the boat's half-dozen passengers with wildlife trivia and local history as we navigated through the Intracoastal Waterways spotting dolphins and egrets along the way. Another highlight was visiting The Bishop Museum of Science and Nature for an up-close look at its handful of rescued manatees that will soon be released back into the wild. This well-maintained museum, located in downtown Bradenton, features two floors of exhibits dipping into South Florida's past, plus an impressive planetarium.

Where To Eat

Plenty of local eateries drew us in with their small-town feel and home-cooked fare. For a local experience, we headed to Ginny's & Jane E's, an island staple with an eclectic mix containing a cafe, bakery, and store. Here, you can grab a giant cinnamon roll (get there early—they sell out quick), borrow a book to read from the cafe library, or peruse the colorful gift shop.

Lunchtime took us to the waterfront dining at Anna Maria Oyster Bar on the Historic Bridge Street Pier. We munched on heavenly coconut shrimp, tuna poke stack, and calamari as we watched the boats bobbing in the water.

One night, we ordered melt-in-your-mouth eggplant and chicken parmigiana dinners to go from Vinny's Italian Kitchen so we could eat in our resort's nautical-inspired kitchen. For an upscale experience, dine at the Waterline Resort's restaurant, Chateau Anna Maria, for fresh ingredients, seafood, and prime cuts.

For our final just-us-girls meal before our drive back to Orlando, we lunched at the elegant Pier 22, the go-to place for weekday power lunches. Walking past the full sushi bar opposite the enormous aquarium, we snagged a table overlooking the Manatee River. We savored the Bruschetta Chicken with tangy balsamic glaze and a mammoth Angus burger from the scratch kitchen as we soaked in the last of Anna Maria.

We wish we could have stayed longer to explore more of the enchanting island. But for this mother-daughter duo, we relished the postcard-perfect getaway filled with Old Florida charm.

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