I touched down in Sarasota earlier than expected thanks to Allegiant’s surprisingly punctual flight from Appleton. That alone put me in a good mood - because let’s be honest, “early” and “budget airline” don’t usually go hand in hand. Next up: the rental car. The Hertz Chevy Malibu waiting for me looked like it had survived a couple of hurricanes and a demolition derby. The bumper was hanging on by a thread, paint peeling like a sunburnt tourist, but the AC was ice cold, so I wasn’t about to complain.
With the windows down and the salty breeze hitting my face, we made a beeline for Lido Key Beach. The wind was no joke - it was the kind of gust that tries to steal your hat and rearrange your hairline. The sand beneath my feet was covered in tiny shells, crunching like nature’s Rice Krispies. I kicked off my shoes and walked along the shore, soaking in the warm air and the sound of waves crashing. The water looked inviting, clear and warm enough to make a Wisconsin guy like me want to jump in - but the wind had other plans, so I just dipped a toe to check the temperature.
Then, just around the bend, I spotted the kind of boat that makes you question your life choices. A sleek, gleaming statement boat with triple 300 Mercury motors. It was a beast - the kind of ride that says, “Yeah, I own the water.” I stood there, wind whipping my face, feeling a pang of jealousy. I wasn’t on that boat, but man, I wanted to be.
Hungry and ready to refuel, we tracked down the Old Salty Dog restaurant. The place had a laid-back vibe, perfect for families and dogs alike - I saw plenty of both. Dana, our server, was friendly and efficient, making sure we felt right at home. The fish sandwich was a bit dry, but it had decent flavor. The fries were your classic kind, nothing fancy but satisfying. The real winner was the key lime pie - tart, creamy, and just sweet enough to make me forget the fish’s shortcomings. Sitting there with a waterfront view, watching boats bob in the harbor, I felt like I’d found a little slice of Florida’s charm.
After lunch, we headed just outside of town to our VRBO trailer. It was a cute little setup tucked behind a beautiful home - newer, clean, and cozy. The only hiccup was the USB ports, which had clearly been through the wringer and didn’t all work. But the AC was blasting, the bed was comfortable, and the place had this fun, campground vibe - like glamping, but without the fancy price tag. The trees around gave it a peaceful feel, though a little yard cleanup would make it perfect.
So yeah, day one in Sarasota was a solid start. If you’re wondering what to do in Sarasota, I’d say hit up Lido Key for some shelling and beach time, grab a bite at the Old Salty Dog, and find yourself a cozy spot to crash - even if it’s a trailer with a few quirks.
Thinking about a trip? Sarasota’s waiting, shells and all. Just bring a windbreaker - and maybe a boat loan application.
Day two started with a quick run to downtown Bradenton to check out the Riverwalk and marina. The vibe was chill-boats bobbing, joggers passing by, and that salty river breeze mixing with the scent of fresh-cut grass. From there, we made our way to Emerson Point Preserve and the nearby 3rd Point, a nature lover’s dream. We strolled along the shore, spotting a pink roseate spoonbill standing tall like a flamingo on steroids, some osprey circling high above near the observation tower, and a few carbs hanging out by the canoe launch (okay, maybe I mean crabs). The views were stunning-Tampa Bay stretched wide, the mangroves swaying gently, and the sun playing peek-a-boo through the clouds.
Next up was a sweet detour to Vimpire Penguin, a shaved ice cream spot decked out with quirky, colorful décor that felt like stepping into a candy-coated dream. The ice cream was just the right mix of refreshing and indulgent-a perfect pick-me-up for a warm Bradenton afternoon.
Then came the plan to catch the sunset at Robinson Preserve. If you haven’t been, Robinson Preserve is a sprawling 680-acre coastal gem tucked into northwest Bradenton. It’s a mix of mangroves, salt marshes, tidal creeks, and coastal wetlands, all stitched together by miles of walking and biking trails. The preserve boasts observation towers that give panoramic views over Tampa Bay and Anna Maria Island, plus kayak launches and picnic spots that scream “day well spent.” It’s the kind of place where you can lose yourself in nature’s soundtrack-bird calls, water lapping, and the rustle of mangroves.
We raced to the preserve’s tower, hoping to catch that perfect golden-hour glow. But, well… let’s just say we arrived a little late. The sun had already dipped below the horizon, leaving behind a soft afterglow instead of the fiery sunset we’d hoped for. Still, we snapped some photos and videos-twilight over the wetlands has its own quiet kind of beauty. The observation tower gave us sweeping views of the preserve’s diverse habitats, and even in fading light, the place felt alive and peaceful.
On the way back to the RV, we swung by 88 Live Piano Bar. The night was just getting started. A local band was tearing through classic rock tunes when Dawn, a server with a voice that could stop traffic, jumped on stage and absolutely rocked the house. We ended up chatting with Eric, a bartender who’s practically a Bradenton institution, and his girlfriend, who bartends there and-get this-is from Appleton. Small world alert: the singer’s family is from Lake Geneva. Talk about a Midwest invasion in Florida!
If you’re hunting for things to do in Bradenton, don’t miss Emerson Point’s birdwatching, Vimpire Penguin’s shaved ice, and a sunset attempt (even if you’re fashionably late) at Robinson Preserve. Top it off with a night at 88 Live Piano Bar for some genuine local flavor.
Ready to chase sunsets and discover Bradenton’s hidden gems? Pack your binoculars and your sense of adventure-this town’s got stories waiting to be told.
I woke up to a lazy Florida morning, the kind where the sun’s already working overtime and the only thing on my mind is a fresh mango. Let me tell you, nothing says “vacation mode” quite like eating a mango straight off the counter with juice running down your arm. We took it slow, packed up, and hit the road north to New Port Richey to see some friends. The plan? Cruise the coast, make a few scenic stops, and soak up whatever Florida threw at us.
First, we somehow missed the exit for the Sunshine Skyway Bridge. I figured, “No big deal, we’ll just catch the next one.” Wrong. That little mistake turned a quick drive into a three-hour crawl through Florida’s finest traffic. By the time we made it to St. Pete Beach, I’d memorized the back of every bumper from Sarasota to Tampa.
Parking at St. Pete Beach? Six bucks an hour, and you’d think they were selling beachfront gold. The bathhouse was rough-looked like it hadn’t seen a mop since spring break ‘98. But the beach itself? Pure velvet sand, blindingly white, and the kind of wind that’ll exfoliate your face for free. We walked, people-watched, and let the sun do its thing. No complaints there.
Back in the car, we headed up the coast to Tarpon Springs, which felt like a full day’s drive on its own. The town is famous for sea sponges, and the downtown is as cute as advertised-think old-school Florida with a Greek twist. Of course, parking was another ten bucks, and the hunt for a bathroom became a full-blown side quest. The Sponge World store? No bathroom. The couple outside? Laughed and pointed us to the visitors center across the street. Paid parking, no spots. We finally found a spot a block away and wandered into a little village of shops. Sponges everywhere, but don’t expect bargain prices. Still, it’s a cool spot if you like quirky shopping and vintage salvage-some of the old doors and oddball antiques in the salvage store were worth the stop.
After picking up a sponge (because when in Rome…), we punched in our friend’s address and, naturally, ended up at the wrong building. That detour tacked on another 22 minutes, just in time for the day’s grand finale: a gray Nissan Altima rear-ended us at a stoplight. I pulled over, and the car took off. So, what do you do? You chase them, of course. After a few corners, they finally pulled into a gas station. I got out, asked for the plate, and got a classic “It’s my boss’s car” from three guys who looked like they’d rather be anywhere else. Hit-and-run, Florida style. Sometimes you just have to laugh it off.
Finally, we made it to our friends’ place-a beautiful home that felt like an oasis after the day’s chaos. Quick shower, then out to the Crab Shack for dinner. This place is old, rustic, and crawling with cats, but the seafood was incredible. We were so into the food and the band playing that I barely remembered to take any pictures. The place sits right on Milkers Bayou, and even though it was dark, you could tell it’d be a killer spot to hang out during the day. Definitely my kind of joint.
The night ended swapping stories with friends who are full-blown boat nuts. They’re buying a 40-foot catamaran to sail around the world, and their boat plans are nothing short of jaw-dropping. They’re even starting a travel vlog, so keep an eye out-I’ll be sharing their adventures soon.
If you’re looking for things to do on Florida’s Gulf Coast, take it from me: expect the unexpected. From mango mornings to hit-and-runs, every day’s an adventure. And if you end up at the Crab Shack, order whatever’s fresh and thank me later.
Day four started slow and easy, hanging out with our friends in their beautiful Florida home. You know those mornings where you just kick back, sip coffee, and soak in the quiet? Yeah, that was us. But then things got interesting: we dressed up and tagged along to a dance competition they were competing in. Not exactly my usual scene, but hey, watching people bust moves with laser focus and a little friendly rivalry was surprisingly fun. Plus, it’s always cool to see something new and cheer on friends doing their thing.
After the dance floor drama, we hit the road back toward Bradenton Beach. This time, we took the Tower Bridge over St. Petersburg, and let me tell you, that bridge is a game changer. Smooth sailing, no traffic jams, and a killer view of the water below. If you’re in the area, take that bridge every time - it’s a serious time saver.
We rolled up to our oceanfront condo, and wow - this place was something else. Huge sliding glass doors opened up to an uninterrupted view of the Gulf, waves rolling in like a slow-motion movie scene. There was a bit of a hiccup with the cleaning (because, hey, sometimes things happen), but we made it work - no trip ruined here.
After settling in, we made a quick run to Publix for groceries. The prices surprised me - not bad at all. So if you’re watching your wallet, cooking in your condo is definitely the smart play. Then it was time for a stroll down the beach to the Coconut Hut, a cute little spot right on the sand. We grabbed drinks and dinner just in time for the sunset. Heads up: nothing here is cheap. A little mixer with Crown Royal ran $12, and a paper plate with a fillet of grouper set us back $38. But the vibe? Totally worth it. Sitting there, watching the sun dip below the horizon with the salty breeze in your face, you kind of forget about the price tag.
Bradenton Beach itself is stunning - soft sand, gentle waves, and that laid-back Florida vibe that makes you want to slow down and stay awhile. If you’re planning a trip, I’d say splurge on the condo, cook some meals, and treat yourself to a sunset drink at Coconut Hut at least once.
Day five was all about slowing down and soaking in the Florida beach life. We kicked off the morning right, hanging out at the condo and then inviting a friend and his son over to join us for a day on the sand. The beach here is something else - soft, powdery sand that feels like walking on a cloud, and the kind of wide-open views that make you forget your phone exists.
We grabbed some folding chairs, set up camp, and settled in to soak up the sun and salty breeze. The water was warm and inviting, and while we were wading around, a few small fish darted past like underwater speedsters. Then, out of nowhere, a sleek 4-foot barracuda cruised by, giving us a little thrill and a reminder that this beach has some serious marine life.
After a bit, we decided to stretch our legs and walked south along the shore toward Cortez Beach. The walk was peaceful, with the ocean on one side and the soft crunch of shells underfoot. We made our way out onto the fishing pier, where a few locals were casting lines and swapping stories. One guy told us the fishing here is unpredictable but fun - you never know what you might catch, which sounds like a good excuse to keep trying.
Back at the condo, we whipped up some dinner and then took a quick trip up to Anna Maria Island to check out Bean Point. If you haven’t been, Bean Point is one of those hidden gems - a quiet, pristine beach with crystal-clear water and a laid-back vibe that feels like a well-kept secret. We strolled along the shore, taking in the pretty views and enjoying the calm atmosphere. It was the perfect low-key day after a few busy ones.
Day 6 on Anna Maria Island started like a postcard-barefoot on Cortez Beach, the sun just waking up and painting the sky in soft pastels. The sand was cool underfoot, dotted with shells like tiny treasures left by the tide. The salty air carried the promise of adventure, and I was ready to soak it all in.
From the beach, I wandered up to Bridge Street, the lively spine of Bradenton Beach. This place is a delightful jumble of small shops, quirky boutiques, and bars that look like they’ve been there forever-because they have. The scent of fresh coffee mingled with sea breeze, and golf carts zipped by with cheerful locals waving “Hey y’all!”
One stop that caught my eye was the Bridge Tender Inn, a full-on Packer bar nestled right here in paradise. Green and gold flags fluttered in the Gulf breeze, and I couldn’t help but chuckle at the sight of cheeseheads in flip-flops. I made a mental note to come back later for a cold one and maybe a game.
At the end of the street, the Bridge Street Pier stretched out over the water, a perfect spot to watch pelicans perch like old fishermen swapping tales. A dolphin cruise boat bobbed gently at the dock, and I knew this day was about to get even better.
After a quick stop back at the condo, we grabbed the car and headed over to Cortez Island, home to one of Florida’s oldest fishing villages. Our first mission: the famous Star Fish Company. Alas, we arrived just after closing, but no worries-there was still plenty to explore.
Down the road, the Swordfish Grill & Tiki Bar beckoned with its waterfront deck and live music. We settled in with cold drinks, the band’s easy groove blending perfectly with the gentle lapping of the marina waters. The pelicans seemed to approve, nodding along as boats drifted lazily by. It was the kind of place where time slows, and worries float away on the breeze.
Back to the Bridge Street Pier for our dolphin cruise, tickets in hand and excitement building. The boat slipped through the Intracoastal, the captain sharing local lore and pointing out landmarks as we cruised toward the north tip of Cortez Island.
Then came the magic-dolphins playing near the seawall, leaping and splashing like they were putting on a private show. A bald eagle soared low over the water, regal and rare, a perfect Florida moment.
The cruise continued to Longboat Pass, where the sky exploded in fiery oranges, pinks, and purples. For $35 a head, this 90-minute ride felt like a steal-a front-row seat to one of nature’s best performances.
After docking, we popped into the Packer bar for a quick look, but the crowd was thick and lively, so we headed back to the condo. With the giant sliding doors wide open, we cooked fresh grouper, the aroma of lemon and butter mingling with the ocean breeze. We ate to the soundtrack of crashing waves and the fading glow of the sunset-a perfect end to a perfect day.
If you’re searching for “live events near me Anna Maria Island FL,” “Anna Maria Island nightlife,” or just the best “things to do in Bradenton Beach,” take it from me: start with a morning walk, add a little island adventure, and finish with dolphins and deck drinks. That’s the Anna Maria Island way.
Got your own Anna Maria Island stories or favorite spots? Drop them below, or tag a friend who needs some sunset magic in their life!
We kicked off Day 7 with a plan: make a run down to Fort DeSoto Park, just south of St. Petersburg. The drive itself is half the fun, crossing the Sunshine Skyway Bridge again - that thing’s like a roller coaster for your car, with water stretching out in every direction. You can’t help but feel like you’re driving on the edge of the world.
Parking at Fort DeSoto was a steal - just $6 for the whole day. First stop: Gulf Fishing Pier. This massive pier was buzzing with anglers, and we even spotted a few dolphins cruising nearby. Walking all the way out, the views of blue water, diving birds, and fishing lines made it feel like we’d stepped into a postcard.
Next, we checked out the old fort. The big guns and historic walls were pretty cool - a neat reminder that this place has seen its share of history. The gift shop? Meh, nothing to write home about, but hey, we gave it a look.
Then we geared up with sand shoes and headed to the North Beach, trekking out to the farthest tip of the point. This spot was next-level cool - a little cove called Sand Dollar Beach dotted with boats bobbing gently in the water. We did some shelling and found some impressively large shells. I almost grabbed one, only to realize it was a crab - surprise!
The real highlight? A school of small fish swam right past us, and then, out of nowhere, a roughly 3-foot hammerhead shark came cruising through, chasing the fish. Super cool to see, but also a little reminder that standing in the water with a shark nearby is not for the faint of heart.
We spent most of the day soaking up the sun and salt air before heading back. On the way home, we swung by Anna Maria Island for some well-deserved ice cream - a perfect sweet finish to a day full of nature and adventure.
Back at the condo, we cooked dinner while watching the waves roll in through the giant sliding glass doors. There’s something about eating good food with the ocean as your backdrop that just makes everything better.
Our last morning in Florida started slow and sweet, just like the trip itself. We took a peaceful walk along the beach, the sand still soft beneath our feet and the ocean breeze carrying that salty, sun-warmed scent that’s impossible to forget. Even though we noticed some spots showing the scars of recent storms, the beauty of the coastline was undeniable. It’s that bittersweet feeling-you know you have to leave, but the place doesn’t quite want to let you go.
After soaking in the morning calm, we packed up and headed north toward the airport. But of course, we couldn’t resist a little detour. Near the airport, we cruised through Indian Beach, a gorgeous neighborhood dotted with stunning waterfront homes that made me seriously reconsider my life choices. We stopped to overlook Sarasota Bay, watching boats glide lazily across the shimmering water. It was the perfect spot to reflect on the trip and snap a few last photos.
Driving past the Ringling Museum, I made a mental note: next time, we’re definitely stopping here. The place looks like a cultural treasure trove with so much to explore-art, history, gardens-you name it. Sarasota has so much to offer, and this trip was just the tip of the iceberg.
All in all, it was a great trip, full of beaches, good food, new friends, and plenty of Florida sunshine. Leaving is always the hardest part, but I’m already plotting my next visit.
