Plan the perfect trip for two, romance included

If you’re looking for a little romantic getaway, it’s hard to do better than the authentic Florida feel of the Bradenton area. My partner, Bri, set out to reconnect with a place she felt deeply connected to in her childhood, while I was aboard to understand how to make the most of a couple’s getaway in the present. Not a bad gig, to be sure. 

There’s a leisurely pace and charm here that is utterly unique, and when you sprinkle in just the right mix of adventure, beautiful views, and add a criminally underrated restaurant scene to the mix, you end up with something special.

by Chris Mitchell

At its core, what makes the Bradenton Area such a worthwhile place to visit is that you can access that feeling of stepping into the past, and embracing that feeling that not everything you need to do has to be done in a rush – all while noting that this is a destination with its eyes set firmly on the future, and, like a fine wine, will only be getting better with age. 

So, if you’ve decided that, like us, you wouldn’t mind basing yourself on Anna Maria Island and exploring all the surrounding area has to offer alongside your partner, then what should you focus on? Well, I’m awfully happy you asked.

Get Up Close & Personal With Dolphins

One of the most memorable ways to experience the natural beauty of Anna Maria Island is from the water, and few do it better than Anna Maria Island Dolphin Tours. These small-group and private excursions are led by knowledgeable captains like Chris, whose roots in the local boating and fishing community stretch back generations.

The waters surrounding Anna Maria and Sarasota are shallow and warm — ideal for the resident population of bottlenose dolphins who call this area home year-round. These dolphins are actually the baseline population for dolphin research globally, studied since the 1950s by the Chicago Zoological Society. 

They’re so well known, in fact, that most of them have names, earned through unique dorsal fin shapes: Bangles, Flip Flop, and the like. Chris pointed out several of them on our tour, casually identifying them by fin like old friends. He talked with genuine reverence about how dolphins work together to navigate tropical weather and how they can communicate up to two miles underwater. 

“See that bridge in the distance? That’s two miles — they can talk across that,” he said.

You could see that Chris wanted the ultimate experience for us, that it meant something to him that this all meant something to us. The whole experience felt serendipitous, from the dolphins themselves, to the fact that as our boat approached the bridge, Chris’s wife and son happened to be crossing it, and waved happily. Is there any better attestation to the small town, community feel that you can find here?

As sunset hit, and we basked in the wonders of this little adventure, I remember Chris turning to Bri and I and noting, simply, “I’ll never get tired of these trips. Mother Nature always makes you a different painting.” By the way, if you’re short on time, but still want to get out on the water, simply consider ditching your car for the day, and get out on the Gulf Islands Ferry. Who knows? You might see a dolphin on your ferry ride!

Stay Steps from the Beach at Silver Surf Gulf Beach Resort

Every morning, I looked forward to getting a cup of coffee, and some great options for breakfast on the run, before we took it down to Silver Surf Gulf Beach Resort’s private beach access. We’re talking steps away from the waves, my friends. The staff here felt like family we just hadn’t met yet, and it was immediately clear that, while this was our first time here, for many guests this was their home away from home. You’d hear people come in for breakfast, and decide that it was already time to book in for next year – and the staff would help them do that in the best possible way. 

It’s one of those spots on Anna Maria Island that manages to feel both unpretentious and effortlessly charming. It’s not flashy, but that’s part of the appeal, quite honestly, and it matches the vibe of “authentic Florida.” 

The rooms are clean and comfortable with island-inspired decor, and many come with kitchenettes, ideal for anyone who wants to toss together a lunch in case they’ve got some afternoon adventure in the works. But the real star here, as I’ve noted, is the private beach access, reserved just for guests. There are loungers, umbrellas, and those panoramic views of the Gulf you’ll be dreaming about long after you leave.

Taking a meeting one day by the heated pool out back – well that wasn’t a bad touch, either. How’s that for work life balance?

Make Time for Robinson nature Preserve

On the northern edge of Bradenton, just a short drive from Anna Maria Island on most days, you’ll find Robinson Preserve. As they like to say, this is “where saltwater meets sawgrass.” We had initially planned to rent a kayak, but the weather wasn’t on our side, so we went all in on hiking/taking a stroll. We didn’t quite get to cover the 600 acres of restored coastal wetlands, but we sure got a taste for it, and were treated to birds aplenty, especially herons and ospreys.

One of the best ways to take it all in is from the observation tower. Climb to the top and you’re greeted with panoramic views over the preserve and out toward Tampa Bay — a reminder that Florida’s wild side is every bit as spectacular as its beaches. And if you’ve got kids in tow (or just feel like one), the NEST building nearby often hosts interactive environmental exhibits and programs, giving you a deeper appreciation of the ecosystem you’re wandering through.

I, naturally, played on some of the structures meant primarily for kids – but it was only to ensure that they were in good order, of course. And they were. 

It can sound cliché or redundant at times to talk about places where “time slows down,” but the Robinson Preserve really is one of those places. It’s a place to get perspective, and to let worries melt as you get a taste of some stunning natural surroundings. 

It was a little rainy and windy when we visited, but that didn’t stop us from loving every minute of it. Whenever it starts raining and we’re on the road, I playfully remind Bri (and myself) that, thankfully, we’re not made of sugar, so we can embrace a touch of rain. 

Get Your Restaurant Fix 

We’ll start where our toes are still sandy — Sandbar Seafood & Spirits. Whether it’s fresh grouper, Gulf shrimp, or just a glass of wine timed with the sunset, it’s the classic coastal Florida experience. Order the key lime pie. Trust us. If you can time it properly, get there right around sunset, as it’s something special to behold, and keep your eyes open for sand art, largely in the form of epic sand castles. I also loved that they had plenty of local beers on tap.

For something a bit more elevated, quite literally, head to the Oak & Stone. The panoramic views over downtown Bradenton are just the beginning. It’s a casual spot with serious beer credentials, boasting an impressive self-serve wall of rotating craft brews. From hoppy local IPAs to rich porters, there’s always something new to try. Grab a seat outside, take in the breeze, and let the taps be your guide.

The Doctor’s Office on Anna Maria Island was a place we adored, and not just because the owner was a Nova Scotia transplant. The bar channels a speakeasy vibe without the pretension. The cocktails are thoughtful and inventive, and if the smoked salmon is on the menu, don’t even think twice (and same goes for the lobster escargot). It’s actually based in a former doctor’s office, and you’ll definitely notice that they lean into that theme, from the decor, to the cocktails, to their menu at large. We ended up becoming friends with the folks seated near us at the bar, and I get the sense that is not an uncommon occurrence. 

But if there’s one meal we’re still talking about weeks later, it was the romantic meal we shared at Taverna Toscana. Nick, our server, guided the entire evening with ease — pouring just the right amount of wine, sharing stories, and finishing off the meal with a table-side pour of limoncello (and really, who doesn’t love that?).

The restaurant may be relatively new (opened in May 2025), but it feels like a fixture already. From the six-hour strawberry reduction atop their cheesecake to the way each dish is seasoned perfectly, it’s clear there’s a lot of intention going into how they do things here. 

Enjoy the Breeze at North Shore Cafe 

If you want to lean into a perfect morning, then heading to the northern tip of Anna Maria, and stopping by North Shore Cafe is the right move. Bri had her coffee, I had my matcha, the sun was shining high in the sky, and we enjoyed a touch of shade under their outdoor patio’s palm trees. The mural in the back is also a spot that you’ll want to snap the perfect couple’s vacation photo!

Be sure to pop into their boutique before you head out, and then walk up and down Pine Avenue, popping into other local shops and doing a touch of breezy island shopping.

For Your Next Couple’s Getaway – Think Bradenton, Anna Maria Island and Longboat Key

Bri and I are fortunate to travel a lot, and that’s why it’s all the more powerful when we feel very taken with a place. Just writing about our time there makes me want to do what we saw so many others who were there do – plan to come back again. They have a nearly 95% return rate for a reason! 

We’ve been all over Florida, but we’ve never been somewhere like this, and it’s not just about the vibes on Anna Maria Island, it’s about the access you have to Bradenton and the surrounding area at large, ensuring that, whatever you and your partner are looking for, you’ll find it here in droves.

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Nostalgia travel

Nostalgia travel is a trend for a reason–it brings back fond memories from the past in a place that’s special to you. Here, upwards of 90% of visitors come back to this area again and again. It’s easy to see why.

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