Anna Maria Island 'Old Florida'

Every great vacation rental business is run by a destination ambassador who introduces the town or city to visitors in a clear and authentic way. Sometimes it's through interior design and decor: items that have been handpicked with great thought. Other times, it’s through tips and introductions in the local community. And when choosing the right property for vacation, I try to seek out a combination of both: a property that tells a story — whatever that story might be. Back before tourism was such big business, Florida was known for its slower pace of life: small towns were powered by mom and pop shops, kids were safe to roam freely, and things were simple and easy. Things were quaint, but great. This era is fondly referred to as “Old Florida” — and it’s all but disappeared with the onset of technology and development — once quaint beach destinations now home to resorts and expansive strip malls. But remnants of Old Florida charm do still exist if you look for them carefully.

My ambassador of Old Florida was Nancy McAleer, who lives most of the year with her husband Michael in Montreal — some 1500 miles away. Nancy's part of an increasingly growing kind of vacation rental professional who manages their vacation rental businesses from afar with the help of technology and old-fashioned persistence. When you ask Nancy if she thinks a remote host can achieve the same quality as a host who lives on-site, she’s almost offended — claiming when done properly, the remote recipe works even better because it forces you to be almost overly-prepared for anything that might come your way. Nancy's vacation rental story starts off like many: adversity forced her to find a new path forward. And as if the idea of starting a vacation rental business wasn’t challenging enough, Nancy also went in on the project with close friends. The final product is Sirenia By the Sea, a 5-bedroom vacation home on the water that represents much more than a place to lay your head: it’s where groups come together to recharge their batteries: it’s where families re-group to enjoy the important stuff.  How Nancy built her business wasn’t rocket science. But as I would learn in the days to come, it wasn’t dropped into her lap either.


I’ve always loved the idea of painting. But it’s always been purely aspirational: I envision my dream home as having a room dedicated solely to painting, overlooking some scenic pass, with my easel, canvas, maybe even a tattered color pallet like Bob Ross. When booking my rental in Anna Maria Island, Nancy mentioned the important role that art plays in her beach town — a perfect chance to develop my skills! Via email, Nancy introduced me to Cory Wright, a prominent local artist you can see painting beach landscapes and giving watercolor boot camps to kids and adults alike. Since her adult classes would fall outside of my scheduled visit, Cory suggested I join a kids’class at the The Studio at Gulf & Pine studio where she teaches. As my contemporaries began to arrive, we shared some small talk, before diving into three different kinds of fish paintings. On my right was a pretty famous artist named Brooklyn and to my left was Gigi, who specialized in seahorses. As we began to build out our paintings, Cory explained how her children’s classes seem to exhibit a kind of unrestrained creativity — way more so than her adults who are always so concerned about messing up. We started off with outlines, and were then encouraged to fill in the rest however we saw fit. And by the end, when it was time to show our work to the waiting parents, this may sound cheesy, but I was reminded how much I really do enjoy art and how often I let it intimidate me from actually getting started.


One of the best parts of choosing a vacation rental and being introduced to locals is in the form of insider tips. At the end of watercolor class, Mason's mother suggested I explore the annual Stone Crab festival located in the nearby fishing town of Cortez. Stone crab is one of my absolute favorite foods on the planet so there was no way to pass this up. I invited Cory along with her husband John, and learned about the history of Cortez, a hard-working community that seems to have successfully staved off many of the threats of economic development that are so common elsewhere in Florida. I learned that the Cortesians (as they call themselves) are more than just proud people. They’re highly self-sufficient. During the Depression years, Cortez was the only community in the United States that required no federal aid, subsisting on plentiful catches of mullet. And between colossal hunks of stone crab meat, Cory and John’s parenting values seemed to coincide: it’s the importance they place on exploration and independence with their kids that fits perfectly in Anna Maria Island: you can definitely feel this comfort as a visitor too.


When I travel, I love to ask my vacation rental connections about interesting running routes — they’re almost always more challenging and interactive than a hotel treadmill and they allow you to see new layers of a destination. Cory’s husband John was just the insider I needed. Robert, a representative of the show’s sponsor, aBundle, had flown into town late the previous night, and as the sun was just peeking over the horizon, we explored the waterfront promenade and one of AMI’s precious nature preserves. Relatively few people take advantage of these parks, John explained. But we did. And meandering up to the little mountain top to look out over the bay, it was one of the most serene ways I can imagine starting my day.


Hoping to get a taste of AMI from the sea, Nancy had the perfect contact for me: Yetta and Steve of AMI Outfitters, something of a landmark on Pine Street just a few blocks from my rental. The shop retains that hand-picked charm that big box stores and online outlets seem to so sorely lack these days. Yetta comes from the world of PR, and Steve brought his previous life as a nature photographer — the perfect duo to run an outdoorsman shop: and while they work their butts off 6 days a week, on the 7th day Yetta lets Steve go fishing, and when she does, he invites his clients to tagalong in that classic Old Florida way, basically free of charge. After hopping into his truck and parking at the local boat ramp, Steve asked me to help lower the boat into the water by holding on to two specific ropes. Having learned the basics of fly fishing with Hunter in Blue Ridge, I put my skills to work and almost immediately began catching fish. Steve was gracious as could be — pointing out rays, dolphins, and the importance of choosing the right partner, both in business and in life. Passing by Cortez, the town I met a day earlier with Cory and John, I asked if we could stop by Starfish — a simple dockside restaurant I had learned about day before. It was here that Steve shared nuggets of his previous life as one of the first employees of Eagle Creek, one of the most renowned outfitter brands in the world. Steve has a clean way of looking at development in places like Anna Maria Island.


And while we didn’t catch anything significant on the water that day, we did make it back in time for sunset: sunsets are outrageously good in AMI and one of Nancy’s top recommendations for guests is to hire AJ Latteri of The Loft 5 Catering for a beach picnic. When she’s not hosting open-air farm-to-table dinners or cultivating relationships with surrounding organic farmers, AJ is on a mini-mission to bring back the picnic culture and using her service was a real luxury for me as a vacationer: being able to unpack a beach blanket, drinks, veggie kebabs with Israeli couscous, plates and silverware all without doing literally any work was pretty much the best way to end my day. Before packing up, I met a few locals who were at first pessimistic about the idea of a travel show about Anna Maria Island. They helped me understand that a wave of development and money were stressing the fabric of the town at its seams.


Since Nancy manages Sirenia by the Sea from abroad, she doesn’t have the chance to interact most her contacts in person. In many cases, she’s never actually met them: And this can be a really challenging thing: complete strangers in someone's home and around town can be really painful if not hosted properly. But what Nancy lacks in physical presence, she makes up for with smart investments. Investments in the right people on the ground: people like Chelsie and her company Gulfside Cleaning Solutions. A reliable cleaning crew might just be the most important part of a remote host’s business because Nancy knows she can count on Chelsie’s team if things go awry. And also, smart investments in the right amenities: This is where the sponsor of this episode, is worth introducing: they’re a company that offers hotel-tested products to vacation rental professionals. What used to be only available in huge bulk, is now accessible to people like Nancy with one or two properties. Spending a little bit more on durable sheets or the right sets of towels also reduces her workload a great deal. For someone with preciously limited time, these kinds of investments go a long way.


Nancy’s hospitality from afar is best epitomized by the Cponies, a tour that Nancy books for guests on a regular basis, yet one she had never experienced herself. I had the pleasure of joining Nancy to visit the Cponies — which was one of the weirdest tours ever. After a safety briefing and introduction to each of the Cponies, which are basically undercover unicorns, we saddled up and headed to the sea. Once my horse, Dreama, let loose a few of what my guide Jen called sea souvenirs, we got a quick photo. Dreama was pretty calm, moseying into the ocean, and I was surprisingly at ease too: what I typically dislike about horse riding is the distance between you and the hard ground. But with Dreama, it transformed into a surreal experience: when we got deep enough, the horses lifted off and I couldn’t help but laugh hysterically as Dreama began swimming…and fast. To get the idea, combine one life-sized My Little Pony with a new boat engine. The ponies love swimming by the way: Jen has been a lifelong horse enthusiast and noticing how much her horses loved entering the sea to cool off, she began to offer tours and things took off. People travel from around the world to experience the Cponies: it’s an experience I don’t think I’d ever have signed up for had it not been for Nancy and her enthusiasm. And it was cool bring things full circle and see her finally experience it too.


I’ve always felt the local food scene can tell a lot about a destination food is like translation dictionary that allows travelers to use things that we know, to understand things that we don’t. And since restaurant recommendations are such a personal component of the vacation rental host’s repertoire, I accepted Nancy's readily. And once introduced me to Sean Murphy…I knew things were about to get real. Sean is one of AMI’s most fabled restauranteurs, with a handful of establishments and initiatives under his wing. I met him first at his bar, The Doctor’s Office (named after a local doctor, whom I’d come across the next day), where after about 15 seconds of small talk, Sean arrived with what looked like an antique bird bath. By the time we left the Doctor’s Office for dinner it had filled up and become a Star Wars Bar mix of patrons from all walks of life. We then headed over to Sean’s flagship restaurant, Beach Bistro, which has the unexpected feeling of an old-school railway car, set extraordinarily front and center on the beach. Sean tells the story of old Florida through his food. And you could see that hospitality was something engrained in his personality: stopping by various tables to greet locals and visitors alike.


To get another understanding of what AMI is all about, Nancy reached again into her little black book and introduced me to Captain Dev who, with his big smile, quick-wit, and take-the-bull-by-the-horns attitude, embodies a generation of Floridians for whom tourism is both a problem and a solution. After years in the Navy, Dev moved back to AMI — the place he grew up and knows like the back of his hand. The original plan with Dev was a half-day trip out to Egmont Key, but due to the weather we decided instead to do a tour of his childhood landmarks. There was the rope swing he discovered when he first got his boat license, the abandoned islands where as a teenager he used to sneak off to party with friends, and the ship wreck — a sunken molasses boat from the 1920’s that you’d never know about without insider guidance. Dev's memories of the “Old Florida” aren’t necessarily gone, but they’ve changed in many ways. Dev’s dream house, for instance — a waterfront home he’s admired since childhood — would today cost an estimated $2M. How does one ride this wave of change in their own favor? Dev likes to think it’s by going with the flow, and by keeping his business and personal relationships tight. On paper, Dev is a boat captain who took me out on the water for some fun. But his value to my trip represented something much greater than that.


Eventually, all great vacations come to an end, and on the final night before I left one of the things that really began to crystalize for me in Florida was how all the people I’d met — Dev and his wife Kourtney, Steve and Yetta, Cory and John, AJ and her business partner Shelby, Nancy and her husband Michael, and Sean — despite their totally different backgrounds and professions, ages, and interests — pretty all much described what they loved about Anna Maria Island in the exact same way. I invited them all over to my vacation rental for the evening, introducing many to one another for the first time in person! Despite our different walks of life, everyone at dinner spoke a common language of AMI and that’s a powerful thing. For a vacation rental destination, when both the residents, business owners, and visitors have a precise understanding of what’s being offered and what is not, there’s synergy there, collective wisdom seems to thrive. I thought it would be nice to commemorate this magic with the help of Cory, who was able to whip up a lovely new wall hanging for Sirenia by the Sea.