Gay Travel & Gay Love Can Happen In A Small Town. Cue The Music

This week’s Travel Thursday piece is a mix of travel and love, a hybrid post about a destination in the middle of nowhere and a couple that is making a big gay impact in very small town America.


While packing up for a press trip, I received a message that the public relations company wanted to add an additional quick stop onto the end of my itinerary. “You just have to meet these guys. We all love them, they’re great. They’re known as ‘The Boys of Chokoloskee’.” The suggestion to me was to do an airboat ride, then stop into this couple’s Cuban restaurant for lunch and then head home.

I looked up this Chokoloskee place and realized that it was truly in the middle of nowhere. Actually, go to nowhere, and then take the road further away from nowhere, then go over a causeway, and then you’ll be either in the middle of the Gulf of Mexico, the last bit of the Everglades, or Chokoloskee… or all three. The map looks more daunting than the beautiful drive it is from either Naples (50 minutes) or Fort Lauderdale (1 hour 40 minutes) or even Miami (1 hour 40 minutes). 


Related Post: Picturesque Naples Is Open for Business and Welcomes All

Since I was driving back from the Florida West Coast city of Naples to the East Coast gay mecca of Fort Lauderdale, I thought, why not and responded in the affirmative to adding the brief stop onto my Thanksgiving Weekend journey to seek out gay life in Southwest Florida. Just a few hours after saying yes in an email to meeting these so called “Boys of Chokoloskee”, I received a friend request on Facebook, saw it was someone who lived in Chokoloskee, said yes to the friend request, and sent him a “see you soon” message. 

Well that was just the beginning of the warmth and hospitality and kindness I was given over my 24 hour stay in Chokoloskee. The Facebook chat went like this:


After that exchange and a little more, I was so looking forward to a Cuban restaurant, a stay at a mid-century motel, and a boat ride out into 10,000 islands and the gulf of Mexico. Little did I know, the activities would be umpteen more times exciting that I would have thought and that I would meet one of the most loving, impressive, kind, most authentic gay couple, heck any kind of couple I had every met.

From Naples, I had a quick swamp boat ride at Wooten’s Everglades Tours. The everglades are more grasslands and mangrove patches that the swampy forests of Louisiana so it was a good and different experience than I had before. 

And then it was time to meet the boys. 


As I pulled up to the HavAnnA Café (they use Anna in the spelling to honor family members), I was a little surprised for all in front of the restaurant and on the lawns beside the building and across the street were Ferraris, Maseratis, Corvettes, and other luxury cars. Was I at a Michelin Star Restaurant and didn’t know it? I found out later that being at the end of the road, at the end of the earth has its positives as everyone wants to drive there to see what is there, and then they are hungry. And the website for the restaurant (image shown below) shows you how big Chokoloskee is, you’re seeing the whole thing. It was an island until the 1950s when a causeway was built to tie it to the mainland.

The restaurant was welcoming, very busy, great food, fun staff (there were more than just the gay boys/owners working there from our community). I enjoyed my time watching this little restaurant handle a great rush from this luxury car club plus the usual crowd.  


The boys… okay, they have names, David and Aaron… the boys used my showing up as an excuse to ditch out after closing a little earlier than usual (check their website for seasonal days and hours) so we could get out onto the gulf to see the wildlife and watch the sunset. They’re not in the boat chartering business themselves (they have great recommendations when you come to visit), but they do run the Parkway Marina and have their own personal boat and were very kind to take this Chokoloskee virgin out into the middle of nowhere. But they were so comfortable to be around, trusting, cute, kind, and real so I hopped in and went for an amazing ride. 

After seeing a flock of over 100 American White Pelicans (wingspan of over 9 feet), multiple other bird species, and my first green sun flare sighting, we headed back from the gulf and I settled into the Parkway Motel

My room was gosh-darn cute!  When you say 1950’s motel, yes, that is exactly what it is and I loved it. Of course, Instinct has covered St. Regis, Ritz, W, Faena stays and those were full of luxury and what not and we look forward to staying in places like that again, but to be honest, this little Parkway Motel was a flash back into simplicity and comfort. I’m looking forward to my return. But maybe next time I may look at staying at one of their other Parkway Motel offerings as they also offer for those that don’t want to share walls with others separate homes to book. I think I might check out the D. Hooker Fishing Lodge (the D stands for Dirty) which is a 3 bedroom doublewide trailer. The boys are making it work and having fun.


So what did I do in little Chokoloskee? I experienced what the boys were offering this Chokoloskee virgin. They have the HavAnnA Café, the Parkway Marina, and the Parkway Motel. They were all great fun and new experiences. I’m originally from rural Central Maine, an Eagle Scout, and this was a return to some simpler times to enjoy the simple things, outdoors things, the well done things, the things done with pride, and a great splash of nature and care. 

What was also beyond evident during my time with David and Aaron were two POWERFUL things that were so palpable, it was great.

Number One: the love, respect, acceptance, and appreciation people have for these two men. And its not just the 1,100 residents of Chokoloskee, but they are known from Naples to Fort Lauderdale (and I am sure beyond) for the loving guys that they are. 


After the boat ride in the gulf, we cleaned up and went out to have a late dinner and go to a couple of bars in Everglades City, the closest city on the mainland, population 400, but there were more bars and restaurants there than in Chokoloskee. It was fun to see, where ever we went, David and Aaron were always greeted with excitement and open arms. I thought I was hanging out with the mayors of the island and the city. In a small town and area like that, everyone knows everyone and everyone knows everyone’s business. Of course it was known that these two gay men were married, but that was not a negative here, it was just a demographic fact, a bit of info, not a divider or a hinderance. But they also owned a motel, a marina, and a restaurant in the area, probably a fifth of Chokoloskee island, so they should be well-known.

Number Two: the love Aaron and David have for each other. Think relationship goals, real feelings, open about your feelings for each other in public, and just exuding happiness when together… yeah, I hated them. Kidding! It was just so positive and real and reassuring that there is hope for a good and healthy relationship out there. I’ve seen them a couple of more times since my stay at the Parkway and they’re still those great guys and a great couple to know, to appreciate, and to admire. 

I did catch up with Aaron and David to explore a little more about their relationship and their live in Chokoloskee and them being a gay couple in the middle of the Everglades. 

They were happy to share some thoughts about what is going on in current politics and in their lives.

Aaron (left) explains how he met David (right). Photo taken from their wedding video

Instinct: Thanks for agreeing to answer some of my questions since our last meeting and with all the changes that have happened in Florida politics.

David: With all the recent anti-LGBTQ press in Florida and Naples Pride recently getting approved for the parade, only to be smacked down with a ‘ No Public Open Air Drag Performances Allowed’ rule, an article highlighting our story will hopefully bring more compassion and understanding that we’re not the bad guys here. In fact, we love the same thing many conservatives around the state do; fishing, nature, wildlife, stars at night, birding, and recreation with family and friends. Love is Love! And #LoveWins Always and in All Ways.

I want you to know, that as a Young Teenage Man questioning what it means to Be Gay, I gravitated to an Instinct Magazine while in a Barnes and Nobles with Friends after school. I felt a sense of taboo, but thumbed through it. I read articles about ‘Being Open in the Work Place’, and remember the feeling that it’s Ok to be Gay, cause there are Professional Gays in the real world with successful careers. It was a positive trajectory uplifter for my sense of self, and who and what I can be when I’m truly me. 


Here we are ~20 Years later, and I’m Honored and Grateful for this Opportunity. 

Earlier on in their relationship

How did you two initially meet and was it love at first sight?

Aaron: We first met at DrYnk Bar in Wilton Manors, one of my friends introduced us. That was my lucky day.


David: That was the first time we met, at DrYnk Bar, but I think when the magic actually happened was seeing Aaron come into the bar with different groups of friend each night and I was like, “Who is this guy!” I see him walk in through the door and I see him go walk to a group of people and talk with them, and I didn’t want to really jump on him as soon as he arrived right then, so I was talking to my own group, and then I turned and said “Hey hey hey” while walking forward and rolling my shoulders and …

Aaron:  … and I knew I was in love right there (both laughing and saying hey hey hey hey).

David: And that was it..

In Unison:  Oh and that New Year’s kiss.


David: I was showing him the back yard wasn’t built out at DrYnk, it wasn’t finished as of yet, and I said, you know what, it’s the end of the year, we’re about to start a new year and I pushed him up against the wall and took a kiss.

Aaron: Don’t tell them that

David: and you know what, he gave it right back, so it counted.


And where was the wedding? 

Aaron:  Chokoloskee is my home town, the wedding was here.  We are the first openly gay couple on the island, we had the first gay wedding on the island. We were worried at first, just for a little bit. But you know the town, the churches, the community has fallen in love with us and have made us feel super comfortable. The small Everglades town of Chokoloskee, everyone was buzzing, “Oh, my god, we’re going to go to their wedding.”

** the Boys shared their wedding video with me. Eyes and cheeks were so wet with happy tears.  


What is your favorite thing to love about each other? 

David: The thing I love most about Aaron is his authenticity, he is genuine, he is real, he keeps me grounded, he brings that childlike enthusiasm to situations and it keeps me humble, keeps me laughing and it keeps me out of my mental space as I get cerebral sometimes.

Aaron: He is funny, he is caring, and when we are together, I feel safe and secure. The love that he shows me, even when he is grumpy, it is amazing, his smile, those beautiful eyes. I’ve never felt this way, I could go on and on.

We get along great, I think we compliment each other amazingly, because we re better together. I’m a lucky man.


David: I’m the lucky one.

What has COVID been like for the two of you? Has it brought you closer together?


David: The COVID 19 Shelter in Place Mandate was tough for the both of us. Bars were deemed non-essential, so while I was out of a paycheck, I was also thinking to myself how I’m showing up, just might not matter in society. Aaron’s plumbing company Honest Plumbing took off. As more and more folks stayed home, they wanted to fix and upgrade things around the house. We began working together on a few bigger jobs, and saw the synergy instantaneously. 

Life in the big city led to a lot of unrest during that time, so we started spending more time in Aaron’s home town of Chokoloskee, about an Hour & 1/2 away from Fort Lauderdale. Living in South Florida most of my life, this hidden Old Florida Heritage Site was new to me and we spent countless days fishing and recreating in the great outdoors of Everglades National Park and the 10,000 Islands. A simple approach to daily living where sunrise, sunsets, and the tides dictate daily affairs had me geeking out on nature’s wonders and reminded me of my collegiate pursuits in Environmental Science. 

So when the opportunity to steward Chokoloskee’s 1st Fishing Camp Parkway Motel and Marina, previously owned by the Smallwood Family, came up, we thought to ourselves if more folks got together to go fishing, where baiting a hook, keeping the line tight, and reeling her out of the mangroves and away from the propeller to catch and release or keep the slot limit, we’d be living in a different society all together. And so far so good! Happy Hour Sunsets on the docks brings the whole trailer park together at Parkway. 

Aaron: Yes, we bought a boat and went fishing for a month during the shut down. 


What is it like running multiple business together with your partner?

David: It’s actually a real treat to work daily alongside the man you love. From fuel duties on the docks at the Parkway Marina to working the fryer and flat top at HavAnnA Café, we’re constantly having fun and whistling at each other. It’s rigorous work where we sacrifice our weekends and holidays, but it’s also challenging to find reliable consistent help in a frontier town that’s still in a boom-or-bust pocket of Florida. Nearly 90% of all our annual earnings are realized during the four Winter months when the annual population of Chokoloskee swells from ~180 folks in the summer to ~3,000 in the Winter. But, it’s not a bad life, and when the right and perfect people show up ready and willing to support our vision for the restaurant, motel & marina here in Chokoloskee, we’ll be living the dream. Until then, we’re not afraid of hard work and sweat equity, doing our part to support the community and visitors from all over the world. 


Aaron: Challenging, but rewarding. We’re better together, and growing something with your partner as you’re growing in love is the best thing I can ask for. 

Has the topic of adopting or having kids via surrogate ever come up?


David: As a former Miami-Dade High School Science Teacher, positively impacting the next generation is in my soul, but we’ve both agreed that adopting kids at this time would be way too much on our plates as small town entrepreneurs. #NoFussGus, our American Bulldog crossed with Dalmation Mutt greets us on the front porch daily with his wiggle waggle tail, and reminds us to take it easy. But maybe someday we’ll re-evaluate the topic. 

Aaron: Not surrogate, but adopting because there are so many kids out there. We’re both on the fence, so never say never. 


What is the best advice you would give to anyone who is looking for love out there but hasn’t found it?

David: Once you get passed the check-lists and double clicks, drop into your heart space and follow your intuition. If it feels good and is fun go for it. But always keep it real and stay honest. 

Aaron: Keep an open heart and an open mind. And say hello to everyone.

Whatever you’re called, David & Aaron, #GoodVibeTribe, The Boys of Chokoloskee, Instinct can only wish you the best. Thanks for sharing your lives, your businesses, your beginnings, your love with us. Thanks for showing that love is love, in a big town, in a small town, in the middle of the Everglades, in the political climate we have in a red state. Love is strong and thank you for showing us how strong love can be. Yeah, sure, you’re ambassadors for our community and visibility is everything these days, but you’re also just two humans with a great joy to share and who doesn’t want to be around that.

And if you want to be around that, take a drive across the Everglades some weekend and see they Boys at the end of line on Route 29. 

2 thoughts on “Gay Travel & Gay Love Can Happen In A Small Town. Cue The Music”

  1. Love this article SOOOOO much! Aaron is my cousin. I just moved to Florida from San Diego and look forward to visiting and connecting with my family. I am so happy to see that Aaron & David are getting some great acknowledgement…Wonderful article!
    Peace & Love !


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