The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

Rent a local Key West

Rent a local: What better way to get to know Key West?

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


Earlier this week, Ranger Ed and I did happy hour at The Grand Cafe on Duval with two visitors who’d never been to Key West. They were winding up a four-day “introductory course” to the island a bit foot sore and weary and primed for a return trip.

I’m a sucker for listening to first-time Key West visitors. They never start a sentence with “well, it’s certainly not what it used to be …” First timers are lovers in bloom. Every picket fence is a joy; the chickens worthy of a point-and-shoot (camera, not gun; I knew some of you would ask); and, they look right past a shop worn store front, a pothole or an iguana with hibiscus on his brain and poop on the sidewalk.

We asked these first timers what they expected before arrival and what they actually experienced: First a pause and then a tumble of wonder that Key West is so much more than the lower end of Duval; that the arts, history and architecture are so wholly unexpected based on the world-wide reputation for drinking and carousing; that, well, there are so many stories behind the Key West Mystique.

They’d expected an island resort catering to water sports, eating and drinking, walking around, shopping and most definitely beaches. (We took a sidebar moment to talk about “there are no natural, sandy beaches in Key West because of the reef, etc., and no one ever tells visitors beforehand. And, yes, you really do need water shoes.)

They found all that of course. It was when I asked what surprised them the most that we got an earful about not knowing all the “real” things about Key West.

Happy hour at the Grand Cafe Key West
Happy hour at The Grand Cafe in Key West

“Tonight was our best night, because we got to hear the back stories and the history from locals. Wouldn’t it be great if everyone new to the island could have a happy hour with a couple of locals as part of their trip?”

I joked, “you mean, sort of like rent-a-local”? But, the more I think about it, there’s no reason rent-a-local couldn’t be the seed for a significant business model. (Someone has to come up with a better marketing name, but you ought keep that “rent-a-local” thing because that’s what everyone will call it anyway.)

How would Key West Rent-a-Local work?

The mission is simple: Connect like-minded visitors to local hosts knowledgeable in history, arts, culture and architecture for an opportunity to enjoy each other’s company and learn more about the island. (Heck, I suspect locals and snowbirds would ante-up, too.)

It might work like this: A couple visiting Key West is interested in Key West architecture. Rent-a-Local connects those visitors to specific hosts and experts on the island for a one-on-one get-to-know-you: an architect or someone from HARC or one of our architectural and historical walking tour experts. Or how about a package of Florida Keys trees, plants and eco-systems? Or a military history package? We’d be limited only by our imaginations.

Heck, we could pick the local hosts from the City of Key West’s Ambassador Program. Everybody who is, was or wanted to be in the know has been through those classes and would make great hosts. Ambassadors can even make the wastewater treatment plant sound interesting. But I digress.

Rent-a-Local puts together packages that include that happy hour or lunch with a local expert or host and a day or several days of already existing local tours and lectures. There’s no shortage of exceptional experts, nor of organizations, venues and not-for-profits already providing programs and entertainment. Rent-a-Local pays a flat fee stipend to the host to cover the time, food, entertainment.

Locals know all these things are part of Key West. We know our theaters and galleries; we know who does the best walking tours and who does great historical programs. We know whom to call and what fundraisers are the most fun. So, it’s understandable if we are slightly affronted when we hear visitors say they don’t know much about Key West except for Duval and the ubiquitous marketing that shows beautiful beaches, clear water and a palm tree.

Despite the nose a bit askew, we know it’s true. Visitors pre-arrival aren’t seeing and hearing a comprehensive, consistent message about the other Key West, the one that so intrigued our guests this week.

More to the point, there’s no easy way to access and plan a vacation built around those things. There are concierges for snorkeling, bar hopping, restaurant dining and sunset sailing and they’ll put together a wonderful package. But if you’re looking for less sun-water-and-alcohol, you’re pretty much on your own to dig it out.

And, this wouldn’t be about creating more work for a handful of people and local organizations. The programs, venues and events are already available. There will be no shortage of locals willing to spend a couple hours with a couple of visitors –and those visitors will be happy to pay for the VIP experience. I’m not talking about asking local hosts to spend a day with strangers — though if they were willing and the price were right, go for it.

Take for instance, the “happy hour with the historian” from the Key West Arts and Historical Society. Rent-a-Local would make sure that program is in a package either as “in-person” or online. There’s no reason for KWAHS to do new stuff or for its staff to take on additional one-on-one time with visitors.

Same thing for visitors interested in “things that grow in Key West.” The Key West Garden Club and the Key West Tropical Forest & Botanical Garden are wonderful destinations to include in a package. Don’t forget a walking tour of pocket parks and the Truman Waterfront. I’m sure there are Master Gardeners who’d be willing to talk plants over cocktails with like-minded visitors.

There is only one stumbling block: Cash for marketing. And, I don’t mean a few thousand dollars on social media or some half-done email blasts. I mean professional level, target marketing to reach potential visitors who want a taste of how locals live and what we love. This new approach could be a significant help to local organizations trying already to reach this visitor audience. You keep doing what you’re doing well. Rent-a-Local coordinates the packages and local hosts that will bring visitors to you — and eventually to your fund-raising mailing and membership lists.)

So, there you have it. Someone’s going to do good for the local arts, culture, historical, environmental and not-for-profit communities — and there’s likely a tidy space for profit to be had. All I ask when it’s launched is that you let Ranger Ed and me be among the hosts — and invite our two visiting guests for the grand opening. Ed can entertain forever on Fort Zach and I like listening to people who love the island. Cat people would be a plus. What’s not to like about an occasional happy hour with new friends?

Oh. PS: I’ve shopped this idea with some locals none of whom have suggested I’m a lunatic. At least not to my face.


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