Key West, According to Sam

You know their politics. Do you know their favorite local musician?

As Key West casts its final votes, Mayor “DeeDee” Henriquez and Commissioner Sam Kaufman are approaching the point where there are only so many more policies and campaign promises they can explain before the race is called.

But amid the flurry of campaign events, social-media arguments and controversial mailers, there may still be room to learn something else about the candidates: where they eat, what they recommend, and how they spend their time when they’re not at City Hall.

Palm and Prejudice sent both candidates the same survey of fewer than 20 deliberately nonpolitical questions, asking about their favorite restaurants, festivals, sightseeing spots, local recommendations, and the places they return to.

The idea was simple: get a taste of Key West through two distinct personalities who have spent years serving the community and, along the way, experienced plenty of what the island has to offer.

Commissioner Kaufman's responses, published below in full, reveal a public servant whose love for Key West is as a result of diverse music tastes, embracing eclectic social circles, and maintaining a schedule that keeps him on the move through a bustling island.

Which eatery or bar do you wish more people knew about?

One place is El Siboney Restaurant. It’s a true Key West staple that is family-run, consistently great Cuban food, and the kind of place locals have loved for years. It’s authentic, welcoming, and dependable. Places like El Siboney are part of the heart of our community, and I always encourage people to check it out and support our local favorites.

What is your standard coffee order and where do you get it?

I usually go with a simple Americano. Honestly, with how busy things have been, I’m usually making it at home or in the office. But when I do get out, I like stopping by Keys Coffee Co. or Cuban Coffee Queen. It’s a great way to start the day, and I always try to support our local businesses because they’re such an important part of what makes Key West special.

What was the most honest conversation you ever had in this town that happened over food or drinks?

Over the years, both as a commissioner and as an attorney, I’ve had hundreds of honest, sometimes difficult conversations with people in this community. A lot of those happen over coffee. People open up about real issues about housing, jobs, family struggles, and concerns about City Hall. Sometimes they’re emotional, sometimes blunt, but they’re always important. Those conversations stick with me. They’re a big part of how I understand what people are going through and why I take this work so seriously.

Tell me about the last time you had a truly bad meal here. You can leave the name out or preferably say where were you, did you stay, did you say anything or just paid and left?

I honestly don’t remember having a bad meal in Key West. We’re really lucky to have so many great places here. If I ever did, I’d probably just pay and leave quietly. I’m not someone who likes to make a fuss.

If a friend is visiting for 24 hours, where are the three places you try to take them?

It’s tough to pick just three, but I’d start with the Southernmost Point Buoy. You have to do it at least once. Then I’d take them to Mallory Square for sunset, and take a stroll over to the Key West Bight. It’s one of those classic Key West experiences that never gets old.

And I’d make sure we spend some time at the beach, either Higgs Beach or just walking along the water. That’s where you really get a feel for what makes this place special.

How do you tip in Key West if you understand how the town really works? What does tipping say about a person here?

Our local economy runs on the people who serve, support, and take care of this community every day. I always tip on the higher end usually 25% or more because I know how hard people work here and how important that income is, especially with the high cost of living in Key West.

I also encourage visitors to do the same. When you come here, you’re not just enjoying the island, you’re part of the local economy. Tipping well is one of the simplest and most direct ways to support the people who make Key West what it is.

Tipping here says a lot about you. It shows respect. It shows you value the people behind the service. And it shows you understand that supporting locals isn’t just something you say, it’s something you do.

How do you avoid looking like a tourist here and what is the one mistake that immediately gives someone away?

The great thing about Key West is that you don’t have to try to fit in. Just come as you are. Everyone belongs here, and that’s what makes this place so special. If anything, the one mistake is trying too hard or treating it like just a party stop. Key West is a real community with people who care about each other. Be yourself, be respectful, and you’ll feel right at home. That’s why I love this city and feel so grateful to be here.

What is your favorite local festival?

I really enjoy Taste of Key West because it brings the community together and supports important causes. The Holiday Parade is another favorite because it’s great to see families and neighbors come out. I also love Goombay Festival and the Conch Republic Independence Celebration as they really capture the spirit of Key West: culture, history, and a community that knows how to come together and celebrate.

Is there a visual or performing artist in Key West whose work you return to? What draws you in? Where did you first encounter them?

It’s hard to pick just one because Key West has such a strong arts community. Julia [Kaufman's wife] and I really enjoy the local theater especially the shows at Waterfront Playhouse, Red Barn Theatre, and Tennessee Williams Theatre. What makes it special is the mix of talented local performers and artists who come in from outside, together they put on shows that are always high quality, entertaining, and unique.

A lot of my first experiences with local artists came just from living here going to shows, attending events, and seeing how much talent we have all around us. Key West’s commitment to the arts is one of the things that make our city so great!

If you could book one local musician or band in Key West and everyone had to listen, who would it be?

We have so much talent here, but I’d start with Tony Baltimore. He’s a great example of our local music scene, talented, engaging, and always puts on a fun show. We were also lucky to have some incredible local musicians perform at my campaign kickoff including C.W. Colt, Happy Dog, Jericho, Cayman, Jeff Clark, Izzy Zaidman, Larry Baeder and Terri White, Jess and Jill, and more. It really reminded me how much talent we have right here in Key West. And there are so many others, Caffeine Carl [who passed away after this interview], all bringing people together through music.

Which author or poet—living or dead—do you feel best captures the spirit of Key West, and why does their work still matter today?

It’s probably Ernest Hemingway. He wrote in a way that feels real, just simple, direct, and honest. That’s what reminds me of Key West. People here are genuine. They say what they mean, they look out for each other, and they don’t try to be something they’re not. His writing still matters because it reflects that kind of life appreciating the moment, the people around you, and the place you call home.

Name someone in town people would never guess you’re close to. Is there an interesting story of how that bond formed?

That’s a tough one, because one of the things I value most about Key West is how connected everyone is, you end up building relationships with people from all walks of life.

Over the years, I’ve gotten close with people I probably wouldn’t have met anywhere else, whether through my work as an attorney or serving in city government. A lot of those relationships started with a simple conversations sometimes over coffee, sometimes helping someone through a difficult situation and grew from there.

That’s what makes Key West special. It’s a small town where real connections form in unexpected ways, and those relationships stick with you.

How do you keep a secret in a town that runs on them?

You keep it by respecting people.

Key West may feel like a small town where everyone knows everything, but trust still matters. Whether it’s in my work as an attorney or in city government, people come to you with things they expect to stay private and you honor that.

At the same time, there’s a difference between personal trust and public responsibility. When it comes to government, decisions should be made in the sunshine, openly and transparently.

At the end of the day, your reputation is everything here. If people know they can trust you and that you’re honest about how decisions are made, that’s what really matters.

What do you think about people who clap for the sunset?

I think it’s great. It’s a reminder of how much people truly enjoy being in Key West. Visitors come here to experience something special, and that moment just watching the sunset and appreciating it together really captures that feeling. It may seem simple, but it shows how much this place means to people. And as locals, we’re lucky to live somewhere that brings that kind of joy to others every day.

What is one thing you regularly do to keep the weirdness of Key West alive?

I think the best way to keep the “weirdness” of Key West alive is to encourage people to be their authentic selves. Key West has always been a place where people feel free to express who they are, and it’s important we protect that. I try to lead by making sure people feel welcome, respected, and comfortable being themselves.

If we keep that spirit - open, inclusive, and a little different, that’s what keeps Key West special.

If someone asked whether Key West is truly “for everyone,” what’s the honest response?

Yes! Key West is for everyone.

That’s been part of who we are for a long time. People come here from all walks of life, and what makes this place special is that you can be yourself and feel accepted.

But we can’t take that for granted. It’s something we have to keep protecting by making sure people feel welcome, respected, and safe.

I also hear from people who feel let down by the current administration at City Hall. That matters. Everyone should feel welcome not just in our community, but in their own City Hall. That’s a big part of why I’m running to restore that sense of trust and make sure everyone feels heard and included again.

That’s what “One Human Family” really means, and it’s something I believe in and will always stand up for.

If Key West could talk back to you, what do you think it would say about the choices you’re making for it and about who you are in this town?

I think Key West would say: keep showing up, keep listening, and keep doing what’s right.

This is a community that values honesty, independence, and people who are willing to stand up when it matters. I’ve tried to do that and sometimes it’s not easy, but it’s important.

And I think it would also say: don’t forget who you’re doing this for. This town is about people. Families, workers, small businesses, and neighbors who care about each other. If I stay focused on that, being honest, listening, and putting the community first then I’m making the right choices for Key West.