Some people know the Florida Keys from the highway. The Howerton Group knows them from the water — from the seat of a bike at dawn, from the bow of a boat at golden hour, from a sandbar so quiet you can hear the tide. For this family-led team at Brenda Donnelly Real Estate, island living isn’t a destination. It’s a daily rhythm they’ve built their lives around.
In our ongoing series introducing the people behind the brand, we asked The Howerton Group to share the spots, rituals, and hidden corners that make the Keys home. Consider it an insider’s map — drawn not from a guidebook, but from a life genuinely lived on the water.
Their Go-To Dish
The team loves all the fresh local fish the Keys have to offer, but their go-to is the fried shrimp platter at Square Grouper. It’s the kind of unfussy, perfectly done island fare that tastes even better with salt air and a view.
Where the Atmosphere’s Just Right
For ambiance, a favorite is the front patio at MoonDog — though there’s also an inside space and a back patio to choose from. Eclectic, fun, and full of great people-watching, with food they call amazing. It’s exactly the kind of easy, characterful spot that captures the Keys’ unpretentious charm.
A Hidden Corner Most Visitors Miss
One of the team’s favorite quiet pleasures is a bike ride down South Street at night — heading from White Street toward New Town. There’s no traffic, just stillness and a string of gorgeous homes glowing softly in the dark. It’s a side of the island most visitors never slow down enough to see.
A Morning Ritual Worth Waking For
Mornings often begin on two wheels, biking to a favorite coffee spot, Frenchies — a small, intimate place tucked off the beaten path. It’s the kind of unhurried start that sets the right tone for an island day.
The Architecture They Love
Architecture is a big part of why this team fell in love with Key West. It feels like stepping back in time. What they love most are the gates and front doors — the entryway to a home. There’s something about that first threshold that tells you the whole story of a house before you ever step inside.
Where They Shop
A favorite stop is Key West Aloe, where the products earn high marks — the sunscreen above all. For a team that spends as much time on the water as this one does, it’s a fitting choice: local, dependable, and made for life under the island sun.
A Neighborhood Built for the Water
A favorite waterfront community is Jolly Roger on Little Torch Key — all-waterfront lots that sit remarkably close to open water and the Gulf, with no bridges in the way. For a boater, that’s the dream: easy, consistent access and amazing boating right from the dock. It’s the rare neighborhood built entirely around life on the water.
Dining by Boat
Ask the team about the perfect waterfront meal arrived at by boat, and the answer is Geiger Key Marina. The fish-camp vibe is pure old Key West — easy docking, a great atmosphere, and live music. It’s the kind of place that reminds you why the slow, salty side of the Keys is so worth protecting.
A Sandbar Worth the Trip
And then there’s the favorite escape of all: Content Keys. Heaven on earth, they call it — the bluest water, sand as soft as flour, and a quiet you rarely find, with few other boaters around. Best of all, it’s a short cruise from the dock. It’s the kind of place that makes the case for waterfront living all on its own.
Find Your Place in the Keys
The Howerton Group’s Keys are ones of open water, quiet sandbars, and homes that begin with a beautiful front door — the kind of life that turns a property into a place you never want to leave. Backed by the team’s combined strengths in presentation, negotiation, construction insight, and attentive coordination, they help clients see both the lifestyle and the practical realities behind every waterfront move.
If you’re dreaming of your own place on the water — in Little Torch Key, Key West, or anywhere across the Florida Keys — The Howerton Group would love to help you find it.
Reach out today to begin the conversation — and let us help you find your place on the water.
About The Howerton Group
Together, Michelle, Wil, and Sam operate as The Howerton Group, a family-led real estate practice grounded in trust, continuity, and a shared commitment to client care. Their combined strengths — strategic presentation and negotiation, construction and infrastructure insight, and attentive transaction coordination — provide clients with well-rounded guidance at every stage of the process.
This integrated approach ensures clarity, responsiveness, and practical expertise, supporting informed decisions and a seamless real estate experience throughout the Florida Keys.