OFF THE PATH KEY – WEST’S SOUTHERNMOST HOUSE IS MORE THAN A MANSION - A group of people walking in front of a building - Palm trees
Southernmost House owner and operator Michael Halpern recently converted the southernmost, 1400 block of Duval Street into a public plaza that soon will feature outdoor table seating for the Southernmost House’s new Seaside Café as well as the Southernmost Beach Café on the other side of the plaza. MANDY MILES / Keys Weekly

During the seasonal changes of October, the Keys Weekly will explore less-traveled outdoor escapes often overlooked by locals and tourists here in the Florida Keys. From Card Sound Road to the Southernmost Point, the Keys offer a spectacular collection of miraculous nature trails, parks and outdoor wonders that rarely make the mainstream to-do lists on TripAdvisor and Google. For those looking for an escape within the escape, this series offers an insider’s guide to some of the less-traveled and unique destinations near your front door. So invoke your inner Robert Frost and take a turn “off the path.” 

Southernmost House – More than a Mansion

Sure, we all know the Southernmost House as the stately pink mansion at the southern end of Key West’s Duval Street. The 1896 home once featured a single bedroom on the second floor, but now has nine hotel rooms inside, four cabanas outside lining the zero-entry pool and five rooms across the street in The Original Lopez House.

But not everyone is aware of the new pedestrian plaza that recently replaced the 1400 block of Duval Street out front, where planters, outdoor sculptures and tables soon will welcome weary visitors and hungry diners.

In addition to the new plaza, the mansion doubles as a museum, boasting a significant collection of historical documents.

“We have a collection, all in one room, of eight original letters signed by Ernest Hemingway,” said general manager Monroe Holloway. “My favorite Hemingway letter is the one addressed to the Museum of Modern Art in New York City that encloses his annual dues and asks the MoMA to change his address to Whitehead Street in Key West.” 

In addition to the Hemingway room, in the lobby of the Southernmost House hangs an oath of office that Lyndon B. Johnson signed aboard Air Force One to become president of the United States following the assassination of President John F. Kennedy. There were three such oaths signed on that fateful day. One of them made its way to the Southernmost City.

Monroe Holloway, general manager of the Southernmost House, demonstrates a working phonograph made by Thomas Edison that is on display at the Key West mansion that boasts a significant collection of historical documents and artifacts. The property also features the Seaside Cafe food truck with outdoor seating and access to an adjacent public beach and a public pedestrian plaza that recently replaced the southernmost block of Duval Street. MANDY MILES / Keys Weekly

The museum also has on display a working phonograph built by Thomas Edison.

And finally, there’s the food truck.

OFF THE PATH KEY – WEST’S SOUTHERNMOST HOUSE IS MORE THAN A MANSION - A group of people sitting at a bus stop - Palm trees
The relatively new Seaside Café is a food truck that’s located at the Southernmost House. Chef Rafe Halpern has curated and created a menu that satisfies every taste. There’s a salad, coconut shrimp, conch fritters, truffle fries and pizzas that have been described as the “best in town.” But don’t leave without trying Chef Rafe’s lobster salad on his honey butter biscuits. Oh. My. God. MANDY MILES/Keys Weekly

Seaside Café opened just a few months ago, but Chef Rafe Halpern has already captivated a loyal local following with his wood-fired pizza, truffle fries and lobster salad on honey butter biscuits. 

Combining history, honey butter biscuits, a pedestrian hangout and decadent hotel, have a new look at an old favorite.

Mandy Miles drops stuff, breaks things and falls down more than any adult should. An award-winning writer, reporter and columnist, she's been stringing words together in Key West since 1998. "Local news is crucial," she says. "It informs and connects a community. It prompts conversation. It gets people involved, holds people accountable. The Keys Weekly takes its responsibility seriously. Our owners are raising families in Key West & Marathon. Our writers live in the communities we cover - Key West, Marathon & the Upper Keys. We respect our readers. We question our leaders. We believe in the Florida Keys community. And we like to have a good time." Mandy's married to a saintly — and handy — fishing captain, and can't imagine living anywhere else.