Sea captains, sportsmen, cigar magnates, artists, adventurers, authors, politicians, rumrunners — a cross section of the swashbuckling men who helped shape modern-day Key West, the quirky outpost at the Southernmost Point of the continental United States that feels like another world entirely. The Florida Keys destination ranks among the country’s most exotic tropical escape hatches, with plenty of luxury hotels and resorts to choose from. For a charming, authentic stay that evokes the days of Hemingway and Bob Dylan, the Key West Historic Inns collection is second to none.
This assemblage of historic buildings in Old Town’s best neighborhoods are living chronicles of the island’s colorful past, each telling stories of the adventurous types who once roamed these same streets. They offer an intimate alternative to big-brand resorts while preserving the area’s architectural and cultural heritage. And you can choose the part of town that most appeals to you and what you’re looking for in Key West.
Key West Historic Inns comprises five boutique properties: Ridley House, Winslow’s Bungalows, Lighthouse Hotel, Ella’s Cottages, and Fitch Lodge, each representing different chapters of the island’s story. All have been carefully updated to preserve original architectural detail while offering modern luxury hotel amenities.
For the drive from Miami to Key West over the scenic Overseas Highway we opted for a BMW Alpina XB7, a rare $150,000-plus ultra-luxury performance SUV, courtesy of Miami’s blue-chip Braman Automotive, one of the largest and most prestigious BMW dealerships in the USA. Alpina creates exclusive, high-performance versions of BMW vehicles that emphasize refined power and style over raw aggression.
With only about 1,700 hand-built cars produced annually, each Alpina undergoes a unique process where engines are hand-assembled at Alpina’s Buchloe facility before being integrated with BMW bodies and returned for final interior upgrades. The XB7 is Alpina’s interpretation of BMW’s flagship X7 SUV—“extensively re-engineered for enthusiasts who value extraordinary speed paired with luxury.”
Departing Miami in the XB7, we basked in the allure of US Highway 1—the legendary Overseas Highway. As the Seven Mile Bridge unfolded before us, the XB7’s 631-horsepower V-8 delivered effortless acceleration while the hand-stitched Lavalina leather cabin and adaptive air suspension kept the journey supremely comfortable. The glass-roofed interior framed stunning views on both sides as we passed through the legendary Keys.
“The BMW Alpina is for drivers who truly appreciate performance and craftsmanship,” Alex Shack, Chief Operating Officer of Braman Automotive, tells us. “The XB7 strikes a rare balance—serious speed and power, but refined and intentional. That resonates in Miami, where our clients want performance and presence, but also exclusivity. It’s a car you recognize immediately if you know what you’re looking at.”
The XB7’s Alpina-tuned 4.4-liter V-8 Bi-Turbo engine delivers 631 horsepower and 590 lb-ft of torque, accelerating from 0-60 mph in 4.1 seconds with a 180 mph top speed. It features BMW’s 48-volt mild-hybrid system paired with an 8-speed Sport Automatic transmission and all-wheel drive. Signature Alpina design elements distinguish it from standard X7 models: unique front apron with enlarged air intakes, split LED headlights with Swarovski crystals, illuminated kidney grille, and four distinctive oval exhaust pipes.
The cabin showcases hand-finished luxury with exclusive Lavalina leather upholstery, intricate hand-stitching, an Alpina-designed digital instrument cluster, and a glass iDrive controller engraved with the Alpina logo. Options include six-seat configuration with electric captain’s chairs, Sky Lounge LED panoramic roof, extended Merino leather, and Myrtle Luxury Wood trim. Exclusive Alpina paint finishes like Alpina Blue and Green Metallic further distinguish the XB7.
Among the five Key West Historic Inns properties, Ridley House and Winslow’s Bungalows represent the collection’s most compelling contrasts. Ridley House brings serious historical credentials through its three connected buildings on Caroline Street, including a Bahamian Eyebrow Building listed on the National Registry of Historic Places. The eyebrow architectural style—where the roof extends to shade second-floor windows—represents classic “Conch Republic” construction techniques brought by Bahamian settlers in the 1800s.
The buildings date to the late 1800s and served as private residences for families who prospered during Key West’s golden age, when the island was one of America’s wealthiest cities per capita thanks to maritime salvaging and cigar manufacturing. White picket fences separate guests from the street, while interiors showcase high ceilings, original woodwork, and architectural details from that golden era. The location puts guests in a quiet residential pocket while remaining steps from bustling Duval Street and Old Town’s galleries, restaurants, and various attractions.
Winslow’s Bungalows sits in Old Town’s vibrant center on Truman Avenue, steps from Duval Street. The property occupies multiple historic structures built in the late 19th and early 20th centuries that transitioned to hospitality use as Key West reinvented itself following cigar manufacturing’s decline and the Overseas Railroad’s 1912 arrival, which opened the island to mainland visitors.
This resort-like property features unique rooms across numerous compounds with three pools and a poolside bar. Buildings cluster around pools and pathways where tropical plants fill every space. Where Ridley House whispers quiet charm, Winslow’s creates a social atmosphere where guests naturally congregate. The proximity to Duval Street makes it the collection’s most convenient base for first-timers who want to experience everything Key West offers, from dive bars to fine dining and everything in between.
Travelers planning multiple Key West nights might choose Winslow’s for a social, resort-style visit, then move on to Ridley House for a quieter, historically focused experience. First-time visitors can choose based on proximity to priorities—Lighthouse Hotel for museums and landmarks like the Hemingway House, Fitch Lodge for seaport access, Winslow’s for Duval Street nightlife, or Ridley House for architectural significance.
Old Town’s walkable scale makes the collection’s various locations practical. The distance between properties ranges from a few blocks to maybe a mile, all easily covered on foot, by bicycle—or BMW. Miami is known for its impressive array of supercars and ultra-luxe rides, and most of them come from Braman Automotive, which caters to celebrities of all stripes as well as the well-heeled and enthusiasts of beautiful automotive art. Although it showcases several of the best luxury brands, BMW is one of its top marques, embodying as it does the perfect blend of pedigree, design and driving thrills.
With over 20 strategically-positioned locations in the area and annual sales exceeding 40,000 vehicles, Braman “has established itself as more than a dealership—it’s a gateway to the world’s most coveted automobiles,” the company notes. As Miami’s exclusive authorized dealer for many elite marques including BMW, it’s the ultimate sign of success when a client receives the keys to a new six-figure piece of automotive art. And there’s no better way to test out your new wheels than with a jaunt down the Overseas Highway to one of Key West Historic Inns’ picture-perfect places to stay.
