Beards, bulls, and the best week of summer in Key West 🧔‍♂️

Hemingway Days is coming, plus the rise and fall of the island's cigar empire.

Author

Florida Keys Road Trip
July 14, 2026

Welcome to another week on the Overseas Highway! 

We are officially in the thick of summer, which means the water is warm, the days are long, and the island chain is buzzing with energy.

This week, we are looking ahead to one of Key West's most iconic and eccentric celebrations: Hemingway Days. Whether you are a literary buff, a fishing enthusiast, or just someone who appreciates a good beard, this is a week you won't want to miss. We are also diving into the fascinating history of Key West's cigar industry, a booming era that once made the island the wealthiest city in Florida.

Grab a cold drink, find some shade, and let's get into it.

🧠 TRIVIA TIME

What Guinness World Record does a Lower Keys elementary school hold?

(Answer at the bottom of the newsletter)

📰 MILE MARKER ROUNDUP

Hilton Key West Resort & Marina Opens on Stock Island

A brand new resort property officially opened its doors on July 1, bringing a fresh waterfront option to the increasingly popular Stock Island area.

Coast Guard Rescues Overdue Diver Off Key Largo

A timely reminder of water safety: the U.S. Coast Guard successfully rescued a diver who was reported overdue off the coast of Key Largo on July 11.

16,000 Corals Returned to Keys Reefs

In a massive conservation effort, the Coral Restoration Foundation has successfully returned 16,000 corals to ten different reef sites as part of Mission: Iconic Reefs.

45th Annual Key West Marlin Tournament Approaches

Coinciding with Hemingway Days, this prestigious fishing tournament runs July 22-25, drawing anglers from all over to chase the elusive blue marlin.

🤝 PARTNER SPOTLIGHT

Beat the Summer Heat — A Keys Survival Guide

July in the Florida Keys is beautiful, but it is undeniably hot. To make the most of your summer trip, you need a strategy. The secret is all about timing. Plan your outdoor adventures—like kayaking, paddleboarding, or snorkeling—for the early morning hours before 10:00 AM, when the water is glassy and the temperatures are still tolerable.

When the midday sun hits its peak, retreat indoors. This is the perfect time to explore air-conditioned attractions like the Key West Butterfly & Nature Conservatory, the Florida Keys Eco-Discovery Center, or the History of Diving Museum in Islamorada. Embrace the daily 3:00 PM rain shower as a natural cool-down; it is the ideal excuse to duck into a waterfront bar for a quick refreshment. Once the sun begins to set, the islands come alive again, perfect for sunset celebrations or even a night kayaking tour to see the bioluminescence.

2025 Pictures with the Bulls and the Hemingway Look-A-Likes

📖 DEEP DIVE: Hemingway Days 2026

If you happen to be in Key West during the last week of July, you might think you are seeing double. Or triple. Or a hundred times over. That is because the 45th Annual Hemingway Days festival is taking over the island from July 22 through July 26, bringing with it a tidal wave of white beards, khaki safari shirts, and literary enthusiasm.

Ernest Hemingway lived in Key West from 1931 to 1939, a highly productive period during which he wrote "To Have and Have Not" and portions of "For Whom the Bell Tolls." The island left an indelible mark on the author, and today, the island returns the favor with a five-day celebration of his life, work, and sporting passions.

The undisputed highlight of the week is the Hemingway Look-Alike Contest, held at Sloppy Joe's Bar—Papa's favorite watering hole. Over a hundred stocky, white-bearded hopefuls take the stage across multiple nights, vying for the coveted title of "Papa." The competition is fierce, but the camaraderie is genuine, with past winners returning to judge the new crop of contestants.

But the festival is not just about looking the part. The schedule is packed with events that honor Hemingway's diverse interests. On Friday, July 25, the Conch Republic Seafood Co. docks host Papa's Fish-Off, where competitors cast lines using traditional Cuban Yo-Yos (hand lines). Later that evening, athletes will gather for the Hemingway 5K Sunset Run. Saturday brings the Caribbean Street Fair to Duval Street, followed by the delightfully absurd Running of the Bulls, featuring wooden bulls and costumed Papas parading through downtown. It is a uniquely Key West spectacle that perfectly captures the island's irreverent spirit.

🏴‍☠️ LORE & LEGENDS: The Rise and Fall of Key West's Cigar Empire

Long before it was a tourist mecca, Key West was an industrial powerhouse. In the late 19th century, the island was the undisputed "Cigar Capital of the World," a booming hub of tobacco and trade that made it the largest and wealthiest city in Florida.

The story begins in 1831, when William Wall, a shipwreck survivor who had washed ashore a few years earlier, opened the island's first large-scale cigar factory. But the industry truly exploded during Cuba's Ten Years' War (1868–1878). Fleeing the conflict, thousands of Cuban refugees made the short journey across the Florida Straits to Key West. Among them were highly skilled torcedores (cigar rollers) who brought their craft, culture, and traditions to the island.

By 1890, this one-by-three-mile island was home to an astonishing 200 cigar factories. Nearly 80 percent of the 18,000 residents were involved in the industry, producing up to 100 million cigars annually. The factories themselves were marvels of the era, designed with large north-facing windows to catch the breeze and illuminate the work floors.

Perhaps the most fascinating aspect of this era was the tradition of the "lector." Because the work of rolling cigars was tedious and repetitive, the workers pooled their own wages to hire a reader. Sitting on an elevated platform above the factory floor, the lector would read aloud for hours—everything from daily newspapers and classic novels to fiery political tracts. This unique practice made Key West's cigar workers some of the most educated and politically informed laborers in America.

The empire, however, was not meant to last. The Great Fire of 1886 devastated the city, destroying 11 factories and much of the downtown area. While the industry briefly recovered, ongoing labor strikes and unionization conflicts eventually drove the major factory owners away. Vicente Martinez Ybor relocated his operations to Tampa, founding Ybor City, which soon claimed the title of Cigar Capital. By 1931, the last of the large factories in Key West had closed its doors. Today, only a few of the massive brick and concrete factory buildings remain, standing as quiet monuments to the era when Key West was built on smoke and leaves.

🧠 TRIVIA ANSWER

In 2019, 887 people simultaneously performed the Baby Shark dance at Sugarloaf School, setting a new Guinness World Record.

Keep your windows down and your watch off.

The Florida Keys Road Trip Team

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