Discover Roosters, Rum & Coastal Charm

Written By Jennifer Rogers

Your Guide for Getting to Know Key West

Have you ever seen the movie Knight and Day? There’s a memorable moment at the end of the movie where Cameron Diaz’ character June turns to Tom Cruise’s character Roy and asks, “are you with me, or without me, with me, without me?” Seconds later, they’re flying down a narrow road in a convertible - hair flying freely in the wind - heading south to the tip of the continent at Cape Horn. It’s the kind of romantic scene that sparks instant wanderlust.

Key West is the Atlantic’s own version of that “end of the road” moment. Tucked away at the southernmost tip of the Florida Keys, it’s where Highway 1 collides with turquoise waters and the slow rhythm of island life - nowhere left to go.

Key West is an island made of coral rock, with a rugged shoreline where mangroves meet the sea and sunsets paint the sky. Its beaches are not the typical white sand beaches you expect from Florida. Rather, they are more secluded, tucked into coves, unspoiled, intimate, and private.

The island is equally well-known for its lively nightlife and historic residents. Located at the center of it all is the iconic Duval Street - a mile-long stretch of quirky dive bars, historic buildings and neon signs. Here, you will find the legendary watering hole Sloppy Joe’s that Ernest Hemingway once frequented drinking whiskey and rum, swapping stories.

But Hemingway wasn’t its only famous resident. Key West was also home to Tennessee Williams, author of a Street Car Named Desire and Cat on a Hot Tin Roof, four-time Pulitzer Prize winner Robert Frost, and Jimmy Buffet who found inspiration for many of his songs here. Even President Harry S. Truman was a short-term resident, spending many months of his presidency at a spot now known as the Little White House.

TABLE OF CONTENTS

GETTING THERE

Key West sits at the very tip of the Florida Keys where the Gulf of Mexico and Atlantic collide. It is the southern most island in the chain and the southernmost point of the continental U.S. In fact, it’s just 90 miles from Cuba which is why it became a natural refuge for so many Cuban exiles, cigar makers, and revolutionaries whose influence left a lasting mark on its rich cultural history.

Closest Airport: The closest airport to Key West is the Key West International Airport (EYW) located just a few miles from downtown. The airport is very convenient but also very small so flights can be expensive and limited.

Another popular option is to fly into Miami, rent a car and drive the Keys. The scenic journey down the Overseas Highway (Route 1) is truly breathtaking. The stunning 113-mile route crosses over 40 bridges connecting the islands of the Florida Keys together. Much of the way, you will be surrounded on both sides by panormaic views of turquoise water making it a lasting, memorable experience. The drive takes approximatley 3-1/2 to 4 hours, but is worth it if you have the time.

KNOW BEFORE YOU GO

Before you pack your bags and start your journey, here are a few key things to keep in mind.

  • If flying to Key West, you may want to avoid renting a car. Getting from the airport to downtown is easy and most of the island is walkable. Parking is limited and expensive.

  • Transportation from the aiport includes car rentals, taxi service, rideshares like Uber and Lyft, and companies that deliver scooter and bicycle rentals.

  • Pre-book airport transportation ahead of time to avoid long wait times.

  • Bikes and scooters are great options for getting around once on the island since traffic gets congested and parking is limited. You can also rent golf carts which helps with parking and navigating narrow streets.

  • There is a bus/trolley loop that operates around Duval Street.

  • Pack casual attire. Flip-flops and casual wear are acceptable pretty much everywhere. If you make a dinner reservation, ask about the dress code just in case.

  • Key West is more expensive than mainland Florida especially during peak season in winter and spring so budget accordingly.

  • Visiting during “shoulder season” (September/October) is typically less expensive but prepare for more rain.

  • Embrace the island time vibe as things move at a much slower, relaxed pace here including service and traffic.

  • Drink plenty of water as the tropical climate (and those cute umbrella adorned cocktails) can easily leave you dehydrated.

  • Although Key West is pretty safe, keep an eye on belongings just like you would any other crowded, tourist town.

Weather & Climate - Key West tends to be warm and tropical all year round, but here are some things to keep in mind:

  • Summers can be very humid making the heat more intense. Day time temps usually get up into the mid-80s to low-90s.

  • Summmers can also be very wet. Key West gets quite a bit of rain from June to November, and occasional thunderstorms are common.

  • The busiest times to visit are winter and early spring (December through April) due to perfect sunny and dry weather.

  • Hurricane season runs from June to November.

WHERE TO STAY

Hyatt Centric Key West Resort & Spa

A Hidden Waterfront Oasis - located at 601 Front Street, Key West, Florida.

Located right at the waterfront in Old Town Key West, the Hyatt Centric Key West Resort & Spa is the ideal spot to stay. With views of the Gulf and adourned in traditional Key West style - think tin roofs, pastel-hued architecture, white patios, and tropical accents - it offers exactly what you are looking for during your stay.

It is located on Front Street, just off Duval steps from Mallory Square and everywhere else you want to be.

This boutique hotel offers about 120 comfortable, tastefully decorated rooms each with its own private balcony, many of which have an ocean view. The rooms are spacious and private.

Here are just a few of the room amenities:

  • Private balconies or patios

  • Bath robes

  • Keurig coffee makers with pods

  • Mini Fridges

  • Big screen TVs with streaming services like Google Stream and On Demand

  • Daily housekeeping

  • In-guestroom Peloton rentals.

  • Air conditioning and ceiling fans

  • High-speed internet

  • Games and books for guests

There is a pool for lounging with a jacuzzi, a poolside bar Blue Mojito Bar & Grill, chaise-lounges near the water and access to the shore. They have a gift shop, dry cleaning services, and a gym. There is also an incredible upscale restaurant with views of the Gulf - Four Flamingos, a Richard Blais Key West Kitchen. They even have an on-site sanctuary for rescued sea turtles.

Jala Spa at Hyatt Centric Key West Resort & Spa offers a sancturary for guests to unwind and relax with spa treatments inspired by the island’s natural elements and beauty. Below are some of the treatments offered all of which require an appointment.

  • Massages - Signature Jala, Deep Tissue, Hot Stone, Swedish, and more.

  • Facials - Anti-Aging, Pore Detox, Microdermabrasion, and more.

  • Body Treatments - After Sun Rescue Treatment, Island Glow, Anti-Aging, Nourishing, and more.

  • Enhancements like CBD, hot oil scalp massage, eye treatment, lip exfoliation, waxing, and more.

The resort also offers concierge services to help you plan your days with access to numerous excursions including:

  • On-site bike rentals (complimentary with some packages).

  • On-site golf cart rentals.

  • Sunday yoga.

  • Jet ski rentals at the property.

  • Excursions and curated experiences like sunset cruises, diving experiences, and fishing charters, most of which conveniently pick you up right at the property like Sea Monkey Charters.

THINGS TO DO

Key West is a thriving and vibrant island community with an endless list of things to do. Whether you’re seeking outdoor adventures like snorkeling and fishing, bar-hopping along lively Duval Street, or wandering through art galleries and historic sites like the Ernest Hemingway House, there’s something here for everyone. And when you’re ready to slow down, grab a colorful cocktail adorned with a tiny umbrella and take in the iconic Key West sunsets - some of the most unforgettable in the world!

Hemingway House & Museum - Ernest Hemingway called Key West home for nearly a decade. Today, visitors can tour his well preserved home including the upstairs loft where he wrote some of his most famous works including portions of A Farewell to Arms and other notable titles. The home is filled with historic photographs and personal artificats that offer a glimpse into his life and adventerous spirit.

While here, you will undoubtedley encounter descendants of Hemingway’s six-toed cat. Dozens of these charming polydactly residents, descendants of Hemingway’s original pet cat Snow White, roam the property freely and are taken care of by a dedicated team of staff including a full-time veterinarian.

In the garden near the pool, take a close look at the ground and you might spot a famous penny embedded in the concrete. As the legend goes, Hemingway got into a heated argument with his wife Pauline over the cost of the pool, throwing it down in frustration exclaiming, “you might as well take my last damn cent!” - and its been there ever since.

Mel Fisher Maritime Museum - Located in the heart of Old Town Key West, the Mel Fisher Maritime Museum offers a captivating glimpse into the world of shipwrecks and sunken treasure.

Legendary treasure hunter Mel Fisher spent 16 relentless years searching for the wreck of the Spanish galleon Nuestra Senora de Atocha, finally striking gold quite literally in 1985. Today, visitors can explore a remarkable collection of gold bars, silver coins, ancient weapons, sparkling jewels, and other artificats from this and other wrecks as they tour this fascinating museum and learn the captivating history behind each treasure.

Duval Street - No trip to Key West would be complete without taking a walk down legendary Duval Street and its neighboring streets, home to some of the most iconic bars in the country incluidng Hemingway’s old haunt Sloppy Joe’s and other dive bars like The Green Parrot (A Sunny Place for Shady People), The Speakeasy Inn & Rum Bar, Willie T’s, and Fat Tuesday. Be sure to also take a peak at The Smallest Bar, a quirky, tiny space to grab a drink.

Key West Lighthouse & Keeper’s Quarters Museum - Located across the street, just steps away from the Hemingway House, is the Key West Lighthouse. Climb the 88 steps to the top of this 1800s lighthouse for a stunning panoramic bird’s eye view of the island off an observation deck.

Today, the lighthouse also serves as a charming little museum honoring the island’s maritime heritage. Exhibits include nautical tools, historic photos, and personal items belonging to past keepers of the lighthouse.

Mallory Square - Set along the waterfront, this iconic square is a vibrant market featuring open-air booths with local artisans selling handmade arts and crafts, along with boutique shops and souvenir stands. Street performers add to the lively atmosphere and each night, the square comes to life around sunset as it offers a phenomenal view of the sun setting over the Gulf.

Key West Aquarium - The Key West Aquarium, the island’s only aquarium, opened its doors in 1935, and remains one of the oldest aquariums in Florida. Here you will find large tanks full of tropical fish, sharks, eels, jellyfish, and even sea turtles. There is a hands-on touch tank filled with conchs, horseshoe crabs, sea cucumbers, urchins, and starfish. They also feature live shark and stingray feedings and a special exhibit dedicated to caring for injured sea turtles.

The Truman Little White House - This state historic site served as the winter home of President Harry S. Truman during his presidency between 1946 to 1952, and was later visited by several other presidents. Today, it operates as a museum offering a rare glimpse into the personal, intimate workspace of a sitting U.S. President. Guided tours, VIP tours, and other packages are availalbe to visitors allowing them to explore the home and its history.

Butterfly & Nature Conservatory - The Key West Butterfly & Nature Conservatory houses over 50 species of free-flying butterflies from across the globe alongside over 20 exotic birds in a glass-dome tropical habitat. Visitors can enjoy vibrant pink flamingos, flowering plants, and soothing waterfalls in a tranquil, peaceful setting.

Fort Zachary Taylor Historic State Park - This Civil War-Era fort offers an intriguing look into 19th century military history and architecture. Visitors can explore at their own pace with self-guided tours or join a guided tour offering insights into the fort’s rich history.

Fishing Charters - You don’t need to be a sesasoned angler to enjoy a day out on the water. Guided fishing trips are availabe for all skill levels, offering a chance to to fish in crystal-clear turquoise waters for tarpon, snapper, grouper, and more.

Sunset Cruises - Key West is an incredible place to experience a susnet cruise aboard a catamaran or schooner. Whether you’re seeking a quiet, romantic evening or a more lively celebration, there’s variety of options to choose from.

With its perfect weather, Key West offers an endless list of outdoor adventures and ways to get outdoors and explore including:

  • Snorkeling

  • Diving

  • Parasailing

  • Jet Skiing

  • Kayaking & Stand-Up Paddleboarding

  • Bike Rentals

  • Scooter Rentals

  • Sandbar Boat Charters with Sea Monkey

Ghost Tours - Key West offers historic ghost tours that take you to famous haunted spots like the Oldest House, the Key West Cemetery, and haunted inns known for paranormal activity. Guides share chilling stories about restless spirits and legendary figures. Choose from walking tours, trolley rides, and ghost cruises on the water.

Southernmost Point - No trip to Key West would be complete without a visit to the island’s most iconic landmark - the Southernmost Point. This popular photo spot for tourists is just 90 miles from Cuba and is the southern most point of the continental U.S.

This is also home to the Southernmost Beach and Cafe where you can grab a cold drink and a snack while visiting.

BEST DAY TRIP

Dry Tortugas National Park - Located 70 miles west of Key West where the Gulf of Mexico meets both the Atlantic Ocean and Caribbean Sea is one of the most remote and rewarding national parks in the U.S. - Dry Tortugas National Park. Just getting there is an adventure. You can only reach it by seaplane or a ferry ride offering sightings of giant sea turtles, huge spotted stingrays, and jelly fish drifting just below the surface.

What’s unique about Dry Tortugas is that over 95% of the park’s 100 square miles lies beneath crystal-clear turquoise waters teeming with marine life. It is a sanctuary for sea turtles and an incredible spot to snorkel, dive, or just relax on the beach.

At the heart of the park, lies Fort Jefferson, a 19th century fortress that once protected the Gulf of Mexico shipping lanes with a long history.

Long before it was a national park, the remote islands of Dry Tortugas held a legendary place in history. Named for the abundant “tortugas” (Spanish for turtles) found here, the islands became famous for being a hideout for notorious pirates of the 17th and 18th century who launched raids from the island on Spanish treasure fleets. The surrounding treacherous coral reefs and frequent hurricanes also made the Dry Tortugas a hotspot for shipwrecks, adding to its storied past.

RESTAURANTS & BARS

Key West is well-known for its vibrant bars and is world-famous restaurant culture. Here’s a quick guide on the best spots.

Best Coffee & Breakfast Spots:

Best Lunch Spots:

  • Pan Am / First Flight Island Restaurant & Brewery

  • Schooner Wharf Bar

  • Blue Heaven

  • 5 Brothers Grocery & Sandwich Shop

  • Ana’s Cuban Shop

Best Spots for Dinner:

Best Bars in Key West:

GREAT SUNSET SPOTS

There are so many incredible spots to watch the sunset in Key West. Below are just a few of the more popular ones. Be sure to arrive early to pick your front row seat especially at the more crowded spots like Mallory Square and Sunset Pier.

  • Mallory Square

  • Fort Zachary Taylor Historic Park

  • Latitudes on Sunset Key

  • Higgs Beach Pier

  • Sunset Pier

  • White Street Pier

  • Any sunset cruise

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Jennifer Rogers
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