Enjoy Key West and the Florida Keys
Hello Key West Travelers
Welcome to Enjoy Key West, your ultimate guide to experiencing the vibrant charm of Key West and the breathtaking beauty of the entire Florida Keys! Whether you’re dreaming of lively Duval Street nights, serene days by the beach and beautiful turquoise waters, or exploring the unique history and natural wonders of this island paradise, EnjoyKeyWest.com is here to help you plan an unforgettable adventure. Get ready to discover the best of the Keys, from delicious dining and thrilling water sports to hidden gems and iconic sunsets.
When to Visit Key West: Finding Your Sweet Spot
Forget what you think you know about high season! November often gets crowned the best month in Key West by locals, and for good reason. You’ll find minimal crowds and perfect weather, making it an ideal time to explore.
While mid-December through March is traditionally peak season, bringing heavy traffic to the Overseas Highway and Seven Mile Bridge, the period from November to mid-December offers a fantastic sweet spot. Crowds start to thin, and the weather is truly “out of this world.”
Interestingly, even with the heat and humidity, summer is becoming a second high season, especially popular with families and European travelers. So, depending on what you’re looking for, Key West has a “best” time to visit just for you!
Insider Hotel Advice & Local Insights
Planning where to stay in Key West and the Florida Keys can be a big decision, and that’s where we come in. This entire Key West and Florida Keys travel guide was designed by insiders to help you find the perfect lodging option. We’re not just online; we’re locals who know many of the Key West hotels by heart, offering unique advice you won’t find anywhere else.
Whether you’re visiting on a budget, enjoying a family vacation, or traveling to Key West for business, our “Where to Stay” section will guide you to accommodations that perfectly suit your needs. Looking for more than just a place to sleep? Our featured stories and “Related Stories” offer plenty of ideas and tips to help you get the most out of your visit to the Key West area.
Remember, to Enjoy Key West, you can book online, or for personalized recommendations, give us a call at 954-969-0069. We’re ready to share just how much we know about Key West and the Florida Keys!
Editor’s Choice to Enjoy Key West Hotels
Margaritaville Beach House Key West
2001 S Roosevelt Blvd, Key West, Florida 33040
Previously known as Sheraton Suites Key West and The Barbary Beach House, underwent an $18 million renovation before its rebranding. This Key West resort is conveniently located near the airport…
Almond Tree Inn
512 Truman Avenue, Key West, Florida 33040.
The Almond Tree Inn, your serene adults-only oasis nestled in the vibrant heart of Key West. Here, you’ll discover the perfect fusion of authentic Key West charm and sophisticated modern amenities…
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL 33040
Hyatt Key West Resort and Spa is right in the heart of Old Town Key West. From here, it’s just a short walk to the vibrant Mallory Square and the romantic Sunset Pier. Duval Street, with its lively array of shops, bars, and…
Editor’s Picks: Top 3 Key West Restaurants
Blue Heaven
729 Thomas St, Key West, FL 33040
(305) 296-8666
Blue Heaven offers a Caribbean-American cuisine menu in an unforgettable outdoor setting. Dine under canopies of trees with free-roaming chickens and cats, soaking in the truly bohemian atmosphere. They’re renowned for their spectacular brunch, featuring towering Key lime meringue pie and delicious pancakes, as well as fresh seafood and jerk chicken for lunch and dinner. Typically open daily for Breakfast, Lunch, and Dinner, though it’s always wise to check their website for current hours and live music schedules.
Latitudes
245 Front St, Key West, FL 33040 (Sunset Key Cottages)
(305) 292-5394
For an unparalleled upscale dining experience, Latitudes offers Contemporary American, Seafood, and Caribbean cuisine. Expect exquisite dishes crafted from fresh, local ingredients, served in a breathtaking oceanfront setting. Breakfast, Lunch, and Dinner daily (check their website for specific hours). Access is via a short, complimentary ferry ride, and advanced reservations are highly recommended due to its exclusive ambiance and popularity.
Santiago’s Bodega
7305, 207 Petronia St #101, Key West, FL 33040
(305) 296-7691
For a delightful and social dining experience, Santiago’s Bodega in Key West offers a globally-inspired tapas-style menu. Enjoy an array of small, flavorful plates perfect for sharing, from fresh seafood and savory meats to inventive vegetarian options. They’re open daily from 11:00 AM to 10:00 PM, serving lunch, dinner, and a popular happy hour.
Getting Around Key West: Ditch the Car!
Navigating to Enjoy Key West is all about embracing the island vibe – and that means leaving your car behind whenever possible. Scooters and bikes are the go-to for locals and savvy travelers, offering the freedom to explore at your own pace. In fact, walking is often your best bet for short distances, letting you soak in the charming streets and vibrant atmosphere.
Why the car-free push? Parking in Key West is notoriously scarce and pricey, with daily rates easily adding up. If your plan is strictly to soak up the Key West scene and stay within the island, you really don’t need a rental car at all.
However, if you’re keen on exploring the wider Florida Keys – from Islamorada to Marathon – a car becomes a necessity to truly experience the iconic Overseas Highway and all it has to offer. Just be prepared to park it once you’re back in Key West!
Key West Weather: A Tale of Two Seasons
Key West offers distinct weather experiences depending on when you visit.
Summers (June-August) are classic tropical, with average high temperatures typically in the upper 80s to low 90s Fahrenheit (30−34∘C). Expect the heat to come with higher humidity and frequent, though usually brief, afternoon thunderstorms. These tropical downpours often pass quickly, leaving behind fresh, clean air, but it’s wise to avoid driving during the heaviest parts of the storm.
Winters (December-February), however, are a true escape. Key West enjoys a consistently pleasant climate, with average temperatures hovering around 75 degrees Fahrenheit (24∘C). The humidity is significantly lower than in summer, making for incredibly comfortable days and evenings. Plus, the water temperatures remain perfect for swimming, typically in the low to mid-70s Fahrenheit (21−24∘C), meaning you can enjoy the ocean year-round.
Key West Hot Topics
Transportation
Key West is a small, walkable island, making exploration easy and enjoyable! While many of Old Town’s charming streets and attractions are best explored on foot, here are the top ways tourists get around…
Tours
Key West offers an incredible array of tours to suit every interest, whether you want to explore on land, by sea, or even dive into its more mysterious side. It’s a fantastic way to enhance your visit and discover the island’s unique charm, history, and natural beauty.
Bars
As the sun sets, Key West’s bar scene awakens, offering everything from historic pubs rich with local lore to lively open-air spots with live music. Whether you’re after a handcrafted cocktail in a quiet corner, a vibrant party, or a classic Key West experience with a cold drink, you’ll find your perfect spot.
Exploring Key West: Your Guide to Trolley Tours
One of the best ways to discover the magic of Key West, especially if you’re a first-time visitor, is by taking a trolley tour! These charming, narrated journeys offer a relaxing and informative way to see the island’s most iconic sights and delve into its unique history.
You have two excellent options for trolley-style tours in Key West, both known for their engaging experiences:
The Old Town Trolley Tour
This is your go-to if you love flexibility. The Old Town Trolley operates as a hop-on, hop-off service with numerous stops around the island. This means you can alight at any of the key attractions like the Ernest Hemingway Home, the Southernmost Point, or Mallory Square, explore at your leisure, and then simply re-board a later trolley to continue your adventure. The tour features live, entertaining narration from knowledgeable conductors who share fascinating historical facts and local anecdotes, covering a wide route that includes not just Old Town but also areas like Fort East Martello. A full loop typically takes about 90 minutes if you stay on board.
The Conch Tour Train
Step back in time with the “world-famous” Conch Tour Train, a Key West tradition since 1958. This distinctive open-air “train” primarily focuses on a comprehensive loop through the historic Old Town district. While it offers fewer hop-on, hop-off stops than the trolley, its live narration provides a detailed and charming overview of Old Town’s rich history, architecture, and quirky stories. The full, continuous ride usually lasts about 60-70 minutes, making it perfect for a concise and classic Key West sightseeing experience.
Which Tour is Right For You?
- Choose the Old Town Trolley if you want the freedom to explore many different locations at your own pace throughout the day.
- Opt for the Conch Tour Train if you prefer a quintessential Key West experience with a focused, narrated journey through the heart of Old Town.
Both tours offer an exceptional way to get acquainted with Key West, learn about its vibrant past, and pinpoint the spots you’ll want to revisit!
A Family of Florida Keys Islands
Key West
Islamoratha
Key Largo
Pine Key
Marathon
Key West
Islamoratha
Key Largo
Pine Key
Marathon
Welcome to Key West: History, Charm & Island Life
Welcome to Key West, the captivating island paradise at the southernmost tip of the continental United States. Here, turquoise waters meet a vibrant, bohemian spirit, steeped in a rich and colorful history.
Stroll along the lively Duval Street, where music fills the air, unique shops beckon, and delicious dining awaits. But beyond the vibrant facade, Key West holds a fascinating past. It was once the wealthiest city per capita in the U.S. thanks to its “wrecking” industry, salvaging treasures from the treacherous reefs.
One of Key West’s most enduring legacies is its connection to legendary author Ernest Hemingway. He made this island his home for most of the 1930s, finding inspiration for classics like “To Have and Have Not” within its laid-back charm. Visit the iconic Ernest Hemingway Home and Museum, where you can explore his former residence, writing studio, and encounter the famous six-toed cats said to be descendants of his beloved pet.
Discover stunning sunsets at Mallory Square, explore pristine coral reefs, or simply relax on a white-sand beach. Key West offers an unforgettable blend of natural beauty, cultural richness, and endless opportunities for adventure and relaxation, all wrapped in a uniquely historic package. Come experience the magic of this charming island!
Enjoy Key West Marilyn Monroe
You’re right to point that out! Key West does indeed have a famous Marilyn Monroe statue. Here’s an updated blurb that includes it:
Enjoy Key West: Marilyn Monroe
Step into the timeless allure of Hollywood’s golden age with Enjoy Key West Marilyn Monroe! This unique experience offers a captivating blend of Key West’s vibrant charm and the iconic legacy of Marilyn Monroe.
What to Expect
- Iconic Marilyn Monroe Statue: Get your camera ready! A life-size statue of Marilyn Monroe, capturing her legendary “Seven Year Itch” pose with her skirt billowing, is a must-see landmark in Key West. It’s perfectly situated in front of the Tropic Cinema on Eaton Street, making for an unforgettable photo opportunity.
- Marilyn-Themed Decor: Immerse yourself in a world inspired by the legendary star, with carefully curated decor that evokes the glamour and sophistication of Marilyn’s era.
- Unique Photo Opportunities: Beyond the famous statue, discover various Monroe-inspired backdrops and props to capture even more memorable moments.
- Key West Vibe: While paying homage to Marilyn, the essence of Key West’s laid-back, artistic, and free-spirited atmosphere is seamlessly woven into the experience.
- Perfect for Fans: Whether you’re a devoted admirer of Marilyn Monroe or simply looking for a distinctive and engaging activity in Key West, this is an experience you won’t want to miss.
Come and discover a truly special way to Enjoy Key West through the lens of one of history’s most enduring icons, and be sure to strike a pose with the iconic Marilyn Monroe statue!
X
TikTok
The Bull & Whistle Bar: A Key West Legend
Step into a true Key West institution at The Bull & Whistle Bar, often just called “The Whistle.” This iconic three-story establishment on Duval Street isn’t just a bar; it’s a living piece of Key West history, dripping with stories and local character.
Housed in a building dating back to the early 1900s, The Bull & Whistle has seen it all. It started life as a boarding house, then became a notorious brothel, and later, during the Prohibition era, a secret speakeasy and even a hideout for smugglers. Its walls could certainly tell a tale or two!
Today, The Bull & Whistle offers three distinct experiences under one roof:
- The Bull (Ground Floor): This open-air bar is always buzzing with live music and a lively crowd. It’s a classic Key West experience, perfect for soaking in the energy of Duval Street.
- The Whistle (Second Floor): Head upstairs for a more relaxed vibe, with pool tables, games, and a spacious wrap-around balcony that offers fantastic views for people-watching below. It’s a favorite haunt for locals, known for its authentic Key West charm.
- The Garden of Eden (Rooftop): For the truly uninhibited, the rooftop offers a clothing-optional experience with panoramic views of the island. By day, it’s a unique sunbathing spot; by night, it’s a vibrant space with a DJ, perfect for dancing under the stars.
The Bull & Whistle embodies Key West’s independent spirit and colorful past. It’s a must-visit for anyone looking to experience the authentic, historic, and wonderfully quirky side of the island!
The Stories Podcast is sponsored by
