Key West: America's Caribbean Paradise
Table of Contents
Introduction: Where the Road Ends and Paradise Begins
At the southernmost tip of the United States, where US-1 finally dips its toes into the turquoise waters of the Straits of Florida, lies Key West—a vibrant, colorful island that feels more Caribbean than American. This 4-mile-long, 2-mile-wide paradise has been captivating visitors for centuries with its laid-back atmosphere, rich history, and spectacular sunsets that paint the sky in fiery hues each evening.
Key West's unique identity stems from its fascinating blend of Cuban heritage, literary history, naval significance, and bohemian spirit. It's where Pulitzer Prize-winning authors like Ernest Hemingway and Tennessee Williams found inspiration, where presidents like Harry Truman established winter White Houses, and where pirates, wreckers, and fishermen built fortunes from the sea. Today, it remains a sanctuary for artists, free spirits, and anyone seeking refuge from mainland conventions.
The island's vibe is best described as "island time meets creative energy." There's a palpable sense of freedom that comes from being surrounded by water on all sides—a feeling that rules are made to be bent and life is meant to be enjoyed. The pace slows, smiles come easier, and the famous "Duval Crawl" from beach to bar becomes a way of life. Yet beneath the festive surface lies a deeply historic community with beautifully preserved architecture and traditions dating back centuries.
Why Visit Key West? For the world's most spectacular sunsets, the vibrant nightlife along Duval Street, the fascinating literary and pirate history, the incredible water sports and fishing, the unique blend of Cuban and American cultures, the stunning coral reefs for snorkeling, and the simple joy of watching the world go by from a porch swing in America's southernmost city.
How to Get There
Reaching this island paradise is an adventure in itself, with the journey building anticipation for the tropical escape ahead.
Air Travel
Key West International Airport (EYW) offers convenient access just minutes from Old Town. Major airlines provide regular service:
| Airline | Direct Flights From | Notes |
|---|---|---|
| American | Miami, Charlotte, Dallas | Most flights connect through Miami |
| Delta | Atlanta | Seasonal service to other hubs |
| United | Chicago, Houston, Newark | Seasonal variations |
| Silver Airways | Various Florida cities | Regional connector |
The Overseas Highway Drive
The iconic 113-mile drive from Miami to Key West along US-1 is one of America's great road trips, crossing 42 bridges including the famous Seven Mile Bridge:
| Starting Point | Distance | Approximate Drive Time | Route Highlights |
|---|---|---|---|
| Miami | 160 miles | 3.5-4 hours | Scenic ocean views, Islamorada, Marathon |
| Fort Lauderdale | 190 miles | 4-4.5 hours | Adds extra coastal scenery |
| Naples | 240 miles | 5-5.5 hours | Across Alligator Alley to Miami then south |
Ferry & Bus Options
Key West Express
High-speed ferry from Fort Myers Beach (3.5 hours) and Marco Island (4 hours). Beautiful approach by water with dolphin sightings common.
Greyhound Bus
Regular service from Miami with several stops along the Keys. Affordable but longer travel time.
Florida Keys Shuttle
Private shuttle service from Miami and Fort Lauderdale airports directly to Key West hotels.
Where to Stay
Key West offers diverse accommodations from luxurious resorts to charming historic inns, each capturing a different aspect of the island's personality.
The Casa Marina Resort
Historic Waldorf Astoria property with the largest private beach in Key West. Built in 1920, this resort combines old-world elegance with modern luxury.
Location: Southernmost End
Price Range: $$$$
Sunset Key Cottages
Private island luxury just 500 yards offshore. Accessible only by boat, these West Indies-style cottages offer ultimate privacy and spectacular sunsets.
Location: Sunset Key Island
Price Range: $$$$
Ocean Key Resort & Spa
Waterfront luxury at the foot of Duval Street. Features a private marina, full-service spa, and spectacular sunset views from its restaurant.
Location: Duval Street/Waterfront
Price Range: $$$$
The Gardens Hotel
Lush tropical oasis in the heart of Old Town. This historic property features beautifully landscaped gardens and a tranquil pool area.
Location: Old Town
Price Range: $$$
Pier House Resort & Spa
Befront resort with private beach, full-service spa, and excellent dining. Perfect balance of location and relaxation.
Location: Duval Street/Waterfront
Price Range: $$$
Curry Mansion Inn
Charming Victorian bed and breakfast with rich history. Includes daily breakfast and evening wine reception.
Location: Old Town
Price Range: $$$
Key West Hostel
Budget-friendly option with dormitory and private rooms. Social atmosphere with pool and common kitchen.
Location: Old Town
Price Range: $
Eden House
Key West's first clothing-optional hotel, known for its bohemian atmosphere and friendly social scene.
Location: Old Town
Price Range: $$
Southernmost Hotel Collection
Several properties near the southernmost point offering good value and excellent locations.
Location: Southernmost Area
Price Range: $$
What to See: Main Attractions
Southernmost Point
The iconic concrete buoy marking the southernmost point of the continental United States stands just 90 miles from Cuba. This brightly painted landmark is one of the most photographed spots in Key West, with lines often forming for the perfect vacation picture. While the actual southernmost point is on private property nearby, this marker has become the symbolic "end of America."
Pro Tip: Visit early morning or late afternoon to avoid the longest lines. The surrounding area features beautiful views and historic homes worth exploring.
Ernest Hemingway Home & Museum
Where Nobel Prize-winning author Ernest Hemingway lived and wrote from 1931 to 1939. This Spanish Colonial-style home contains original furnishings and Hemingway memorabilia, but the real stars are the approximately 40-50 polydactyl (six-toed) cats who roam the property—descendants of Hemingway's original cat, Snow White.
Highlights: Hemingway's writing studio (separate from the main house), the first swimming pool built in Key West, and the beautiful tropical gardens.
Pro Tip: The knowledgeable guides share fascinating stories about Hemingway's life in Key West beyond what you'll read on placards.
Mallory Square & Sunset Celebration
Each evening, two hours before sunset, locals and visitors gather at Mallory Square for the legendary Sunset Celebration—a daily festival celebrating the end of another day in paradise. Street performers, local artisans, food vendors, and musicians create a carnival-like atmosphere as the sun dips below the horizon.
Don't Miss: The famous "cat man" with his trained house cats, breathtaking aerialists, and the classic "sunset" photo opportunity.
Pro Tip: Arrive at least an hour before sunset to secure a good viewing spot and enjoy the entertainment before the main event.
Harry S. Truman Little White House
This historic site served as President Harry S. Truman's winter White House during his presidency (1945-1953). Perfectly preserved with original furnishings, it offers a fascinating glimpse into presidential history and Cold War politics. The guided tours are exceptionally informative, bringing to life Truman's working vacations in Key West.
Interesting Fact: Truman spent 175 days of his presidency here, and subsequent presidents including Eisenhower, Kennedy, and Clinton have used the facility.
Things to Do: Island Adventures
Water Activities
- Snorkeling at coral reefs
- Scuba diving to wrecks
- Sunset sailing cruises
- Deep sea fishing
- Jet ski tours
- Parasailing
- Dolphin watching tours
- Stand-up paddleboarding
Land Activities
- Duval Street bar crawl
- Historic home tours
- Ghost tours
- Bicycle tours of Old Town
- Art gallery hopping
- Butterfly Conservatory
- Key West Lighthouse climb
- Fort Zachary Taylor exploration
Tours & Experiences
- Conch Tour Train
- Old Town Trolley Tours
- Food tasting tours
- Literary walking tours
- Pirate history tours
- Sunset champagne cruises
- Private sailing charters
- Seaplane tours to Dry Tortugas
Signature Experiences
Sunset Celebration at Mallory Square: More than just watching the sunset, this daily festival embodies Key West's free-spirited culture. Street performers, local artisans, and food vendors create a carnival atmosphere as the sun performs its nightly spectacle. It's a must-do experience that captures the essence of Key West.
Duval Crawl: The famous mile-long stretch of Duval Street from the Gulf of Mexico to the Atlantic Ocean offers some of the best nightlife in Florida. The "crawl" involves sampling the diverse bars, from the historic Sloppy Joe's to the clothing-optional Garden of Eden.
Dry Tortugas National Park: Accessible only by boat or seaplane, this remote national park 70 miles west of Key West features Fort Jefferson, spectacular snorkeling, and some of the most pristine natural environments in America. The journey is part of the adventure.
Food & Drink: Conch Republic Cuisine
Traditional Dishes to Try
- Conch Fritters: Deep-fried balls of conch meat, peppers, and spices
- Key Lime Pie: The official state pie, made with Key lime juice
- Cuban Sandwich: Pressed sandwich with roast pork, ham, Swiss cheese, pickles, and mustard
- Stone Crab Claws: Served chilled with mustard sauce (in season Oct 15-May 15)
- Yellowtail Snapper: Local fish often prepared whole with Key West spices
- Conch Chowder: Tomato-based soup with conch, vegetables, and spices
Restaurant Recommendations
| Restaurant | Cuisine | Price Range | Notes |
|---|---|---|---|
| Blue Heaven | Caribbean/American | $$$ | Legendary breakfast, roosters in courtyard, Key lime pie |
| Louie's Backyard | Upscale Caribbean | $$$$ | Spectacular ocean views, fine dining experience |
| El Siboney | Cuban | $ | Authentic Cuban home cooking, family-owned |
| Half Shell Raw Bar | Seafood | $$ | Waterfront casual dining, fresh oysters and seafood |
| Nine One Five | Global Fusion | $$$ | Romantic setting in historic mansion |
| DJ's Clam Shack | Seafood | $ | Best fried clams and casual seafood |
Bars & Historic Pubs
Sloppy Joe's
Key West's most famous bar, originally opened in 1933. Hemingway's regular haunt features live music and plenty of history.
Green Parrot Bar
Authentic local dive bar with great music and no pretense. A favorite among Key West residents.
Hog's Breath Saloon
Famous for its "Hog's Breath is better than no breath at all" motto and live entertainment.
Shopping: From Tacky to Tasteful
Art Galleries & Local Crafts
- Gingerbread Square Gallery: Oldest gallery in Key West featuring local artists
- Key West Aloe: Skin care products made with local aloe vera
- Alan S. Maltz Gallery: Wildlife and landscape photography
Unique Boutiques
- Key West Island Books: Independent bookstore with local focus
- Fast Buck Freddie's: Eclectic department store with unique gifts
- Coconut Grove: Bohemian clothing and accessories
Souvenirs & Food Gifts
- Kermit's Key West Key Lime Shoppe: Everything key lime
- Peppers of Key West: Hot sauces and spices
- Key West Handprint Fabrics: Locally designed tropical fabrics
Culture & Local Life
Key West's culture is a vibrant tapestry woven from Bahamian, Cuban, and American threads, with a strong emphasis on individuality and celebration. The island has long been a refuge for those who march to the beat of a different drum, creating a community that values personal freedom, artistic expression, and living in the moment.
Festivals & Events
| Event | Time of Year | Description |
|---|---|---|
| Fantasy Fest | Late October | 10-day costume festival with parades and parties |
| Key West Literary Seminar | January | Gathering of renowned authors and literary enthusiasts |
| Hemingway Days Festival | July | Celebration of Hemingway with look-alike contest |
| Conch Republic Independence Celebration | April | Commemorates Key West's "secession" from the US |
Local Vibe & Community
Key West residents, known as "Conchs," are famously independent and proud of their island home. There's a strong sense of community despite the constant influx of tourists, with locals supporting local businesses and preserving island traditions. The pace of life follows the sun—active and energetic during daylight hours, then slowing to appreciate the spectacular sunsets before the nightlife awakens.
Practical Information
Best Time to Visit
- December-April: Peak season with perfect weather
- May-June & November: Shoulder seasons with fewer crowds
- July-October: Low season (hot, humid, hurricane risk)
Weather & What to Pack
- Lightweight, breathable clothing
- Rain jacket (especially summer)
- Swimwear and cover-ups
- Comfortable walking shoes
- Sunglasses, hat, and reef-safe sunscreen
Money Matters
- Currency: US Dollar
- Credit cards widely accepted
- ATMs available throughout island
- Tipping standard (15-20% at restaurants)
Local Tips: Key West is generally safe, but use normal precautions with valuables. The sun is intense—reapply sunscreen frequently. Many restaurants don't take reservations—be flexible with dining times. Parking is limited and expensive—consider walking, biking, or using public transportation. Stay hydrated in the tropical climate.
Hidden Gems: Off the Beaten Path
Fort Zachary Taylor Beach
Often overlooked for more famous beaches, this state park offers the best swimming and snorkeling in Key West, plus historic fort ruins to explore.
The Key West Cemetery
Fascinating historic cemetery with above-ground tombs and humorous epitaphs that reflect Key West's unique sense of humor.
Nancy Forrester's Secret Garden
Hidden oasis with rescued parrots and lush tropical vegetation, offering a peaceful escape from the crowds.
Itineraries: Making the Most of Your Visit
2-Day Weekend Itinerary
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| Saturday | Breakfast at Blue Heaven, Hemingway House tour | Southernmost Point, beach time at Fort Zachary Taylor | Sunset at Mallory Square, dinner at Louie's Backyard |
| Sunday | Conch Tour Train, Key West Lighthouse | Snorkeling trip, Duval Street shopping | Sunset sail, casual seafood dinner |
5-Day Comprehensive Itinerary
| Day | Activities |
|---|---|
| 1 | Arrive, settle in, explore Duval Street, sunset at Mallory Square |
| 2 | Historic Old Town walking tour, Hemingway House, Truman Little White House |
| 3 | Full-day snorkeling and sailing excursion to coral reefs |
| 4 | Butterfly Conservatory, beach time, ghost tour in evening |
| 5 | Bike rental to explore residential areas, last-minute shopping, farewell dinner |
Nearby Destinations
Dry Tortugas National Park
70 miles west of Key West, this remote park features Fort Jefferson, spectacular snorkeling, and pristine natural beauty. Accessible by ferry or seaplane.
Marathon
About 1 hour drive north, this Middle Keys community offers the Dolphin Research Center and beautiful Sombrero Beach.
Islamorada
Approximately 1.5 hours north, known as the "Sportfishing Capital of the World" with excellent restaurants and resorts.
Key West captures the imagination like no other American destination. It's where the rules of the mainland soften, where history whispers through gingerbread architecture, where the sunset is celebrated like a daily holiday, and where the spirit of adventure meets the tranquility of island life. Whether you come for the history, the nightlife, the water sports, or simply to watch the chickens cross the road, Key West will leave you enchanted and planning your return before you've even left.
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