Discover Key West - Where History Meets Island Paradise
Uncover Key West's charm! Explore historic sites, vibrant nightlife, delicious seafood, and stunning sunsets. Plan your perfect escape to this southernmost point today.
Nestled at the very tip of the Florida Keys, Key West is a vibrant island city where turquoise waters meet historic charm, creating a unique blend of laid-back island life and lively cultural experiences. Known for its picturesque sunsets, quirky character, and rich history, this southernmost point of the continental U.S. invites travelers to discover a world apart where flip-flops are always in fashion and the margaritas flow freely.
Key West offers an irresistible allure with its tropical climate, vibrant arts scene, and fascinating past. From the literary haunts of Ernest Hemingway to the naval history of the Truman Little White House, every corner tells a story. The island’s surrounding reef system provides incredible opportunities for snorkeling and diving, while its streets buzz with live music, delicious Cuban-inspired cuisine, and the legendary nightly Mallory Square Sunset Celebration. It’s a place where you can relax on a pristine beach in the morning and dance to a live band on Duval Street by night, making it ideal for those seeking both adventure and relaxation.
Seasonal Weather Guide
Plan your perfect getaway with our detailed seasonal forecast.
The Conch Republic Charm: Where History Meets Bohemian Spirit
Key West pulses with a rhythm all its own, born from a colorful past of pirates, poets, and presidents. This island’s unique blend of Bahamian, Cuban, and American influences is palpable in its vibrant architecture, spicy cuisine, and the famously independent spirit of its residents, often called “Conchs.” Explore the narrow lanes of Old Town, and you’ll find charming Victorian homes, lush gardens, and hidden courtyards that whisper tales of bygone eras.
Beyond its physical beauty, Key West thrives on a bohemian soul. It’s a sanctuary for artists, writers, and free spirits, reflected in its numerous art galleries, lively street performers, and a welcoming, inclusive atmosphere. The island encourages exploration, from its fascinating museums to its vibrant nightlife, ensuring that every visitor finds a slice of paradise that speaks to their inner adventurer or their need for blissful relaxation.
Things to Do
Unforgettable experiences await you.
Mallory Square Sunset Celebration
Gather with street performers, artisans, and food vendors to watch Key West's legendary sunset. This nightly ritual offers a vibrant atmosphere and stunning views over the Gulf of Mexico.
Snorkeling or Diving in the Coral Reef
Explore the diverse marine life and vibrant coral formations of the Florida Barrier Reef, one of the largest in the world. Numerous boat tours offer excursions for all skill levels.
Visit the Ernest Hemingway Home & Museum
Tour the beautiful former residence of the famous author, Ernest Hemingway, where he lived and wrote for over a decade. Admire the Spanish Colonial architecture and meet the descendants of his polydactyl (six-toed) cats.
Stroll and Explore Duval Street
Walk down Key West's most famous street, bustling with lively bars, unique shops, art galleries, and diverse restaurants. It's the heart of the island's entertainment and nightlife.
The Icons You’ll Want to See
Ernest Hemingway Home and Museum — Step into the former residence of the legendary author, a beautiful estate filled with antiques and, famously, over 50 six-toed cats descended from Hemingway’s own pet. Allow 1-1.5 hours for a guided tour and self-exploration.
Mallory Square Sunset Celebration — An iconic, free nightly festival where street performers, artists, and food vendors gather to celebrate the spectacular Key West sunset. Arrive at least an hour before sunset to secure a good viewing spot and enjoy the pre-show entertainment.
Southernmost Point Buoy — A must-visit landmark marking the southernmost point of the continental U.S., just 90 miles from Cuba. Be prepared for a queue, especially during peak times; consider an early morning visit for fewer crowds.
Truman Little White House — Florida’s only presidential museum, offering a glimpse into where President Harry S. Truman spent 175 days on vacation and conducting presidential business. Guided tours provide fascinating historical insights into his time on the island.
Fort Zachary Taylor Historic State Park — Home to a pre-Civil War fort and one of Key West’s best natural beaches with clear, calm waters perfect for swimming and snorkeling right offshore. An ideal spot for history buffs and beach lovers alike; plan for half a day to enjoy both.
Key West Lighthouse & Keeper’s Quarters Museum — Climb the 88 steps to the top of this historic lighthouse for unparalleled panoramic views of the island and surrounding waters. The museum explores the lives of Key West’s lighthouse keepers.
Essential Guide
Everything you need to know.
Must-Visit Spots
Local Cuisine
Where to Stay
Travel Tips
Planning Your Visit
Key West is easily reached via Key West International Airport (EYW), or many visitors opt for the scenic 3.5-4 hour drive down the Florida Keys Overseas Highway from Miami (MIA) or Fort Lauderdale (FLL). Once on the island, getting around is a breeze without a car; it’s incredibly walkable and bike-friendly, with rentals available (approx. $15-$25/day). The Duval Loop free bus service circles Old Town, making major attractions accessible. Accommodations range from charming guesthouses to luxury resorts, but booking well in advance (especially November-May) is crucial, as prices can be $250-$500+ per night. Always hydrate well and use high-SPF sunscreen; the Florida sun is intense year-round.
When to Visit
Choose the perfect time for your adventure.
Peak Season: Mid-November to May
Pros
- Pleasant, dry weather with comfortable temperatures
- Lower humidity and less chance of rain
- Vibrant atmosphere with many events and activities
- Ideal for outdoor activities like snorkeling and sailing
Cons
- Highest prices for flights and accommodations
- Most crowded, especially during holidays and spring break
- Requires booking well in advance
- Can be difficult to find parking and reservations
Shoulder Season: Early November, Late May, Early June
Pros
- Good weather before the extreme summer heat or after hurricane season
- Fewer crowds than peak season
- Potentially lower prices for lodging and activities
- Still plenty of events and open attractions
Cons
- Transitioning weather can be unpredictable
- Early hurricane season risk in June
- Humidity starts to increase in late spring
- Some popular activities might start to wind down or become busier towards peak season
Off-Peak: July to October
Pros
- Significantly lower prices for hotels and flights
- Fewer tourists, offering a more relaxed experience
- Warm ocean temperatures perfect for swimming and water sports
- Opportunities to experience local life without the crowds
Cons
- High heat and humidity can be uncomfortable
- High risk of hurricanes and tropical storms
- Frequent afternoon thunderstorms can disrupt plans
- Some establishments may have reduced hours or be closed for renovation
The ideal time to visit Key West is from November to May, when the weather is pleasantly warm, dry, and less humid (temperatures average 70s-low 80s F). June through October brings higher temperatures, humidity, and the risk of hurricanes, though prices for flights and accommodations tend to be lower.
From its vibrant street life and rich historical tapestry to its breathtaking sunsets and crystal-clear waters, Key West offers an unforgettable escape into a world where relaxation and adventure coexist, leaving every traveler with a piece of its quirky, free-spirited charm.
Sample Itineraries
3-Day Key West Explorer
A perfect blend of history, relaxation, and iconic Key West experiences, from Ernest Hemingway's home to Mallory Square's sunset celebration.
-
Day 1: Island Arrival & Sunset Sail Serenity
- Morning (9:30 AM - 12:30 PM)
Start your Key West adventure by immersing yourselves in the literary legacy of Ernest Hemingway. Head to the Ernest Hemingway Home & Museum (907 Whitehead St). This beautifully preserved house, famous for its resident polydactyl cats, offers guided tours providing fascinating insights into Hemingway’s life and work. Allow approximately 1.5 - 2 hours for the visit.
- Practical Tip: Arrive shortly after opening (usually 9:00 AM) to beat the crowds.
- Cost: ~$18 per person.
- Distance: Most accommodations in Old Town are within walking distance or a short ride.
- Afternoon (12:30 PM - 5:30 PM)
From Hemingway’s home, take a leisurely 10-minute walk (approx. 0.5 miles) south to the iconic Southernmost Point Buoy (Whitehead St & South St) for a quintessential Key West photo opportunity. Expect a short line for photos. Afterwards, stroll just one block east (approx. 0.1 miles) to the enchanting Key West Butterfly and Nature Conservatory (1316 Duval St). Spend about 1 hour wandering through a tropical haven filled with hundreds of vibrant butterflies and exotic birds.
For a casual lunch, consider Blue Heaven (729 Thomas St), famous for its outdoor atmosphere, live music, and excellent food (try the Key Lime Pie!). It’s about a 10-minute walk from the Butterfly Conservatory.
- Cost: Southernmost Point is free. Butterfly Conservatory: ~$17 per person. Lunch: $40-$80.
- Evening (5:30 PM onwards)
Prepare for a breathtaking Key West experience: a sunset sail. Walk or take a short rideshare to a departure point like the Historic Seaport. Companies like Fury Water Adventures or Sebago Watersports offer catamaran sunset sails (often including open bar and appetizers). This elevates the traditional Mallory Square sunset experience with stunning ocean views. The sail typically lasts 2 hours.
After returning to shore, enjoy a delicious dinner. For a vibrant atmosphere and fresh seafood, Half Shell Raw Bar (231 Margaret St) is a local favorite, or for a more upscale setting, consider Louie’s Backyard (700 Waddell Ave) for oceanfront dining.
- Cost: Sunset Sail: ~$80-$100 per person. Dinner: $100-$180.
- Practical Tip: Book sunset sails in advance, especially during peak season.
- Morning (9:30 AM - 12:30 PM)
Start your Key West adventure by immersing yourselves in the literary legacy of Ernest Hemingway. Head to the Ernest Hemingway Home & Museum (907 Whitehead St). This beautifully preserved house, famous for its resident polydactyl cats, offers guided tours providing fascinating insights into Hemingway’s life and work. Allow approximately 1.5 - 2 hours for the visit.
-
Day 2: Ocean Exploration & Historic Charms
- Morning (9:00 AM - 1:00 PM)
Embrace Key West’s aquatic side with a snorkeling adventure. Head to the Historic Seaport (e.g., Greene St docks) for a morning reef snorkeling trip. Many operators, such as Fury Water Adventures or Sebago Watersports, offer 3-hour excursions to the shallow coral reefs, including gear and basic instruction. This is a fantastic way to see the vibrant marine life of the Florida Keys.
- Practical Tip: Wear a swimsuit under your clothes, bring a towel, sunscreen, and a hat.
- Cost: Snorkeling Trip: ~$60-$80 per person.
- Afternoon (1:00 PM - 5:30 PM)
After your snorkeling adventure, grab a casual lunch at a spot near the harbor like B.O.’s Fish Wagon (601 Caroline St) for classic conch fritters and fish sandwiches, or Garbo’s Grill (409 Caroline St) for gourmet street food. Afterwards, delve into presidential history at the Harry S. Truman Little White House (111 Front St), a short 5-10 minute walk (approx. 0.4 miles) from the Historic Seaport. Take a guided tour to learn about its role as a winter retreat for several presidents.
From there, take a 10-minute walk (approx. 0.5 miles) south to the Key West Lighthouse & Keeper’s Quarters Museum (938 Whitehead St). Climb the 88 steps to the top for panoramic views of the island.
- Cost: Lunch: $30-$60. Truman Little White House: ~$25 per person. Lighthouse: ~$17 per person.
- Evening (5:30 PM onwards)
Spend the evening exploring the lively atmosphere of Duval Street. Enjoy pre-dinner drinks at a classic Key West establishment like Sloppy Joe’s Bar (201 Duval St) or Green Parrot Bar (601 Whitehead St) for local flavor and live music.
For dinner, indulge in the culinary scene. Consider Santiago’s Bodega (207 Petronia St) for delicious tapas in a charming setting, or Sarabeth’s Key West (530 Simonton St) for a more refined American menu.
- Cost: Drinks: $30-$60. Dinner: $100-$200.
- Morning (9:00 AM - 1:00 PM)
Embrace Key West’s aquatic side with a snorkeling adventure. Head to the Historic Seaport (e.g., Greene St docks) for a morning reef snorkeling trip. Many operators, such as Fury Water Adventures or Sebago Watersports, offer 3-hour excursions to the shallow coral reefs, including gear and basic instruction. This is a fantastic way to see the vibrant marine life of the Florida Keys.
-
Day 3: Fort, Flavor, & Farewell Feasts
- Morning (9:30 AM - 1:00 PM)
Discover Key West’s unique culture and culinary delights with a guided Key West Food Tour (various starting points, often around Old Town). These tours typically last 2.5-3 hours, taking you off the beaten path to local eateries, providing insights into the island’s history and diverse flavors. It’s a great way to sample different dishes and learn about the local food scene.
- Practical Tip: Wear comfortable walking shoes. Come with an appetite!
- Cost: Food Tour: ~$70-$80 per person. (This also serves as your breakfast/lunch for the morning).
- Afternoon (1:00 PM - 5:30 PM)
After your food tour, head to Fort Zachary Taylor Historic State Park (601 Howard England Way). This park boasts Key West’s best natural beach for swimming and snorkeling (from shore), as well as a historic fort to explore. You can rent snorkeling gear at the park. Spend a few hours relaxing on the beach, swimming in the clear waters, or walking through the historic fort.
- Practical Tip: The park is about a 20-30 minute walk from the southern end of Duval Street, or a short rideshare ($10-$15). Entry fee: $2.50 per pedestrian/bicycle or $6 per vehicle.
- Cost: Park entry: $5-$10 (depending on transport). Snorkel rental: ~$10-15 per person.
- Evening (5:30 PM onwards)
For your farewell dinner, treat yourselves to a truly memorable experience. Take the complimentary ferry from the Opal Key Resort & Marina to Latitudes on Sunset Key for an exquisite fine dining experience right on the beach, with stunning sunset views (reservations essential, book well in advance). This is a splurge-worthy meal that perfectly caps off your Key West adventure. Alternatively, if you prefer staying on the main island, Cafe Marquesa (600 Fleming St) offers an intimate and highly-rated dining experience.
After dinner, take a final leisurely stroll along Duval Street or the Historic Seaport, soaking in the last moments of Key West’s magical ambiance.
- Cost: Dinner at Latitudes or Cafe Marquesa: $200-$300+.
- Practical Tip: For Latitudes, confirm ferry times and allow extra time for travel to the dock and the ferry ride.
- Morning (9:30 AM - 1:00 PM)
Discover Key West’s unique culture and culinary delights with a guided Key West Food Tour (various starting points, often around Old Town). These tours typically last 2.5-3 hours, taking you off the beaten path to local eateries, providing insights into the island’s history and diverse flavors. It’s a great way to sample different dishes and learn about the local food scene.
5-Day Island Hopper & Relaxer
Dive deeper into Key West's charm, explore surrounding waters with snorkeling or kayaking, and enjoy leisurely evenings on the island.
-
Day 1: Welcome to Paradise & Sunset Spectacle
- Morning (10:00 AM - 12:00 PM) Arrive at Key West International Airport (EYW). Take a taxi or pre-booked shuttle to your accommodation in Old Town. (Taxi/Shuttle Cost: ~$25-40, Time: ~15-20 min). Check in and drop off your bags. Take a leisurely stroll around your hotel’s immediate neighborhood to get acquainted with Key West’s charming architecture and tropical foliage.
- Afternoon (12:00 PM - 5:00 PM)
- Lunch (12:00 PM - 1:00 PM): Head to Blue Heaven (729 Thomas St, ~5-10 min walk from central Old Town) for a classic Key West outdoor dining experience with chickens and cats roaming. Expect a wait, but it’s part of the charm. (Cost: ~$40-60 for two).
- Explore Old Town & Southernmost Point (1:30 PM - 4:30 PM): Walk down Duval Street, taking in the vibrant shops, bars, and galleries. Continue south to the iconic Southernmost Point Buoy (Whitehead St & South St, ~1 mile from Duval Street’s starting point, 15-20 min walk). Snap a photo, then meander back up Whitehead Street, perhaps stopping at the Hemingway Home Museum (907 Whitehead St) for an exterior view to save for a longer visit later. (Admission to Hemingway House: $18/person, if you decide to go in).
- Evening (5:00 PM onwards)
- Sunset Celebration at Mallory Square (5:00 PM - 7:00 PM): Head to Mallory Square (400 Wall St, ~5-10 min walk from upper Duval) for the nightly Sunset Celebration. Enjoy the street performers, craft vendors, and the spectacular Key West sunset over the Gulf of Mexico. (Free, but tips for performers are appreciated).
- Dinner (7:30 PM): Enjoy dinner at Santiago’s Bodega (207 Petronia St, ~5 min walk from Mallory Square), known for its delicious tapas in a lively setting. Perfect for sharing and trying various flavors. (Cost: ~$70-100 for two with drinks). Afterwards, perhaps a casual drink at a Duval Street bar to soak in the nightlife.
-
Day 2: Reef Rendezvous & Maritime Tales
- Morning (8:30 AM - 1:00 PM) Embark on a catamaran snorkeling trip to the Florida Reef, the only living coral barrier reef in North America. Several reputable companies offer trips, such as Fury Water Adventures or Sebago Watersports. Tours typically last 3-4 hours, including sailing time, equipment, and instruction. Most tours depart from the Historic Seaport, accessible by a 10-15 min walk from central Old Town. (Cost: ~$75-95 per person, includes snacks/drinks).
- Afternoon (1:00 PM - 5:00 PM)
- Lunch (1:30 PM - 2:30 PM): After your snorkeling trip, grab a fresh seafood lunch at Half Shell Raw Bar (231 Margaret St, right at the Historic Seaport). Enjoy oysters, stone crab, and other local catches with waterfront views. (Cost: ~$50-80 for two).
- Customs House Museum (2:30 PM - 4:30 PM): Visit the impressive Customs House Museum (281 Front St, ~5 min walk from Half Shell Raw Bar). This historic red-brick building houses artifacts and exhibits on Key West’s history, art, and maritime heritage. (Admission: $15/person).
- Evening (6:00 PM onwards)
- Dinner (6:30 PM): Indulge in a delicious meal at A&B Lobster House (700 Front St, ~2 min walk from Customs House), known for its upscale dining, fresh seafood, and fantastic harbor views. (Cost: ~$150-250 for two, including drinks).
- Nightcap & Stroll: After dinner, enjoy a leisurely walk along the Historic Seaport Bight, admiring the boats and soaking in the relaxed evening atmosphere. Perhaps a final cocktail at a quiet bar like the one at The Marker Resort (200 William St) for a sophisticated end to the day.
-
Day 3: Mangrove Mysteries & Literary Legacy
- Morning (9:00 AM - 12:30 PM) Explore the tranquil mangrove ecosystem of Key West on a guided kayaking tour. Companies like Kayak Key West or Lazy Dog Adventures (located on Stock Island, usually includes shuttle service from Key West or requires a short taxi ride, ~15-20 min, ~$20-30 one way) offer tours focused on wildlife viewing and the unique environment. (Cost: ~$55-75 per person for a 2-3 hour tour).
- Afternoon (1:00 PM - 5:00 PM)
- Lunch (1:00 PM - 2:00 PM): Upon returning to Key West, grab a casual lunch at a local spot like Fausto’s Food Palace (522 Fleming St, central Old Town) for a quick and authentic deli sandwich or a more relaxed meal at Island Dogs Bar (505 Front St). (Cost: ~$30-50 for two).
- Ernest Hemingway Home & Museum (2:30 PM - 4:30 PM): Immerse yourselves in literary history at the Ernest Hemingway Home & Museum (907 Whitehead St, ~10-15 min walk from central Old Town). Explore the author’s former residence, complete with his writing studio and the famous six-toed cats. (Admission: $18/person, cash only).
- Evening (6:30 PM onwards)
- Dinner (6:30 PM): Enjoy dinner at Louie’s Backyard (700 Waddell Ave, ~15-20 min walk or short taxi from Hemingway House). This iconic oceanfront restaurant offers exquisite dining with stunning views, particularly at sunset. (Cost: ~$120-180 for two, excluding drinks).
- Post-Dinner Entertainment: Stroll along the beach near Louie’s or enjoy a drink at their more casual Afterdeck Bar. Alternatively, consider a Key West Ghost Tour (various companies depart from central locations, ~$30/person, 90 min) for a spooky and entertaining end to the night.
-
Day 4: Beach Bliss & Fort Finds
- Morning (9:30 AM - 1:00 PM) Head to Fort Zachary Taylor Historic State Park (601 Howard England Way, ~15-20 min walk or short bike ride from Old Town). This park boasts Key West’s best natural beach with clear waters perfect for swimming and snorkeling (bring your own gear or rent some on-site). You can also explore the historic Civil War-era fort. (Park Admission: $6 per vehicle or $2.50 per pedestrian/bicyclist). Rent bikes for the day (e.g., from Eaton Bikes, ~10 min walk from central Old Town, ~$15-20/day per bike) to easily access the park and explore later.
- Afternoon (1:00 PM - 5:00 PM)
- Lunch at the Beach Café (1:00 PM - 2:00 PM): Enjoy a casual lunch at the café located within Fort Zachary Taylor State Park (Cost: ~$30-40 for two).
- Art & Culture (2:30 PM - 4:30 PM): Bike back towards Old Town and explore the vibrant Whitehead Street Art Gallery scene or visit the Audubon House & Tropical Gardens (205 Whitehead St, ~5 min bike ride from Mallory Square, $15/person) to admire its historic furnishings and lush gardens.
- Evening (6:00 PM onwards)
- Dinner (6:30 PM): Treat yourselves to a romantic and elegant dinner at Latitudes on Sunset Key (245 Front St, ferry departs from behind the Opal Key Resort, reservation required well in advance). Enjoy the stunning beachfront dining with your toes in the sand. (Cost: ~$200-300 for two, including drinks and ferry fee). The ferry ride itself is part of the experience.
- Live Music: After returning from Sunset Key, find some live music at a classic Key West establishment. Green Parrot Bar (601 Whitehead St, ~5-10 min walk from the ferry dock) offers a genuine local vibe and great bands.
-
Day 5: Farewell & Final Flavors
- Morning (9:00 AM - 12:00 PM)
- Leisurely Breakfast: Enjoy a final leisurely breakfast. Try Banana Cafe (1215 Duval St, ~10-15 min walk from central Old Town) for a unique Caribbean-inspired breakfast or a classic American breakfast at Frenchie’s Café (529 United St). (Cost: ~$30-50 for two).
- Last-Minute Souvenirs & Stroll: Spend some time picking up any last-minute souvenirs on Duval Street or wandering through the side streets of Old Town, admiring the charming houses and gardens one last time. Perhaps revisit a favorite spot for a final photo.
- Afternoon (12:00 PM onwards)
- Departure: Depending on your flight schedule, have a light lunch or grab a quick bite. Take a taxi or shuttle back to Key West International Airport (EYW) for your departure. (Taxi/Shuttle Cost: ~$25-40, Time: ~15-20 min).
- Morning (9:00 AM - 12:00 PM)
Explore Neighboring Areas
Ready to visit Discover Key West - Where History Meets Island Paradise?
Let AI build your perfect itinerary in seconds.