Your Perfect Key West Escape

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Advisor - Bryant Blakeslee
Curated By

Bryant Blakeslee

  • Key West

  • Arts & Culture

  • Beaches

  • LGBTQ+ Travel

  • Food & Wine

  • Coastal

  • Entertainment

  • Relaxation

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Curator’s statement

Imagine a place that captures your heart time and time again, a tropical paradise that beckons you to relax and unwind. Key West is that place for me. With its friendly atmosphere, laid-back vibes and an abundance of amazing food and nightlife. The walkable streets and the welcoming locals make it a safe and inviting destination to slow down and immerse yourself in its charm. If you're looking for the perfect escape, Key West is where you need to be.

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Where to stay in Key West

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Things to do in Key West

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Best things to do in Key West

Key West offers a diverse range of activities that cater to all interests, from history buffs and nature lovers to foodies and adventure seekers. Here are some must-do activities that will make your Key West experience truly unforgettable:

  • Ernest Hemingway Home and Museum - Explore the former residence of the legendary writer, complete with lush gardens and descendants of his famous six-toed cats. The museum offers a glimpse into Hemingway's life and works, and the charming grounds are a peaceful retreat in the heart of Old Town.

  • Southernmost Point Buoy — Snap a photo at this iconic landmark, marking the southernmost point of the continental US. It's a must-see spot and a great place to reflect on your Key West adventure. Arrive early to avoid the crowds and get a picture-perfect shot.

  • Mallory Square — Join the nightly Sunset Celebration with street performers, local artisans and breathtaking views of the sun setting over the Gulf of Mexico. This lively event is a Key West tradition and a fantastic way to end your day on the island.

  • Fort Zachary Taylor Historic State Park — Visit this historic fort and enjoy one of the best beaches in Key West. The park is ideal for snorkeling, picnicking and soaking up the sun. Explore the fort's history and then relax on the beach with crystal-clear waters and plenty of shade.

  • Key West Butterfly and Nature Conservatory — Wander through a lush, tropical paradise filled with hundreds of butterflies. The conservatory is home to a variety of exotic birds and plants, making it a stunning and serene place to cool off and reconnect with nature.

  • Kayaking Adventures - Embark on a kayaking tour through Key West’s beautiful mangroves. Paddle through calm waters and explore hidden coves, looking for wildlife like manatees, birds and fish. It's a peaceful and active way to experience the island's natural beauty.

  • Sunset Cruise - One of the best ways to enjoy Key West’s legendary sunsets is from the water. Book a sunset sail for a relaxing evening with breathtaking views of the horizon. Many cruises offer live music, drinks and appetizers, creating a magical atmosphere as you watch the sun dip below the sea.

Explore the art scene

One of my favorite ways to spend a day in Key West is by exploring its vibrant art scene. The island is home to numerous galleries showcasing incredible works by local and international artists. Here are my top picks for an art crawl:

Pub crawl along Duval Street

Duval Street is the heart of Key West's nightlife, stretching from the Gulf of Mexico to the Atlantic Ocean. It's packed with a variety of bars, each offering its own unique atmosphere. Whether you're in the mood for a laid-back vibe, live music or a lively party, you'll find it on Duval Street. Here are some of my favorite bars for a memorable pub crawl:

  • Green Parrot Bar — A local favorite known for its laid-back vibe, live music and cold drinks. It’s the perfect place to start your bar crawl with a slice of Key West history.

  • Sloppy Joe's Bar - An iconic Key West bar with a lively atmosphere and live music. A must-visit for anyone looking to experience the spirit of Duval Street.

  • Hog's Breath Saloon — Famous for its slogan, “Hog’s Breath is better than no breath at all!” This bar offers live entertainment and a fun, casual setting.

  • The Rum Bar at the Speakeasy Inn — A cozy spot with a wide selection of rums and expertly crafted cocktails. Perfect for rum enthusiasts and those looking for a relaxed atmosphere.

  • Alonzo's Oyster Bar - Great for happy hour with half-price appetizers and a scenic view of the marina. Try their oysters and enjoy the waterfront ambiance.

Experience the Vibrant LGBTQ+ Nightlife

Key West is known for its welcoming and inclusive atmosphere, making it a top destination for LGBTQ+ travelers. The nightlife here is vibrant and fun, with several bars and clubs that cater specifically to the LGBTQ+ community. Here are some spots you won't want to miss:

  • Bourbon St. Pub -A popular gay bar featuring a pool, garden bar and drag shows. It’s a cornerstone of the LGBTQ+ scene in Key West.

  • Aqua Nightclub — Known for its fantastic drag shows and lively dance floor. A must-visit for a fun and inclusive night out.

  • 801 Bourbon Bar - Offering drag shows, karaoke and a friendly atmosphere, this bar is a staple of the LGBTQ+ nightlife in Key West.

  • Island House -A gay resort with a popular bar and cafe. It’s a great place to relax, meet people and enjoy the welcoming environment.

Activities for all interests

Day trips:

  • Dry Tortugas National Park — Take a ferry or seaplane to this remote park, home to historic Fort Jefferson and stunning coral reefs. Perfect for a day of history and snorkeling.

Places to eat & drink in Key West

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Culinary scene in Key West

Key West is a food-lover's paradise, known for its fresh seafood, Cuban cuisine and Key lime pie. The island offers a diverse culinary scene that will satisfy any palate. Here are some of my favorite dining spots:

  • Blue Heaven — Famous for its Sunday Brunch, Blue Heaven offers a relaxed dining experience in a historic setting. With roosters roaming the yard and live music often playing, it’s a must-visit for a quirky and enjoyable meal. Their lobster Benedict and key lime pie are particularly popular.

  • Little Pearl — This intimate restaurant is perfect for a quiet dinner, known for its fresh seafood and creative dishes. The cozy ambiance and attentive service make it an ideal spot for a special evening out. Try the scallops or the fresh catch of the day for an unforgettable meal.

  • Cafe Marquesa — Located within the Marquesa Hotel, this elegant restaurant offers a sophisticated menu with a focus on fresh, local ingredients. The beautifully presented dishes and refined atmosphere make it a top choice for fine dining in Key West. Favorites include the seared tuna and the chocolate soufflé.

  • Latitudes - Situated on Sunset Key, Latitudes provides an upscale dining experience with stunning oceanfront views. Known for its exquisite seafood and romantic setting, it’s perfect for a memorable dinner. Be sure to try their lobster bisque and the key lime pie for dessert.

  • Eaton Street Seafood Market — This market is a local favorite for fresh seafood. Their lobster rolls are a must-try, filled with succulent, buttery lobster meat. It's a great spot for a casual, yet delicious meal.

  • Café Solé — Known for its French-Caribbean cuisine, Café Solé offers a delightful dining experience. The atmosphere is charming and intimate, and the menu features a variety of fresh seafood and rich, flavorful dishes. Don’t miss the hogfish or the bouillabaisse.

  • El Siboney - Dive into authentic Cuban cuisine at this beloved local restaurant. El Siboney is famous for its generous portions and flavorful dishes. Try the roast pork or the Siboney steak, both of which are local favorites.

  • Nine One Five -Located on Duval Street, this upscale restaurant offers a creative menu and excellent service. The atmosphere is chic and inviting, making it a great place for a special night out. Popular dishes include the tuna dome and the lobster ravioli.

  • Mangoes -Known for its monthly Drag Brunch, Mangoes is a lively spot with a fun and festive atmosphere. The menu features a variety of delicious options, and the drag performances add a unique and entertaining twist to your dining experience.

  • Thirsty Mermaid — This charming eatery offers fresh seafood and craft cocktails in a relaxed setting. It’s a great place to enjoy oysters, lobster rolls and their signature cocktails.

  • La Te Da - A historic hotel with a lively restaurant and bar. Known for its cabaret shows and vibrant atmosphere, it’s a great place to enjoy a meal and some entertainment.

  • Kermit's Key West Key Lime Shoppe — Famous for its Key lime pie and other lime-infused treats. A visit to Kermit’s is a must for anyone with a sweet tooth. Be sure to try the frozen Key lime pie on a stick.

  • Louie's Backyard — This oceanfront restaurant offers exquisite cuisine and stunning views. Known for its elegant dishes and romantic setting, it's perfect for a special occasion. Don't miss their fresh seafood and innovative cocktails.

  • Cuban Coffee Queen - A must-visit for coffee lovers, Cuban Coffee Queen offers robust Cuban coffee and delicious breakfast sandwiches. Perfect for starting your day with a caffeine kick and some local flavor.

Need to know

Key West is the ultimate escape. Whether you're planning a long weekend getaway or making a port stop on a cruise. Key West has something special for everyone.

How to get around the island

Key West is a compact island that’s easy to navigate. Here are some options for getting around:

  • Biking: Rent a bike to explore the island at your own pace. It's a popular and eco-friendly way to get around.

  • Walking: Many of the main attractions, restaurants and bars are within walking distance of each other.

  • Trolley and conch train tours: These guided tours are a fun way to see the sights and learn about the history of Key West.

  • Scooters and electric cars: Rent a scooter or electric car for a faster way to zip around the island.

  • Public transit: Key West Transit offers bus services that can get you around the island efficiently.

Travel essentials

  • How to get there: Key West is accessible by plane, car, ferry or even cruise ship. The island's airport, Key West International Airport (EYW), is small but well-connected with major hubs. If driving, take the scenic Overseas Highway (US-1) from Miami. Ferries also run from Fort Myers and Marco Island.

  • Packing tips: Pack light, breathable clothing, swimwear, sunscreen and comfortable shoes for walking or biking. Don’t forget a hat and sunglasses for sun protection and a light jacket for cooler evenings.

Local insights

  • Local culture: Key West has a laid-back, welcoming vibe. The locals, known as "Conchs," are friendly and love to share their island with visitors. Embrace the relaxed pace and enjoy the diverse cultural influences.

  • Events and festivals: Plan your trip around some of Key West's famous events such as Fantasy Fest in October, Hemingway Days in July and the Conch Republic Independence Celebration in April.

  • Weather: Key West enjoys a tropical climate. Summers are hot and humid, while winters are warm and dry. Hurricane season runs from June to November, so it's wise to keep an eye on the weather forecasts if visiting during these months.

Safety and health tips

  • Health precautions: Always stay hydrated and use sunscreen to protect against the strong tropical sun. If you're planning on water activities, ensure you’re aware of the safety protocols.

  • Safety tips: Key West is generally very safe, but like any travel destination, it’s wise to stay aware of your surroundings, especially at night. Lock your bikes and be careful with your belongings.

Book Key West tours and activities

  • Exploring Key West is even more exciting when you have the chance to book some of the best tours and activities the island has to offer. From snorkeling adventures to historical tours, booking with a trusted provider ensures you get the most out of your visit. I recommend using Viator for your tour bookings. With a wide range of activities to choose from, you can easily find something that suits your interests and schedule.

Ready to experience the charm and excitement of Key West for yourself? Let me help you plan the perfect getaway! Whether you're looking for a romantic escape, an adventure-filled trip or a relaxing retreat, I’ve got you covered. Contact me today to start planning your unforgettable Key West vacation!

Advisor - Bryant Blakeslee

Travel Advisor

Bryant Blakeslee

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This guide is part of our ongoing series on travel to Key West. Looking for more travel inspiration? Check out my guide, Top 10 Must-Do Activities Aboard Virgin Voyages.