Key West Travel Guide: 10 Things You Can’t Miss

1. Fly Into Key West Airport and Don’t Rent a Car

Key West Airport is a tiny little airport located directly on the island. It recently has had an expansion and renovation is very quaint and comfortable, making you feel like you’re a part of the culture straight off the plan. There are plenty of ride share and taxi options available to carry you to the downtown area or over to Stock Island wherever your accommodations may be. Every time that we have visited Key West we usually take a taxi over to our accommodations and then walk everywhere from there. Key West is an extremely walkable Island measuring around one and a half miles north to south in around 4 miles east to west making it very easy to navigate, walk and explore on your own. In fact, parking is so limited and so tight that we prefer to walk. If you have a desire to explore parts of the island, side-by-side rentals for a day or two are the way to get around the island and feel the wind in your hair.  These rentals are available in several areas in town and are a great way to get around without the trouble of navigating a rental car.

2. Stay Downtown

Each time we have visited Key West we have stayed in a different location off of Duval Street downtown. Some of our favorites are the Southernmost House on the southern end of the island near the southernmost point, The Gardens hotel in midtown, and the Marker Resort at the north end of the island near the marina. All three are great locations for exploring downtown and have incredible pools, relaxation, and that island vibe you’re looking for. These three are highly recommended for their customer service, hospitality, and overall vibe. Our favorite is definitely the Marker which has the most incredible pool bar and daily live music sometimes featuring local bands not to mention the great restaurant onsite, incredible location, and the nearest to the end of the island where the watersports marina is located.

3. Experience the Sunset at Mallory Square

Each evening Around two hours before sunset, Mallory Square becomes alive with street performers, vendors and other artists showcasing their talents and skills. Make sure that you check online to see what time the sunset will occur as this varies from day to day. Get there early to secure a great spot, grab a drink and relax, just to watch all of the festivities and going on around you. A Key West Sunset is nothing short of incredible. We have found the best view to be at the upper end of Mallory Square near the Ocean Key Resort & Spa. In Key West, the earth doesn’t simply let the sun set—it reaches out and takes it, pulling it slowly into the horizon as the sky burns and softens all at once. For a few breathless moments, it feels like the planet itself is holding the light before surrendering it to night. That final sliver of sun clinging to the horizon feels impossibly intimate—like the day whispering one last secret—an instant so stunning you swear the world pauses just to watch it disappear. And when you’re hooked, you will never look at another sunset the same, as if they will stay with you bringing back that island feeling every time.

4. Key West is a Foodie Town

Key West is a true foodie town, where legendary flavors and laid-back island energy come together on every plate. Blue Heaven is an absolute must—famous for its iconic Key Lime Pie and island-inspired dishes, and even more memorable as the backdrop for a Kenny Chesney’s music video for “The Good Stuff”  that perfectly captures the spirit of the Keys. For small plates and big flavor, Santiago’s Bodega is our favorite tapas spot, but be sure to make reservations—it’s popular for a reason.  For an unforgettable, sunset-soaked dinner, Latitudes at Sunset Key delivers pure magic, complete with a short ferry ride that makes the evening feel like an event and dinner on the beach. Don’t miss the lobster pizza at the Seaside Café, breakfast at The Breakfast Club, Too, or a quick jolt of local flavor from Cuban Coffee Queen. Add in historic favorites like El Siboney or Pepe’s Café, and key lime pie on every corner you’ll quickly realize that in Key West, food isn’t just fuel—it’s part of the island’s story.

5. Plan Down Days by the Pool

Whenever you travel, it’s just as important to plan down days as it is to plan adventures—and that’s especially true in an island town like Key West. Give yourself permission to slow down: lay by the pool, sip a cold drink, and let the rhythm of the island wash over you. Those unstructured moments, soaking in the sun and the sounds and the stillness, are what truly recharge your body and renew your soul, so you return home feeling whole again.

6. Remember Key West Beaches are Different than Most

The beaches in Key West are a little different than what you’ll find in most island towns or across Florida—there aren’t long stretches of wide, powdery sand, but instead smaller, more intimate beaches with character and history woven into them. Many of the best beach experiences require a short walk, bike ride, or ferry trip, like Fort Zachary Taylor State Park, Smathers Beach, or a day excursion to nearby islands such as Dry Tortugas or Sunset Key.  Fort Zachary Taylor State Park is a favorite for good reason: it’s one of the few places in Key West where you can truly swim, relax, and snorkel all in one spot. The water is often clear, the shoreline is dotted with coral and rock formations, and you can easily rent snorkel gear, beach chairs, and umbrellas for the day. It’s a perfect example of how Key West beaches aren’t about endless sand—they’re about slowing down, exploring, and appreciating the natural beauty in a more laid-back, authentic way.

7. Watersports Abound

One of the best ways to truly experience Key West is to get out on the ocean and feel the Atlantic around you. Water sports are everywhere—from jet ski tours and parasailing, to paddleboarding and kayaking through the calm mangroves in Stock Island. You can book snorkeling and reef trips from the Historic Seaport or take a catamaran out for sailing, dolphin watching, or sunset cruises. Whether you’re skimming across the water or floating above a coral reef, being on the ocean gives you a whole new appreciation for Key West and the life that surrounds it.

8. Make Time for the Unique Attractions

Key West is packed with iconic attractions that blend history, culture, and pure island character. The Ernest Hemingway Home and Museum offers a fascinating glimpse into the author’s life, complete with lush gardens and the famous six-toed cats, while the nearby Key West Lighthouse provides panoramic views of the island for those willing to climb. The Key West Butterfly and Nature Conservatory is a peaceful, colorful escape, and the Harry S. Truman Little White House highlights the island’s role in presidential history.  No visit is complete without stopping at legendary spots like Sloppy Joe’s Bar, made famous by Hemingway himself, along with other classic watering holes such as Captain Tony’s Saloon, The Green Parrot, and Mallory Square for its nightly sunset celebration. Together, these attractions capture the heart of Key West—where history, storytelling, and a good drink all share the same address.

9. Understand Why Key West is Known as the “Conch Republic”

Key West’s history is as colorful and rebellious as the island itself, shaped by pirates, shipwreckers, cigar makers, and free spirits who never quite fit the mainland mold. That independent streak lives on in the term “Conch Republic,” born in 1982 when Key West jokingly seceded from the United States in protest of a federal roadblock. What started as satire became a badge of honor—symbolizing the island’s humor, resilience, and refusal to take itself too seriously. Today, the Conch Republic isn’t about separation, but about celebrating Key West’s fiercely independent soul and its deep pride in doing things its own way.

10. Embrace the Eclectic Vibe

Key West is a place best experienced when you stop trying to control the moment and start embracing the island’s wonderfully eclectic vibe. From roosters casually roaming the streets to sunsets that feel like daily rituals, the charm lies in the unexpected and the unapologetically laid-back way of life. As the southernmost point in the continental United States, Key West carries a spirit all its own—part history, part rebellion, part paradise. Let these ten tips guide you, but more importantly, let the island show you how to slow down, wander freely, and truly live in the moment.