Ultimate Key West Travel Guide: Top Things to Do, Best Hotels & Must-Try Restaurants

Going to Key West is one of the most rewarding day trips from Miami, and yet I’m always surprised to meet many that have never been. Key West is a place like no other, where people gather from all over the world the world to celebrate it’s unique history, culture, and colorful characters.

I’ve been coming to Key West for years, and live right in the Florida Keys, so I know that Key West has a distinctive flair, and so many hidden treasures that you’ll keep coming back for more. Let’s dive right into this slice of paradise and what it has to offer.

This article is part of my complete Florida Keys travel guide, where I share itineraries, island guides, and essential tips for planning your Keys vacation.

Where to Stay in Key West

Key West is made of many distinct areas, as detailed in my neighborhood guide. For travelers wanting a true taste of Key West, proximity to Duval Street is key. For this reason, I recommend staying within walking distance. This avoids parking hassles and keeps you close to the best restaurants and shopping.

Others prefer a quiet place to get away from the bustle of Duval Street. Stay in one of the sweet boutique hotels or bed and breakfasts in the lush historical neighborhood. If you want a true beach and ocean views though, head closer to the Southernmost buoy at the other end of the island.

Pier House Resort & Spa

You’ll find the Pier House Resort & Spa right at the beginning of Duval Street. It’s barely two blocks to Mallory Square, famous for its nightly sunset festivities, and Sloppy Joe’s, the most famous bar in Key West. Talk about location!

Despite being in a busy part of town, Pier House is tucked away into the landscaping, making it a little oasis amidst the the chaos. You would never guess that they have their own little private beach here too! This is the best place to get a bit of both worlds. I personally enjoyed my stay there, as nothing beats being just a walk away from everything.

Southernmost House

On the more quiet end of town, next to the Southernmost Point Buoy, is the Southernmost House. One reviewer describes it perfectly, “We felt like we were visiting our rich, extended family in the midst of the Gilded Age.” This stunning historic mansion directly faces the ocean for stunning views and a constant breeze.

Southernmost House has a private beach, three pools, a tanning pier, and a restaurant. Choose to stay in either one of the cottages or a room within the mansion. Continental breakfast is also included at this family owned establishment. Great for couples and groups who want beachside relaxation with Duval Street just down the way.

Skip the hassle of looking for flights! Use my Award Booking Concierge Service. I’ll find the flights on points and let you know exactly how to book. 

Andrew’s Inn & Garden Cottages

Tucked into the narrow streets, you’ll find all sorts of accommodation options. Andrew’s Inn & Garden Cottages scores a perfect five stars with guests who are smitten by this oasis right near Duval Street. Here you can start your day with a delicious breakfast, spend your afternoons in the pool, and mingle during their complimentary happy hour.

Ella’s Cottages

Ella’s cottages has a similar location to Andrew’s Inn, which puts it perfectly a block away from the revelry of Duval, making a it a peaceful place with excellent access to all the action. The thoughtful service and daily breakfast baskets make this a special stay.

One reviewer even said “This hotel single handedly change my mind about the charm of boutique hotels.” I couldn’t agree more, hospitality takes the forefront at many boutique hotels in Key West. It makes a huge difference when your hosts know and care about you having the best possible trip.

For more help planning your trip, visit my Florida Keys travel guide to explore island comparisons and sample itineraries.

Best Restaurants in Key West

One of the best parts of visiting Key West is indulging in its incredible food scene. From laid-back seafood shacks serving lobster rolls on the beach to elegant fine dining with ocean views, the island is packed with flavors that reflect its mix of Caribbean, Cuban, and Southern influences.

Over the years of living in and exploring the Florida Keys, I’ve eaten my way through Duval Street favorites, hidden local gems, and late-night pizza spots that hit the spot after a night out. Whether you’re craving freshly caught seafood, or just a slice of pizza and homemade gelato, Key West’s restaurants are as vibrant and memorable as the island itself.

• Blue Heaven – A must-visit for brunch. Known for its Caribbean-inspired dishes, lobster Benedict, and towering Key lime pie, plus a lively garden setting where roosters wander freely.
• Latitudes – Located on a private island (Sunset Key), this fine-dining spot is famous for romantic sunset dinners with dishes like grilled swordfish and lobster bisque. Make a reservation to get access to the ferry to get to Sunset Key.
• Hogfish Bar & Grill – A casual, off-the-beaten-path seafood shack on Stock Island, serving its signature hogfish sandwich, conch fritters, and Key West pink shrimp.
• Louie’s Backyard – Upscale oceanfront dining featuring Caribbean-American fusion, with standout dishes like conch chowder, grilled grouper, and lamb chops.
• The Lobster Shack– Tucked away near South Beach, this tiny, unassuming spot serves some of the best lobster rolls outside of New England. Choose from warm, buttery lobster rolls or a chilled version with mayo, both piled high with fresh Florida lobster. The no-frills vibe makes it perfect for a quick yet unforgettable lunch before hitting the beach.
• Bagatelle– Set inside a beautiful old Conch-style house on Duval Street, Bagatelle combines historic charm with creative cuisine. It’s known for its brunch, where you can sip mimosas on the front porch while people-watching, but dinner is just as memorable, with dishes like seared scallops, short rib gnocchi, and of course, Key lime pie.
• Amigo’s Tortilla Bar– If you’re craving Mexican flavors, head to Amigo’s for casual, fun dining right near Mallory Square. Their fresh, square-shaped tortillas make tacos stand out, and the margaritas are some of the best in town. This is my go-to stop in Key West for a reasonably priced meal, and you can sit at the bar facing the street for a lively view.
• Duetto Pizza & Gelato – Duetto is a tiny pizzeria and gelateria that has earned a cult following for its authentic Italian-style thin-crust pizza paired with homemade gelato. It’s a great late-night stop or just a quick lunch. You can order by the slice or grab one of their delicious focaccia sandwiches for just a few bucks.

Best Bars & Nightlife

When the sun goes down in Key West, the island comes alive with a nightlife scene that’s as colorful and eclectic as its history. From legendary bars that once hosted Ernest Hemingway to lively music venues where the crowd sings along with the band, every night feels like a celebration.

I’ve spent many evenings exploring Duval Street and beyond, and no two nights are ever the same—sometimes it’s sipping a craft cocktail under twinkling lights, other times it’s dancing shoulder-to-shoulder with strangers at a rowdy bar. Whether you want a laid-back evening with a rum drink in hand or a wild night you’ll only half-remember, Key West’s nightlife has something for everyone.

• Irish Kevin’s– This Duval Street institution is a nonstop party, known for its live music, crowd interaction, and cheeky humor. The performers here don’t just play covers — they banter with the audience, get people singing along, and sometimes even pull guests on stage. If you’re looking for a wild, no-frills Key West night out, this is it.
• Sloppy Joe’s– Perhaps the most legendary bar on the island, Sloppy Joe’s has been a Key West staple since 1933 and was a favorite haunt of Ernest Hemingway. They keep the lore going with a Earnet Hemingway look-a-like contest every year. With live bands every night, this is one of those must-visit stops where history and nightlife collide.
• General Horseplay– For a more refined cocktail experience, head to General Horseplay. Located just off Duval, this trendy bar is known for its craft cocktails, creative twists on classics, and stylish atmosphere. The back patio often features live music, making it a great alternative if you want something a bit less chaotic than the Duval Street mainstays.
• Key West Legal Rum Distillery– A true hidden gem, this working distillery offers free tours and tastings where you can sample small-batch, handcrafted rum. The distillers use Florida sugarcane, and flavors range from classic white rum to Key lime and coconut infusions. It’s a great daytime stop to learn a little about the island’s rum-making tradition — and maybe bring a bottle back as a souvenir.
• Salute! On the Beach– One of the few true beach bars in Key West. They make a fantastic Painkiller cocktail, combined with varied menu and a great view, it’s a crowd pleaser!

Top Things to Do

Key West is brimming with history, culture, and one-of-a-kind experiences that make it unlike anywhere else in the world. Over the years of exploring the island, I’ve discovered that some of the most unassuming spots—like the Butterfly & Nature Conservatory—end up being surprisingly magical. Meanwhile bigger adventures—such as a trip out to the Dry Tortugas—are worth every bit of the long ferry ride.

From lively nightly sunset celebrations to tranquil gardens, historic landmarks, and unforgettable adventures on the water, Key West offers something for every traveler. Whether you’re drawn by the history, the nightlife, or the tropical scenery, these top attractions showcase the very best of what makes this island so special.

Mallory Square Sunset Celebration

Every evening in Key West, locals and visitors alike gather at Mallory Square for the island’s most famous ritual — the Sunset Celebration. This nightly festival transforms the waterfront into a lively street fair with jugglers, magicians, live musicians, and vendors selling handmade crafts. The real showstopper, though, is Mother Nature: as the sun dips below the horizon, the sky explodes with fiery oranges and purples over the Gulf of Mexico.

• Best Time: Arrive about an hour before sunset to snag a good spot.
• Cost: Free, but bring cash for street performers and snacks.

Southernmost Point Buoy

The Southernmost Point Buoy is one of Key West’s most photographed landmarks. The brightly painted concrete buoy marks the southern tip of the continental United States, just 90 miles from Cuba. Expect a line for photos, but it’s worth it to capture the memory of standing at the “end of the road.”

• Tip: Go early in the morning to avoid long waits.
• Fun fact: The actual southernmost point of the continental U.S. is a privately owned island 10 miles from Key West. The southernmost point of the entire U.S. is located in Hawaii.

Ernest Hemingway Home & Museum

Step into the life of one of America’s most iconic writers at the Ernest Hemingway Home & Museum. Hemingway lived here in the 1930s, and the house is filled with original furnishings, quirky artifacts, and stories of his larger-than-life personality.

Outside, the lush gardens and famous six-toed cats (descendants of Hemingway’s own pets) wander the grounds. The swimming pool, built at an enormous expense during the Depression, was the first in-ground pool in Key West and remains a highlight. Touring this home feels like a true immersion into Key West’s literary legacy.

• Cost: $19 for adults, $7 for kids 6–12.
• Time Needed: About 1 hour. Includes a half hour guided house tour.

Duval Street & the “Duval Crawl”

Duval Street is the heartbeat of Key West — a mile-long stretch buzzing with bars, shops, art galleries, and restaurants. By day, it’s a lively place to browse boutiques, grab tacos at Amigos, or cool off with ice cream from Mattheessen’s. By night, the energy ramps up as live bands take the stage at Irish Kevin’s, cocktails flow at General Horseplay, and history meets revelry at Sloppy Joe’s, Hemingway’s old haunt. Whether you’re strolling with family during the day or diving into the famous “Duval Crawl” after dark, this street is the island’s main stage.

• Tip: Avoid Fantasy Fest (around Halloween) unless you’re ready for full-on debauchery.

Dry Tortugas National Park

Seventy miles west of Key West lies one of America’s most remote and breathtaking national parks: Dry Tortugas. Accessible only by ferry, private boat, or seaplane, this protected island is home to Fort Jefferson, a massive coastal fortress, and surrounded by crystal-clear waters perfect for snorkeling.

Swim alongside tropical fish near the old docks, relax on pristine beaches, and take in the sheer remoteness of this tropical outpost. For the adventurous, primitive camping is available right on the island. Advanced reservations required, and they fill up quickly!

If you are prone to seasickness, definitely take precautionary measures like dramamine. When I did it we had great weather and saw sea turtles the whole way over, but that gentle rock of the large ferry boat still got me feeling a little nauseous.

• Cost: $200+ for ferry, $400+ for seaplane.
• Time Needed: Full-day trip.

Key West Butterfly & Nature Conservatory

Step into a tropical paradise where hundreds of butterflies flutter freely around you at the Key West Butterfly & Nature Conservatory. As you wander through the glass-domed gardens, exotic birds swoop overhead, flamingos strut by, and vibrant blooms surround you.

It’s a magical escape from the bustle of Duval Street — and almost guaranteed that a butterfly will land on your shoulder. This something I tell everyone to stop in to do for an hour or two while in Key West. It is very different from the other things to do and is a refreshing moment to reconnect with nature.

• Cost: $17.50 adults, $12.50 children 5-12.
• Best Time: Morning, when it’s less crowded.

Sunset Sail

Key West sunsets are legendary, but watching them from the water makes the experience even more unforgettable. Climb aboard a historic schooner or catamaran for a sunset sail, where you’ll sip drinks, feel the breeze, and watch the sky ignite with color from the best seat in town. Some sails are lively with music and drinks, while others are more laid-back and romantic. Either way, nothing beats toasting the sunset out at sea.

While we usually cruise around in our own boat, my family and I really enjoyed the schooner ride. It is so peaceful to be sailing rather than having the hum of a motor in the background. Check what the inclusions are for each tour as some include drinks, a bar, snacks, or even dinner.

Truman’s Little White House

History buffs will appreciate a visit to Truman’s Little White House, once a naval officers’ home turned presidential retreat. Harry S. Truman spent 175 days of his presidency here between 1946 and 1952, making key decisions on foreign policy and the early Cold War. Today, tours of the beautifully preserved house offer a fascinating glimpse into Truman’s time in Key West — right down to his poker table and mid-century furnishings.

• Cost: $24 for adults, or package that includes the Conch Tour Train and Shipwreck Museum for $90.
• Time Needed: About 1 hour.

Key West Shipwreck Museum

Part museum, part immersive theater, the Key West Shipwreck Museum tells the story of the island’s wrecking industry — once its most profitable trade. Kids love the interactive displays, while adults will appreciate the mix of history and entertainment. Be sure to climb the 65-foot observation tower for one of the best panoramic views of Key West.

• Cost: $18 adults, $9 kids.

Key West Beaches

Smathers Beach

Smathers Beach is the largest public beach in Key West, stretching nearly half a mile along the south shore. With soft white sand, calm waters, and plenty of space for sunbathing or playing beach volleyball, it’s ideal for a day of relaxation. You can also rent kayaks, paddleboards, or jet skis, and enjoy a scenic walk along the palm-lined promenade.

Why Choose Key West?

As the (so-called) southernmost point of the continental U.S., Key West is famous for its colorful conch houses, quirky atmosphere, historic sites, and unbeatable sunsets. It’s the liveliest part of the Florida Keys, perfect for those who want a mix of culture, nightlife, and Caribbean vibes.

• Best for nightlife, culture, and history in the Keys.
• A mix of luxury resorts and charming B&Bs.
• Incredible dining scene, from Cuban cafes to fine dining on private islands.
• The only spot in the Keys with true nightlife energy plus plenty of historical attractions.

Tips for Visiting Key West

Before you set off to explore Key West’s unique mix of history, culture, and island fun, here are a few tips that will help make your trip even smoother:

• Plan Ahead for Popular Attractions – Experiences like the Dry Tortugas National Park often sell out, so book your tickets well in advance.
• Pack for the Heat (and Rain) – Key West is warm and humid year-round, with sudden tropical showers. Lightweight clothing, sunscreen, and a reusable water bottle are must-haves.
• Ditch the Car – Parking is expensive and limited on the island. Walking, biking, or hopping on a scooter is the best way to get around.
• Embrace Island Time – Things move a little slower here, and that’s part of the charm. Don’t overbook your schedule—leave room for spontaneous adventures.
• Enjoy Responsibly – Duval Street is famous for its bar scene, but pace yourself and hydrate. The Key West sun makes those rum runners hit harder than you’d expect!
• Catch Every Sunset – Whether it’s at Mallory Square, from the beach, or on a sunset sail, make time to watch the sun dip below the horizon each evening. It’s the quintessential Key West experience.

Key West has a way of blending relaxation and adventure like nowhere else. With a little planning and a sense of adventure, you’ll discover why so many travelers (myself included) can’t help but return again and again.

See my 3 day Key West itinerary to make the most of every moment or my full guide to 1 week in the Florida Keys to cover all the islands on your trip. Compare Key West to my Key Largo, Marathon, and Islamorada guides, and you’ll see how each place has a different feel.

Ready to plan your full itinerary? Explore my complete Florida Keys travel guide for everything you need to know before you go.