There’s a reason Key West sits at the top of countless travel wish lists. This tropical island paradise, where Caribbean charm meets laid-back Florida vibes, is a destination full of pastel-colored houses, turquoise waters, and unforgettable sunsets. Whether you’re a beach lover, history buff, or foodie, Key West delivers an experience that feels like a world away.
Key West is compact and walkable, with most attractions centered in Old Town along Duval Street, Mallory Square, and the Southernmost Point. New Town is quieter and offers more space, but staying close to Old Town keeps you within walking distance of restaurants, bars, and beaches.
Ocean Key Resort & Spa
Ocean Key sits literally at the corner of Duval Street and the Gulf, so you’re steps from Mallory Square and front-row for sunsets at Sunset Pier; its rooms, spa, and sunset-facing dining make it a great choice if you want comfort and instant access to the waterfront. The location and service are excellent especially if you want a luxurious, walkable base for both day and nightlife.
The Southernmost Point Guest House
Located near the iconic Southernmost Point buoy, this historic inn offers ocean views, cozy porches, and unbeatable proximity to South Beach and the Butterfly Conservatory. It’s an ideal stay for those who want to experience the charm of Old Town Key West while being just minutes from the best local attractions.
Casa Marina, A Waldorf Astoria Resort
Casa Marina is Key West’s other classic resort with real beachfront, wide grounds, and a slower, resort-y pace — perfect if you want sand, pools, and a full-service property while still being only a short drive from Old Town. Guests who prefer a hotel-with-beach choose Casa Marina for its space and resort amenities rather than the bustle of Duval.
The Marquesa Hotel
This elegant property blends Victorian charm with lush gardens and serene courtyards, offering a peaceful escape right in the heart of Old Town. Only a short walk from Duval Street, it’s ideal for guests who want tranquility without being far from the action.
The Cabana Inn
A charming adults-only boutique inn located just one block from the legendary Duval Street. The Cabana Inn combines old Key West architecture with lush tropical gardens and a relaxing pool courtyard — perfect for travelers who want a tranquil retreat steps away from nightlife, shopping, and dining.
Key West mixes history, nature, and water-based fun: walk Old Town, visit Hemingway’s house, relax on a sandy stretch at Fort Zachary Taylor, and take a boat trip to see the Keys from the water. Below are five vetted attractions I’d schedule first on any short trip.
The Southernmost Point
No trip to Key West is complete without a photo at the colorful Southernmost Point buoy. It’s one of the most iconic landmarks in Florida, and early mornings are the best time to visit before the crowds gather.
Mallory Square Sunset Celebration
The nightly Sunset Celebration is a lively, free event of performers, food vendors, and sunset watchers — it’s one of the most iconic Key West experiences and a must for first-time visitors.
Ernest Hemingway Home & Museum
A short tour of Hemingway’s house offers history, beautiful gardens, and the famous six-toed cats — it’s compact, informative, and a genuine cultural stop on the island. Tickets are purchased at the gate and tours run throughout the day.
Fort Zachary Taylor Historic State Park
A mix of history and natural beauty, this Civil War-era fort also features one of Key West’s best beaches. Visitors can swim, snorkel, or picnic while exploring the historic grounds overlooking the turquoise waters.
Boating Excursion to Sand bar (private charter/snorkel/cruise)
Book a private or shared boat charter for snorkeling, island-hopping, or sunset cruises — seeing Key West from the water is a different, essential perspective and many local captains run half-day snorkel and sunset trips that include equipment and guidance.
Explore Duval Street
No trip to Key West is complete without a stroll down Duval Street, the vibrant heart of the island. Stretching from the Gulf of Mexico to the Atlantic Ocean, Duval Street is lined with lively bars, unique boutiques, art galleries, and historic landmarks.
Conch Tour Train
A fun and informative ride through Key West’s history and neighborhoods—great for first-timers or those just looking for an easy exploration route.
Key West punches above its weight for food: a compact island that mixes fresh seafood, Cuban flavors, tapas, and creative cocktail-driven small plates. The scene ranges from casual docksides with conch fritters to refined oceanfront dinners — all of which makes food one of the best reasons to spend more than a day here.
Louie’s Backyard
Set in a historic oceanfront home, Louie’s Backyard serves elevated Caribbean-American cuisine. With its romantic patio and sea breeze, it’s one of Key West’s most enchanting dinner spots. Louie’s Backyard offers elevated Caribbean-American cuisine in a romantic oceanfront setting.
Santiago’s Bodega serves tapas-style plates that make sharing fun and adventurous; the menu is Mediterranean-influenced with reliably excellent small plates and sangria. It’s a perfect spot for tasting lots of flavors in one sitting and works well for intimate dinners or groups that want to graze.
Clemente’s Pizzeria offers artisanal wood-fired pizzas with locally sourced ingredients and a warm, rustic setting. Located near Duval Street, it’s a casual yet stylish spot perfect for unwinding after a long day of exploring.
Banana Café
A beloved French-inspired café serving delicious crepes, omelets, and fresh juice. Located right on Duval Street, it’s perfect for a relaxing breakfast before exploring Old Town.
La Grignote
This charming bakery and café offers freshly baked croissants, quiches, and pastries made daily. Its cozy vibe and friendly staff make it a must-stop for a light lunch or mid-morning treat.
Blue Heaven
A quintessential Key West experience with outdoor dining under banyan trees, free-roaming roosters, and famous pancakes. It’s a tropical oasis known for its laid-back atmosphere and hearty breakfasts.
Key West’s nightlife moves from mellow sunset-watching to high-energy bar crawls — Duval Street is the spine of late-night activity, Mallory Square gives you the sunset show, and small dive bars offer local bands and late-night crowds.
Sloppy Joe’s Bar is a Key West institution and Hemingway favorite, Sloppy Joe’s is legendary for live music and its fun, rowdy atmosphere. Grab a cold drink, join the crowd, and experience.
The Green Parrot is loved by locals for its unpretentious vibe and frequent live bands; it’s the best place to hear gritty, local music and mingle with residents rather than only tourists.
Hog’s Breath Saloon is famous for its motto “Hog’s Breath is better than no breath at all,” this iconic bar offers live music, frozen drinks, and great people-watching. It’s a must-visit for anyone looking to experience the island’s carefree spirit.
If you prefer a craft cocktail or a thoughtful, smaller bar, these stand out for quality and character.
General Horseplay is a small, playful spot known for creative cocktails and a fun, kitschy vibe with a great atmosphere if you want an offbeat, craft-forward drink.
The Roost is an intimate, neighborhood-style bar with a rotating lineup of interesting cocktails and friendly bartenders; it’s a good choice when you want a quieter bar with well-crafted drinks.
Virgilio’s back-bar is known for great martinis that blends Italian food with bar-focused craft cocktails — it’s a mellow, refined spot for a well-made martini or classic cocktail before or after dinner.
- Book a hotel in Old Town if you want walkability; pick Casa Marina or a beachfront resort if you want guaranteed sand and longer pool days.
- Make dinner reservations (Key West fills up quickly in high season).
- Pack reef-safe sunscreen and comfortable walking shoes — the islands are best explored slowly, on foot or by rented cruiser bike.
- Packing – Bring beachwear, casual sundresses, and a chic outfit or two for upscale dinners. Check out my beach packing list.