3 Perfect Days in Key West: Sunsets, History & Island Vibes
Where We Stayed: La Pensione Inn
La Pensione Inn is an ideal home base in Key West. It’s a short walk to Duval Street and close to the free Duval Loop bus, making getting around easy. The daily omelet bar breakfast is a great perk and the perfect way to start busy island days.
Day 1: Old Town, Duval & That Famous Sunset
We kicked things off by renting a golf cart, the best way to explore the island at your own pace. Our first stop was the pier, a great spot to ease into island time. For lunch, Bo’s Fish Wagon is a must—fresh seafood and one of the best fish sandwiches in Key West.
Next, we checked out Bob Marley’s recording studio, a quick but interesting stop, then cruised down Duval Street to visit the Ernest Hemingway Home & Museum. Even if you’re not a big literature fan, the history—and the six-toed cats—make it worthwhile. Right nearby is the Key West Lighthouse, which offers great views if you’re up for the climb.
We wrapped up the afternoon at Fort Zachary Taylor Historic State Park, where history meets one of the best beaches on the island.
As evening approached, we headed back out for the Key West sunset, which truly lives up to the hype. Whether you watch it at Mallory Square or along the water, sunsets here feel like an event—locals and visitors pause everything just to take it in. After sunset, we stopped by the Hanging Tree Bar, a laid-back local favorite with a classic Key West feel, before ending the night at Sloppy Joe’s. Live music, strong drinks, and nonstop energy make it a Duval Street icon you can’t skip.
Day 2: Dry Tortugas National Park
Saturday was dedicated to the unforgettable Dry Tortugas National Park—definitely book this in advance. The boat ride itself is part of the experience, and once you arrive, the turquoise water, snorkeling, and exploring Fort Jefferson make this a true bucket-list adventure.
After returning to Key West, we kept the evening casual and enjoyed another stroll down Duval, because there’s always something happening.
Day 3: Duval Nights & Island Energy
Key West nights are something special. Happy hour is a whole vibe here, with drink specials, live music, and an easygoing atmosphere all along Duval Street. Every bar has its own personality, making it fun to wander and see where the night takes you.
Top Happy Hour Picks in Key West
Alonzo’s Oyster Bar – Seaport classics with a view
Happy Hour daily (roughly 4:00–6:30 PM) with half-off well drinks, beer & wine, plus discounted seafood and tapas-style small plates. Great spot right on the water for pre-dinner oysters or drinks before sunset
Boat House Bar & Grill – Waterfront sunset happy hour
Daily happy hour around 4:00–6:30 PM with drink specials and 50% off small plates. Fantastic place for an early evening cocktail while watching boats and colors over the harbor.
Thirsty Mermaid Raw Bar Restaurant – Local favorite with craft beers
Daily happy hour (typically 4:00–6:00 PM) featuring $3 pints and other drink specials, plus discounted bites like wings and seafood. Fun casual vibe not far from Duval.
The Docks Restaurant + Raw Bar – Sunset views on Stock Island
Happy hour includes drink deals and sometimes specials on oysters and sharable seafood, with great views over the commercial fishing harbor—ideal if you’re willing to go just beyond Old Town.
Dante’s Pool Bar & Restaurant (Historic Seaport) – Party pool vibes
Happy Hour Monday–Friday (~4:30–7:30 PM) with BOGO beers & well drinks, specials on fun cocktails like Painkillers and Dark ’n’ Stormys, plus discounted bites like wings, shrimp, and snacks next to the pool
From iconic sunsets and historic landmarks to legendary bars and island beaches, Key West packs a lot into just three days. Staying at La Pensione Inn, getting around by golf cart, and balancing adventure with nightlife made this trip unforgettable. Key West is relaxed, colorful, and full of personality—and it’s a place you’ll want to return to again and again.
