Where We Stayed: La Pensione Inn
La Pensione Inn is a fantastic home base in Key West. It’s a short walk to Duval Street and conveniently close to the free Duval Loop bus, making it easy to get around without a car. A big bonus? The inn offers a made-to-order omelet bar in the mornings, which is the perfect way to fuel up before a day of exploring.
Day 1: Exploring Old Town & Duval Street
We started our trip by renting a golf cart, which is hands-down one of the best ways to explore the island. Everything in Key West is close, and cruising around makes it part of the fun.
Our first stop was the pier, a great place to soak in those classic island views. When hunger hit, we grabbed lunch at Bo’s Fish Wagon, a must-try. The fish sandwich is simple, fresh, and exactly what you want in Key West.
From there, we checked out Jimmy Buffett’s recording studio, a quick stop but a cool piece of music history many people miss. We continued riding down Duval Street, popping in and out of shops and bars, before touring the Ernest Hemingway Home & Museum. Even if you’re not a huge literary fan, the history—and the famous cats—make it worth it.http://hemingwayhome.com
Next door is the Key West Lighthouse, which offers great views if you don’t mind the climb. We wrapped up the day at Fort Zachary Taylor Historic State Park, exploring the fort and relaxing on one of the best beaches in Key West.
Day 2: Dry Tortugas Adventure
Saturday was all about the Dry Tortugas National Park, and this is something you need to book in advance. The boat ride is part of the adventure, and once you arrive, the water is unbelievably clear. Exploring Fort Jefferson, snorkeling, and just being surrounded by nothing but ocean makes this a once-in-a-lifetime experience.
After returning to Key West, we kept the evening low-key—because after a full Dry Tortugas day, you’ll be tired in the best way. drytortugas.com
Day 3: Duval Street & Island Nights
Key West evenings are where the island truly comes alive. Happy hour here is a whole vibe, and you’ll find great drink specials, live music, and laid-back energy all along Duval Street. Every bar feels different, so it’s easy to wander until you find your spot.
Whether you’re listening to live music, people-watching, or just enjoying a cocktail, nights in Key West are effortless and fun.
Final Thoughts
Key West is the kind of place that mixes history, food, beach time, and nightlife without ever feeling rushed. Staying at La Pensione Inn, renting a golf cart, and mixing iconic attractions with casual local spots made this a perfect 3-day getaway. It’s relaxed, walkable, and full of character—exactly what a Key West trip should be.