Looking for a tropical getaway filled with stunning sunsets, crystal-clear waters, and a laid-back island vibe? Key West, Florida, is the perfect destination for those seeking relaxation, adventure, and a taste of the Florida Keys’ unique charm.
From exploring historic landmarks to snorkeling in coral reefs, this 3-day itinerary will help you make the most of your trip to Key West.
What to Know Before You Go
Best Time to Visit
Key West is a year-round destination, but the best time to visit is between November and April, when the weather is warm but not too humid, and hurricane season has passed. Summer months (June to September) can be hot and humid, but they also offer fewer crowds and lower hotel rates.
Where to Stay
For easy access to Key West’s top attractions, staying in Old Town Key West is ideal.
You’ll be close to Duval Street, Mallory Square, and the historic sites. There are plenty of options, from luxury hotels like The Marker or Casa Marina to charming B&Bs like The Mermaid & The Alligator. If you prefer a more peaceful setting, consider staying at a beachside resort near Smathers Beach.
Getting Around
Key West is a small island, and most attractions are easily accessible on foot or by bike. You can also rent scooters or take advantage of the Conch Train for a guided tour. If you’re staying outside of Old Town, taxis or ride-sharing services like Uber are available.
Day 1: History and Sunset Sails
Morning: Ernest Hemingway Home & Museum
Start your trip by exploring the historic Ernest Hemingway Home & Museum, the former residence of the famous author. You’ll see where Hemingway lived and worked, along with the descendants of his famous six-toed cats roaming the grounds.
Mid-Morning: Key West Lighthouse
Just across from the Hemingway House is the Key West Lighthouse. Climb to the top for panoramic views of the island and the surrounding waters. It’s a short climb and well worth it for the stunning photo opportunities.
Afternoon: Lunch on Duval Street
After a morning of history, head to Duval Street for lunch. This bustling street is lined with lively restaurants, bars, and cafes. Stop at Caroline’s Cafe or Sloppy Joe’s for a laid-back meal featuring local seafood, conch fritters, and Key lime pie.
Afternoon: Southernmost Point
After lunch, take a short walk to the Southernmost Point buoy, one of Key West’s most iconic landmarks. Snap a picture at this popular photo spot, just 90 miles from Cuba.
Evening: Sunset Sail
End your first day with a sunset sail aboard a catamaran. Key West is famous for its breathtaking sunsets, and there’s no better way to enjoy it than from the water. Many tours include champagne, live music, and hors d’oeuvres, making it a perfect evening activity.
Day 2: Snorkeling and Outdoor Adventures
Morning: Dry Tortugas National Park
On your second day, take a day trip to Dry Tortugas National Park, one of the most remote and beautiful national parks in the U.S.
Accessible by ferry or seaplane, this stunning island offers crystal-clear waters perfect for snorkeling, exploring the historic Fort Jefferson, and relaxing on pristine beaches. Be sure to pack a picnic and enjoy the day surrounded by nature.
Afternoon: Relax on Fort Zachary Taylor Beach
If you prefer to stay closer to Key West, spend the afternoon at Fort Zachary Taylor Historic State Park, home to one of the best beaches on the island. You can explore the historic fort, snorkel along the rocky shoreline, or relax under the shade of palm trees. The park also has picnic tables and a small café where you can grab lunch.
Evening: Dinner at Blue Heaven
For dinner, head to Blue Heaven, a quirky, laid-back restaurant known for its tropical garden seating and live music. Try their famous Key lime pie or the Caribbean-inspired seafood dishes. The relaxed vibe and local flavor make it a must-visit spot for dinner.
Day 3: Island Hopping and Local Flavor
Morning: Visit the Butterfly and Nature Conservatory
Start your last day with a peaceful visit to the Key West Butterfly and Nature Conservatory, a serene indoor garden filled with hundreds of butterflies and tropical birds. It’s a tranquil escape from the hustle and bustle of Duval Street.
Mid-Morning: Mallory Square and Historic Seaport
Afterward, head to Mallory Square and the Historic Seaport, where you can explore the shops, visit art galleries, or grab a cup of Cuban coffee at Cuban Coffee Queen. Take a leisurely walk along the waterfront and watch the boats come and go.
Afternoon: Island Hopping by Boat
In the afternoon, consider renting a boat or joining a small group tour to explore some of the surrounding Florida Keys. You can visit nearby islands, snorkel in coral reefs, or simply enjoy a relaxing day on the water. If boating isn’t for you, opt for a guided kayak tour through the mangroves for a closer look at the island’s diverse ecosystem.
Evening: Sunset at Mallory Square
No trip to Key West is complete without experiencing the famous Mallory Square Sunset Celebration. Arrive early to enjoy the street performers, musicians, and vendors that fill the square each evening. Find a spot by the water to watch the sun dip below the horizon in one of the most iconic sunset spots in the world.
Dinner: Latitudes
For your final dinner in Key West, treat yourself to a waterfront dining experience at Latitudes, located on nearby Sunset Key.
You’ll need to take a short ferry ride to get there, but the stunning views and elegant menu make it worth the trip. End your trip with a delicious meal while watching your final Key West sunset.
Tips from a Local:
- Bike It: Key West is a small island, and biking is one of the best ways to get around. You can easily rent a bike for the day and explore the island at your own pace.
- Don’t Miss Happy Hour: Many of Key West’s bars and restaurants have great happy hour deals on drinks and appetizers, usually between 4 and 6 PM. It’s a perfect way to sample local cocktails and seafood at a fraction of the price.
- Wear Sunscreen and Stay Hydrated: The Florida sun can be intense, so make sure you wear sunscreen and bring plenty of water when exploring, especially if you’re spending time at the beach or out on a boat.
- Plan Ahead for Dry Tortugas: If you plan to visit Dry Tortugas National Park, book your ferry or seaplane tickets well in advance as spots fill up quickly, especially during peak season.
- Explore Beyond Duval: While Duval Street is a must-see, don’t forget to explore the quieter parts of Key West, like Bahama Village or the residential streets filled with charming Conch-style houses.