We independently research and recommend any products or places but we may earn a commission if you click on links we provide. Learn More.
Short on time but still want to get the most out of your trip to Key West? No problem! This three-day Key West itinerary will help you make the most out of your time so you can spend more time exploring and less time wandering aimlessly.
Whether you’re after scenic ocean views, cultural landmarks, or unspoiled wilderness, this island packs plenty into its small size. In just three days, you can experience all the island’s main highlights, from Hemingway’s favorite haunts to the sandy beaches and beyond.
Day 1
Welcome to your first day in Paradise! The first day of your three-day Key West itinerary is all about exploring the highlights of Key West and getting a feel for the island.
Check-in
First, you’ll want to get to your accommodation and check-in. Even if you can’t check in until later in the afternoon, you should try to arrive early so you get a full day in Key West. Most hotels and home rentals will let you drop off your luggage before the official check-in time, so be sure to talk with your host before you arrive.
If you’re trying to decide where to stay, consider which type of vibe you’re going for. Key West, though small, offers two distinct experiences depending on which side of the island you explore: the east and west sides. The east side is more residential and less touristy, with one of the biggest beaches on the island. The west side is home to Old Town and its many attractions, including Duval Street, the Ernest Hemingway Home, the Southernmost Point Buoy, and more.
We would recommend staying in Old Town Key West since it is much closer to all of the main attractions. Most of the hotels in Old Town have limited to none parking spaces though so keep that in mind when arriving. This will create for a better experience and it would be better to rent a bike to get around rather than a car.
Brunch
Once you’ve dropped your bags, you can begin exploring Key West. But first, you’ll want some sustenance.
Start your day at a local favorite like Blue Heaven, a quirky outdoor spot in Old Town known for its heavenly pancakes, massive slices of key lime pie, and Key West roosters wandering about. This place is popular and fills up fast, so be prepared to wait for a table unless you get there right when they open (8 am).
Sarabeth’s is another great brunch option. This is a cozy eatery in a historic clapboard building known for its delicious eggs benedict and fresh pastries.
Explore Old Town Key West
After brunch, take a leisurely walk through Old Town, the historic core of the island. Stroll along the colorful streets and admire the charming cottages, lush gardens, and Caribbean-inspired architecture. Here are some of the highlights you can pick and choose from while exploring Old Town.
There are so many places to explore in Key West so we recommend picking a few places you want to see the most. Then start from one side of the island and make your way over to the other side. Here is a map that includes the top must-sees in Key West so you can make a plan on which places are next to each other to make your way across the island.
Whether you want to see the Ernest Hemingway House, the Butterfly & Nature Conservatory, Key West Lighthouse, Harry S. Truman Little White House or Audubon House this is the time to explore some of the top places on your list.
Fine Dining At Latitudes
After a refresh back at the hotel and getting settled in, there’s no better way to highlight your first day in Key West than with a fine dining experience. After exploring some of the island’s highlights, take a 5-minute ferry over to Sunset Key where the restaurant is located.
There you will be treated to dishes with ingredients that are locally sourced and ocean views that make any dining experience that much better. It is important to make reservations ahead of time at this restaurant so be sure to plan ahead.
Day 2
For the second day of your three-day Key West itinerary, it’s time to experience Key West from a different perspective – on the water!
Breakfast
This is a full day, so you’ll want to grab a quick breakfast before getting out onto the water. Cuban Coffee Queen is famous for their strong Cuban coffee and breakfast sandwiches. For something sweet, check out Glazed Donuts, a sweet shop with creative donuts and coffee to go.
After breakfast, make sure to go see the southernmost point because the best time to see it is in the early morning to avoid the crowds. That way you can get in plenty of pictures without having to wait in line.
Dry Tortugas National Park
One of the most unforgettable experiences in Key West is a day trip to Dry Tortugas National Park, a remote park located 70 miles west of the island. Accessible only by boat or seaplane, Dry Tortugas features the historic Fort Jefferson and some of the best snorkeling in the Florida Keys. You can bring your own boat out to the park or catch a ride on the Yankee Freedom Ferry at the ferry terminal on Grinnell Street. The trip takes about two and a half hours, so be sure to get an early start!
Book an excursion on the Water
If Dry Tortugas feels too far for your itinerary, opt for one of Key West’s many water-based excursions. There are tons of gear to rent, tours to book, and adventures to be had right off the island. Some of the top water activities in Key West include jet skiing, sailing, snorkeling, kayaking, and fishing.
Dinner on Duval Street
After a full day of adventure, you’re sure to work up a hearty appetite. For your second night, head to the famous Duval Street – the main drag of Key West. For a more upscale option, try Latitudes, known for its sunset views and gourmet fare. For something more laid-back, DJ’s Clam Shack is a great spot for lobster rolls and conch fritters. After dinner, grab another slice of key lime pie at Kermit’s Key Lime Pie Shoppe. You could also check out the nightlife on Duval Street, where you’ll find live music at fun local bars like Sloppy Joe’s.
Sunset at Mallory Square
As the day winds down, make your way to Mallory Square for the legendary sunset celebration. Street performers, musicians, and food vendors gather nightly to celebrate the sun dipping into the Gulf. Grab a bite to eat and find a spot by the water to witness one of the most beautiful sunsets you’ll ever see.
Day 3
The third and final day on your three-day Key West itinerary is all about slowing down, soaking up the sun, and savoring the island’s easygoing vibes.
Rent Bikes
Key West is best explored at a slower pace, and renting bikes is the perfect way to see the island. Cruise around town, stop for coffee at Funky Rooster Coffee House and explore hidden lanes that you might miss with a car. Once you’re done biking around town, you can hop on the paved path along the A1A and make your way to the beach.
Beach
No trip to Key West is complete without a few hours spent lounging on the beach. Smathers Beach is the largest public beach on the island, with plenty of space for sunbathing, swimming, and renting water sports equipment. You can also visit Fort Zachary Taylor Beach, which offers picnic areas, nature trails, and historic tours of the 19th-century fort located in the park.
Lunch and Shopping
Once you’re ready for a bite, you can head back into town and grab some lunch in Old Town. El Siboney is a beloved Cuban spot known for its authentic flavors, while Garbo’s Grill offers up street food style seafood like fish tacos and shrimp burritos.
Before you leave, be sure to pick up a few souvenirs to remember your time on the island. Duval Street is home to an array of unique shops selling everything from local art to hand-rolled cigars.
Sunset Sail
End your Key West adventure with a memorable sunset sail. Many local companies offer catamaran or schooner cruises where you can sip champagne, enjoy light bites, and watch the final sunset of your trip in style.