Key West is a sun-soaked island paradise at the southernmost point of the continental United States that offers an intoxicating blend of history, culture, and natural beauty. However, due to the sheer amount of things to do in the area, creating your itinerary can seem like a daunting task. That’s where Compass Realty comes in. We’ve created a day-by-day itinerary guide to experiencing the best Key West has to offer. Read our itinerary and make tweaks to suit your tastes to create the perfect Key West itinerary.
Day 1: Historic Immersion & Nightlife
Start your Key West adventure with a morning stroll down Duval Street, the island’s vibrant main thoroughfare. After a stellar local breakfast, head to the Ernest Hemingway Home and Museum. This Spanish Colonial mansion offers fascinating insights into the legendary author’s life and introduces you to the famous six-toed cats that still roam the property.
In the afternoon, visit the Harry S. Truman Little White House, where the 33rd president spent 175 days of his presidency. End your day at Mallory Square for the iconic sunset celebration, where street performers, artists, and food vendors create an unforgettable carnival atmosphere as the sun dips below the horizon.
Day 2: Ocean Adventures
Dedicate your second day to the crystal-clear waters surrounding Key West. Book a morning snorkeling tour to the United States’ only living coral barrier reef, where you’ll encounter tropical fish, sea turtles, and vibrant coral formations. After lunch, take a catamaran cruise that combines dolphin watching with kayaking through the mangrove-lined backwaters.
Reserve the late afternoon for a visit to the Key West Butterfly and Nature Conservatory, where hundreds of butterflies flutter freely in a climate-controlled habitat. For dinner, head to the Historic Seaport district for fresh-caught seafood and waterfront views.
Day 3: Key West Culture & Cuisine
Begin your third day with a visit to the Key West Lighthouse and Keeper’s Quarters Museum, offering panoramic views of the island. Next, join a guided food tour through the historic neighborhoods, sampling Cuban-influenced dishes and learning about the island’s rich culinary heritage.
Cap off the day back on the legendary Duval Street, which is home to an abundance of happening bars. Stop in for a drink, a bite to eat, or a live musical performance; you can find live music on Duval Street every day.
Day 4: Beach & Relaxation
Reserve your final day for pure relaxation at the best beaches in Key West. Whether you prefer swimming, paddling, beach volleyball, or simply soaking up the sun, Key West’s beaches are the perfect places to unlock your happiness. Some of Key West’s top beaches include Smathers Beach, Clarence S. Higgs Memorial Beach Park, and Fort Zachary Taylor Beach.
Where to Stay in Key West
Make your Key West vacation truly exceptional by booking your accommodations through Compass Realty. Our portfolio of well-appointed vacation rentals offers the perfect blend of luxury, comfort, and authentic Key West charm. From expansive vacation homes to modern condos, each property is carefully selected and maintained to ensure your island getaway exceeds expectations.
With prime locations throughout Key West and exceptional customer service, it is no surprise that we are one of the area’s leaders in hospitality. To stay with us, you can make a reservation online or by calling 305-292-1881.
