From juicy sunsets to coral reefs, three days in Key West mean time to soak up the quirky charm of the island escape. Come to join the party crowd, watch ocean sunsets, and take in historical sites, then head offshore to see the Gulf of Mexico’s castaway islands and mangroves. Here’s how to make the most of your time in the Conch Republic.
Day 1: Island Orientation
Find the high points of Key West’s tree-shaded streets and waterfront on a tour through the heart of town by trolley or train. In the afternoon, visit some of the stops in-depth, whether you’re following in Hemingway’s footsteps, browsing the shops at Mallory Square, or gazing out from the southernmost point in the United States. In the evening, snag a coveted spot on a sunset cruise from the waterfront; it’s worth booking in advance to ensure your spot. Since the trips range from sails aboard historical vessels to party boats with free-flowing drinks, you can make the night as relaxing or wild as you want.
Day 2: Offshore Explorer
With a full day to explore you can head as far as Dry Tortugas National Park, a cluster of islands with powdery beaches, coral reefs, and a historical military fort. Alternatively, simply snag a kayak, paddleboard, Jet Ski, or cruise boat to see everything from mangrove forests to the surrounding reefs. For an up-close look at the bright corals of the Florida Reef, choose a tour that goes beneath the waves: glass-bottom boat cruises and snorkeling trips give you perfect views, and beginner-friendly dive trips mean you don’t need certification to try scuba diving in Key West.
Day 3: Conch Republic Relaxation
Start your last day with a slow walk on the sand of Higgs Beach, known for catching the best morning light on the island. Instead of committing to lunch in a single restaurant, explore the best of Key West food, from fresh-caught seafood to Key Lime pie, on a food tour of downtown. It’s a shortcut to finding the best bites on the island, with plenty of themed options that offer a delicious take on the history and culture of the Florida Keys. As daylight fades, head to Mallory Square to catch one final Key West sunset alongside celebrating crowds and oddball buskers. Toast your final night with a drink in one of Key West’s many bars—they range from wild daiquiri joints to historic Hemingway hangouts perfect for a leisurely cocktail.