Ask any Floridian what you should do as a first-time visitor to Key West and you’ll receive dozens of different suggestions. In fact, you could visit multiple times and still notch a few “firsts” into your belt on every visit. That’s what I did.
My maiden Key West trip was with the family, hitting the landmark sites in Old Town. My second was discovering an appreciation for the sand and sea. My third—well, let’s say I followed its famous bar scene all the way to Mile Zero. During your first visit to Key West, you’ll want to fill three days with on-water activities, historical sites, and plenty of fruity cocktails.
Always dress like you’re spending the day on the boat.
If you only have time for one thing, make it the Ernest Hemingway Home and Museum.
Your first day in Key West should be as limitless as possible, so instead of jumping on a tour right away, make it a DIY day. Renting a kayak allows you to explore whichever waterways you desire, whether that’s just off the beach or up to another key.
You’ll want to recuperate after a long day of paddling. A haunted history tour aboard a trolley is an excellent way to learn about the island while kicking back and relaxing—that is, unless you see a ghost.
Spending the day drinking and fishing on a boat is a lifestyle for many Key West residents. Join them for a few hours on a catamaran tour where whatever you don’t throw back into the water will be fileted for you to enjoy back on the island.
There are dozens of spectacular places to watch the sunset in Key West, but gazing at the sky from the water is a visitor favorite. Let a sunset cruise with a full bar and plenty of hor d’oeuvres be the shining highlight of your trip.
Make a convenient visit to the Dry Tortugas National Park. You’ll board a catamaran and sail to this historic landmark, which is 100 square miles (25,900 hectares) of open water, coral reefs, and several small islands. You can also check out Fort Jefferson—a 16-acre (6.5-hectare) coastal fortress.
If you’ve only got an hour to devote to one final activity in Key West, make it a parasailing trip. Your last glimpse at this beautiful island from high in the sky will be a memory that etches itself into your heart forever.