How to do Key West in Three Days

The ribbon of road, US Highway 1, leads you over forty two bridges, revealing sublime tropical scenes and turquoise water views throughout a necklace of islands trailing West from the Southern tip of Florida. As you cross the final link in your journey, the Cow Key Bridge, you know you have arrived at the ultimate destination, Key West.  How long will you be joining us for? Like most people you probably didn’t book for a long enough stay.  That’s ok, you can always come back but for now let us tell you How to do Key West in Three Days!

You can go no further, nor would you want to, once you discover all this unique two by four mile island paradise has in store for you. No need to rush. You’re on island time here. Slow down and savor each day of your Key West experience.

Enter the welcoming island on Roosevelt Boulevard and forget the GPS navigation. Go right for the Northern Business Loop or left for the Southern Route. Once you reach your lodging location, you can give your vehicle a rest. Key West is a walkable town, and easily accessible by renting a bicycle or scooter. Your hotel may even provide one for you or you can message our Concierge for help.

Check in and leave unpacking for another time. Treat yourself to the sunshine and fresh air by taking a relaxing stroll in the neighborhood. Whether you’re staying in an Old Town bed and breakfast, or a posh resort setting, notice you’re never far from local restaurants, shops and of course, the sparkling Atlantic or Florida Gulf waters. Check here for our favorite Key West Accommodations.

Feel comfortable asking a friendly local (like Amber) you meet on the street for recommendations of a tasty island meal. Key West is home to delicious options found at food wagons and hole-in-the-wall venues you may not find on your own. 

After you’ve gotten acquainted with your surroundings, you’ll snuggle into your comfortable bed to the sounds of the island breezes through the palm trees. Sleep peacefully and dream about a full day of Key West adventure.

If you’re curious about the history and sights of Key West, begin your day with a ride on the Trolley or the Conch Train. The narration of the drivers is interesting and humorous as they relate stories and island lore. Several stops along the way allow you to get off, take your time to sight see, and re-board later. Morning tours can be less crowded and following your tour, you may want to revisit a few places you saw earlier in the day.

After your island tour, brunch or lunch in an open air eatery and sample some fresh from the Keys seafood and famous Conch fritters. Ask about the signature cocktail wherever you are, always tops in originality and flavor. Or try a local beer. 

If your historical curiosity about Key West is peaked, don’t miss the red brick Customs House Museum on Front Street for insights on the early days of island life, as well as ever changing exhibits focusing on the people and personalities that have contributed to Key West’s diverse population. So named for its original location on the waterfront, Front Street is home to several historical structures re-purposed into shops, restaurants and a live performance theater. A small park in front of the theater is populated with the bronze busts of Key West’s most prominent historic citizens.

If a taste of contemporary culture is what you’re looking for, head for nearby Duval Street, the main North to South thoroughfare crossing Key West. Along this two mile stretch you will find a wide assortment of entertainment, shopping, dining and artistic options. Be sure to pop into the famous Emeralds International to see the best Conch Pearl collection in the world. Of course people watching is often the most entertaining as tourists, locals, and all sorts of interesting people converge each day and well into the night along this lively street.

The Northern end of Duval, famous for countless bars and constant music in the air is always the most active scene. The further South you travel on Duval Street, galleries may outnumber the bars. Find a relaxing, sandy beach at the Southernmost end to reward yourself for crossing the entire island . Also a popular restaurant, the Southernmost Beach Cafe awaits to replenish you with island style food and refreshing drinks.

A trip to Key West is not complete without witnessing the Sunset Celebration on Mallory Square. Part street fair, part circus, this early evening venue draws all island visitors to be entertained and awed by talented street performers, and local artisans selling their creations. Then the moment arrives for the photo op you’ve been waiting for as Mother Nature takes center stage, and her golden sun sinks into the watery horizon.  

As night falls over the island, will you head for the lights and excitement of Duval Street? Or will you opt for a moonlit walk with feet in the sand along South Roosevelt’s Smathers Beach? Whichever your choice, reserve tonight for a scrumptious dinner. Key West boasts more than 150 restaurants, each offering a distinctive take on island fare and the most delicious local seafood.

As morning light greets your final day in Key West, what have you missed? You’ve walked the charming neighborhoods, you’ve peddled a bike from end to end, you’ve ridden the informative trolley, but you haven’t appreciated the view of Key West from the water. After all, Key West is an island and today you’re headed for adventure on the surrounding brilliant blue waters.

Pick you speed. Pick your vehicle. For a fast and invigorating ride, hop on a wave runner to circumnavigate the island, or pilot a sail boat to test your sailing skills. If you’re still in relaxation mode, there’s nothing like the gentle ride of a paddle board or kayak to explore the calm back waters and lush mangroves.  

You may choose to leave the helm of your craft to the experts. Sit back and enjoy a day or sunset sail excursion on the waves aboard the majestic. There’s something about being surrounded by water that refreshes and renews. If you happen to be here during a full moon, you MUST go on a Full Moon Sail. Message our Concierge for help finding one.

Take your final hours to collect a souvenir or two, some renowned Key Lime pie, a signature Key West bracelet or a precious silver coin from Mel Fisher’s Treasures. And don’t forget to make your reservations for your next visit. Stay in the Key West loop by following our Facebook page and messaging us to get started. We can help you with any questions you may have.

You know you will be back. It’s a Key West guarantee.