A Day Trip to Key West

A Day Trip to Key West

If you’re visiting Islamorada, there is certainly plenty to do right in town that will keep you busy and active throughout your whole trip! However, many visitors look into making a day trip to Key West to experience the Florida Keys most famous destination. The drive is just a little over 1.5 hours, so you can certainly pack a full day in especially if you hit the road early! We’ll give you a full day-long itinerary that will let you experience the best of Key West but have you back in Islamorada by bed time.

Early AM – Depart Islamorada

Photo Yelp

To make sure you get the most out of your day trip, head out first thing in the morning. Stop by Bob’s Bunz which opens at 6am every day and is the perfect stop for a quick coffee & pastry on-the-go on your way out of town. Midway Cafe also opens at 7am and has a great breakfast menu for a quick bite and “the best coffee in the Florida Keys”.


Arrive in Key West

Wondering where to park in Key West? Find a spot at one of the many parking garages that have spots available for up to 10 hours. Once your ride is tucked away head over to the Front St. Depot near Mallory Square to start your day.

Conch Train Tour

This fun train tour can seem like a tourist trap, and Key West is certainly small enough to easily explore on foot, but if you have children or enjoy commentary and stories about local history then this train is a fun way to learn more about some of the iconic spots in Key West. You can hop on/hop off making it flexible and easy to discover things on your own schedule!

Photo: conchtraintour.com

Ernest Hemingway House

Tours are only 30 minutes and provide a ton of awesome stories and information about the life of one of the greatest writers of all time. Plus, you’ll get the scoop on the famous six-toed cats that reside on the property and the reason behind why Hemingway’s wife built (at the time) the most expensive swimming pool in town. Fun and informative for adults and kids.

Photo: theculturetrip.com


Time to grab lunch! The options for good lunch spots in Key West are limitless. Near the Hemingway House, Blue Heaven, Santiago’s Bodega & Mangoe’s Cafe are all popular spots for fresh seafood and lunch fare. If you decide to hop back on the train or head north after your tour, Amigos Tortilla Bar, DJ’s Clam Shack and Caroline’s Cafe all offer solid lunch options.


Shopping on Duval St.

Walk up and down Duval St. for tons of shopping. With everything from touristy t-shirt shops, to name brands and local artisans, you could get lost for hours exploring the shops of Key West! Check out big names like Ron Jon Surf Shop, Tommy Bahama & Lilly Pulitzer. Also make sure to check out some local favorites like Green Pineapple boutique and Key West Aloe.

Southernmost Point

As you make your way down Duval shopping, you can eventually dead end at Southernmost point. Alternatively, you can also catch this during one of the stops on the Conch train tour or earlier in the morning after Hemingway House. Snap a photo at this iconic landmark to document your trip to Key West!

Happy Hour

By now your group might be ready for a snack or a beer. Look no further than Sloppy Joe’s or Hog’s Breath Saloon – both famous Key West mainstays worth checking out and stopping by for a drink. If you’re still up for some time on your feet, you can bounce around to a few of the many bars that line Duval St.

Photo: sloppyjoes.com


Photo: Yelp/Flaming Buoy

Time for dinner! It’s almost hard to offer suggestions for dinner because there are just SO many fabulous options. Here are some tried and true Key West favorites: Bliss Restaurant, Prime Steakhouse, Little Pearl, Bien, Hot Tin Roof, The Flaming Buoy Filet Co.


There is actually a full dessert restaurant called Better Than Sex – maybe worth a look if someone in your group has an insatiable sweet tooth! For most of us, ice cream and key lime pie will do just fine. Stop by Kilwin’s Chocolate & Fudge, Wicked Lick, Kermit’s, and Key Lime Pie Co. for sweet confections of all kind.

Key Lime Pie Co.

Sunset at Mallory Square

If you can stick around to catch the sunset at Mallory Square, definitely do! Depending on the time of year this could happen before or after dinner. The sunsets in Key West are legendary for a reason and you’ll quickly understand the bustle and crowds that congregate there daily to catch this magnificent wonder.

Photo: mallorysquare.com

Back to Islamorada

In just a little under two hours, you’ll be back home in Islamorada! Ready to get a good night’s sleep and take on the next day of activities. While Key West is definitely worth seeing, being back in Islamorada offers tons of less crowded opportunities to experience the Keys at their finest and most beautiful.