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The Perfect Day in Key West - Travel Itinerary

Welcome to Key West! Also known as the Conch Republic, this almost 8 square mile island is America’s Southernmost city and lies just 90 miles north of Cuba! Known for its turquoise waters, lively nightlife, world-class water sports, and of course… Key Lime Pie, Key West is one of those places that everyone should visit at least once! There’s enough to do in Key West to keep you busy for more than a few days, but if you’re a time-crunched traveler like us, then we’ve got good news for you… You can cover a lot of ground in Key West in a short amount of time! We only had one day to do, see, and eat as much as possible, and we did just that! From eating the famous Key Lime Pie at Blue Heaven Restaurant to strolling down the world-renowned Duval Street to watching the sun go down from a 65-foot catamaran with a cold drink in hand, our time in Key West is something we won’t soon be forgetting. We hope this itinerary/travel guide will help you plan and make the most of your time in Key West!

Looking for accommodations for your time in Key West? Check out some of our recommendations HERE!

Be sure to check out our “One Day in Key West” vlog for a closer look at our time on this beautiful island!

Now, let's get to it...

8:00 am: Coffee/Breakfast

  • Blue Heaven (729 Thomas St)

Described as “Floridian-Caribbean cuisine” Blue Heaven’s dining area is a private courtyard that was once home to Earnest Hemingway's boxing matches (yes, you heard that right). And when I say “private courtyard”, that doesn’t stop the chickens from roaming through the dining area pecking the ground for scraps, or the cats from lounging in any sun-soaked patch of brick in the shady breakfast oasis. Now that you understand the setting, let’s talk about the food! We ordered three of their most popular dishes… 1.) The Lobster Benedict which is a toasted English muffin topped with a generous portion of lump lobster meat, a perfectly poached egg all covered with lime hollandaise, and let me tell you, this dish is as delicious as it sounds! 2.) The Banana Pancakes which were some of the best we’ve ever had. They’re not trying to reinvent the wheel on this one, just simply doing an excellent job at creating a flawless version of a classic. 3.) And no visit to Blue Heaven would be complete without ordering a piece of their famed Key Lime Pie which has been featured on numerous TV shows and is said to be country star Kenny Chesney’s favorite! The nearly 6-inch thick meringue on this pie is beautifully toasted on the outside and soft and airy on the inside, the Key Lime filling is tart and creamy, and the graham cracker crust is sweet, buttery, and crumbly… In other words… It’s the perfect Key Lime Pie!

It is worth noting that Blue Heaven opens at 8 am and is first-come, first-serve (no reservations) for Breakfast and Lunch. Wait times can easily be upwards of an hour just to get a table, so we recommend getting there early! We arrived around 8:30 am on a weekday in May and were seated immediately, but by the time we left around 9:45 am the wait was already upwards of a half hour.

Note: When looking for parking near Blue Heaven (or anywhere in Key West for that matter), be sure NOT to park in any space marked "Resident Parking".

Other Options:

  • Banana Cafe (1215 Duval St)

  • Cuban Coffee Queen (5 Key Lime Sq)

  • Glazed Donuts (420 Eaton St)

  • La Grignote (​​1211 Duval St)

9:30 am: Explore Old Town Area and beyond

Notable Sites/Activities:

  • Duval Street

  • Rum Distillery Tour (Key West First Legal Rum Distillery or Papa’s Pilar Rum Distillery)

  • The Hemingway Home & Museum

  • Key West Shipwreck Museum

  • The Conch Tour Train

  • Harry S. Truman Little White House

  • Key West Lighthouse Museum

  • Key West Butterfly & Nature Conservatory

  • Florida Keys Eco-Discovery Center

  • Key West Cemetery

12:30 pm: Lunch

  • Garbo’s Grill at Hanks! (​​409 Caroline St)

This husband-&-wife-run food stand/trailer (ensconced behind Hank's Hair of the Dog Saloon) has been featured on Food Network’s Diners, Drive-ins, & Dives and serves up an eclectic and inventive offering of tacos, burritos, and burgers. Their Korean beef short rib tacos are a crowd favorite and the Umamiburger smothered in chipotle Gouda won Guy Fieri’s heart in one bite! Needless to say, Garbo’s is worth a visit during your time in Key West.

Other Options:

  • El Siboney (900 Catherine St)

  • BO’s Fish Wagon (801 Caroline St)

2:00 pm-4:00 pm: Jet Ski Tour w/ Fury Water Adventures

From jet ski tours to snorkeling tours to parasailing to bike and golf cart rentals and so much more, Fury Water Adventures is THE place to find your adventure when in Key West! We took the 90-minute guided jet ski tour, and while the weather wasn’t ideal for our time on the water, we still had a good time, so we can only imagine how much fun it would be when the water and wind is calmer.

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2:00 pm-4:00 pm: Beach Time

There is a common misconception that Key West is lined with pristine, white-sand beaches, but in all honesty, it couldn’t be much further from the truth. Due to the fact that Key West is home to America's only living coral reef (the third-largest coral reef in the world) the shoreline is mostly made up of ground coral, which means that most of the picturesque beaches that you have in mind when you think of Key West (i.e. Smathers Beach, Higgs Beach) are all man-made. The only natural, white-sand beach on the island (that I know of) is Fort Zachary Taylor Beach. Regardless if they’re natural or man-made, they are beautiful and worth a visit! So, here are a few of our top picks!

  • Smathers Beach

  • Higgs Beach

  • Fort Zachary Taylor Beach

5:00 pm-8:30 pm: Snorkel/Sunset Cruise w/ Fury Water Adventures

When it comes time to watch the sunset in Key West, there’s no better place to do it than from the water in our opinion. Combine those sunset views with a little snorkeling adventure, and you’ve got a pretty incredible evening on your hands! And that’s exactly what we did with Fury Water Adventures on their “Rum & Reggae” snorkel and sunset combo cruise! After a short ride out on their state-of-the-art, 65-foot catamaran, you’ll have a 30-45-minute snorkeling session where you’ll get to see North America’s only living coral reef up close and personal! After taking in the underwater sites, you’ll climb back aboard the boat for world-class sunset views and bottomless rum punch and beer. We loved our afternoon and evening with Fury Water Adventures SO much and can’t wait to visit again and experience more of their tours and rentals!

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5:00 pm-8:30 pm: Sunset Celebration at Mallory Square

Every evening about 2 hours before sunset locals and tourists alike gather along the shore at the Mallory Square Dock to watch that big orange ball sink into the Gulf of Mexico. This free celebration includes street performers, magicians, jugglers, local artists, and vendors that together (along with the star of the show… the sunset) make up one of the most popular attractions in Key West… The Mallory Square Sunset Celebration!

Note: Depending on the time of year that you visit, the times on this itinerary will change due to the sunset time changing, but if you’re visiting in the spring or fall, these times will be roughly accurate. That said, if you’re not enjoying the sunset on the water (like we did), Mallory Square is our pick for the best place to celebrate sunset!

9:00 pm: Dinner

  • Conch Republic Seafood Company (631 Greene St)

This restaurant serves up “Conch & Caribbean-style” dishes in a laid-back, open-air setting with incredible views of the seaport & marina. We had the conch fritters that were served with a delicious house-made Key Lime Mustard dipping sauce, and the St. Kitts Pasta was to die for! It's lightly blackened shrimp served over crab-stuffed ravioli with spinach, sun-dried tomatoes, and parmesan that is finished with a zesty lemon and garlic cream sauce... Without a doubt, one of the best pasta dishes that we’ve ever had. The "Catch of the Day" fish sandwich was a little basic, but that’s to be expected from a simple dish like that. I had hoped that they would elevate it with a gourmet bun, or special sauce, but that wasn’t the case. Nonetheless, our overall experience was a positive one and we would definitely recommend giving Conch Republic Seafood Company a try on your visit.

Other Options:

  • Hogfish Bar and Grill (6810 Front St)

  • Amigos Tortilla Bar (425 Greene St)

And just like that, your day in Key West has come to an end! We hope that this has helped you plan and make the most of your Key West vacation! If you did find it helpful, please consider heading over to our YouTube Channel and subscribing for more travel content, and following us on Instagram. It would mean the world to us!


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