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5 Day Ultimate Itinerary: the Florida Keys

Turquoise waters, historic towns, vibrant sea life, and stunning sunsets make the Florida Keys the ultimate tropical destination in the USA! I just spent 5 days exploring these beautiful islands, and I'm here to tell you the best things to do on your Keys vacation with this 5 day ultimate itinerary!

This post is sponsored by the Florida Keys & Key West Tourism Development, but all opinions and thoughts are my own.

Where are the Florida Keys?

The Florida Keys are a chain of islands located off the southern coast of mainland Florida. Composed of coral and limestone, the islands curve southwestward for about 220 miles (355 km) from Virginia Key in the Atlantic Ocean (just south of Miami Beach) to Loggerhead Key of the Dry Tortugas in the Gulf of Mexico (Britannica, 23).

The history of the Keys is very extensive and the islands were originally inhabited by Native American people. But, the first permanent settlers arrived about 1822 and engaged in fishing and salvaging shipwrecks (Britannica, 23).

Approximately 1,300 islands make up the Keys, but there are 5 main regions: Key Largo, Islamorada, Marathon, Big Pine Key & the Lower Keys, and Key West. Each region has its own unique character and is popular for different things.

The two regions I visited during my time, that I recommend to you are Islamorada and Key West. Islamorada is known as the sport fishing capitol of the world, and the backcountry here is perfect for fishing, kayaking, and more! Key West is the southernmost city and is actually closer to Havana, Cuba than Miami! This city has a rich history, quaint streets, upscale restaurants and shopping, and a great nightlife.


Best time to visit the Keys?

There really is no bad time! Although typically, the best time to visit the Keys is between November-March, aka during their dry season.

The Keys has two seasons, like much of the Caribbean, the wet/hurricane season during the summer months (May-Sept) and the dry season during the winter months (Oct-April). Seaweed can also appear to be more prevalent on the beaches during the summer months.

Temperatures during the winter months range from a high of 75-79F and a low of 67-72F. During the summer months the temperature doesn't get much hotter with a high of 85-91F and a low of 77-81F, but it is very humid in these months which will make it feel hotter.

Read more about the weather in the Keys on the Florida Keys Tourism website here!


How to get around the Keys?

Since the Keys are made up of many different islands to see the most during your trip I strongly recommend renting a car. I suggest you fly into Miami International Airport (MIA) and rent a car at the airport (we did Budget car rental, but I didn't have a good experience with them, there are many other companies to rent from as well). From there, you will drive down the iconic US-1 towards the Keys and it only takes about an hour to get to the first island, Key Largo, from the airport.

You can read more information on the best way to get to the Keys by land, air, and sea on the Florida Keys Tourism website here.


5 Day Ultimate Itinerary

Day 1: Fly into Miami and Drive US-1 to the Keys

Welcome to Florida! Today you will fly from your home base to Miami International Airport. There you will pick up your rental car and start on your way to the first island you're visiting which is Key West! The drive in total is roughly 3.5 hours from Miami to Key West (depending on traffic), so just know that you may want to book a flight that gets in earlier in morning/afternoon.

Drive the scenic US-1 to Key West, and be sure to take your time. It is a gorgeous, once in a lifetime drive with many opportunities to pull over and admire the beauty!

Since you will spend most of today driving, tonight will be more chill to get settled in. Upon arrival into Key West, check into your hotel. I recommend staying at the Perry Hotel Key West! It is such a beautiful property, and conveniently has a free shuttle bus that takes you to the heart of downtown Key West, which is so nice because it's a bit of a nightmare (and expensive) to find parking on your own.

Once you're settled into the Perry Key West, take the hotel's shuttle into Old Town Key West and grab dinner at Half Shell Raw Bar. Located in the Key West Historic Seaport, the casual Half Shell Raw Bar serves fresh seafood, from fish and chips to its famous Half Shell conch ceviche. Diners sit at picnic-style tables and can gaze over the water to watch boats come and go, while enjoying local seafood such as Key West pink shrimp. I loved this restaurant, the chill vibes and delicious food makes it a great first place to go on your trip in the Keys!

Day 2: Exploring Key West

Good morning in Key West! Today you should take the day to explore Old Town Key West and all it has to offer (which is a lot)!

I recommend starting your day off by going to the famous, Blue Heaven. Home to the most “heavenly” breakfast in Key West (think seafood eggs Benedict and homemade banana bread), this shuttered blue building has a century-old history of entertaining islanders on Petronia Street in the historic Bahama Village neighborhood. Through the years, the venue has hosted cock fighting, gambling and Friday-night boxing matches refereed by Ernest Hemingway. Today, diners enjoy Keys, Caribbean and seafood specialties and memorable meringue-topped Key lime pie. The ambiance is so tropical and chill, and the food will not dissapoint! It's a great way to start off your day in Key West.

Next stop of the day, check out the famous 'Southernmost Point Sign' for a picture! This is an iconic landmark because it's the southernmost point of the United States, and is only 90 miles from Cuba! It's actually closer to Cuba than it is to Miami. I recommend coming here earlier in the morning for a picture because a long line forms in the afternoon full of people waiting for their picture.

Just down the street, you will find the beautiful Ernest Hemingway Home & Museum. Ernest Hemingway lived and wrote in Key West for nearly 10 years, finding solace and great physical challenge in the turquoise waters that surround this tiny two-by-four-mile island. At this Whitehead Street property, guests can step back in time and visit rooms and gardens where the Nobel Prize winner spent the most prolific period of his writing career. Notable features include the island’s first swimming pool and a colony of cats, many of them six-toed, supposedly descended from a sea captain’s feline given to the author. Hemingway wrote many of his classic works in the second-story studio that adjoins the Whitehead Street house. Among them: “Death in the Afternoon,” “For Whom the Bell Tolls,” “The Snows of Kilimanjaro” and “The Short Happy Life of Francis Macomber.” He used Depression-era Key West as the locale for “To Have and Have Not” — his only novel set in the United States. This is a must visit spot in Key West, and you can purchase a pass on the spot!

Across the street from the Hemingway Home, you will find the Key West Lighthouse. It is so beautiful and filled with so much history. The current lighthouse opened in 1848 with a woman as its Keeper; nearly unheard of during the 19th century. In the years following, the Key West Lighthouse underwent a number of upgrades including the installation of a Third Order Fresnel Lens, an extension to the tower which allowed the light to be seen from a greater distance, the addition of Keeper’s Quarters, and finally the electrification of the light. In 1969, the U.S. Coast Guard decommissioned the Key West Lighthouse since there was no longer a need for a full-time Keeper due to technological advancements.

Today, this sentinel of the sea stands as a museum dedicated to Key West’s maritime heritage and to the men and women who bravely kept the light burning through the threats of war and weather. Today, visitors can walk up the 88 steps to the top of the light as well as explore the belongings, photographs, and words of the lighthouse Keepers and their families who lived a now obsolete, yet never forgotten, way of life.

Now that you've learned more about the history of the island, I recommend seeing the natural beauty! Clarence S. Higgs Memorial Beach was my favorite beach on Key West, and if you want some time to relax and soak up the rays I recommend coming here.

After a fun-packed day of sightseeing, it's time to end it with a relaxing sunset cruise! I did mine through Sebago Watersports and we really enjoyed it! They provide free drinks, and a relaxing cruise around the coastline of Key West on a spacious catamaran! It's the perfect way to end your day.

After your sunset cruise I'm sure you will have worked up an appetite. So, I recommend stopping by the famous Conch Republic Seafood Company for dinner! They serve fresh dock-to-dish dining in the building formerly known as the Singleton Fish House and Ice Plant. For many years, local shrimpers unloaded, processed, and shipped thousands of pounds of Key West Pink Shrimp from this location.

Photos courtesy of

Day 3: Leave Key West, Go Kayaking, and Head to Islamorada

Today's the last day in Key West, so I recomend spending this morning by exploring it a different way - through the mangroves! We did a glass bottom kayaking tour with Get Up and Go and absoutely loved it! This was my first time doing glass bottom kayaking, and I fell in love. This tour goes through mangroves, beautiful waterways, and the water is sooo clear. And keep your eyes peeled for some exciting nature and marine life in the Florida Keys backcountry! I saw a sea turtle, many sharks, and endless fish during our tour!

After your adventure on the water, it's time for some R&R on the beach. On your way from Key West to Islamorada you will find this beautiful beach, Sombrero Beach which is more of a hidden gem. It's a great local spot to chill for a bit before continuing on your way.

Located across the street from Sombrero Beach, you'll find the Turtle Hospital. Opened in 1986, the Turtle Hospital treats injured sea turtles and, when possible, returns them

to the wild. Educational tours introduce visitors to the resident sea turtles and the hospital's curative programs for loggerhead, green, hawksbill and Kemp's ridley turtles. The hospital is believed to be the world’s only state-licensed veterinary hospital dedicated solely to the treatment of sea turtles. Reservations are recommended for tours, so you can learn more and book your spot here!

Photos courtesy of

Continue on your way, and check into your hotel in Islamorada. I recommend staying at the Fisher Inn Resort & Marina which is an affordable, waterfront hotel right off US-1. Fisher Inn Resort & Marina offers guests a modern, stylish and comfortable place to stay while visiting Islamorada. The resort features vibrant rooms with useful amenities like kitchenettes with refrigerators and free WiFi. They have a variety of rooms such as a Seaside Villa situated steps away from the sand or choose an intimate Tarpon Room.

Tonight I recommend a local favorite Italian spot, the Italian Company. It was some of the best Italian food I've had in awhile and is only a few minutes away from the Fisher Inn! I got the penne alla vodka, and it was so delicious! They also have amazing Neapolitan-style pizza that I would strongly recommend.

Day 4: Snorkeling, and Exploring Islamorada

Good morning from Islamorada, the island known for beautiful water, fishing, snorkeling, and more! I recommend doing one of those things today; such as snorkeling with Islander Girl Snorkel & Tour. I had this tour booked and, unfortunately due to poor weather, it got cancelled, but I still recommend this company as they have 5 stars on Google with over 800 reviews. Islander Girl’s snorkel shop is owned and operated by a mother/daughter team that grew up right here in Florida Keys doing what they do best: diving and snorkeling!

For lunch today in Islamorada, an option is to visit Robbie's Marina. Robbie’s Marina is an eclectic mix of outdoor shops, food vendors and tarpon feeding. You can also grab a bucket of fish to feed the tarpon or enjoy watching everyone else getting up-close and personal with the huge fish. The Hungry Tarpon Restaurant and Bar offers a large menu with a variety of options for the entire family.

Go back and hang out at the Fisher Inn before dinner time. They have free kayaking and SUP's for guests that you can take out and explore the mangroves that are right out front of the property. It's really beautiful, and a fun, free, relaxing activity to do!

Before dinner, head over to Florida Keys Brewing Co. I got a tour of this brewery and fell in love with their story, products, and the vibe. They have been brewing up tasty beers in Morada Way’s Arts and Cultural District since March 2015 and they infuse their brews with local flavors such as Key limes, citrus, and local honey.

PRO TIP: If you visit on the third Thursday of the month, there will also be a beautful art market on the street in front of the brewery! We were lucky that it was going on while we were there and I got a beautiful, handmade bracelet from a local artist.

Tonight, enjoy dinner at the beautiful restaurant Marker 88. This was my favorite restaurant we visited because not only is the food amazing, but the vibes cannot be beat. From ocean to plate, guests can expect an extensive selection of new and globally inspired dishes providing a simple yet extraordinary dining experience in the heart of Islamorada. Since 1967, Marker 88 has been a Florida Keys dining institution. Their fresh takes on seafood, steaks, pasta, and hand-crafted cocktails deliver a culinary experience that is unique and unparalleled to the Keys. Its picturesque sunset views, beachfront dining, extraordinary food & beverage program, and dockside service lend the perfect atmosphere for all to enjoy one of the Keys' most iconic dining experiences imaginable.

Day 5: Day at Leisure, and Drive Back to Miami to Depart Home

Today is your last day in the Keys. You can start your morning by visiting the beautiful Gardenia's Bistro on your way out of town. This is a delicious cafe located within a beautiful flower shop! It's definently a hidden gem.

Enjoy the drive on US-1 one more time before making your way back to mainland Florida, and departing out of Miami International Airport.



In conclusion, the Florida Keys are a beautiful chain of islands with endless things to do! From snorkeling, to kayaking, to relaxing on the beach, to shopping, to concerts, and more, there's really something for every kind of traveler. If you are considering a trip there, I hope this inspires you to book that flight! And be sure to reference if you need any more help planning your trip!

And one last thank you to the Florida Keys Tourism Board for hosting me during my time on the islands, I had an amazing time and know I will be back one day!

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