The BEST 5 Day Florida Keys Itinerary in Paradise!

Are you dreaming about visiting the Florida Keys and looking for the perfect itinerary?

The Florida Keys are my favorite place on Earth, and I don’t say that about just anywhere!

I grew up visiting the Keys as a kid because my dad was raised there! I even got married in the Keys, and now my husband and I return at least once a year!! I’ve been to the Florida Keys countless times, and I can say without a doubt they are worth a visit (or two or three).

In this blog post, I’ve put together all my knowledge on the Keys into an epic 5 Day Florida Keys itinerary. This itinerary is perfect for those with just under a week to spend in the Keys and want to see the top highlights.

You’ll get to snorkel in the clear waters of Islamorada, drive over the Seven Mile Bridge, see the iconic historic sites of Key West, and more!

So, keep reading if the Florida Keys are on your bucket list and you need a done-for-you itinerary!

Overview of the Florida Keys

The Florida Keys are a sun-soaked string of islands stretching from the southern tip of mainland Florida down to the vibrant island of Key West.

Spanning 113 miles, the Florida Keys are one of the most stunning and unique destinations in the U.S. They are connected by one major road and 42 bridges, the most famous of which is the Seven Mile Bridge!

As you drive through the Keys along the Overseas Highway, you’ll be treated to some of the most beautiful ocean views in the world, with the turquoise waters of the Gulf of Mexico on one side and the Atlantic Ocean on the other. It takes around 2.5 hours to drive from one end of the Keys to the other!

While there are over 800 keys in the Florida Keys archipelago, not all of those are inhabited! Instead of going Key by Key, it’s easier to break the Keys up into three main areas: the Upper Keys, Middle Keys, and Lower Keys.

Here’s a quick overview with a fun map that showcases the different areas!

• Upper Keys: Main areas are Key Largo and Islamorada. Known for the amazing diving, snorkeling, and fishing.
• Middle Keys: Centered around Marathon. A nature lover’s paradise with pristine beaches and wildlife encounters, plus the Seven Mile Bridge!
• Lower Keys: Key West, the lively heart of the Keys, brimming with history, culture, and non-stop fun, plus other off-the-beaten-path keys like Big Pine Key

In this itinerary, you’ll have the opportunity to explore all 3 main areas of the Keys! And you can also check out my Ultimate Florida Keys Travel Guide for a more detailed breakdown of each major Key.

How to Get to the Florida Keys

How you will arrive in the Florida Keys will depend on where you are traveling from! Some options are more convenient than others, which I will cover below!

Flying into the Keys

If you are arriving to the Florida Keys from outside the state of Florida, you will likely be flying into the Keys!

Technically, the only major airport in the Keys is Key West International Airport (EYW). EYW is a small airport located right in the heart of Key West, making it easy to jump straight into the action as soon as you land. However, it can be pricey to fly into EYW, and they are limited routes and airline choices,

On the other hand, many visitors choose to fly into Miami International Airport (MIA) or Fort Lauderdale-Hollywood International Airport (FLL) due to lower costs and more flight options.

Miami Airport is only around an hour’s drive from Key Largo (the uppermost Key), with Fort Lauderdale Airport just over 1.5 hours away. So, it is totally doable to start your Florida Keys itinerary from one of these airports! You can even add a day of sightseeing in Miami or a trip to the Everglades to your itinerary.

⭐ Pro Tip: I personally recommend booking one-way flights for your Florida Keys trip. If you can, fly into Key West and out of Fort Lauderdale or Miami (or vice versa). This way, you do not have to drive the length of the Keys twice. ⭐

This itinerary assumes you are starting your journey from Fort Lauderdale or Miami airport and ending in Key West, but it can easily be reversed!

Renting a Car in the Keys

No matter where you fly into, this itinerary will require a rental car. As mentioned above, the Florida Keys stretch over 100 miles. If you want to explore them properly from Key Largo to Key West, you’ll need a rental car!

I personally love using DiscoverCars.com. Not only do they have an amazing cancellation policy, they also secure you the best price by comparing costs across all the major rental car companies!

For the Keys, I recommend booking a fuel-efficient car, as you’ll be driving a good amount, and gas prices tend to be a little pricier in the Keys.

If you are able to book one way flights, you can pick up your rental car at the Miami or Fort Lauderdale airport, and drop it off at the Key West airport!

🚗 Check pricing and availably of rental cars for your Florida Keys adventure here!! 🚗

Driving from Other Parts of Florida

For Florida locals who love road trips, driving to the Florida Keys from other parts of Florida is a fantastic option! The Overseas Highway (U.S. Route 1) connects the Florida mainland with the Keys, offering breathtaking ocean views the entire way.

Here are the approximate drive times from major Florida cities:

• Miami to Key Largo: ~1 hour
• Orlando to Key Largo: ~4 hours
• Tampa to Key Largo: ~5 hours

I personally make the drive from Orlando to the Keys at least once a year!

⭐ Pro Tip: When driving through South Florida to get to the Keys, try avoiding rush hour traffic, especially in Miami. Rush hour is typically 7am-10am and 4pm-7pm! In addition, traffic into the Keys on Friday afternoons and out of the Keys on Sundays can be particularly brutal. ⭐

Day 1: Arrive in the Keys

Alright, it’s time to get into this 5 Day Florida Keys itinerary!! Your adventure begins in the Upper Keys, where the water is crystal clear and the pace is slow (which is very different from Key West).

Morning: Driving into Key Largo

Whether you fly into FLL or MIA, make your way south towards the Keys on the Florida Turnpike or I-95. Once you reach Florida City, you’ll get on “The Stretch”, the 18-mile section of US1 that connects Florida City to Key Largo.

After passing over the Jewfish Creek Bridge, you’ll find yourself in Key Largo!! Key Largo is the largest Key of the Florida Keys and is home to John Pennekamp Coral Reef State Park, the USA’s first undersea park!

For this itinerary, you’ll be staying in the neighboring town of Islamorada instead of Key Largo. However, feel free to stop anywhere in Key Largo that catches your eye on the way to Islamorada!

Afternoon: Arriving in Islamorada

Just 30 minutes south of Key Largo is the wonderful town of Islamorada, my favorite part of the Florida Keys! While you can absolutely stay in Key Largo instead of Islamorada for the first leg of this itinerary, I prefer Islamorada thanks to its incredible restaurants, breweries, and variety of things to do!

Depending on what time you arrive, you can grab lunch or head straight to your hotel to check in. If you have time for lunch, head over to the iconic Tiki Bar at Postcard Inn Beach Resort & Marina (now called Three Waters).

This laid-back beachfront bar is a local favorite and the birthplace of the Rum Runner cocktail, a must-try when in the Keys. They also have delicious and fresh seafood like fish sandwiches, conch fritters, and more!! It’s one of my favorite spots in the Keys.

After lunch, check into your hotel (more on that in a sec), explore the resort, lay by the pool, and take advantage of the free kayaks or paddle boards that most hotels have!

Evening: Sunset Dinner at Lorelei’s

For your first dinner in the Keys, head to Lorelei Restaurant & Cabana Bar, one of my favorite restaurants in not just Islamorada but all of the Keys. Just look for the giant mermaid on the side of the road!

Located right on the bayside, Lorelei has unbeatable sunset views, live music, and some of the freshest seafood around. Order some fish dip and a tropical cocktail, and be sure to stay until the sun dips below the horizon—it’s one of the best sunset spots in the Keys!!

We always come back here at least once during every trip to the Keys, whether for lunch or for dinner, and are never disappointed!

Where to Stay in Islamorada

Another great part of Islamorada is the variety of places to stay! Whether you are looking for a beachside bungalow or a luxurious resort, Islamorada has something for you.

Here are my personal favorite hotels in Islamorada!

1. Cheeca Lodge & Spa – This luxurious resort offers everything you need for a perfect stay, from beachfront rooms to a nine-hole golf course. It’s a great spot for couples and families alike.
2. Islander Resort – A casual and family-friendly resort with direct beach access, comfortable rooms, multiple pools, and plenty of activities.
3. The Caribbean Resort – My fav resort in the Keys (where I got married!). 22-unique Caribbean-style homes, a small marina, and gorgeous zero-entry pool. Perfect for large groups! Read more about the Caribbean Resort here.
4. The Moorings Village – Known for its elegance, luxury, and privacy, this resort offers beautiful cottages set among palm trees and lush gardens. It’s perfect for a romantic getaway! Also where Bloodline was filmed.

➡️ For more details, make sure to check out my full guide on the Best Hotels in Islamorada!

Day 2: Snorkeling, Beers, and a Sunset Dinner

Morning: Breakfast and Snorkel Tour

Today, you’ll get a taste of what the Upper Keys are all about: the incredible underwater landscapes.

Start your day with a quick breakfast at your hotel. Or if you want to eat out, you can check out Midway Cafe in the heart of Islamorada! They have incredible pastries and coffee (one of the only true coffee bars in the Florida Keys).

After breakfast, it’s time to hit the water for one of the most memorable experiences the Florida Keys has to offer: snorkeling. The waters of the Florida Keys are part of the Florida Keys National Marine Sanctuary and help make up the only barrier reef in North America.

In my opinion, the snorkeling in Islamorada is the best in the entire Florida Keys, which is another reason I recommend staying here!

There are tons of snorkel tours in Islamorada, but I recommend booking one that takes you to Cheeca Rocks or Alligator Reef (though this will depend on weather). This Sundance Watersports tour is a perfect option! The waters around Alligator Reef are INSANE, and there is soo much wildlife under the lighthouse.

If you are interested in seeing the Christ of the Abyss statue, you’ll need to book a snorkel tour out of Key Largo. The statue is located in John Pennekamp Coral Reef State Park and one of the most famous snorkel spots in the Keys!

If you’re looking for a bit longer day out on the water, another great option is to book a snorkel and sandbar combo tour.

The Islamorada Sandbar is one of my favorite things to do in Islamorada! Thanks to the shallow water, boats can park right on the sandbar and spend the day relaxing in the water! And with an organized tour, you don’t need to rent your own boat to visit!

Afternoon: Lunch and a Brewery

After working up an appetite snorkeling, head to the Shrimp Shack in Islamorada for a laid-back lunch. This no-frills spot serves some of the freshest shrimp in the Keys. Need more convincing? It was also featured on Diners, Drive-Ins, and Dives!

Next up, spend your afternoon sampling local craft beers at Islamorada Brewing & Distillery. This casual spot offers a variety of house-made brews, including their popular Sandbar Sunday beer, perfect for a sunny day in the Keys.

If you prefer something stronger, try one of their rum or vodka cocktails made with spirits distilled on-site.

They also have a fabulous outdoor beer garden, food truck, and backyard games. It’s very dog and kid friendly!!

P.S. If you are a beer lover, you can also head down the road to the Florida Keys Brewing Company, which is equally as good, and do a little brewery crawl.

Evening: Sunset Dinner at Morada Bay Beach Cafe

If you still have time leftover in the afternoon, I recommend relaxing by your hotel pool and spend time doing nothing! The Keys are all about relaxing after all.

Then, end your day with a sunset dinner at Morada Bay Beach Cafe, another one of my favorite waterfront restaurants in Islamorada.

This open-air restaurant offers tables right on the beach, so you can dig your toes into the sand while enjoying Caribbean-inspired dishes like grilled yellowtail or Cuban-style pork.

It’s also right on the bayside, which means more epic sunset views!!

Or, if you are looking for something a little more upscale, you can go to its sister restaurant right next door, Pierre’s Restaurant. Located inside a colonial-style home, Pierre’s is a French fusion restaurant with a gorgeous interior and beautiful balcony seating!

Day 3: Feeding the Tarpon& Marathon to to Key West

Morning: Tarpon Feeding at Robbie’s

Today is a long day, so I recommend waking up early to fit in as much as possible!!

Start your day at the famous Robbie’s of Islamorada. No trip to Islamorada is complete without visiting Robbie’s, as it’s become one of the most popular stops in the Keys! For this reason, I recommend arriving first thing in the morning before the crowds do.

This way, you’ll hopefully have the docks all to yourself to feed the tarpon, which is what Robbie’s is known for! For a few bucks, you’ll get a bucket of bait fish and get to hand feed tarpon right off their dock.

Be careful though, they do have sharp teeth and they jump fast out of the water!

Before or after your tarpon feeding, grab breakfast at Robbie’s on-site restaurant, aptly named the Hungry Tarpon! They have delicious food here and killer Bloody Mary’s, and they open bright and early at 6:30am.

Robbie’s is also a great place to do some shopping, as they have tons of vendor stands selling everything from artwork to clothing!

Evening: Arrive in Key West

By the evening, you’ll arrive in Key West, the southernmost island in the Florida Keys and the final stop on your itinerary! Once you check into your hotel, head into Old Town for dinner and a night out on the town.

For dinner, two amazing options are Hot Tin Roof and Blackfin Bistro. Hot Tin Roof offers upscale dining with sunset views over the water, perfect for a special night (we celebrated our anniversary here!).

Blackfin Bistro has a cozy, intimate vibe (even though it’s right off Duval) with a menu full of local seafood and elevated American classics. We loved this spot!!

Before or after dinner (depending on sunset timing), make your way to the Sunset Pier Bar for a frozen drink with live music and colorful views of the ocean. It’s one of the best spots in Key West to catch the sunset while sipping on a tropical cocktail!

From there, stroll down iconic Duval Street, known for its buzzing energy and eclectic bar scene. Some of the most popular spots include Sloppy Joe’s (a Hemingway favorite), Green Parrot Bar (a laid-back live music dive), Rick’s (multi-level bar with dancing), and The Rum Bar (tiny but packed with top-shelf rum).

⭐ Pro Tip: Duval Street can get a little rowdy as the night goes on. Most places become 21+ after dark, so if you have young kids, you might not want to stay out too late! ⭐

Where to Stay in Key West

Similar to Islamorada, Key West has a range of accommodation options to suit every traveler, from luxury resorts to charming bed-and-breakfasts. However, Key West tends to be a bit pricer than the Upper Keys, especially if you want to stay in Old Town near the main attractions.

In addition, while there are some larger hotels in Old Town, they tend to be more on the luxurious side. Airbnbs and vacation rentals in Key West Old Town are very common since the island is so tiny and compact and can be a bit more reasonably priced.

Then there is New Town, the eastern side of the island closer to the airport. New Town is only 5 minutes away from Old Town, but you can save you a lot of money by staying here! Even when staying in New Town, you don’t really need a car once you get to Key West.

Most New Town hotels have free shuttles to Old Town, or you can rent bikes! Parking in Old Town Key West can be scarce and pricey, so I recommend taking advantage of the free shuttles wherever possible.

⭐ Pro Tip: If you want to save some money, you can drop off your rental car at the Key West Airport when you arrive, since you won’t really need it for your last 2 days!

Here are my top recommendations for places to stay in Old Town and New Town Key West:

New Town Hotels (a quieter area, ideal for families):

• Havana Cabana at Key West (Budget/Moderate)
• Parrot Key Hotel & Villas (Moderate)
• Margaritaville Beach House (Moderate)
• The Perry Hotel and Marina (Moderate)
• Hilton Garden Inn (Moderate)

Old Town Hotels (closer to the action, ideal for first-time visitors):

1. Almond Tree Inn (Moderate)
2. Ocean Key Resort (Moderate/Luxury)
3. Pier House Resort & Spa (Moderate/Luxury)
4. Casa Marina Key West (Luxury)

For more recommendations and insights, check out my full guide on Where to Stay in Key West!

Need help planning your trip to the Florida Keys?

$19.99

As a Florida local who’s visited the Keys over 20 times, I’ve put all my knowledge and insider tips into this Florida Keys Digital Travel Guidebook!! 

This guide offers everything you need in one place – from where to stay and what to do, to the best times to visit and essential driving tips.

With detailed breakdowns of each Key, 2 sample itineraries, a packing checklist, plus an exclusive Google Map with over 100 pinned locations, it’s designed to make your trip easy and unforgettable! 

GRAB YOUR COPY HERE!!

Day 4: Old Town, Beaches, and a sunset Cruise

Morning: Explore Old Town Key West

Key West is known for its vibrant history, lively nightlife, and laid-back charm. Today, you’ll dive into all the best that Old Town Key West has to offer.

Start your day with breakfast at the quirky and beloved Blue Heaven, a must-visit for any Key West trip. This colorful, open-air restaurant is known for its delicious food and its unique atmosphere, where chickens and cats roam freely.

I’m still dreaming about their famous lobster eggs benedict and towering Key lime pie we had, sooo yummy!

After breakfast, it’s time to explore Old Town by foot. This historic area is home to many of Key West’s most famous attractions, including:

• The Ernest Hemingway Home and Museum – Visit the home of the famous author, where you can tour the house and gardens, meet the six-toed cats that roam the property, and learn about Hemingway’s life in Key West.
• The Key West Aquarium – A small but interesting aquarium where you can see local marine life up close.
• Harry S. Truman Little White House – The former vacation home of President Harry S. Truman, this historic house offers guided tours that give insight into Truman’s time spent in Key West.
• Southernmost Point Buoy – The most photographed landmark in Key West! This buoy marks the “Southernmost” point of the contiguous USA. It’s free to take a photo, but expect a line!
• Key West Lighthouse – Located across from the Hemingway House, this historic lighthouse offers panoramic views of Old Town and the coast. Climb 88 steps to the top, and check out the small museum that shares stories of Key West’s maritime history.

Afternoon: Lunch and Beach Time

For lunch, head to Louie’s Backyard, a Key West institution with stunning oceanfront views and an upscale menu that focuses on fresh, local ingredients. This is the perfect spot to enjoy a leisurely meal while taking in the beauty of the island.

After lunch, spend your afternoon relaxing at Smathers Beach, one of the only sprawling white sand beaches in the Florida Keys! With its soft white sand (that was actually imported from the Bahamas) and calm waters, Smathers is ideal for swimming and sunbathing.

Plus, it’s one of the few free things to do in Key West!

If you don’t mind paying a small entry free, you can also check out the beaches with a side of history at Fort Zachary Taylor State Park. This park spans 54 acres at the end of Key West and has some incredible blue water and great snorkeling opportunities from shore!

Evening: Sunset Cruise

One of the best ways to end your day in Key West is with a sunset cruise. This is personally one of my favorite things to do in Key West, especially for couples visiting Key West!

Several companies offer sunset sailing tours that take you out into the waters surrounding Key West, where you can watch the sky change colors as the sun dips below the horizon. Most cruises offer drinks and appetizers, and some even have live music and dancing.

You can read more about the different options in my guide on the Best Sunset Cruises in Key West! Or, if you are looking for my top recommendation, you can’t go wrong with this Sebago Watersports Sunset Sail!

best sunset cruise in key west

Sebago Watersports Sunset Sail

• Duration: 2 hours
• Cost: $80
• Rating: 4.5/5 stars⭐
• Includes: Open Bar, Live Music, Appetizers

book it here!

Day 5: Water Adventures and Sunset Farewell

Morning: Jet skiing or Dry Tortugas

On your final day in the Florida Keys, make the most of your time with a fun-filled day of water adventures and a sunset farewell.

I actually have two options for you depending on your budget and interests when it comes to water adventures.

If you are looking for a full-day adventure and unforgettable day trip, you can hop on a ferry or take a seaplane to Dry Tortugas National Park, home to the historic Fort Jefferson.

Located about 70 miles west of Key West, the Dry Tortugas are a group of remote islands surrounded by crystal-clear waters, coral reefs, and abundant marine life. The main attraction is Fort Jefferson, a civil-war era fort in the middle of the ocean!

The ferry ride takes about 2.5 hours each way, so plan for a full-day adventure!! Once you arrive on the island, you can snorkel, explore the fort, and soak in the natural beauty of this remote paradise.

Pro Tip: If you are visiting the Keys in the winter time, I’d probably skip Dry Tortugas, especially if you are prone to seasickness. We did this in December and the seas were very rough, which led to a lot of people (including myself) getting sick on the ferry! ⛴️

If you’d rather stay closer to Key West (and save some money), I recommend booking this Jet Ski + Sandbar tour that takes you around the entire island!

You’ll get to zoom through the waters, explore hidden mangroves, and even stop at a sandbar! It’s a thrilling way to experience Key West from a whole new perspective, and many tours offer the chance to spot dolphins, rays, and other marine life along the way.

(Since you already snorkeled in the Upper Keys, I recommend jet skiing in Key West, since the snorkeling is much better in Islamorada anyways!)

Afternoon: Lunch + Bike Ride Around Key West

For lunch, you have tons of options in Old Town. We loved grabbing a bite on the water in the Historic Seaport! Or, head to Kaya Island Eats for some incredibly fresh seafood.

After lunch, slow things down with a leisurely bike ride around Key West. Many hotels and rental shops (like Eaton Bikes) offer bikes for rent, and it’s one of the best ways to explore the island. Ride past colorful conch houses, charming streets, and historic landmarks.

Take the afternoon to explore any of the Key West activities you missed yesterday and maybe do some souvenir shopping since it’s your last day! If you haven’t strolled down Duval during the day yet, this is the perfect time to do so!

Don’t forget to eat some Key Lime Pie, or my personal favorite, chocolate-covered key lime pie on a stick. There are tons of places that sell this in Key West, but my favorite is Kermit’s Key Lime Pie Shop!

Evening: Watch the Sunset at Mallory Square or Enjoy Dinner on Sunset Key

For your last night in the Florida Keys, you have to end it with one last epic sunset viewing! Since you already did a sunset cruise last night, there are two other locations I recommend watching from.

One option is the famous Mallory Square Sunset Celebration, a nightly event with street performers, live music, and food vendors. This square offers unparalleled views of the sunset over the Gulf of Mexico, and you’ll get awesome pictures of the sunset sailboats floating by. I recommend arriving early for a good seat on the water.

If you prefer a more intimate and romantic experience, another great option is to have a sunset dinner on Sunset Key. Sunset Key is quick 7-minute ferry ride away from Key West (you can see it from Mallory Square).

On the island, there is one restaurant, Latitudes. You will need a reservation in advance to dine here and get to the island. But with its private island setting and unbeatable views, it’s the perfect way to cap off your time in the Florida Keys!!!

FAQs About Visiting the Florida Keys

Florida Keys Packing List

Your packing list for a Florida Keys road trip will be very similar year-round, as there’s no harsh seasons in this part of the USA (except the summer heat). There might be a cold front in the winter requiring a sweater or jeans, but for the most part, you can get away with shorts, tshirts, and flip flops year round.. what a life right?!

Aside from normal items like clothes, there are some essentials I recommend for your trip to the Keys, whether or not you’re visiting in the summer, the winter, or somewhere in between! Make sure to check out my guide on What to Wear in Key West for more details!

1. Sunscreen (and lots of it!): I will scream this from the mountain tops until I am blue in the face! If you are going to be oustide, you need to wear sunscreen. I highly recommend Supergoop! Their matte screen and unseen suncreen are next level – you will forget you even have it on! So no excuses, wear your SPF and protect yourself from those harmful rays!

2. Snorkel Gear: If you have your own snorkel gear, I highly recommend bringing it on your trip to the Keys since you will be in the ocean a lot. If you don’t have your own, it may or may not be worth buying it. For example, if you’re doing a snorkel tour on your trip, they will likely provide gear for you. But if you know you are going to use it often, buying a quality snorkel set is a great investment!

3. GoPro: If you’re visiting the Florida Keys, you will be swimming in the ocean (as long as you follow this itinerary). With the different shades of blue, the tropical fish, and the gorgeous coral heads, there is so much to document under the water, and a GoPro is the perfect tool to capture it all! I also highly recommend this floating hand grip, which will make sure you don’t lose your GoPro even if you drop it underwater (ask me how I know).

4. Polarized Sunglasses / Hat: To protect yourself while you’re in the sun and out on the water! Polarized glasses will also help cut the glare on the ocean so you can see the wildlife! I love this inexpensive two pack from amazon! 

5. Water Shoes: Okay by water shoes, I mean shoes that can get wet! not those dorky tourist shoes…lol! I have these Reef sandals that are totally waterproof and are great for outdoor adventures like kayaking, taking on a snorkel boat, etc. 

Shop My Florida Keys Favorites Here!

Final Thoughts

I hope this 5 day Florida Keys itinerary has shown you just how much the Keys have to offer!! In my opinion, a Florida Keys road trip needs to be on everyone’s bucket list.

So many people I know only visit Key West, and skipping places like Islamorada and Marathon are doing a true disservice to the Keys!! Whether you’re snorkeling at Alligator Reef Lighthouse, walking across the Seven Mile Bridge, or watching the sunset in Key West, there are magical experiences at every turn in the Keys!

If you enjoyed this post and want to explore more of the Florida Keys during your trip, start with the Upper Keys and check out this Guide on Key Largo to Islamorada!

Don’t forget to pin this post for future planning!!!