The Perfect 5 Day Florida Keys Itinerary for First Timers

In this article, I’m sharing the perfect 5 day Florida Keys itinerary, ideal for first time visitors. The Florida Keys are a pretty epic American road trip destination. You’ll find yourself driving along an overseas highway, hopping between different tropical islands.

I’m basing this itinerary off my most recent trip to the Florida Keys, in which I road tripped from Miami Airport to Key West and back again with my friend Mary, exploring multiple keys along the way.

Let’s get to it.

5 Day Florida Keys Itinerary: An Introduction

This 5 day itinerary is designed for first time visitors to the Florida Keys to give you an overview to each of the main keys. Maybe you have been to Key West before, but this is your first time exploring the keys as a whole.

Did you know that the Florida Keys are made up of about 1,700 islands, all connected by a 113-mile overseas highway? Yep, you’ll be road tripping over water in this epic itinerary.

How Many Days Do You Need in the Florida Keys?

In my experience, five days is the minimum amount of time required to road trip the Florida Keys, if you’re planning to visit more than just Key West.

Below I’m sharing the ideal Florida Keys itinerary for first timers, spread across five full days. Note that I say five full days, because this itinerary does involve travel in and out of Miami Airport on days 0 and 6.

You can read my itinerary in much more detail below. I’ve designed the itinerary with general activity lists, rather than restricting you hour-by-hour, because I think that’s more helpful (and digestible, as a reader!).

Let’s get to it!

Car Rental for a Florida Keys Road Trip

You’ll need to rent a car for this Florida Keys road trip, unless you live in Florida or are driving down!

Reserve your rental car at least a few weeks in advance, to avoid any car shortages. Then, pick it up at the rental car counter at Miami Airport.

I recommend Discover Cars for car rental in the Florida Keys, because they show you the best deal from many different companies. You can filter by your personal preferences, such as size of car or insurance level.

Day 0: Fly to Miami

Highlights: Arrival to Miami, pick up rental car.

Your task for “day zero” is just to fly into Miami (or Fort Lauderdale) and pick up your rental car. Of course, you could do this early on your first full day instead, but personally I enjoyed doing this the night before so we had a fresh start for our road trip in the morning!

Where to Stay

Stay somewhere close to the Miami Airport. We stayed at the AC Hotel Miami Airport West for one night and I recommend it. It was a quick drive from the Miami Airport, and the hotel itself was sooo nice and comfortable with some high tech amenities.

Where to Eat

Have a quick dinner. For your first night, I recommend you just grab a quick meal before the adventure starts tomorrow.

Mary and I actually popped by Chipotle for takeout, which we ate in our room at the AC Hotel!

Doral City Place is another option very close to the AC Hotel Miami Airport West. It’s a large shopping center with lots of restaurants.

What to Do

Fly into Miami. Obviously!

Pick up your rental car. This took us a surprisingly long time (1 hour) with the lines at the car rental station, so be sure to account for that possibility.

Relax in hotel. Mary and I actually ended up watching The African Queen (which we were able to play via Youtube on the massive TV in our AC hotel room). This was as “research” for our steamboat ride on day 1 – read about that below!

Day 1: Miami to Key Largo to Islamorada

The first full day of your 5 day Florida Keys itinerary is all about the upper keys. You’ll spend the day driving from Miami down to your beach resort in Islamorada, which takes about 2 hours in total with some fun stops along the way in Key Largo (the northernmost key).

Where to Stay

I recommend booking a beach resort in Islamorada. We stayed at Postcard Inn Beach Resort for two nights. This was a great central location for the two days of our itinerary that we spent exploring the upper keys.

Postcard Inn is special because it’s directly on the ocean, and guests have access to paddle boards, kayaks, bikes, and more.

Fun fact: this resort is also where the rum runner cocktail was invented! Obviously, we had to partake.

Book your stay at Postcard Inn here.

RELATED | Best Places to Stay in the Florida Keys (For All Budgets)

Where to Eat

Lunch at Key Largo Fisheries (Key Largo). This is a very “keys” experience and perfect for lunchtime. Eat some super fresh fish or crab (or lobster!) and see the nurse sharks swimming off the dock.

Key lime pie at Keys Chocolate and Ice Cream (Key Largo). If you are like Mary and I, then you’ll obviously waste no time in getting your hands on some key lime pie.

I recommend stopping at Keys Chocolate and Ice Cream after lunch for their chocolate-covered key lime pie on a stick (and yes, it was gluten free!! Read my guide to finding gluten free key lime pie in the Florida Keys here).

Dinner at Twisted Shrimp (Islamorada). A roadside seafood restaurant where you can actually eat IN a boat!

This place is extremely on brand for the keys.It’s laidback, family owned, and the (gluten free) fried shrimp is a delight. It is a great stop for dinner on your first night!

RELATED | Gluten Free Key West and the Florida Keys Guide

Cocktails at Postcard Inn’s Tiki Bar. You HAVE to visit the Tiki Bar for obvious reasons – this is reportedly where the rum runner cocktail was invented!

What to Do

Go on The African Queen Steamboat Tour. Taking this historic steamboat tour is the highlight activity of the first day of your 5 day Florida Keys itinerary. This is literally THE boat that featured in the 1951 adventure film starring Humphrey Bogart and Katharine Hepburn. It’s actually on the U.S. National Register of Historic Places.

I recommend booking a tour for 10am, which is what we did. This was good timing as it gave us ample time to drive down from Miami, and we finished in time for lunch.

It was somewhat surreal sitting in this boat, cruising through the Key Largo canals and out to the ocean and back, after just having watched the movie the night before. Check availability and book your tour here.

Day 2: Islamorada and Key Largo

Highlights: A snorkel tour, charter fishing, and catch-and-cook dinner.

The theme for day two is adventure in the upper keys! This is your day to go snorkeling at the famous John Pennekamp Coral Reef State Park – the first undersea park in the United States!

Unfortunately for Mary and I, it was very windy on this day of our Florida Keys road trip… so our snorkel tour got CANCELED! This was a huge bummer, but nature happens, my friends.

The Keys can be particularly windy so it’s not unheard of for water activities to get canceled. With that in mind, we still had a wonderful day and were able to go charter fishing in the afternoon.

Where to Stay

You’ll spend a second night at your resort in Islamorada. We spent our second night at the wonderful Postcard Inn. I enjoyed having two nights in Islamorada, despite this being a pretty fast-paced 5 day Florida Keys itinerary.

Postcard Inn was a good home base to drive around the upper keys from. Plus, it was so great to have direct beach access, especially after our snorkel tour got canceled!

Where to Eat

Quick breakfast. I recommend having a quick breakfast on day 2, because your itinerary today is pretty packed! Mary and I grabbed some food from the Starbucks by Postcard Inn (notably: the last Starbucks for 90 miles!).

Lunch at The Fish House Restaurant and Seafood Market (Key Largo). I stopped here for lunch to try their famous “Matecumbe” sauce which is essentially fresh fish simmered up with capers, shallots, and other delights. This dish has been featured multiple times on the Food Network – for good reason. Highly recommend!

Dinner at Chef Michael’s (Islamorada). For dinner, Mary and I dressed up and dined in style at Chef Michael’s (reservations recommended). Actually, we ate the fish that we caught earlier that day on our fishing trip – so fun!

This is also the place to try Lionfish – by eating it you are supporting their efforts to cull this invasive species and save the nearby reefs.

What to Do

Snorkeling tour at John Pennekamp Coral Reef State Park. Ideally, you should spend the first half of your day enjoying an epic snorkeling tour off the coast of Islamorada.

Tours last 2.5 hours and depart 9am, 10:30am, 12pm, 1:30pm, and 3pm (for this itinerary, I recommend booking the 9am). Book your tour ahead of time here.

Fishing trip with Bamboo Charters. After lunch, head out on the water again but this time with Captain Matt Bellinger of Bamboo Charters. He’s an experienced fisherman, and will help you catch some Florida Keys fish no matter your experience level.

On our trip, we caught a lot of small snapper, which we saved for a catch-and-cook dinner at Chef Michael’s (arrange this with Captain Bellinger ahead of time). We also had an extremely thrilling hour-long struggle with a giant sting ray – don’t worry, we released it!

Fishing charters can be booked for 8am or 1pm, in groups up to six people, and you can choose a 4-, 6-, or 8-hour option. For this itinerary, I recommend the 4-hour 1pm-5pm option. Book your fishing charter here.

Relax at the beach. Your other job for today? Chill out and enjoy the beautiful Florida Keys beach – with direct access from Postcard Inn!

Of course Mary and I were disappointed when our snorkel tour was canceled, but this didn’t stop us from taking the paddleboards out at Postcard Inn.

Day 3: Islamorada to Big Pine Key to Key West

Highlights: A tropical fruit farm, the Seven Mile Bridge, and Cuban food in Key West.

Drive time: 2 hours

Today you’ll get back into road trip mode, by driving down to Key West and passing over the famous Seven Mile Bridge. The total drive time from Islamorada to Key West is two hours, but you’ll take some fun stops along the way – including a picnic lunch at a very unique tropical fruit farm!

Where to Stay

I recommend staying at The Gardens Hotel in Key West. This was our home for two nights, and I loved it. This hotel is historic, quaint, and has a lovely breakfast and pool.

The location is ideal – you can walk anywhere you want to go in Key West but it’s a couple blocks back so never gets too loud at night. There’s also champagne on arrival and on site parking.

Book your stay at The Gardens Hotel here.

Where to Eat

Breakfast at Mangrove Mike’s (Islamorada). Start your day off with the most Americana vibes diner you could imagine, just a five minute drive from Postcard Inn.

I particularly loved that they had gluten free pancakes! Definitely recommend eating breakfast here on at least one of your days in Islamorada.

Picnic lunch. For lunch, I recommend having a picnic, either at Bahia Honda State Park or at Grimal Gove (a tropical fruit grove that I share more about below!).

Dinner at El Meson de Pepe (Key West). You just have to try Cuban food in Key West and this is a great family-owned place to do it, recommended by locals and easy walking distance from your hotel if you stay at The Gardens Hotel.

What to Do

Visit the Florida Keys History & Discovery Center (Islamorada). After breakfast, your first stop of the day should be this history museum. It’s in Islamorada and only a five-minute drive from Postcard Inn, so it’s an easy way to start our day. During our visit, I learned a LOT about the Florida Keys (did you know it was originally an overseas railroad?).

Drive the Seven Mile Bridge. Your drive today includes this incredible landmark. After passing Marathon and before reaching Big Pine Key, you must first drive over seven miles of turquoise ocean.

Take a tour of Grimal Grove. I absolutely recommend making time to stop at Grimal Grove, a tropical fruit grove in Big Pine Key with a super unique back story. This is the only breadfruit grove in the country and tours include “tropical fruit hunting” and a fun tasting session where you eat breadfruit curry, fried breadfruit, sugarcane juice, and more (AKA, lunch!).

Tours last 75-90 minutes and are available Tuesday to Saturday at 10:30am, 1pm, or 3:30pm (I recommend the 1pm time slot for this itinerary!). Book your tour here.

Get settled at your hotel. After driving another hour, you’ll arrive in Key West! Check in to your hotel (I recommend booking The Gardens Hotel) where you’ll be staying the next two nights.

Check in involves a complimentary glass of champagne, and you may even have time to jump in the pool and say hello to the resident cat and tortoise!

Drinks and nightlife on Duval Street. After a delicious Cuban dinner, make the most of your first night in Key West with a trip to the iconic Sloppy Joe’s – the bar that Ernest Hemingway frequented in Key West. Just a warning: it’s going to be crowded… and sloppy!

The entirety of Duval Street will be bustling, so if Sloppy Joe’s isn’t your vibe then you still have plenty of bars to pick from.

Day 4: Key West

Highlights: full day to explore Key West, literary walking tour, key lime pie, museums, and sunset sailboat tour.

Today you can put the car keys away and devote a full day to exploring Key West!

There are honestly so many things to do in Key West but I’m sharing my personal ideal one day schedule below. If I was to extend this 5 day Florida Keys itinerary into a full week or longer, I’d give extra days to Key West because you only really get a taster with one full day.

Still, it’s a pretty epic day. If you follow my itinerary below, you’ll spend today eating key lime pie, drinking Cuban coffee, exploring on a literary tour, visiting historic sites, and sailing into the sunset with a drink in hand!

Where to Stay

We stayed a second night at The Gardens Hotel, and I recommend you do, too. I took advantage of the hotel’s amenities by swimming in the pool early in the morning!

Key West is the highlight of the Florida Keys for many people, so you definitely want one full day and two nights here.

Where to Eat

Breakfast at The Gardens Hotel. Since our hotel was a bed and breakfast, we just went downstairs to eat a lovely breakfast out on the garden patio!

Coffee at Cuban Coffee Queen. This was a great stop to try the classic Cuban cafe con leche.

Lunch at Date & Thyme. You can really eat lunch anywhere today, but my personal recommendation would be this lovely organic market and cafe. They specialize in grab & go meals like wraps (and ice cream sandwiches!) and have plenty of vegan and gluten free options.

ALL the key lime pie. You’re in Key West, after all, so dedicate some time today to trying key lime pie! We did this directly after lunch.

RELATED | Where to Find Gluten Free Key Lime Pie in Key West

Dinner at Half Shell Raw Bar. For dinner tonight, embrace being by the seaside and head to this casual and quirky bar located in the Key West Historic Seaport.

It will be convenient after your sunset sailing trip ends (more on that, below!). I recommend at least one platter of oysters.

What to Do

Go on a literary walking tour. Key West is known for its vibrant literary history. If, like me, that interests you, then be sure to go on this 1.5 hour tour. You’ll walk through the Old Town of Key West, visiting the homes and haunts of writers like Ernest Hemingway, Robert Frost, Tennessee Williams, Shel Silverstein, and Elizabeth Bishop.

Tours are offered Sundays and Wednesdays at 10am. If that doesn’t match your schedule, you can contact them about a private tour. The cost is $30 per person, and you can book your tour here.

Visit Judy Blume’s bookstore, Books and Books. This is another one for my fellow book worms. Whether or not you go on the literary walking tour you should definitely check out the Books and Books bookstore – this is owned by none other than Key West local author, Judy Blume! You may even see her during your visit.

Explore Key West’s historic sights. After your literary morning, lunch, and a sampling of key lime pie, it’s time to spend your afternoon on more traditional touristic pursuits.

Key West has SO many museums and historic sights. You can really only scratch the surface in one day (but don’t worry, you’ll also have time to visit some sights tomorrow morning).

Personally, Mary and I chose to visit the Mel Fisher Maritime Museum this afternoon. That may seem like an odd choice but we really wanted to see some of the less well-known side of Key West and this museum was fascinating!

Take a sunset sailing trip. Finally, end your day in Key West with an incredible sunset sailboat trip out into the ocean, complete with complimentary cocktails and live music.

Mary and I took this exact sailing trip with Sebago Watersports and it was such a lovely way to end the day. There’s nothing like a Key West sunset seen from the ocean!

Book your sailing tour here.

Day 5: Key West to Marathon

Highlights: Southernmost Point, Ernest Hemingway Museum, Key West Lighthouse, Turtle Hospital, and a stunning beach resort.

Drive time: 1 hour

This is the final full day of your 5 day Florida Keys itinerary, but it’s still packed full of fun activities!

You’ll spend the morning exploring more of Key West, including the Southernmost Point and any museums you missed the day before. Then, you’ll drive north to Marathon where you’ll tour the famous Turtle Hospital, and check in to your hotel where you’ll have an incredible al fresco dinner by the beach.

Where to Stay

You have a couple options of where to stay tonight, depending on when your flight home is. I recommend staying the night in Marathon, before driving back to Miami Airport the following morning. This maximizes your time and gives you 5 full days in the Florida Keys.

Alternatively, if you are flying home on day 5, then you may have to skip some of the itinerary below to drive back to Miami Airport in time for your flight.

Personally, on our final night in the Florida Keys we stayed at Isla Bella Beach Resort in Marathon. This was an incredible accommodation to end our trip on.

It’s luxurious yet surprisingly affordable, directly on the water with pools, beaches, bikes, and beautiful docks with sunrise views. There are also a few restaurants on site and this is where we had dinner – one of the best meals of our trip by far.

Book your stay at Islabella here.

Where to Eat

Breakfast at your hotel or in town (Key West). Get an early breakfast today so you can get out and explore Key West. Either eat the complimentary breakfast at The Gardens Hotel, or check out Green Pineapple Cafe, a favorite of mine which opens at 8:30am.

Lunch at Seaside Cafe at the Mansion. Before you depart Key West, grab a quick lunch at this truly iconic restaurant that’s just steps from the Southernmost Point. Come here for their famous lobster pizza – it will not disappoint!

Dinner at Mahina at Isla Bella. Dress up and enjoy a final dinner in the Florida Keys at this Polynesian inspired restaurant at Islabella, where you can dine al fresco under the stars with a backdrop of ocean waves.

The filet mignon is to die for, and top it off with a key lime pie martini! Reservations required.

What to Do

Spend the morning exploring Key West. There is so much to see in Key West so you’re bound to have some places you still want to go after your full day in Key West yesterday. This is your time to visit them – just check out and have your hotel hold your luggage first!

On our final morning in Key West, Mary and I climbed up the Key West Lighthouse, before taking a tour of the Ernest Hemingway Home (a MUST when in Key West!) and hugging The Kapok Tree.

Then, we checked out the Southernmost Point marker, before getting a lobster pizza lunch. It was a pretty packed morning!

You could easily do the same, or change it up and visit any of the other sights I listed previously.

Turtle Hospital tour (Marathon). This was one of the highlights of my whole Florida Keys road trip! Marathon is home to a world class sea turtle rehabilitation center, and it’s actually open to the public to visit.

Tours are offered on the half hour, from 9am to 4pm, and cost $35 per person. Reservations are highly recommended! Book your tour here.

Relax at Isla Bella. After your turtle hospital tour, return to your hotel and relax before dinner. Soak up your final hours in the Florida Keys!

If you stay at Isla Bella Beach Resort like we did, then I recommend taking a dip in one of the pools.

Final Day: Marathon to Miami Airport

Highlights: Pigeon Key, drive to Miami Airport and fly home.

Drive time: 2.5 hours

All good things must come to an end. On your final day in the Florida Keys, your main job is to check out of your hotel and drive back to the Miami Airport (~2.5 hours driving time) to return your rental car and fly home.

Be sure to give yourself ample time to drive back to Miami before your flight, especially if you’re driving on a Friday or Sunday, due to traffic!

If you have time before you check out, consider taking the complimentary bikes at Isla Bella and riding to Pigeon Key and back. I also recommend checking out the Marketplace at Isla Bella before you leave – it’s an epic 5,000 square foot space with a cafe, perfect for picking up some souvenirs (and lunch for the road) before you depart!

If You Have More or Less Time on Your Florida Keys Roadtrip…

You can shorten or extend my suggested itinerary as needed, based on your flight times.

If I had to cut a night from my 5 day Florida Keys itinerary above, it would perhaps be the final night in Marathon (and just drive directly to Miami Airport). However, Isla Bella Beach Resort was my favorite hotel and a wonderfully relaxing way to end the trip, so it really depends on your travel style.

On the other hand, if I could add days to this itinerary and make it a full week in the Florida Keys, then I’d add a full day in Key West. Another day in Islamorada also would have been useful due to the weather cancellation of our snorkeling trip.

For the ultimate relaxation, I’d also add a couple days at Deer Run on the Atlantic, a sustainable bed and breakfast on Big Pine Key. A girl can dream!

5 Day Florida Keys Itinerary: Final Thoughts

That completes my 5 day Florida Keys road trip itinerary… I hope it’s helpful to you as you plan your own trip to the Florida Keys.

If you have any questions, just leave me a comment below. Happy traveling, and enjoy the Florida Keys!