Key Largo to Key West: Florida’s Most Epic Road Trip Itinerary

If you’re thinking of visiting the Florida Keys, great choice! In my opinion, the best way to see and do everything is to drive from Key Largo to Key West on an epic road trip!! A lot of people visit the Keys and just go to Key West…

Don’t get me wrong, Key West is super fun, but it’s completely different from the rest of the Keys! Going to the Keys and just visiting Key West is like going to New York City and not leaving Times Square.. You’re just not getting the full experience!

The rest of the Florida Keys have such a charm about them, and you really need to experience all the different areas to appreciate it. The drive from Key Largo to Key West is only about 2 hours, so it’s totally doable in a long weekend. However, I recommend spending a week in the Keys to get the full experience!

In this itinerary, I go over exactly how to spend one week in the Keys, starting in the Upper Keys and making your way down to Key West, including things to do, where to stay, and more! So keep reading to plan your perfect road trip from Key Largo to Key West!

Note: This post contains affiliate links. If you click an affiliate link or book through an affiliate program, I receive a small commission at no cost to you! 

The Ultimate Key Largo To Key West Road Trip

Where to Fly Into

For Florida locals, this trip obviously starts from wherever you live! However, if you’re not from Florida, you’re going to have to fly into one of the many Florida airports. You have a few options!

• Fort Lauderdale International Airport (FLL) often has cheap flights to other parts of the country and is only 1.5 hours (~75 miles) from Key Largo
• Miami International Airport (MIA) is the closet airport to Key Largo (only 60 miles) and takes about an hour to get to Key Largo
• Key West International Airport (EYW) is a much smaller airport and will likely be more expensive than FLL or MIA.

My recommendation: If you are able to book one way flights, I’d fly into Fort Lauderdale or Miami and then out of Key West (or the opposite) so you don’t have to drive up and down the length of the Keys twice!

Road Trip Map

I’ve put together the below map with all of my favorite spots from Key Largo to Key West, including restaurants, bars, hotels, and more! You can easily export this map into your own Google Maps so you can reference it during your trip 🙂

Packing List for Key Largo to Key West Itinerary

Your packing list for your Key Largo to Key West road trip will be very similar year-round, as there’s no harsh winters in this part of the USA. 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! It’s my favorite brand ever (not sponspored by them) but I will recommend them forever. 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 gear, I highly recommend bringing it on your trip if you’re planning to be in the ocean more than once (which you should be!). 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 your own snorkel and masks is a great investment!

3. GoPro: If you’re visiting the Florida Keys, you will likely be getting out on the water. 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!

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. 

Days 1-3: Upper Keys

The Upper Keys are my personal favorite part of the Keys, the most notable being Key Largo, Tavernier, and Islamorada. In my opinion, this is where the best restaurants and activities are, and this area truly resembles that “Florida Keys” lifestyle. Key Largo to Islamorada is only 17 miles, so you can really stay anywhere in between the two and tackle the whole area in a few days!

Where to Stay in the Upper Keys

Below is a quick overview of my favorite hotels in the Upper Keys, which includes Key Largo and Islamorada. You can also read more in my guides: Best Hotels in Key Largo and Best Hotels in Islamorada!

Day 1: Check in + Beers at Local Brewery

This itinerary assumes Day 1 is mostly a travel day! After you check into your hotel in the afternoon, I recommend heading to Islamorada Brewing & Distillery for some incredible local vibes. Here you can get Florida-inspired beer, like the Sandbar Sunday, plus some yummy snacks from their food truck!

In the evening, head just down the road to Shrimp Shack for dinner. This place was featured on Diners, Drive-Ins, and Dives, so you won’t regret it!

P.S. If you are thinking of heading to the Florida Keys, don’t forget to check out my Ultimate Florida Keys Travel Guide to help plan your trip!

Day 2: Get Out on the Water + Sunset Dinner

Water Adventures

On your second day in the Upper Keys, it’s time to get out on the water and enjoy what the Florida Keys are famous for! If you’re scuba certified, there are some awesome dives in Key Largo and Islamorada, like Spiegel Grove (wreck dive) and Molasses Reef. If you’re not scuba certified, don’t worry, there’s still plenty to do! 

My favorite spot in the Upper Keys is Alligator Reef Lighthouse. It’s about a 30-minute boat ride out to the lighthouse, and you will be greeted with the most magnificent shades of blue water!

Plus, as you snorkel around and through the lighthouse, you will see tons of wildlife like tropical fish, nurse sharks, octopus, and maybe even some dolphins.

This spot is truly incredible, and you can visit here on a snorkeling tour from one of the many companies in Islamorada. You can read more about snorkeling in Islamorada in my guide here!

Another great option is visiting John Pennekamp Coral Reef State Park, the United States’ first undersea park! Covering 70 nautical square miles, there are lots of great snorkel spots within and near the park, but my favorite (and probably the most popular) is the Christ Statue! You can read more about visiting this iconic spot in my Key Largo Snorkeling Guide!

Whichever snorkeling trip you choose, I recommend going out first thing in the morning. You will have the best weather (and smallest waves) during this time, and hopefully beat the crowds!

If you are not a big snorkeler, another great thing to do in the Upper Keys is go fishing. Did you know Islamorada is actually the sports fishing capital of the world? Throughout the year, you can fish for incredible game like mahi, wahoo, marlin, and more!

Afternoon in Paradise

After your day out on the water, head to the famous Tiki Bar in Islamorada at Postcard Inn for some lunch and drinks. If you drink alcohol, you have to try a rum runner (with a floater!) – it was invented here! In the afternoon, relax at your hotel pool, maybe take a nap in a hammock.. hey, you’re on vacation right?

For dinner, I recommend checking out one of the incredible restaurants on the bayside so you can watch the sunset. Below are my favorites, and you can read more about the Best Restaurants in Islamorada here!

• Lorelei Restaurant and Cabana Bar
• Snook’s Bayside Restaurant
• Square Grouper
• Morada Bay Beach Cafe & Bar
• Marker 88 Restaurant

Day 3: Kayaking, Robbie’s, and Shopping

On your last day in the Upper Keys, head over to Robbie’s of Islamorada. This spot is famous for its tarpon feeding experience, so if that interests you, definitely do it!

After, you’ll be renting kayaks from here and doing one of their incredible backcountry tours! You’ll get to kayak through the mangroves on the bayside and see some incredible wildlife. If you’re looking for something a little more adrenal-pumping, you can also do a jet ski tour, or maybe even parasailing. 

Once your tour ends, have lunch at Robbie’s – their food is delicious! If you’re looking for more adventure in the afternoon, another awesome thing to do is visit Dolphins Plus. This non-profit is a rehabilitation center for dolphins and also offer the chance to swim with them. It is much more ethical than Theater of the Sea, which I DO NOT recommend visiting. 

There are also some great souvenir shops in the Upper Keys you can visit if you’re looking to do a little shopping. My favorites are Shell World and the Rain Barrel.

In the evening, grab some drinks and watch the sunset at your hotel. Or, if you are up for another adventure, you can go on a Key Largo sunset cruise!

If your hotel has a fishing dock, I highly recommend grabbing some poles and doing a little bottom fishing in the evenings! It’s always fun to see what you can catch with a little bit of shrimp or ballyhoo. 

If you need more ideas for activities, make sure to check out my list of the Top 20 Things to Do in Islamorada!

Day 4: Middle Keys and Drive to Key West

It’s time to start Phase 2 of your Key Largo to Key West road trip and start making your way down towards Key West along the Overseas Highway. Don’t worry, you’ll be breaking up the drive with a stop or two in the Middle Keys! If you love animals, the Turtle Hospital in Marathon is absolutely worth a visit. 

Another great stop is Bahia Honda State Park. It’s $8 per vehicle to enter, but it’s totally worth it to spend a few hours on the beach, snorkeling, and just relaxing! Plus, there is an old railway bridge and a spot to rent kayaks and paddle boards.

Note: As you make your way from the Middle Keys to Key West, you will drive over the famous Seven Mile Bridge, which has a pretty unique history you can read more about here.

Another cool thing to do on the drive is visit the National Key Deer Refuge on Big Pine Key!! Key deer are endangered, so the Florida Keys do a lot to protect them. They are the smallest deer species in North America and only live in the Florida Keys! You can see them in the wild driving along No Name and Big Pine Key – it’s pretty awesome!

In the afternoon, finish your drive from Key Largo to Key West and check into your hotel.

Days 5-7: Lower Keys (Key West)

Where To Stay in Key West

As you can see on the map above, if you want to be walking distance to all the main sites, you’ll need to stay in Old Town, but expect to pay a pretty penny! This area is small, with limited parking, but the most gorgeous, Queen Anne style houses and picturesque streets. It’s fun to stay down here but definitely not necessary!

There are plenty of resorts at the top of Key West, and most have shuttles to Old Town for free. We stayed at the Doubletree Hilton and it was perfect! Here are a list of hotels I recommend checking out across the different parts of Key West:

• Havana Cabana at Key West (Budget/Moderate)
• The Perry Hotel and Marina (Moderate)
• Hilton Garden Inn (Moderate)
• The Southernmost House (Moderate/Luxury)
• Ocean Key Resort (Moderate/Luxury)
• Casa Marina Key West (Extreme Luxury)

P.S. You can read more about where to stay and things to do in my perfect 3 Day Key West Itinerary!

Day 5: Water Adventure OR Fort Jefferson + Sunset at Mallory Square

Welcome to Key West! On your first full day, I highly recommend getting out on the water (do you see a theme here?!) Key West has tons of fun adventure activities to choose from. If you snorkeled in the Upper Keys, I would probably skip snorkeling in Key West (you will probably be disappointed – The Upper Keys definitely have the best snorkeling!)

Jet skiing around the island is super fun, and there’s also parasailing, dolphin watching, fishing, and more! GetYourGuide has tons of options – just take your pick!

Fort Jefferson State Park

If you’re REALLY up for adventure, I highly recommend visiting Fort Jefferson State Park at the Dry Tortugas. To get here, you either need to take the 3-hour Yankee Freedom ferry, or you can book a seaplane, but the latter is very pricey!!

Both options book up pretty far in advance, so if you think you want to visit, I recommend looking at your options as soon as possible! You can read more about visiting here.

Fort Jefferson is one of the coolest places I’ve ever visited! It’s a former military installation approximately 60 miles west of Key West in the middle of the ocean! The fort was never finished, but it was used during the Civil War and even held prisoners.

The fort is cool to walk around, plus there are incredible beaches and clear water surrounding the fort that you can snorkel and swim in. You can even camp here if you’re into that!!

Mallory Square

After your morning of adventure, head out and explore Old Town Key West, hit the shops, etc. This area is very walkable and there’s lots to keep you busy! In the evening, head down to Mallory Square to take part in the famous Sunset Celebration.

Here you’ll find street vendors and performers, andddd everyone else in Key West!! Hah. Just kidding, but it is a very popular place to watch the sunset, so expect crowds, and get there early if you want an unobstructed view!

Before (or after) sunset, I highly recommend getting dinner at Hot Tin Roof at the Ocean Key Resort. It was absolutely fabulous, and right on the water!! After dinner, when the sun goes down (cue Kenny Chesney song), one of the most famous parts of Key West comes alive – Duval Street!

If you’re over 21, Duval Street is a fun thing to experience once in your life.. It’s basically a tropical, slightly more tame Bourbon Street in New Orleans. Fair warning: it gets rowdy!!!!

Day 6: Brunch, Bikes, & Beach

On your second day in Key West, head straight to Blue Heaven as soon as they open for the MOST incredible breakfast of your life. The waffles are absolutely to die for. Also, Key Lime Pie as big as your head!! If you did the famous “Duval Crawl” last night, they also have some yummy drinks to cure that hangover!

After brunch, I recommend renting bikes from Eaton Bikes and exploring Key West on two wheels! Key West is extremely bike friendly, and it’s a great way to see the town. Bike over to the  famous Southernmost Point sign and get your touristy photo! Nearby, you’ll also find the Key West Lighthouse, which offers great views of the island, as well as Ernest Hemingway’s House, which is cool even if you’re not a literature lover!

Grab lunch at one of the many places along Duval, and then head over to Smathers Beach and relax in the afternoon. Did you know there aren’t many beaches in the Keys? Luckily, Smathers is one of the most beautiful ones! It’s also one of the best free things to do in Key West!

Another cool thing to do in Key West if the above isn’t your style (or if you have more time) is to take the ferry over to Sunset Key to grab lunch or dinner at the award winning Latitudes Resort. It’s a quick 7-minute ferry, but you have to have a reservation at the restaurant or hotel to get on. The restaurant is pretty incredible and definitely worth a visit!

P.S. Don’t forget to check out my blog post on my Top 25 EPIC Things to Do in Key West!

In the evening, I highly recommend booking a sunset booze cruise. There are lots of options on Viator, but most include bottomless rum punch, live music, and yummy appetizers! It’s the perfect way to spend your last evening in Key West – out on the water! You can read my review of the Best Sunset Cruises in Key West here!

Day 7: Fly Home!

Today is unfortunately the day you leave the beautiful Keys… 🙁 If you have some time before your flight on your last day, feel free to explore Key West a little more in the morning. However, if you have to make the drive back to Fort Lauderdale or Miami on your last day, you need to give yourself PLENTY of time to make it back.. I’m talking A LOT of time.

Traffic in the Keys can get really bad since there is one road in and one road out. An accident can mean hours of delays. Take my word for it.. if you have a morning flight out of Fort Lauderdale or Miami, I recommend leaving Key West the night before and getting a hotel room near the airport instead. If you have an afternoon/evening flight, make sure you give yourself lots of extra time, especially during Miami rush hour!

Final Thoughts

That wraps up my Key Largo to Key West Road Trip itinerary! I hope I’ve shown you how incredibly special the Florida Keys are.

Like I mentioned, there are different ways to tackle this itinerary depending on what flights you can snag.. Key Largo to Key West or vice versa, it doesn’t matter! But booking one way flights will minimize your drive times and allow you to spend more time in paradise! 

If you need more help planning your trip, check out my Ultimate Florida Keys Travel Guide to help be even more prepared for your journey from Key Largo to Key West! And if you have to choose only one Key to visit, here is my Key Largo vs Key West comparison guide!

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