How to plan a Florida Keys road trip

Last updated on May 13, 2024

Have you seen the iconic aerial photos of the Overseas Highway in the Florida Keys – a slim stretch of road and bridges winding its way through the island chain? It’s a scene that’s begging for a road trip and one I’ve finally ticked off the bucket list.

Our Florida Keys road trip didn’t disappoint – I’ve never been anywhere quite like it in the States – a land of turqoise waters and over 100 mangrove and coral islands, dotted with little neighbourhoods where the Florida’s castaways have made their home. 

It makes for one of the USA’s most unique road trip – a chance to drive with water on either side as far as the eye can see on the 7-mile bridge, and with many roadside stops and attractions to explore. 

We did the Miami to Key West drive as a there-and-back, going via the Everglades en route. Depending on your style, it’s a destination where you could adventure for days in its waters or simply bask on the shore. And there’s history, wildlife and culture to explore too. 

Here’s our guide to how to road trip Florida Keys – as with all our itineraries, it’s one you can adapt to suit your tastes, style and age of your fellow travellers.

Let me know if you have questions.

We also have a guide to the best things to do in the Florida Keys with kids, and a round-up of the best Florida Keys family resorts.

How to use this Florida Keys road trip itinerary

We’ve outlined the exact route we did on our Florida Keys road trip, but you can read the section for each individual destination and decide what your own priorities are and adjust accordingly. For example, if you’re keen on diving, you might want to extend your time in Key Largo, or if nightlife and culture is your bag then spend longer in Key West. 

We’ve suggested 5 days for a Florida Keys road trip, but you could easily stretch or shrink that. 

The main destinations I’ve covered are: Key Largo, Key West, Marathon and Islamorada. Another popular spot is Big Pine Key, which you could visit from Key West.

Who is this itinerary for? Families? Couples?

We travelled as a family of four with a 3 and 6 year old, but you could easily adapt this itinerary for whatever the shape of your travel group, be that couples, friend groups or solo travelers.

Why visit the Florida Keys

The Florida Keys are an all-out vacation destination, packed with resorts and hotels all geared towards making the most of their island paradise. The coral island chain is charged with a easy-going attitude, and each of the main individual islands has its own distinct character.

There are water activities aplenty – from fishing to boating to kayaking and SUP – and back on land, there are beaches and wildlife to enjoy. 

If you’re looking for culture, the history of the Keys is no less unique than its environment and there are opportunities to learn about it at places like the Truman House, the Shipwreck Museum and Hemmingway House. 

Plus just stopping at roadside eateries and sampling the nightlife of Key West grants a window into the Florida Keys laidback, offbeat, way of life.

Our Florida Keys highlights

Florida Keys itinerary map

Florida Keys Itinerary at a glance

Day 1: Drive to Key Largo via the Everglades, stopping at the Ernest Coe Visitor Centre and getting a fruit juice from Rob’s Fruit Stand. Check into Baker’s Cay and spend the afternoon relaxing there.

Day 2: Spend the day in Key Largo, enjoying the resort and taking your pick of water activities. Try scuba diving or snorkelling, or take a glass bottom boat tour of the reef.

Day 3: Drive to Key West, stopping at Robbie’s of Islamadora to feed the fish, and having lunch at the No Name Pub near Big Pine Key. Enjoy the views on the 7-mile bridge. Head to Duval Street and do the trolley tour to explore the main Key West sights. Watch the sunset at Mallory Square and have dinner in town.

Day 4: Explore more of Key West, choosing your priorities. Take a day trip to Dry Tortugas, visit the historic homes or do a food tour. In the evening, do a sunset cruise.

Day 5: Drive to Marathon and visit the turtle hospital. You could drive on from here and end your trip this day, or spend an extra night in Marathon or Islamorada, enjoying the beaches and laid-back pace of life.

Florida Keys FAQs

How long do you need for a Florida Keys road trip?

You can drive from Key Largo to Key West in just under 2.5 hours, so this is by no means a road trip with a lot of driving. But you’ll of course want time to explore.

We spent 3 nights in the Keys (1 in each of Key Largo, Key West and Marathon), but I wish we’d had at least one more.

I think 5-6 nights would be ideal to make the most of it all and pack in as much as possible (including that all important relaxation time). I would especially have liked more time in Key West as that has the highest concentration of attractions.

All that said, we had a brilliant time in just 3 nights, so if that’s all you have still go for it – you could also do it in 2 nights if you’re even shorter on time.

In the suggested itinerary above, I’ve stretched our time a bit and laid out 4-5 nights (2 in Key Largo, 2 in Key West and 1 in Marathon or Islamorada). We did it in 3 nights by cutting out days 2 and 4 and packing our Key Largo activities into day 1, and our Key West activities into day 2 and part of day 3.

Florida Keys drive times

Key Largo – Key West: 2.5 hours
Key Largo – Islamorada: 30 minutes
Key Largo – Marathon: 1 hour
Marathon – Key West: 1 hour 10 minutes

When to go to the Florida Keys

All months aren’t equal in the Florida Keys, so you’ll want to plan accordingly. November to April is the busiest time when you’ll find plenty of snow birds escaping the US winter and enjoying the high 70s of the Florida Keys. 

June to October is humid and hot at around 90 degrees and this time also coincides with hurricane season (June-November). It means you can get some great deals, but you might need some flexibility if extreme weather hits – it feels like quite a big risk if you’re travelling from far afield, but more worth it if you’re traveling domestically.

Other things to consider include Spring Break in March (perhaps to be avoided or enjoyed?!), Key Lime Festival in July, peak fishing season in April, and festivals like the Key West Food and Wine Festival in January.

How to get around the Florida Keys

You’re going to need a car to road trip the Florida Keys. We recommend looking for deals with Discover Cars who aggregate prices from all the leading rental companies.  

The one exception is Key West where it’s possible to get around on foot and with public transport. And if you’re going to be sampling the nightlife it’s best to leave that car at home! If you’ve flown directly to Key West and plan to spend all your time there, you could get away without having a car.

How to get to the Florida Keys

We travelled to the Key Largo from Miami airport, which takes about 1.5 hours. You could stop off at the Everglades en route without adding much additional drive time. 

Other routes to the Keys include a flight straight to Key West, or a boat from Key West to Naples or Fort Myers. The boat takes about 2.5 hours.

Our detailed Florida Keys road trip itinerary

Key Largo

Key Largo is the first island you hit when entering the Florida Keys from the mainland. One of the biggest draws is the John Pennekamp Coral Reef State Park, the USA’s only living coral reef. As such it’s ideal for scuba and snorkel lovers. 

There’s also plenty of opportunity for kayaking, hiking and boat trips – and there are some great resorts to base yourself at too (we loved Baker’s Cay)

Things to do in Key Largo

• Go snorkelling in the John Pennekamp Coral Reef State Park. Or for something less intrepid, take a glass bottom boat tour.
• The John Pennekamp State Park and the Key Largo Hammock Botanical State Park also have some good walking trails if you’d prefer to stay on land. Cannon Beach and Far beach are also nice spots within the JP park. 
• Try scuba diving – there are places to both learn and dive
• Visit the Coral Restoration Foundation to learn about the important work they’re doing to protect the barrier reef
• See the African Queen boat, made famous in the 1950s film of the same name. You can even take a trip on it.
• Hang out at Harris Beach, the most popular option for families in Key Largo
• See the birds at the Florida Keys Wild Bird Center (technically in Tavernier)

Where to eat and drink in Key Largo

• Try key lime pie from the Blonde Giraffe Key Lime Pie Factory
• We loved the restaurants at Baker’s Cay, especially Dry Rocks, which had casual Mexican-inspired fare.
• Get one of Harriette’s famous muffins, including key lime pie flavour, at this cute atmospheric diner.
• Key Largo Fisheries Backyard Café is a top pick for seafood
• For a break from seafood, head to the Italian Food Company
• Mrs Macs Kitchen for classic American comfort food.

Where to stay in Key Largo

We stayed at Baker’s Cay, a gorgeous resort with its own beach and plenty of family-friendly amenities. It was our first introduction to the Keys and part of the reason we fell in love with its tropical vibes. Read more in our guide to the best Florida Keys family resorts.

Other options in Key Largo include:

• Bay Harbor Lodge and Coconut Bay Resort – a family-owned resort with comfort and character

• Drift Hotel – a good budget-friendly option in Key Largo.

Key West

While the most far afield, Key West is also the most popular island and has become a haven for cultural outcasts and a famously lively nightlife. It’s the most urban of the islands with an historic downtown filled with bars, shops, hotels and restaurants, mostly centered around rowdy Duval Street. And it’s earned its status as the wild child of the islands for good reason – the parties go on late here!

But, as I say in my guide to the Florida Keys with kids, there’s more to Key West than its nightlife and we loved experiencing it as a family. From pretty streets to communal sunsets and a storied history, Key West is a playground for all ages.

Things to do in Key West

• Head to Mallory Square for sunset and join the daily crowds as they toast the sunset together
• Visit the Ernest Hemmingway Home and Museum where you can learn about the author’s time in Key West where he spent almost a decade. Don’t miss the polydactyl cats, descendants of Hemmingway’s own! The Key West Lighthouse is also nearby.
• Go to Audubon House where John James Audubon drew some of his most famous bird illustrations
• Walk around the historic quarter to see the architecture that characterises Key West 
• See the butterflies at the Butterfly and Nature Conservancy 
• Take a photo at the southernmost point of continental USA (there tends to be a line, so we just took one from afar!)
• Head to Duval Street for the famous Key West nightlife – including Green Parrot Bar and Sloppy Joe’s Bar
• Take a day trip to Dry Tortugas National Park where you can explore the historic Fort Jefferson and go snorkelling in the pristine waters
• Tour the Truman Little White House to see where the past president and other after him spent his summers
• Visit the Key West Aquarium or Key West Shipwreck Musem – both in Mallory Square
• Ride the conch train or take a trolley tour around the town for an easy way to see the main sights and learn about Key West history and culture
• Or for something more spooky, do the ghost tour
• If you’re into forts (I’m not!), there’s also the Fort Zachary Taylor State Park where you can learn about the civil-war era fort.
• Do a day trip to Big Pine Key and Bahia Honda State Park to see a wilder, quieter side of the keys

Where to eat in Key West

• Blue Heaven is famous for its breakfasts and has a good dinner menu too. There is a bar of the same name just opposite, which was great for people watching!
• Grab a slice of pie from Kermit’s Key West Key Lime Shop
• Cuban Coffee Queen has a few branches and does an excellent, strong coffee
• Get your gourmet donuts from Glazed Key West
• Best option of all – do a food tour of Key West to learn more about the town as you munch your way around it.
• On your way into Key West, take a detour to Big Pine Key and the No Name Pub – a cool bar that also serves food (can be tricky to get a table though)
• Date and Thyme is a popular restaurant with good veggie options
• We didn’t visit, but we heard Better than Sex dessert restaurant is as good as it says!
• For a unique experience, you can ride a floating tiki bar!

Where to stay in Key West 

We stayed at Oceans Edge, around 15 minutes from downtown, which has the benefit of being away from the town’s noise, but the inconvenience of having to get there and back. There is a free shuttle if you don’t want to use the car.

All rooms have an ocean view and it’s all done in a pretty boardwalk style with white clapboard walls and pretty balconies or porches.

Read more in our guide to the best Florida Keys family resorts.

Other good places to stay include: 

Marathon

Marathon is growing a reputation as a good base for families, and we agree it’s a good choice. The central island between Key West and Key Largo is best known for its beaches, especially Sombrero Beach, which has some of the island’s best sand. 

It also has the turtle hospital where you can do a tour and learn more about their rescue and conservation work – a great family attraction.

And we loved where we stayed at the beautiful Isla Bella Beach Resort. 

Things to do in Marathon

• Do a tour of the sea turtle hospital to learn about how they rescue and care for these endangered creatures. It was a highlight of our time in the Keys.
• Spend some beach time at Sombrero Beach or Bahia State Park – both popular family options near Marathon
• Get up close to aquatic life at the Florida Keys Aquarium Encounters 

Where to eat in Marathon 

• Our hotel in Marathon, Isla Bella, had some great dining options, including Mahina, a Polynesian-inspired restaurant
• Barracuda Grill is a popular spot for seafood (as a vegetarian, I can’t personally vouch for this, but the reviews are excellent!)
• Another popular option is Porky’s Bayside Restaurant and Marina

Where to stay in Marathon

We stayed at the Isla Bella Beach Resort, a huge beachfront resort that takes full advantage of its location with oceanside pools and restaurants, private beaches to relax on, and hammocks to enjoy the views. It’s the epitome of an island resort paradise. Read a full review in our guide to the best resorts in Marathon.

Other options in Marathon include:

Islamorada

Islamorada is the sport fishing capital of the world, which is the main draw for many of its tourists. But it’s also a beautiful spot and has some good resorts, so it’s a good stop if you want to break up the journey between Key West and Key Largo, or simply experience a quieter part of the island. 

It also has a beautiful beach and an artists enclave filled with studios and galleries.

Things to do in Islamorada

• Go to Robbie’s of Islamadora to feed the massive tarpon fish. There are also boat trips from here, and the complex of restaurants and shops is a quintessential Florida Keys experience. 
• If you’re into fishing, there are lots of fishing charters to choose from (definitely not my vibe!)
• Go to pretty Anne’s Beach where the shallow waters are perfect for kids (albeit too shallow for swimming)
• Explore the Moarda Way Arts District and all its artists’ studios and galleries, especially on third Thursday of the month when they open late.
• Go to the History of Diving Museum 

Where to eat in Islamorada

• Mrs Mac’s Kitchen is a popular roadside spot with kitsch décor and hearty meals in Islamadora
• Robbie’s of Islamadora has a quirky low-key restaurant with walls and ceilings lined with dollar bills
• Get a cinnamon roll from Bob’s Bunz
• Try a flight of beer at the Florida Keys Brewing Company 
• Morada Bay is a lovely beachside restaurant serving Caribbean-style and American food
• Chef Michael’s is a more upscale option that’s a destination in itself

Where to stay in Islamorada

We didn’t stay in Islamorada, but places that caught our eye include:

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