July 20, 2017

USA: 4 days on a Florida Keys road trip!

Driving down the Florida Keys from Miami to Key West is a really great road trip!

You could nip down to Key West from Miami, at the very bottom, in a couple of hours, but we spent 3 days taking our time…

We love a road trip in the USA, hubby and I. He gets behind the wheel and navigates on the wrong side of the road with our GPS that we bring from home, and I give him “helpful” advice along the way 😉

There’s certainly enough to do and see to take four or five days – or even longer if you’re the “slow travel” kind and have more time. Although the travel time from Miami to Key West is only about three hours if you just want to put your foot down and get down there.

Here is my four day itinerary suggestion for your Florida Keys road trip:

Florida Keys map

The Florida Keys stretch 180 km (113 miles) from Miami to Key West and the islands (or keys) are linked by a series of bridges: engineering wonders of concrete that snake across the ocean between mangroves, swooping from sea level to sky, and each key is a little different to the last. And of course the feat of the Seven Mile Bridge is one to take photos of!

The road to Key West is only one or two-lanes most of way, so it can be slow going if you get behind some numpty who never checks their rear view mirror, or worse, get caught up in a queue because of an accident.

Key west drive from Miami

Heading down the East Coast’s Highway 1 from Miami

However neither of those situations befell us and we tootled down from Miami, stopped to meet the folks who work for REEF at Key Largo fighting the scourge that is the lion fish (more on that below), had lunch in the fishing village of Marathon and finally arrived at Mile Zero in Key West a leisurely 4 or 5 hours later.

Starting our road trip in Miami…

You can’t see the Keys without first spending a night (or three) in Miami! Even if you’ve been before like we have, it’s a great excuse to stay in a different part of this groovy city, check out some new things or revisit the tried and true of South Beach before loading up on car snacks and heading south.

This time we stayed at the YVE Hotel in downtown Miami as we flew in late and wanted to hit the road the next day. It’s located in a great spot if you’re heading off on a cruise as it’s right there beside the Port of Miami and across the road from Bayside Marketplace which is heaving with restaurants, bars and shops. It was ideal for our one-night stopover. Oh and summer rates start at $99!

YVE Miami

Walking back from dinner to our lit up hotel!

YVE hotel view Miami

The view out our window looking towards Bayside Marketplace

1st stop: Key Largo

Key Largo is the first key, about an hour’s drive from Miami Airport where we had Uber’d to pick up our rental car so we could return it to the same location and fly out at the end of the week.

As part of my research of things to do and see on our Florida Keys road trip, I came upon the topic of the lionfish and the monstrous eco disaster that this pretty little, yet venomous, aquarium fish is wreaking on the Keys, the Gulf of Mexico and all the way down to South America. So my first stop was to visit the team at REEF who are trying to battle the plague. You can read all about the lionfish in my previous post here >>

Don’t expect Key Largo to be a metropolis. In fact if you blink you could miss it and suddenly you’re on your way through to Islamorada!

But you may know that Key Largo is home to the quirky Jules Undersea Hotel where you need to don a wetsuit to get to your room and spend the night sleeping underwater (which would freak me out!) and it’s also a great place to learn to SCUBA. In fact all of the Keys are famous for fishing, diving and snorkeling but they are also surrounded by mangroves so while ocean sports are easy to come by, so too are kayaking and bird watching.

Tip: Sunsets are also something to make time to celebrate on the Keys, so head Gulf side each evening for a cocktail with a view at any of the restaurants or bars around the little marinas or beaches.

Click here for Key Largo restaurants >>

Florida keys sunset

Sunset at Morada beach, Islamorada

Castaway's Marathon

The marina outside Castaway’s restaurant, Marathon

2nd stop: Marathon

The next key you’ll come to heading south is Islamorada (where the Netflix series Bloodline is set), but we scooted through to Marathon as we were staying at Islamorada on the way back.

Marathon is at mile marker 48 (heading south to 0), and as I was on a quest to seek revenge and eat the infamous lionfish I was recommended to visit Castaway’s, hidden off the main highway on a sleepy marina that I honestly wouldn’t have looked twice at if I didn’t know. In fact we never would have even found it, but I’m glad I had the tip to stop. It’s Marathon’s oldest restaurant and one of the few places where you can get lionfish on a plate.

It’s a bar/slash/diner that looks like it’s been here for ever and is frequented by locals. But what makes it unique is that they serve up lionfish as sushi – and use the head and tail for presentation. There may be a billion trillion lionfish eating the native fish out of house and home on the reefs below, but I played my part and ate one!

Click here for places to eat in Marathon if you’re in the mood for a pit stop >>

Eating lionfish in Marathon FL

I played my part and ate some lionfish!

3rd stop: Key West

I love Key West! It’s officially mile zero of Route 1 at the very bottom of the Florida Keys – you can pose for a selfie by the sign.

Stay in the old town where it’s just so quaint, and I’d suggest two or three nights here.

We arrived around mid afternoon and checked into our hotel (see details below) in a refurbished 100-year old two-story wooden house with wrap around verandas. It was only a couple of blocks from the main street, Duval, which is lined with brightly painted wooden shops and restaurants serving cocktails, key lime pie and fresh seafood, as well as lots of little beachy boutiques for sun dresses, souvenirs and a few art galleries.

Scroll through the pics to see what we did in Key West.

Chelsea House Key West

We had the upstairs room at cute, historic Chelsea House

Duval St Key West

Shopping on Duval

Art in Key West

I love to buy art when I travel and spent about an hour in here!

Ernest Hemingway's house

Ernest Hemingway’s house in Key West

Colourful key west houses

Walking to dinner at Blue Heaven past these cute buildings

Blue Heaven's garden

Blue Heaven’s garden


3 things to do in Key West

1  I nearly didn’t visit Ernest Hemingway’s house as time was tight, but I’m so glad I did! This should be on your list, even if just to see the 53 cats who live here and are descendants from Snow White, a cat with six toes on each paw given to Hemingway’s son. Just about all of them have 24 toes and I loved them! But the house itself is preserved as his ex-wife left it (he had moved to Cuba when she stayed on here). It’s a fascinating insight into the author and the man.

2  I took a helicopter flight over Key West where I could see some of the famous ships lying wrecked on the ocean floor and which were a huge industry as businesses were set up just to salvage the many ships that wrecked on the coral reefs 100 years ago with cargo that would be valued at $7 million by today’s value. We could see sharks floating in the clear water and flew over the US Army special forces base where guys dressed in black were in the pool – probably practicing near drowning techniques!

3  Eat key lime pie! And believe it or not there are a few ways to make this tart meringue pie… grab a take away version at Kermit on Duval or sit down and enjoy it outside under the trees strung with lights at Blue Heaven. Actually Blue Heaven is definitely worth going to for dinner. The bright blue wooden shuttered building was once the venue of cock fighting and boxing refereed by local resident Ernest Hemingway. It was a billiard hall and an ice cream parlour in the basement, a dance hall, a playhouse and a bordello on the second floor and since 1992 it’s been a restaurant complete with roaming chickens and a few cats. Tables are indoors and outside under trees strung with lights. No bookings are made, you just rock up when you’re ready, pull up a seat at the bar where the bartender will make your cocktail of choice and wait for them to come find you.

Ernest Hemingway's cats

47 of the 53 cats that live at Ernest Hemingway’s house have 6 toes on each paw!

US Special forces base Key West

See the guys in black in the pool at the US Special Forces base?

Where to stay in Key West

I absolutely loved our huge room with lush bathroom in the historic colonial Chelsea House, one of six hotels which is part of the Historic Key West Inns, cute wooden properties within walking distance of everything you want to do, see and eat.


4th stop: Islamorada

On our way back we had a flight to catch about midday from Miami, so opted to stay within 90 minutes of the airport just in case the road got jammed. It was also a long weekend, so you never know! As it happened we whistled through with plenty of time to spare.

We stayed at Islander Resort, a Guy Harvey Outpost. Named after the famous designer, this is a fantastic family resort with self catering rooms and two pools and a beach restaurant located right on the beach. There are barbecues dotted around the site so a good time for groups too – and a coin operated laundry which I availed myself of the minute we arrived!

Islander resort jetty

Kids love to fish off this jetty

Islander Resort Guy Harvey Outpost

The pool and restaurant on the beach at Islander Resort

What to do in Islamorada

You’ll see Robbie’s at the end of the bridge just south of Islamorada and this is a fun spot with loads of activities for everyone. Boating, snorkelling, tarpon fish feeding, shopping among the souvenirs, dining on the water’s edge and a few beers. You take tours from here or rent your own boat or equipment – and plan to spend two or three hours. Even if you’re not staying in Islamorada, stop for lunch at Robbies, it really is fun.

Watch the sunset with a cocktail or over dinner at any of the eastern beach restaurants. I grabbed a table on the veranda at Morada Bay along with the many families and friends gathered at tables on the sand in front leading all the way to the shore and watched the sleepy sun drop into the other side of the world while munching on tortillas and guac.

Robbie's shops

Beach house shopping at Robbie’s!

Robbie's boat hire

Rent a boat or take a kayak out for a paddle from Robbie’s


For more information and everything you need to know about the Florida Keys. jump onto www.Fla-Keys.com

My visit to Florida was assisted by American Airlines on our huge 4-week trip and we paid no baggage fees as we were on the one itinerary! Now there’s another tip 🙂


















About Megan Singleton


Hi, I'm Megan Singleton and I'm the word slinger of this travel blog as well as on radio every week and a few newspapers and mags from time to time. I set off on this travel writing journey 18 years ago and I've pretty much always got a suitcase half packed (or half un-packed!)I'd love you to join me on Facebook or Twitter and sign up for monthly newsletters if you want loads of travel tips, advice and deals!

"USA: 4 days on a Florida Keys road trip!" - What do you think?

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  1. Joanne Anderson on

    Hi, loved your blog. So much great info. What did you mean about being on the one itinerary and not paying for baggage fees?

    • Megan on

      Hi Joanne, if you’re on an international ticket that also includes domestic flights through your travel agent, it can be considered as the one intl ticket and baggage fees are usually included/waived. Of course if you use other domestic airlines it won’t apply.


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