Road Trip to Key West The Backpacking Housewife

Miami to Key West on US Highway One by Greyhound Bus!

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I want to share with you one of our most exciting road trips – one of the great All-American Road Trips in fact – the one hundred and sixty-five-mile iconic road trip from Miami to Key West on Overseas Highway also known as US Highway One. And how we ended up doing this road trip by Greyhound Bus! 

We’d arrived in Florida USA at the end of May not realising it was Memorial Weekend. That’s a bit crazy I know – when it’s one of the biggest and busiest holidays of the year in the US – but, in our defence, we had been travelling for a while off-grid.

We’d just landed in Miami from Honduras Central America – and we were feeling a bit of culture shock about being back in the first world – and somehow we’d also lost track of time.

In Miami the weather was hot and the atmosphere was crazy as we joined the jostling crowds walking on cordoned-off on Ocean Drive to slowly explore the famous beach and the colourful Art-Deco area on that busy holiday weekend.

The Backpacking Housewife on Ocean Drive Miami Beach Florida
Miami was hot and crazy as we joined the jostling crowds on Ocean Drive

But soon, it made sense to us to head out of town, and so we decided to take a road trip – one we’d always aspired to do one day – and that was to travel down to The Florida Keys.

All the way to Key West and to the southernmost point of the USA on Highway One.

It seemed to us that The Florida Keys would be the perfect destination to get away from the hustle and bustle of the tourist hotspots of Orlando, Miami, Fort Lauderdale, Daytona Beach and the Space Coast.

We knew The Keys were connected by bridges and causeways and so I did a bit of research online to discover that there are actually forty-two bridges connecting these islands.

The longest is of course the famous Seven-Mile Bridge.

The shortest is Harris Gap which is only thirty-seven feet long.

And, each island that makes up the Florida Keys offers unique features and the first one you encounter is Key Largo, which promises some of the best diving, snorkelling, fishing and boating experiences in the Keys.

As the backpacking husband is a very keen scuba diver, we decided to stop off for a couple of nights on Key Largo, to allow for some diving and for sightseeing and to enjoy some laid-back nightlife before continuing on our road trip to Key West.

I couldn’t wait to experience all that Key West had to offer us.

The history, the romance, the Hemingway House, food, drink, and the tropical ambience for which Key West is so famous!

We had thought about renting a classic red Mustang convertible for our classic road trip. I’d imagined us driving over the famous bridges in style and with the sun on our faces and the wind in our hair.

But, when we saw the sheer amount of crazy traffic coming in and out of Miami, we started to consider options that would leave the driving to Key West to someone else.

Instead, we decided to travel from Miami to Key West on US Highway One by Greyhound Bus.

What could be more iconic than a Greyhound bus in the USA?

We viewed it as a bit of an adventure. You can find out about Greyhound Bus routes and schedules and bus stops and how to buy tickets online. The buses are comfortable, clean, and well equipped. They have planned rest stops, so you can stretch your legs, and also get some refreshments along the way. It’s a great way to travel!

So, we took the Greyhound bus to Key Largo – which only took a couple of hours – and was a very pleasant and interesting ride through the everglades on Highway One.

Our driver advised us to keep a sharp lookout for alligators along each side of the road where it was a mangrove swamp and, although I did so, to my disappointment I didn’t actually see one.

Key Largo

The Backpacking Housewife Key Largo
We stayed two wonderful nights on Key Largo for diving and sightseeing

We stayed two nights on Key Largo and we had a wonderful time.

We stayed at The Holiday Inn Key Largo. It’s right next to the marina and so we had a wonderful view from our room. We were also mere steps away from the dock, where the tourist attraction and original – but renovated – steamboat ‘The African Queen’ that had starred in the movie with Bogart and Hepburn, in 1951.

The Florida Keys are home to the USA’s only coral barrier reef.

The Florida Keys Marine Sanctuary was established to preserve and protect the reef that is teeming with marine life and coral formations. There are also dozens of dive centres in The Keys offering dive experiences and courses. Most sites are a short boat ride away and there are both shallow reefs for snorkelers and deeper reefs for experienced divers.

The backpacking husband dived with Horizon Divers, Key Largo.

After having a wonderful time in Key Largo, we set off on the second leg of our road trip that would take us all the way to Key West, and we met with the Greyhound Bus across the street from our hotel.

I was delighted to snag front seats, so that we had an uninterrupted view of the road ahead of us and all the famous bridges, through the bus’s large clear windscreen.

Unexpectedly, one of the very best things about this bus trip was meeting all the people riding on the bus. There were about a dozen other people heading down to Key West. Sitting near to us were two older ladies and behind them other couples of various ages. Across from us, a young man, travelling solo. We all got introduced and we got chatting about where we were all from – and I suppose as the only two Scottish people on the bus – we were something of a novelty to everyone else as they were all from different places in the US.

Everyone was incredibly friendly and interesting and the atmosphere onboard was chatty and lively – almost party-like as we shared our travel stories and all the drinks and snacks we’d all brought on board.

From Key Largo, Islamorada is the next Key in this chain and is in fact a village of islands and canals and offers some of the best sports fishing.

Then it’s Marathon Key which is also an island chain of over a dozen connected islands stretching over a distance of 10 miles.

From Marathon – you drive over the famous 7 Mile Bridge – one of the longest bridges in the world.

There is a feeling of total awe as you cross the Seven Mile Bridge – it feels like you are flying over the ocean with azure blue waters on either side of you – and we had a great view from those front seats on the bus.

The Backpacking Housewife travelling by Greyhound Bus on the Seven Mile Bridge Florida to Key West
Front seats on the Greyhound bus and our views over the Seven Mile Bridge!

On the Lower Keys, which have lovely names like Big Pine Key, Little Duck Key, Ohio Key and Sunshine Key, Summerland Key, Big Torch and Little Torch Keys, Cudjoe Key, Sugarloaf Key, Big Coppitt Key, Stock Island and the uninhabited Saddlebunch Keys.

The Rest Stop

We paused our journey at a roadside burger place and rest stop, to have a bite of lunch, to freshen up, and to restock on drinks and snacks and by this time, everyone on the bus was good friends.

The two older women told us they liked to collect discount coupons (apparently that’s a very serious thing in the USA) and they insisted on handing out discount coupons to all of us on the bus so that we could all get a burger and fries, and ice cream, and a drink – all for $5.

I don’t think those serving at the burger place that day had ever sold so much for so little as we all lined up to place our food orders and hand over our discount coupons!

On The Greyhound Bus

Then, a little later and back on the Greyhound bus, I started up a conversation with the young man travelling alone.

He told me he was a musician from New Orleans. He generously shared with me his top tips for ‘N’awlins’ and his list of recommended music venues – which I hastily jotted down in my notebook – as well as the best place to go for both music and for a traditional ‘crawfish boil’.

He told us all the bars to drink at – the music scene to look for – and to pay the cover fees to enter music venues on Frenchman’s Street as that was the very best way to see the greatest artists and hear the best in jazz and blues for which ‘N’awlins is famous.

I told him that New Orleans was somewhere I’d always wanted to go to and that I had a kind of fascination for it. The music, the food, and the history.

And, unbeknown to us at that time, the list of places and the generous recommendations that he had shared that day, would go on to become our template for a fabulous never to be forgotten adventure in New Orleans just one week later.

Because at that time we hadn’t yet made any firm destination plans for what we might do next or where we might go after Key West. We were living like free spirits at that time, leaving space in our lives for spontaneity, and that really worked out well for us because – as it turned out – just a week later, with our list of places to explore in New Orleans, we would decide to fly there directly from Key West.

And, who knew – when we’d stepped onto that bus – that a fateful meeting with a stranger, would shape our future travel plans?

You can read about our amazing time in New Orleans in a post I’ve written entitled New Orleans – Jazz, Blues, Oyster Bars and Voodoo.

Key West

Key West absolutely lived up to my high expectations. It’s almost like a Disney town in its perfection.

We eventually arrived in Key West – as the backpacking husband and I were celebrating a wedding anniversary – with the money we’d saved from not having to car hire a red Mustang convertible – we had booked to stay in a very nice room at the boutique The Lighthouse Hotel.

It was just a ‘mango throw’ away from the Key West Historic District and Duval Street. Our accommodation was a small and beautifully appointed cottage with a patio out front and just across the street from The Hemingway House.

The Backpacking Housewife at Key West
We explored all Key West has to offer – I even got a couple of small tattoos!

As there are so many places to choose to stay in the Florida Keys – from big-name resort hotels, smaller motels and private B&Bs – I recommend you search the hotel websites on the internet and check with online booking agents for the best deals.

But, as a top travel tip, if you find the place you really want to stay at is fully booked on a booking site then in my experience it’s always worth calling the accommodation directly to check that’s the case.

You might get lucky as we did with our stay at The Lighthouse.

Top Things To Do In Key West

Things To Do In Key West The Backpacking Housewife

Entertainment and Dining: The food and entertainment at the Keys are spectacular. From fine dining to bar food you won’t find better. You will be certain to find a place and a plate and price to suit your taste. Don’t forget to check out Jimmy Buffett’s Margaritaville on Duval Street – it’s the original and exactly where you will find the Perfect Margarita!

Shopping: The shopping in Key West centres around Duval Street, where you can find everything from a bargain souvenir to a world-class piece of art.

Conch Tour: The entire island features the clapboard homes and architecture that it has become famous for and taking the Conch Tour Train – as we did – is probably the best way of seeing it all.

Souveniers: While in Key West, I also got the ultimate in souvenirs, as I got a new Tattoo: I had a couple of yoga style wrist tattoos of a lotus flower and an Om at The Southernmost Tattoo Shop in the USA on Duval Street!

Sightseeing. We also enjoyed The Shipwreck Museum and the view of Key West from the top of the Old Wreck Spotting Tower and while we were in Key West there happened to be a special Ernest Hemingway Exhibition at the museum.

Ernest Hemingway was the winner of the Pulitzer Prize for Writing Fiction in 1953 and the Nobel Prize for Literature in 1954 “for his mastery of the art of narrative, most recently demonstrated with The Old Man and the Sea, and for the influence he has exerted on contemporary style”.

In the Key West Museum, there were lots of exhibits and pictures and movie posters all reflecting Hemingway’s work, but the centrepiece was a bronze sculptor capturing a young, enthusiastic and adventurous Hemingway, fishing off his beloved boat ‘Pilar’.

As a writer myself, I was engrossed and enthralled by the life of Hemingway, and so after exploring the Hemingway Exhibition, I was particularly keen to tour the Hemingway House.

Ernest Hemingway’s first visit to Key West in 1928 was only meant to be a short stopover, but once he’d felt the sun on his face, inhaled the salty air and met the locals, he knew it would be his home with his second wife Pauline.

The Hemingway House

The Hemingway House Key West: I loved walking through the airy rooms and book-lined hallways.

The Hemingway House is impressive and has the distinct air and rich ambience of old-world elegance. A high brick boundary keeps the property private but the view from the first-floor wrap-around porch takes in not only the garden but the adjacent street in what is an affluent residential part of town.

I loved walking around the airy rooms and the book-lined hallways, taking in all the family photographs and the personal effects. I could almost pretend I was a house guest exploring the place while Ernest and Pauline (Hemingway’s second wife) had just popped out momentarily.

You can read lots more about my fabulously interesting visit to the Hemingway House in my post: The Hemingway House – Key West.

In Key West, Hemingway became an avid sports fisherman. In 1938 he established a world record for catching seven Marlin in one day. He also garnered a reputation for hard drinking with his new friends Josie ‘Sloppy Joe’ Russell, fisherman Eddie ‘Bra’ Saunders and his brother ‘Burge’ and later Toby Bruce who became his right-hand man and life-long companion.

There is so much to do throughout the Florida Keys and Key West absolutely lived up to my high expectations. It’s so clean and so pretty, almost like a Disney town in its perfection. It’s historic (by American standards) and its buildings and wooden clapboard houses with wrap-around porches and white picket fences give the place a surreal look and Hemingway’s house is a prime example. I loved finding out about one of my writer heroes.

Plus, the food is fabulous and the restaurants are plentiful. In the Hemingway tradition, bars are a fun feature too. Sloppy Joe’s Bar is still there. Duval Street is eye-popping in that there is so much to see and this is where I would urge you to look both left and right in case you miss something. Art galleries. Museums. Fabulous restaurants. Bars. Souvenir shops.

There’s a Walgreens shop housed in a disused but iconic theatre frontage. The original Jimmy Buffett’s Margaritaville. Marylin Monroe statue is a great photo opportunity outside The Tropic Theatre. Key West is almost a theme park in all that it offers!

So, if you ever do find yourself in Florida, I would urge you to head out of Miami on Highway One – perhaps on a Greyhound bus – and explore the Florida Keys. 

Tell me, are the Keys on your Florida wish list?

Or have you experienced Key West?

If so, how did you get there?

Get in touch and let me know!

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Go Wander Wild -

I loved reading about your road trip experience from Miami to Key West. Your descriptions really made it come alive for me. Happy travels!


Thank you for leaving your comment. I’m delighted to inspire you through my writing and my road trips!

nadia -

From key largo to key west ,
bus stop is on the walgreen side or burgerking side?

Tomorrow we leave from key largo i cannot found proper station 🙁


Sorry I missed replying in time and hope you got the bus okay. The bus stop from Key Largo to Key West is on the opposite side of the main road to The Holiday Inn Key Largo – I remember we crossed over the main road to find the stop. Have a great time in Key West! Janice xx

Lee-Anne -

I wanted to do this trip when I was in Florida (for a business trip in Orlando) but simply didn’t have the time. I ended up spending a couple of days relaxing in Sarasota instead. Reading this I wish I had down the Keys trip now. It’s being promoted to the top of my wanderlust bucket list.


Sarasota is perfect for relaxing – I love that coastline and have been several times to relax there myself – but as you can tell from my post I have great enthusiasm in recommending The Keys to you and Key West is very special indeed. Tag me when you post about this trip! xx

Jonno -

Sounds like a great trip, we love going by bus or train rather than driving. Far more relaxing and you get to see much more of where you’re going. What a cool adventure.


It really was fabulous and fun and the people we met on the bus were amazing too!


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