The Great Western! Key West, US of A… – A Guest Post by Towelintherain

I am thrilled to announce the return of a regular guest poster, towelintherain, back from his travels in Florida’s Key West!  Check out his useful tips, hints and advice for making the most out of this beautiful part of the US.

Here’s towelintherain’s previous post at The Rough Guide to a Lonely Planet – Shoestring Munich – A Guest Post by towelintherain.

Also, towelintherain’s Tumblr can be found here –


Key West, The last outpost of the Florida Keys, is closer to Havana than Miami. The southernmost city in The United States of America and self-proclaimed ‘drinking town with a fishing problem’ is a haven for the artistic, where endearing carnage and tropical tranquillity coexist like hydrogen and oxygen. Unfortunately, it can be madly expensive, but there are ways of significantly reducing the cost of an escape to this blissful, balmy paradise.

Getting There

Driving is good fun, but you might need an International Driving Permit. You can rent a car from about $50 and most major rental firms have a branch at each end. Just get yourself on Highway 1, get off the mainland and kick back as you count down the mile markers. It takes about four hours from Miami, but it’s easy and it’s beautiful once you hit Key Largo. Just be careful of the toll roads as some agencies don’t cover for that cost.

You can fly with American Airlines from Miami or Fort Lauderdale, but you’ll be paying around three dollars a minute for a 45 minute flight.

Greyhound buses are the cheapest if travelling alone, but they take a long time and are pretty infrequent. I would, however, recommend avoiding the private shuttle firms. Maybe it’s an American thing that this British man doesn’t get, but their online reviews are mixed at best and getting into minibuses offered by a host of rather random companies I don’t recognise or necessarily trust isn’t something I make a habit of.

Staying There

There’s not much of a Couchsurfing scene and no hostels as such, but there are a couple of hotels with hostel dorms. I stayed in Not Your Average Hotel, which was an absolute diamond, secure, friendly, free breakfast, swimming pools, great location, free wine (well, it is Key West) for less than $50 a night. There’s also Seashell Motel, which I’m told isn’t as good, and a 4 bed dorm apartment on AirBnB, but they’re pretty much the only other places to lay your head for less than $100 a night, unless you want to camp.

Getting About

Key West is pretty small, only about a mile by a few miles wide, but it’s worth spending about $20 to rent a bike for a couple of days. Yes, you can get everywhere on foot, but walking even a couple of miles can get pretty draining on a hot day, so having a bike makes the whole island super accessible and gets you right into the less trodden but equally lovely parts of town.

Far away ocean views (source – towelintherain)


Much like any city, you have everything from street vendors and supermarkets to fancy restaurants, and much like Key West, it’s all quite pricey, but the further away you get from the top half of Duval Street, the more affordable it becomes.

You’ll find plenty of nice restaurants in the side streets and alleyways around the bottom half of Duval Street, or by Key West Marina on Caroline Street, with servings of the lush local Snapper, Conch and Hog Fish aplenty for around $20 dollars or less, while quaint little cafes are dotted around the residential streets and further out beaches for some single figure sustenance.

You can’t move in Key West without seeing the gorgeous Key Lime Pie, so there’s no need to pay more than about $4 to get a good slice. After a great deal of thorough research, which I felt was very important to conduct, I found the best value ones to be from the street side vendors and pie shops, like Kermit’s at 802 Duval Street.

You could try a Conch Salad as well if you can; it’s a limey, lemony, peppery fish salad that’s very refreshing on a hot day.

Museums and Attractions

You can spend a small fortune on museum entry at around $10 to $15 a go, but if you fancy some maritime history at the Shipwreck Museum then you can buy a bulk ticket and save a few bob on the Aquarium, Truman Annexe or Ernest Hemingway House, which I think is a must see. Some, like the Hemingway House, have free and regular guided tours once you get inside, which are well informed and well worth it.  Did you know that Hemingway employed a champion boxer just to fight him when he was drunk? Me neither. Other museums, dependent on what you fancy, include the USCGC Ingham warship and the highly recommended Fort East Martello Museum by the airport, featuring a local superstar haunted doll called Robert.

Several free attractions include the oldest house and gardens in Key West, the Florida Keys Eco Discovery Centre, the Key West Distillery Tour and parts of the Key West Studios.

Free art galleries in general are a big thing here; you can’t fail to stumble across dozens of the things, day or night, so just pop in, meet some artists and try to bag a free drink if you’re feeling thirsty.

Hemingway’s house (source – towelintherain)

Other Free or Nearly Free Stuff

Self-Guided Tour: If you don’t want to pay another $20 or $30 for a guided tour, which I’m told are overrated, then you could try the completely free Key West Historic Marker Tour, covering dozens of locations. Just find the addresses at your leisure and look for the plaques on the walls, then call the listed number for a more detailed guide if you’re able (although it’s likely to be very expensive from a non US phone).

Southernmost Point: Sitting at the end of Whitehead Street is one of the most famous landmarks, essentially a large land buoy that signifies you’re at the southernmost point of the USA. It’s not the greatest thing in town and there’s often a bit of a queue, but it’s worth it for the photo opportunity.

Fort Zachary Taylor State Park: Hiding behind the naval air station, $2.50 gets you and your bike access to a nice secluded beach area, all the food and facilities you’d ever need and access to Fort Zachary Taylor for a bit of ramshackle American military history.

Aids Memorial: Back in the day, Key West was a haven for the gay community. Next to the White Street pier is a powerful reminder of a less tolerant time, while the support of a certain Brewing Company is a powerful reminder that you’re still in America!

Mallory Square Sculpture Garden: This small garden off Wall Street is packed full of free history about some of the island’s most influential and infamous people.

Eyes on the Street: You can find some good stuff painted or engraved on the ground all over the city, while quirky street art lines various backstreet walls. It helps you understand the heartbeat of the place and how threatened it is by rising sea levels.

Key West Island Books: Admittedly, this could get expensive, but at 513 Fleming Street is a little bookshop that’s full of books about Key West and books by Key West locals that could easily have you cursing your baggage allowance.

Sunset: Yes, it’s a cliché must see in every tourist guide, but it really is that good. Thousands flock to Mallory Square every night to watch the stunning fall of the sun into the sea. You can even swig a bottle of Key West Sunset ale while you watch it. Although I wouldn’t bother forking out for the sunset boat ride, all that does is stop you from having a silhouette of a boat to add to the view, but you could try it from a few different locations and see what you find. The sunset flash also doubles as a go button for the nightlife in nearby Duval Street. Speaking of which…

Historic marker 41 (source – towelintherain)
Toweliintherain at the Southernmost Point (source – towelintherain)
Part of the Aids Memorial (source – towelintherain)
Mallory Square Sculpture Garden (source – towelintherain)
Ground art (source – towelintherain)
Sunset at Mallory Square (source – towelintherain)


Every night is an excuse for a party around Duval Street, especially the top half, right from sunset to around 4am (assuming you can last that long, which I normally can’t). $2 street beers are plentiful from late night shops and street vendors, while many of the bars are mostly open air. If live music is your thing then you’ll find free entry to more all American music than you can shake a stick at, most nights of the week, in The Green Parrot, Rick’s, Willie T’s, Captain Tony’s, The Bull and plenty more besides. The top floor of The Bull is a also a ticket entry ‘clothing optional’ bar called The Garden of Eden, if you want to experience normal a bit differently.

If you want to really go full on Key West then head down during Fantasy Fest in late October, a sort of Key West Mardi Gras which I caught the first half of by pure dumb luck. People really go all out to express themselves here, from the Zombie Bike Ride to some amazing body art, via lots of imaginable and unimaginable kinds of carnage.

Yet in all of that, if you want a super tranquil evening then just get yourself anywhere that isn’t Duval Street and peace out in the fresh night air.

In truth, it was hard to tell Fantasy Fest Key West from a regular Key West night out, but either way, you can have a lot of good fun after dark, Fantasy Fest or not.

Live music at Rick’s (source – towelintherain)
Zombie bike ride (source – towelintherain)


Key West is a marvellous place to go if you get the chance, peaceful and sunny by day, bonkers (if you seek it) by night, as friendly as it is forward thinking and full of history on every corner. The only real downside is how expensive it can be. As you leave the island, a sign asks you to come back soon, which can make you wonder if you’re sad to be leaving a paradise or happy that you’ve found one. Either way, if you go then have a great time!

©Pulped Travel 2016. All rights reserved.

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