Luxury Backpack Guide To Key West

backpacking Key West

Key West has a really good sense of humour…

Just look around you or chat to a few of the locals – even the gravestones are funny! The original Islanders who lived here were so far from the goings on in the mainland they picked up a slower Island peculiarity that made life that little bit different. The tourists that arrived were fascinating, and everything ‘normal’ seemed a bit – well, funny!

By the time you see the sign that tells you that you made the journey and you are there, all your stresses will have evaporated in the heat, and there is no way life can be taken seriously anymore.

Key West is the Southernmost point of the US…

You are just a hop, skip and a jump away from Cuba. In many ways you feel like you are already there, sipping Cuban coffee, a fine cigar in your hand (if that’s your thing). But there is also a lot of the deep South influence in Key West, and it is dripping in American history and authenticity. The combination of the two is what makes this place so unique, and so hard to leave.

Key West

Have a drink –  Kick off your shoes – This is Key West!

Firstly, Key West is expensive. You pay the price for paradise. Just a quick glance around at the fine buildings and tourist spots as soon as you arrive makes you realise that it ain’t going to be cheap. However, here I am… as ever, your luxury backpacking saviour – I’ve whipped up a Key West guide for you who want to have a fabulous time knowing full well you did it on a damn tight budget!

Key West

Key West

Getting To Key West

You can fly to Key West International, however flights to Miami are generally cheaper, and the drive is then about 4 hours. Renting a car is your best bet, plus it’s a beautiful drive – 4 hours of ocean views and a total of 42 bridges (including the seven mile bridge which is breathtaking). However, for the thrifty among you, the bus is great. Take the Greyhound from Miami, rather than a private shuttle, and then the local buses are great for getting around once you are there.

Key West


This is where shit gets expensive. But amongst the array of glitzy hotels there are a few hostels, and the ones I found were in the BEST locations. My pick is Not Your Average Hotel, which has small lux dorm rooms (4 beds) and one of those is female only. Average is around $50 per night (about as cheap as it is going to get here) and they have 3 pools and 2 jacuzzis, and the place is as swish as a beachside hotel.

If you are looking for a different experience, there are lots of sailboat options on Airbnb which from around $75 upwards per person you can have your very own boat to sleep on for the night. The boat we ended up with was very ‘no frills’ but the quiet calm of being out on the water as opposed to the busy town was lovely. Their are a few which charge one flat rate for the boat, so if there are a few of you travelling together it becomes really cost effective.

Key West

Key West

Food and Drink

Happy Hour is the holy grail of drinking cheap. You can’t define it – or what hour it is going to be, but you can be damn sure that you will be able to find cheap cocktails at some point in the day in almost every bar. The Key’s motto is “It’s 5 o’clock somewhere” and so daytime drinking is more than acceptable. Keep a look out f0r happy hour signs, and be sure to make those hours your drinking time.

Luxury Backpack favourite Secret Happy Hour: Opposite the Hemingway Museum is a glorious hotel called the Lighthouse Court Hotel which, if you slip through the gate and behind the building, has a luxurious poolside bar that is open to the public. It’s always a quiet spot, and they have a great happy hour in the afternoon with $5 cocktails.

My other Happy Hour picks are: Kelly’s, which makes their own beer, Alonsos Oyster Bar which has half price food during happy hour, Agave 308 Tequila Bar for fabulous cocktails ($6 on happy hour), and The Porch for its range of cask beers.

Key West

Key West

Must Do’s

Beach – A beach town this may be, the beaches are not what you may expect, and are small and over-crowded. Instead try Fort Zachary Taylor State Park for a beach day and snorkelling.

Day Trip – Fort Jefferson – An unfinished, abandoned fort on Garden Key in the Dry Tortugas national park about 70 miles off Key West. You have to take a ferry but this is worth a day of your time for the stunning surroundings and beauty of this man-made giant against the natural surroundings.

Culture – Hemingway Museum – Although it costs $13 per person to get in, the house is stunning as are the gardens, and a visit to Key West is not complete without a visit – read more here. Breathe in the history, and take a copy of The Old Man And The Sea to a watering hole afterwards to get the true experience.

FREE – Cemetery – Be sure to take a stroll around the cemetery. It is really peaceful, and it’s location makes it the most beautiful place to rest I’ve ever seen – it’s the highest point in Key West. Plus – look out for the funny gravestones!

FREE – Make sure you take some time to get yourself a little lost wandering the side streets and taking photos of the beautiful houses. There really is no where with prettier beach houses than Key West.

Key West

Key West

DO YOU have any great tips to add to this guide? If so please comment below so that other readers can experience your recommendations.

Happy Travels!

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