Bar hopping in Key West

The Hedonist: What to see and where to be seen

Once home to Ernest Hemingway and Tennessee Williams, this two-by-four mile island at the tail end of the Florida Keys is made for pleasure seekers. I arrive at Key West's tiny airport and pick up a taxi to Sunset Key Island (001 305 292 5300; westinsunsetkeycottages.com) – a minuscule private island off the mainland that's sprinkled with mint-green cottages. I'm greeted by a porch with rocking chair, then inside, a yard-high bed. It all combines to make me feel as if I've stepped into the pages of a Ralph Lauren summer catalogue.

After unpacking, I head back to the main island to Duval Street. Despite its popularity among Florida University students and the LGBT crowd, the buzz of Key West's nightlife is a few notches below the all-night fist-pumping further north-east in Miami. I start with dinner at Square One (001 305 296 4300; squareonekeywest.com), an upscale eatery whose owner, Michael, greets guests with the enthusiasm of a long-time local. Michael clearly pays similar attention to the food because the specials and signature crab cakes are incredible.

Down the road, Nine One Five (001 305 296 0669; 915duval.com) is a charming restaurant owned by a British expatriate, Stuart Kemp, whose creative cuisine integrates some of the best of British with the fresh flavours of the Keys.

After dinner it's on to one of Key West's oldest bars, Afterdeck at Louie's Backyard (001 305 294 1061; louiesbackyard.com). Walking into Louie's feels like crashing a neighbourhood block party where everyone knows each other. Luckily, the drinks are strong and after a few Louie's Passions, I seem to have adopted a South Florida drawl – a sign it's time to move on.

I head to the most rambunctious bar on the island – Sloppy Joe's (001 305 294 5717; sloppyjoes.com). Another Key West institution known for pulling in a crowd of frat boys and blonde sorority girls, this is where the regrets of youth are made. I've only been in for a few seconds when the first tequila body-shot comes. The rest is history.

It's morning and my hangover needs nursing so I head over to Blue Heaven (001 305 296 8666; blueheavenkw.com) for a Bloody Mary and lobster omelette. No-nonsense waitresses dole out equal servings of attitude and coffee; and just about every face from last night is here.

Sufficiently stuffed, I jump on board the Conch Tour Train (001 888 916 8687; conch tourtrain.com) to see the island by day. Initially, this ride sounds like tourist-trap hell, but drinks are allowed on board. The tour takes in sights such as Harry S Truman's Little White House, Hemingway's home, Audubon House and the 1912 Flagler train station.

But the best part of being in the Keys is its location in the Gulf of Mexico, so I head out to sea on a private boat with Dolphin Safari Charters (001 305 797 5491; safaricharters.com) to do a bit of snorkelling and dolphin-spotting. I crack open a couple of cold beers while dolphins swim by, as the sun gradually sets over the pale-blue waters.

As night falls, it's back to Duval Street for key lime pie at Kermit's Key Lime Pie Shoppe (001 800 376 0806; keylimeshop.com). The zingy pies work a treat, before another night of cocktails.

A Hedonist's Guide to ... (Hg2) is a luxury city guide series for the more decadent traveller. For more information , see hg2.com

PROMOTED VIDEO
Have you tried new the Independent Digital Edition apps?
News
One of the 'princesses' in the video
videoYouTube reinstates sweary video after takedown for 'violating terms'
Life and Style
Could you tell the difference between this and an organic alternative?
food + drink

Culinary experts in The Netherlands thought it was 'fresh' and 'tasty'

Life and Style
Six of the 76 Goats' cheese samples contained a significant amount of sheep's cheese
food + drink
News
Russell Brand arriving for the book launch in East London
peopleRussell Brand cancels his book launch debate due to concerns about the make-up of the panel
Arts and Entertainment
Contestants during this summer's Celebrity Big Brother grand finale
tvBroadcaster attempts to change its image following sale to US
Life and Style
tech

Of all the computers Apple has ever made there’s only one that Steve Jobs had to sell his car to finance

News
New look: Zellweger at Elle's Women in Hollywood awards on Monday

Actress sees off speculation about her face in an amazing way

Travel
ebookHow to enjoy the perfect short break in 20 great cities
Arts and Entertainment
Sarah Dales attempts to sell British Breeze in the luxury scent task
tvReview: 'Apprentice' candidates on the verge of tears as they were ejected from the boardroom
News
Call me Superman: one of many unusual names chosen by Chinese students
newsChinese state TV offers advice for citizens picking a Western moniker
Arts and Entertainment
film

Marvel has released first teaser trailer week early after it leaked online

Arts and Entertainment
Awesome foursome: Sam Smith shows off his awards
music22-year-old confirms he is 2014’s breakout British music success
News
Let’s pretend: KidZania in Tokyo
educationKidZania lets children try their hands at being a firefighter, doctor or factory worker for the day
Independent Travel Videos
Independent Travel Videos
Simon Calder in Amsterdam
Independent Travel Videos
Simon Calder in Giverny
Independent Travel Videos
Simon Calder in St John's
Independent Travel Videos
Latest stories from i100
Have you tried new the Independent Digital Edition apps?
Independent Dating
and  

By clicking 'Search' you
are agreeing to our
Terms of Use.

ES Rentals

    iJobs Job Widget
    iJobs Travel

    SCRUM Master

    £30 - 50k (DOE) + Benefits: Guru Careers: We are seeking a SCRUM Master to joi...

    Franchise Support Assistant

    £13,520: Recruitment Genius: As this role can be customer facing at times, the...

    Financial Controller

    £50000 - £60000 per annum: Sauce Recruitment: A successful entertainment, even...

    Direct Marketing Executive - Offline - SW London

    £25000 - £30000 per annum + benefits: Ashdown Group: A fantastic opportunity h...

    Day In a Page

    How could three tourists have been battered within an inch of their lives by a burglar in a plush London hotel?

    A crime that reveals London's dark heart

    How could three tourists have been battered within an inch of their lives by a burglar in a plush London hotel?
    Meet 'Porridge' and 'Vampire': Chinese state TV is offering advice for citizens picking a Western moniker

    Lost in translation: Western monikers

    Chinese state TV is offering advice for citizens picking a Western moniker. Simon Usborne, who met a 'Porridge' and a 'Vampire' while in China, can see the problem
    Handy hacks that make life easier: New book reveals how to rid your inbox of spam, protect your passwords and amplify your iPhone

    Handy hacks that make life easier

    New book reveals how to rid your email inbox of spam, protect your passwords and amplify your iPhone with a loo-roll
    KidZania lets children try their hands at being a firefighter, doctor or factory worker for the day

    KidZania: It's a small world

    The new 'educational entertainment experience' in London's Shepherd's Bush will allow children to try out the jobs that are usually undertaken by adults, including firefighter, doctor or factory worker
    Renée Zellweger's real crime has been to age in an industry that prizes women's youth over humanity

    'Renée Zellweger's real crime was to age'

    The actress's altered appearance raised eyebrows at Elle's Women in Hollywood awards on Monday
    From Cinderella to The Jungle Book, Disney plans live-action remakes of animated classics

    Disney plans live-action remakes of animated classics

    From Cinderella to The Jungle Book, Patrick Grafton-Green wonders if they can ever recapture the old magic
    Thousands of teenagers to visit battlefields of the First World War in new Government scheme

    Pupils to visit First World War battlefields

    A new Government scheme aims to bring the the horrors of the conflict to life over the next five years
    The 10 best smartphone accessories

    Make the most of your mobile: 10 best smartphone accessories

    Try these add-ons for everything from secret charging to making sure you never lose your keys again
    Mario Balotelli substituted at half-time against Real Madrid: Was this shirt swapping the real reason?

    Liverpool v Real Madrid

    Mario Balotelli substituted at half-time. Was shirt swapping the real reason?
    West Indies tour of India: Hurricane set to sweep Windies into the shadows

    Hurricane set to sweep Windies into the shadows

    Decision to pull out of India tour leaves the WICB fighting for its existence with an off-field storm building
    Indiana serial killer? Man arrested for murdering teenage prostitute confesses to six other murders - and police fear there could be many more

    A new American serial killer?

    Police fear man arrested for murder of teen prostitute could be responsible for killing spree dating back 20 years
    Sweetie, the fake 10-year-old girl designed to catch online predators, claims her first scalp

    Sting to trap paedophiles may not carry weight in UK courts

    Computer image of ‘Sweetie’ represented entrapment, experts say
    Fukushima nuclear crisis: Evacuees still stuck in cramped emergency housing three years on - and may never return home

    Return to Fukushima – a land they will never call home again

    Evacuees still stuck in cramped emergency housing three years on from nuclear disaster
    Wildlife Photographer of the Year: Intimate image of resting lions claims top prize

    Wildlife Photographer of the Year

    Intimate image of resting lions claims top prize
    Online petitions: Sign here to change the world

    Want to change the world? Just sign here

    The proliferation of online petitions allows us to register our protests at the touch of a button. But do they change anything?