Key West Guyd: The End of the Gay World (Part 2)

Danny Hilton
Authored by
Danny Hilton
London Correspondent
May 13, 2013
11:58 a.m.

If you missed the first part of my Key West post, you can read it here. I give a general intro to this magical place, where I stayed (Big Ruby’s Guest House), Hemingway House and a catamaran snorkeling trip with Andrew from Austin. Here’s part two!

Oceanside Lunch
Our next stop was a late lunch on the beach at Sun Sun, one of the restaurants at the stunning Casa Marina, a Waldorf Resort Hotel. We got there at 4pm, a bit late for lunch, so they were ‘in between menus’ – although this hardly seemed to matter when we saw what was on offer. While we waited, we checked out the beautiful hammocks on the beach, which were extremely comfortable, until Andrew knocked my cocktail over, directly into my crotch. I held my head high as I walked back to our table, pretending it didn’t look like I’d just wet my pants (thanks again Andrew).

sun sun food

This picturesque scene didn’t last long. Andrew is already ripping a prawn to shreds off camera.

As I dried off, we feasted on Conch Fritters (a local dish of shellfish mixed with onion, pepper, flour and spices, a must try while in Key West), huge king prawns, spicy seafood chowder and pulled pork. With a few more cocktails I was soon dry, full and happy.

Before we knew it, we were whizzing back to Schooner Wharf for our sunset sail mini-cruise. Taxis are not super-cheap here, but they are with you pretty fast. Any store or reception desk will be happy to call one for you. If you cycle (I don’t, long story) then there is probably no better place in Florida to do it than in Key West.

about to board...

About to board… Little did we know we’d be hoisting the sails ourselves! Ooo-Arr!

Champagne Sunset Sail
This mini-cruise on the 105 foot Schooner, America 2.0, was even more wonderful than it sounds. The feeling of being on a real sail boat was totally different from the catamaran earlier on. As we glided out into the Gulf of Mexico my few remaining stresses melted away. The champagne made it even better. We were all made to feel part of the crew – I hoisted the sails (butch moment, good for triceps), and me and Andrew even had a go at steering. We weren’t exactly pros as you’ll notice from our (and the crew’s) expressions…

woopsie sailing andrew

Our hunky daddy Captain tries to get Andrew to steer in the right direction…
woopsie sailing

While I get told off for inadvertently taking us a bit too close to Cuba

drinking on ship 111

We were soon reassigned to a job we were both much more skilled at: drinking

Back on dry land, with the fear of an international incident out of the way, it was time to get on with some more drinking. The nightlife in Key West mid-week is relaxed, fun and friendly. During the weekend I can only imagine it gets even more so. I ended up singing Cher very drunkenly at a karaoke bar. Luckily, there is no photo or video evidence of this…

Island House
We ended up at Island House, where things were really hotting up. This infamous gay men’s resort has a pool, Jacuzzi, health club and ‘cultural centre’ (cabins, cruise areas) upstairs that really comes alive in the nighttime. Again, luckily there’s no photo or video evidence. Instead, here’s a typical night time scene at Island House… before the action begins… You can read a full review of Island House here.


The awesome Island House at night

Getting There
I got to Key West via a thirty minute flight from Miami International Airport. I got back to Miami on the shuttle bus, with a few stops at some of the other Keys along the way, which took about four hours. I’d recommend both options – I felt like a true adventurer seeing the awesome scenery of the Keys from the air, but it was lovely to see the different personalities of each Key as we drove through them. The four hours went by very fast.

Key West Pride
This year’s pride runs from June 5th to June 9th, and with a street fair, pride parade, pool parties, dance parties, sunset sails, comedy, film, live performers and a giant rainbow flag that stretches from one end of the island to the other, this is set to be one of summer’s unmissable events. I hope I can make it! I hope Andrew can too.


The famous Key West Pride rainbow flag stretches from one end of the island to the other


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