Saturday, August 29, 2015

Top 10 posts on Key West Lookout

Here are the top 10 most read articles on this blog since I started Key West Lookout in 2009. Key West Lookout is written by me and only me. I am a regular Key West visitor, and have been taking vacations in Key West since 1998. My aim is to provide the best, most comprehensive and most up-to-date Key West vacation guide on the planet. See you in Key West! This blog was last updated on 31 August 2015.

#1: Best time of year to visit Key West

#2: Key West hotels

#3: Top things to do in Key West

#4: What to do in Key West when it rains

#5: Key West restaurants

#6: Gay Key West

#7: Best cocktails and martinis in Key West

#8: Key West guesthouses

#9: Planing a Key West vacation

#10: Key West pictures

  • Crazy Key West - 25 of my funniest, silliest pictures from the last 10 years in Key West. Yes, Key West is eccentric and a little mad.


Tuesday, August 25, 2015

Cheap hotels in Key West

Here are my 5 tips for finding cheap Key West hotels and B&Bs and then my top recommendations. Take your time to find the best cheap value places as there few good cheap options here in Key West.

Monday, August 24, 2015

Planning a Key West visit

This post will help if you're planning a Key West visit or vacation and have questions like when to visit Key West, how long to stay, when is the rainy season, what are the best budget hotels, and how to get to Key West. Here's the Key West truth from a fellow Key West visitor.
Planning a Key West visit. Make sure you've done your planning. This picture is taken during the summer when crowds are much fewer
This post will answer these questions:
  • When should I visit Key West?
  • How many days should I stay? Is a weekend too short?
  • How to get to Key West?
  • How bad is the traffic?
  • Where to stop off on the way down the Keys?
  • How long to stay in Key West?
  • Do you need a car / what to so with the car while in Key West?
  • What to wear in Key West?  How formal is Key West?
  • Where to stay and what to do?
  • How good is Key West for children?
So click on the link below and let's get going....

Saturday, August 22, 2015

How long to stay in Key West?

How long to stay in Key West for your vacation is a key question. I think one week is the right length for a Key West vacation. Maybe you are thinking that visiting for only a long weekend is ok but Key West is a little off the beaten track (after all basically it's 127 miles down a dead end road) and as a result you'll spend too much of your vacation actually getting here so a little longer is better.

A week is not perfect of course. The perfect amount time to stay in Key West long as you can! For most visits Key West will be hotter, sunnier, livelier and way more fun than what you have waiting back home - so there is good reason to stay as long as you can. Plus there are hundreds of bars and restaurants and lots to do as well as great weather so you can chill by the pool and relax.

Here's how your stay might look over different time periods:

Wednesday, July 1, 2015

Most beautiful Key West houses and homes

There are some very expensive and beautiful homes in Key West. They are all in Old Town Key West and so very walkable in an hour if you are in a rush or a few hours if you just randomly wander down a few streets in Key West.

Here are a just a few highlights to make you want to come to Key West and also to make you jealous of these beautiful and historic homes.

I think this is my favorite Key West home, 1029 Fleming Street. Immaculate white and all the elements of the house work together in perfect harmony. Very Key West Old Town it also helps that this house is very imposing and also huge. The second image below shows the side view, showing how long the house is. It's not so uniform from the side, for example the 4 sided feature, which I think  makes it even more interesting.

One of the most beautiful homes in Key West - 1029 Fleming Street

Wednesday, June 10, 2015

What to do in Key West when it rains

If you're reading this then it's probably raining in Key West and you're looking for ideas about what to do. First I'm sorry it's raining and I hope it passes soon. Anyway, what to do? The traditional answer in Key West when it rains is: Drink! You have a multitude of choices and you'll find the bars packed today if it's raining. But there are alternatives, read on...
What to do in Key West when it rains. Here on Duval Street someone has a different option than a rain poncho.  

Sunday, May 24, 2015

Inga from Aqua Key West

Inga is the most outrageous and funniest drag queen at Aqua nightclub in Key West. This post is all about her - in honor of her hard work as show director, the amazing costumes and the work each night putting on a great drag show.

The show is called Reality is a Drag, every night at Aqua on Duval Street in Key West. To find out more about this highly recommended show - see my post here. Inga's been at Aqua for 18 years and  all the drag queens that perform here are super talented and excellent but try to choose a night Inga is on the bill.

Here's Inga and her various crazy costumes over the years....

Inga and me, Key West David

Inga in her 4 hands outfit - this is probably the funniest outfit I have seen - classic

Saturday, March 14, 2015

Key West history

For a tiny place Key West has a massive history. 

Here's a super summary of Key West's distinguished and crazy history: Ponce de Leon was the first European, setting foot on the Key West swamps in 1521. 

Then not much happened for 300 years until businessman John Simonton purchased Key West in a Havana bar in 1822 for $2000. Greene, Whitehead and Fleeming laid out the island plan in 1829 (and stole for themselves the names of the best streets).  

Life in Key West was then dominated by - in turn - shipwrecking, sponging and cigar making, all of which left their particular marks and scars on the city. 

Saturday, February 7, 2015

Seaplane to Dry Tortugas and Fort Jefferson

The Dry Tortugas are a group of small islands 70 miles west from Key West and visiting them by seaplane is the best thing I've ever done from Key West and one of my highlights of the year. The flight is only at 500 feet so the ocean views are stunning but that's only a warm up for the island itself which is dominated by the huge Fort Jefferson, the largest brick made structure in the Americas. Then there's the beach and snorkeling. I visited Key West for years without visiting the Tortugas and that was a mistake - make sure you include the Dry Tortugas and Fort Jefferson in your itinerary.
View of Fort Jefferson and the snorkeling area in front from the seaplane at the Dry Tortugas
Here are 11 things that are cool about a seaplane trip to the Dry Tortugas:
  • You get to fly in a small, 12 seat seaplane! That's cool!
  • You get amazing aerial views of Key West on take off and landing
  • For most of the flight you're at only 500 feet so you see loads of turtles, dolphins and other marine life in the water
  • You get to see all the lonely keys and sandbars between Key West and the islands - along with informative commentary from pilot
  • You're immersed in the Caribbean colors of the ocean - beautiful blues and greens
  • When you land on water at the Dry Tortugas experience how soft a water landing is
  • If you go on the morning trip you arrive 90 minutes before the ferry so you have the fort and island to yourself, which is awesome and makes a real difference
  • Fort Jefferson, with its 16 million red bricks, is very photogenic
  • As is the vista out to open ocean which includes the Dry Tortugas lighthouse, 157 feet high, a few miles away on Loggerhead Key
  • The snorkelling, very close (like 10 metres) off the island, is easy to do and good. Much better than any snorkelling in Key West
  • The colors, clarity and contrasts are stunning and you end up with some amazing photographs. The photos you see below are the set I'm most proud of across all my tens of thousands of photos of the Florida Keys - see below
FAQs - visiting the Dry Tortugas

Saturday, January 10, 2015

2014 changes in Key West

Key West 2014
What in Key West changed for the better and what changed for the worse in 2014? Here is my annual review of Key West changes - a personal selection. If you want a comprehensive list then read the Citizen! I do this every year and you can see links to previous years' reviews at the end of this post.

The two anncouncements offering the most impact were not new or surprising and had been brewing for years:

US to normalise relations with Cuba - 90 miles from Key West
Cuba came whole lot closer to Key West in December when President Obama announced more normal relations with Cuba, including relaxing travel barriers for vacations to Cuba. Subsequently, Cuba was named the #2 top destination in the New York Times's 2015 list.

This has potential for profound impact on the closest US real estate to Cuba (e.g. Key West) and could well mean a lucrative tourist route starting between the two. Day trip to Havana, anyone?

The alternative prediction for Key West is a reduction in cruise ship traffic because they choose to stop off / divert to new, interesting, different Cuba rather than good ol' Key West (which regrettably is looking more indistinguishable from all Caribbean / sunny destinations with each passing year).

Sunday, November 30, 2014

When is the best time of year to visit Key West?

Best time to visit Key West is January to May
Most visitors say the best time to visit Key West is January to May because the weather is perfect: it's not unbearably humid yet, and it's so cold at home. In fact, from November to March Key West is the hottest place in the entire contiguous USA. As a result, it's peak season, very busy and super expensive in Key West in these months. The off season (June to December) has its charms, but big downsides too, as I explain below, including a month by month guide.

Let's start with some Key West best time of year Frequently Asked Questions….

Saturday, November 15, 2014

Key West Lookout photo blog

Key West Lookout, this blog, is part photo blog and photographs and images of Key West have always been a vital part of the blog from the beginning. There must be more than a thousand images on this blog by now, with more being added all the time. And these selected carefully from the tens of thousands of pictures I have taken in Key West over the years.

Here's my picture of the week, I LOVE it!
Pelicans in free flight during Key West sunrise
click below for more picture of the week...

Saturday, November 8, 2014

Fantasy Fest 2014 live

7 November 2014. Well Fantasy Fest 2014 is well and truly over. Amazing fun, great events, little inhibition and tens of thousands of beads later. No rain for the main events on Friday and Saturday, and actually great weather. It was super busy on the Saturday of the main parade. Well done to all the people who selflessly organise, and raise money around, Fantasy Fest.

The best: Ten times better than Saturday's parade, and the best event of Fantasy Fest overall, was the Masquerade March on Friday. Brilliant! Key West locals you're the best. We had an amazing party again. The variety and creativity of fancy dress was amazing!

Here's looking forward to Fantasy Fest 2015!


My best 3 pictures: I took hundreds of pictures, so here are a very small number of my favorites....
Of the thousands of costumes and fancy dress creations on the 2014 Masquerade March here is my very favorite 
Fantasy Fest 2014 Masquerade March and my favorite picture overall - the view along Simonton Street of thousands of locals and visitors in full costume
One of the brilliant things about the Masquerade March, where everyone expresses themselves as they wish, is the occasional contrast this philosophy produces, like the one shown above 

Fantasy Fest Key West

This is my guide to Key West Fantasy Fest and I'll answer questions like is it for me, how adult is it, what are the best events and what's the weather like this time of year. If you're new to Fantasy Fest you can get a good idea if Key West Fantasy Fest is for you. Fantasy Fest is a 10-day series of events, parades and parties which runs the last two weeks of October. 

The 2015 dates are 23 October to 1 November 2015. Fantasy Fest always has an annual theme which most people ignore: for 2014 was Anim├ęted Dreams and Adventures, 2015's is All Hallows Intergalactic Freak Show (who thinks these themes up?!).

Fantasy Fest 2014 Key West
Fantasy Fest 2014 Key West
2014 was the 36th annual Fantasy Fest in Key West and the very best events (in my view) come at the end: the Masquerade march on Friday 24 October and the big showpiece event, the parade on Saturday 25 October 2014.

Link on my blog: 2014 Fantasy Fest live blog + 200 pictures

Continue reading for my guide to Key West Fantasy Fest for new visitors and first timers. Please leave a comment in the comments section below, I'd love to hear from you.