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Friday, June 23, 2017

How to Plan Your Key West Trip!



I have a saying about people who travel to the Keys and Key West “ The smart ones leave on Monday, and the really smart ones leave on Tuesdays, and late on Tuesdays at that! Leaving on Sunday, well, let's just say that's not the way to go. If someone leaves on Saturday, they need psychiatric care.

Let's look at the Tuesday departure. A lot of people will come here for one of the many events that are held over the year. Perhaps they are here for The Songwriter's Festival, MOTM, Hemingway Days, The Lobster Fest, Art Festivals, you name it. What do they all have in common? They all end on Sunday. With the events which are more spread out, take the Songwriter's Festival, or MOTM, where there are multiple happenings, they have visitors scampering about town running from place to place. They will see this event at 1 pm, another at 2 pm, yet another at 3:30, another at 5 pm, another at 7 pm, meet their friends for dinner at 8, someplace else at 9. They actually under the delusion that this is a vacation. The fact is, they are busting their ass twenty times more than they do the other fifty-one weeks of the year!

Most people leave on Sunday. What happens is that they go home completely exhausted! Yes, they saw all kinds of things, people, and events which truly enriched their lives. However, what they didn't do on their vacation, is relax. Instead, they ran themselves through the ringer.

Leaving late Tuesday afternoon, or evening makes so much more sense. If you leave Wednesday it's even better. Give yourself some time to decompress. Relax a little. Take some time for a stroll at night and smell the jasmine. Sit on the veranda of The Cork and Stogie and have a libation, watching the world go by, as the trade winds breeze through your hair. Sit in the garden at Hemingway's house and read one of his books that you can pick up at the small store there. Perhaps a day at Fort Zachery Taylor enjoying the fort itself, or the beach. Perhaps a Conch Train ride will fit your style? It's loaded with historical information!

There are loads of choices of things to do where you can just relax, and take it all in.

Remember: Rushing around is a mainland mentality. When in the Keys, do as the locals do.


I'm seeing more and more people arriving here twice a year. They will come initially for an event, as mentioned above, but they will return for a second trip, solely for the relaxation aspect. They're back to smell the aforementioned Jasmine if you will. They don't have to be anyplace at any time. Additionally, right now in the summer, rates are at their lowest. Someone was telling me they were paying $139 a night. Other rooms were less and others more. However, it makes so much sense on so many levels ranging from the chill out factor to the economic factor.


One of the interesting things that happen here is when visitors arrive into town, they will rush up to us, wide-eyed with exuberant and excited looks on their faces, arms outstretched, hollering like mad people “YES!!! WE'RE IN KEY WEST! LETS PARTY!!!!”

This, of course, is one of the things that one signs up for when they move here. All of us were like that when we came as visitors, to begin with. However, living here in a day to day life is different than visiting for a week. While it is different than visiting, I will say that I don't want to live any place else in the world! I used to work with a very intelligent and insightful guy named Andy Colby. Andy would say sometimes “This town will chew you up and spit you out if you're not careful”. Andy was right too. I lost track of those who left the islands with serious alcohol conditions.

Sometimes those visiting will have the go here, go there, go here, go there agenda. They need to relax! HA HA!

As for us, we generally pace ourselves. We live here. We have professions we need to perform at.

                                         Caribbean Club, Key Largo

On rare occasions, people will ask us “Where do you go for vacations? After all, you live in a vacation destination”. I always laugh when someone says “Key West is so laid back”. Yeah, go to the two hundred block of Duval at midnight. That's Hell on wheels, out of control at 200MPH. That's not laid back.

What we do is head to the other end of the Conch Republic. That's laid back! Some asshole from the lower Keys started a rant saying that the upper Keys, Key Largo to Marathon, was just an extension of Miami/Dade. What a load of complete bullshit, and that's the nicest way I can put it. Key Largo, Islamorada (say Isle more ah dah), Layton... have the exact same amount of keys magic as the lower Keys. I spent thirty years hanging out there, as well as playing there and it's truly magnificent. There are loads of great places to stay. Ours is Sunset Cove, in Key Largo!

I always recommend staying a day or two in the upper Keys when heading to Key West! 

E) Whatever you do and wherever you go, be sure to get out on the water. Sunset cruises are the perfect answer. Inexpensive and not too time-consuming. Plus, they have open bars on them as well.

For the best 10 bars in the Florida Keys, check this blog from a few years ago!

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