Received a DM the other day from a visitor to Key West.  They were leaving the next day and wanted to fill their last day with lots of fun.  Sadly, they couldn’t find a tour that had any open seats.  Which led to the question… when is the best time to book a tour when heading to Key West?  Quick answer… before you arrive. Egads, you mean I should pre-plan my vacation? My response?  Yes and no.

I am the first person to cringe at a preplanned agenda while traveling.  I want time for spontaneity and the ability to take advantage of what’s happening at that moment.  But… I do have a broad outline of what I want to do, see and try before I arrive anywhere.  As you plan your Key West trip, ask yourself what are my trip’s goals?  Specifically, what are the items on your “must do/must see” list?

Before you arrive

Before your vacation, decide what are the most important things you want to see and/or do.  In Key West, it may be a sunset sail or fishing or a play, or a concert.  Whatever it is… pre-plan that, then leave days free to fill in with spur-of-the-moment ideas.  While in Key West, that may be an afternoon at the bar listening to a great band or wandering through the many shops and galleries on Duval.

Any activity that is dependent on the weather, such as sunset sails and fishing, I always suggest you plan those early in your trip.  So, if Mother Nature decides to bring in a small craft advisory or an evening of rain showers, the cruise or charter can easily be moved to a later day in your trip.

But… I like spur-of-the-moment plans…

I get that too. But, here is the risk you run… you may not get to do the activity you really wanted.

So, if you wake up and it’s a rainy day, plan some indoor activities.  Go visit the aquarium, the butterfly conservatory, or any of the many museums in town.  (These are affiliate links which means, I will earn a small commission if you use these to book your activities) Plans can be flexible.  Trust, me I get it.  Nothing makes me cringe and stress more than a totally set-in-stone, minute-by-minute, vacation agenda.  Yikes, really?  Because those agendas never plan for an afternoon of sleeping off a few too many brunch Bloody Mary’s by the pool.

When is the best time?

The best time to plan for your must-do things is … before you arrive.  Really, really want to go fishing?  Then you will need to book that early.  Want to see the Dry Tortugas?  Those tours fill up months ahead of time.  Those fill up quickly.  Sunset cruises happen every night in Key West.  Probably can get a seat on one of the many boats going out, but if your heart is set on a specific cruise, then pre-plan that.  Want some ideas of what to do while in Key West… and book ahead of time?  Check out our tour page.  

Bottom line, arrive with some plans set … a broad outline of the vacation but leave room for spontaneity.  After all, isn’t that the idea when you shift over to Island Time?  A vague idea of the day, but time set aside for a few boat drinks by the pool.