18 Hardest Holes (in order of difficulty for me)

The ultimate challenge - one my friend Don would love to try - would be to play a mythical course with the 18 hardest holes from the executive courses in The Villages.  (Each is based on hitting from the gold tees) This 18-hole course is a par 57 with three par fours: Palmetto 8 is the longest hole from gold, so it's an automatic qualifier.  Then there's Longleaf 3 with its signature Oak Tree and Pelican 6 because it has every hazard possible!  The rest are par threes.  Most play long, upwards of 180 yards.  There are a few shorter shots with lots of trouble: Pelican 1 is obvious - it's the hardest opening shot in town.  Roosevelt 5 and Hill Top 4 fit this description too.  Most are beautiful, but there are a few clunkers like Okeechobee 3 and Gray Fox 6 - both are completely non-descript, void of anything compelling, they just play super long and hard.  The most treacherous back-to-back stretch is Bacall 7 & 8.  And special recognition to Red Fox 9 and Sweetgum 8 - they were the first entrants to this list back in my first month in town! I lost a lot of balls to these two back then!  Still do today.     

What hole would you nominate for these lists?

Many are pictured below with a few honorable mentions as well.  You can read all about each course by clicking the link underlining each.  Or access all the courses by clicking this blue button below>

The 18 Hardest Executive Holes

The most famous tree in The Villages sits dead center of the par four third hole at Longleaf.  Your second shot will undoubtably be altered.  Virtually no drive off the box can avoid the trouble you'll find on your second shot.  Playing at sunset will be the only sense of peace you'll get on the most challenging par four in the bubble! 

Red Fox 3 has no landing zone other than the green.  And that's about 150 yards away and the size of a postage stamp!  But don't just mail it in - keep your head down and fully follow through or you'll be seeing red all day!

The 6th hole at Gray Fox is an anomaly for this course.  It's unattractive.  At one of the best-looking courses in town, #6 really sticks out.  Likewise, you need to get your biggest sticks out to reach the green 179 yards away.  There's sand on the front right exactly where I land a fading drive.  And the green is narrow with a lot of rolls.  Left is your safest bailout but be careful to not hit the cart path on the fly!  Yep, it's got all types of challenges - just not looks!  

Pelican 1 is the Hardest Opening Shot in The Villages.  There is a hole out there.  Somewhere!  Look closely for a piece of cloth fluttering in the wind - there may be a hole below that!

The center of the narrow green on Sweetgum 8 is 178 yards away.  It was the first entrant to this list back in February of 2020.  Ever since it has befuddled me between the water, the sand and the thinly available green.  Blasting one into orbit is the only way to land this one! 

At just 140 yards, Roosevelt 5 is one of the shortest of the Hardest, so you should be able to drop a short iron shot from this uphill tee box.  But you better be precise.  The ball loves to funnel toward the pond or under that tree - and that's if you can carry the traps.  The prevailing wind will likely offset the downward trajectory too - lots of stuff to consider on this short little golf shot! 

The only clear visual you get at Bacall 8 is the 40-yard snaking sand trap that covers much of the front. There's only 20 yards of landing zone on the narrow green so you will have to be pin point to match this pretty approach. 


By the time I get to the 8th at Bacall, I'm so pummeled by the previous 3 holes that I'm happy with Bogey.  I'm sure Lauren said that too many times!  

The 8th at Palmetto is one of the longest drives you can take, uphill, usually into the prevailing wind - need I say more?

See the red barn?  It's easier to spot that then the green.  Maybe it's all the marshland in the middle of Red Fox 9 that maximized the distraction.  At just 153 yards, it seems this should be easier.  But it just isn't.  Your shot needs to come in high to stick the landing as the green and surrounding fringe funnel everything away downhill.  At 184 from the black tees is simply impossible! 

How about a little marshland Scarecrow?  Yes, I modified a line from the Wizard of Oz, but Mangrove 4 elicits the same scary reaction! Is there a green over there somewhere or just scary marsh?  Of the 168 yards from gold, about 150 of it is marsh.  But there is a humorous aspect to this hole - there's so little land on the other side that the drop zone over the bridge is so close to the green you could almost putt it!  

Bogart 3 plays uphill from 170 to a small green protected by a triplet of traps - two you can see and one in the back that's unseen, just to surprise you.  If you can thread the needle to land the green you should join the tour.    

Bacall 7 plays longer than it looks.  And it looks plenty long.  Water, a nasty frontal bunker and a run-away left side make it more of a Bogey hopeful than Lauren was in real life! 


This picture is taken from the 9th fairway across that pond.  You can see the flag tucked behind the upward sloping trap.  

Chaos.  That's Pelican 6 in a nutshell - or rather an eggshell.  Lots of marsh, sand and trees separate you from the green.  At least it's a par four so you can take your time on this scenic flight! 

The 9th at Briarwood is one of the most difficult closing holes in town.  178 yards from the gold box, protected by massive traps to the left and a sloped right side landing zone that funnels everything into the tree.  Your last drive of day on Briarwood will be your hardest! 


There's really nothing to Okeechobee 3.  Really, I mean nothing.  Yes, there's some nice-looking trees on the right separating it from Belle Glade's Seminole Championship Nine.  But it's on this list because it's simply long.  And 182 yards of nothingness is still 182 yards.   

Escambia 4 has Everything you want to avoid on a golf shot.  Length - 172 yards.  Sand in front and left side.  Downhill angle begging you to skip it long.  Oh and a bunch of buzzing overhead power lines! Buckle up and foam the runway! 

The 9th at Oakleigh is pretty grimm.  You'll need a long iron or possible driver if the gold tees are back at 180.  And that front bunker covers most of the green.  

You need ice in your veins to play Hill Top 4. It's not the water and sand you can see but the hidden trap on the back that makes it tough to land a shot on this hard deck!  

Honorable Mentions

  • Amberwood 5 - it's long, has the course's toughest green and is full of trees in my slice zone
  • Bacall 5 - have to carry a fully frontal trap to a very narrow green
  • El Diablo 7 - 175 yards with sand and water in my slice zone
  • Heron 9 - Pelican-like blind shot with no fairway to bail to 
  • Lowlands 6 - there's just something about this one that makes it hard
  • Pelican 9 - super long with junk all along the right side
  • Redfish 9 - over water to one of the 9 hardest greens in town.  You don't want your second shot to be chipping downhill 
  • Roosevelt 9 - Of course, your last shot on this course will involve a climb - Bully!
  • Southern Star 3 - long with water all along the right
  • Volusia 3 - funky par 4 where you can't go left off the box and your second shot will need to cover a walled pond to a narrow green.
  • Walnut 6 is the hardest shot on the course - you'll need to thread it through or be jail.  

And check out the full collection of the best holes in The Exec 54 >>>