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!  But the approach is not the only challenge.  Wait till you see the slope of the green.  What a way to start.  

The 5th hole at the new Laurel Oak course is the most talked about new hole in town - it's a monster of a shot.  410 from gold, 430 from black.  Plus, your drive will be over water and the green is the hardest one on the course.  That and the trucks going 80 along the Turnpike to your left makes for an adrenaline rush par 4!  Play it as a par 5! 

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 to the left - 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 5th hole at Bacall is much like Lauren herself: absolutely beautiful, but with a bite. A front bunker stares back at you almost defiantly, as if asking whether you’re worthy of taking on the shot. It takes a perfectly lofted drop shot to hold this green and earn her approval. And this shot begins a treacherous stretch of shots, one of the most demanding in The Villages.  By the time I get to the 8th, I'm so pummeled by this stretch that I'm happy with Bogey.  I'm sure Lauren said that too many times!  

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 under the trees.  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 course, 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 ultimate Pelican beauty and beast shot.  This is the only hole in The Villages that's on this Hardest list as well the Postcard, honoring list that honors the 18 best looking shots.  Congrats to the best hole on the Biggest Bird here!  

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!