GO FOR IT!

The question always arises as to which are the toughest holes to play in this haven of extraordinary courses. We offer the following 18 holes on 18 different Gulfshore area venues as seriously challenging—and will let you decide how to rank them from there. In a dream world, our 18 holes would measure a nightmarish 7,557 yards and play to a par of 74. All distances listed are from the back tees.

Pelican Bay, Club Course,
Naples
Designer: Arthur Hills
Hole No. 5, par 4, 294 yards
We’ll start with the shortest hole on our list, a straightaway shot off the tee that usually is a mid- to long-iron. Big bombers might try to drive the green, but that’s a huge gamble because of the pond in front. A 200-yard drive is much preferred, with an 80-yard carry over water to an elevated green. There are bunkers in front and to the right of a sloping putting surface from a peak at the center.

Wildcat Run Golf & Country
Club, Estero
Designer: Arnold Palmer
Hole No. 9, par 4, 441 yards
This hole has a slight dogleg to the right, with tree trouble on both sides off the tee and a fairway bunker on the left side. Tall pines down the right make it difficult to cut the corner of the dog leg, so most players have a mid- to long-iron second shot to a green protected in front and on both sides by bunkers. The long, narrow multi-tiered green offers a bowl effect that leads to some dicey downhill putts.

Arrowhead Golf Course,
Naples
Designer: Gordon Lewis
Hole No. 18, par 5, 495 yards
With trees down both sides of the fairway, the straighter the better, and fairway bunkers located on both sides also present a major hazard in the path to the green. The fairway narrows considerably for a second shot that also adds a pond protecting the left side of the green, bunkers left and right in front and another back center. A lay-up second shot is probably a wise decision, though longer hitters might want to flirt with a very risky second shot to the green.

Lely Resort Golf & Country
Club, Classics Course, Naples
Designer: Gary Player
Hole No. 12, par 3, 163 yards
A lovely little test with a picturesque lake swallowing wayward shots to the left of the putting surface, which also is protected by deep bunkers all the way around. A cosmetic lava rock pile to the right can also come into play, and if the ball hits there, who knows which way it might ricochet, occasionally even getting a lucky bounce onto the green.

Ritz-Carlton Golf Resort,
Tiburón Golf Club, Gold
Course, Naples
Designer: Greg Norman
Hole No. 3, par 4, 458 yards
Long and straight would be the operative approach off the green, considering the coquina shell waste bunker that runs virtually tee to green down the left side and rolling mounds providing dicey lies down the right side. The putting surface slopes slightly down to the left and also is protected by shell-filled bunkers all around.

Valencia Golf Club at
Orangetree, Naples
Designer: Gordon Lewis
Hole No. 3, par 5, 615 yards
Our longest hole is a three-shot beast with water running down the entire right side and two fairway bunkers down the left side off the tee. The second shot also includes fairway bunkers down the left and a putting surface protected by deep bunkers on the right. If you’ve got that 350-yard driver in your bag, followed by a 250-yard 3-wood, then by all means go for it in two, if you dare.

Marco Island Marriott’s
The Rookery at Marco
Designer: Joe Lee
Hole No. 16, par 3, 159 yards
A peninsula green features water front, right and back and not much room anywhere at all for a bailout shot to dry land. Also to be avoided, a bunker that protects the front left of the putting surface and swings all the way around to the back right of the green.

Hammock Bay Golf & Country
Club, Naples
Designers: Peter Jacobsen and
Jim Hardy
Hole No. 15, par 4, 471 yards
Our longest par 4, this straightaway test is protected off the tee by bunkers down the right side of the fairway. A long-iron shot onto a generous green also must clear bunkers on the left and right sides of the putting surface.

Naples Beach Hotel &
Golf Club
Designer: Ron Garl
Hole No. 18, par 4, 398 yards
A tee shot on this Naples landmark course must come through a narrow 40-yard cut with water down the right side. A second shot also must clear a pond in front of a small green, which also is protected by bunkers on the left front and right back. Shots too far over the back toward the nearby clubhouse are considered out of bounds.

Naples Heritage Golf &
Country Club
Designer: Gordon Lewis
Hole No. 2, par 4, 449 yards
A lateral water hazard runs down the left side from tee to green, and there is out of bounds on wayward shots to the right. Two fairway bunkers down the right side about 275 yards from the back tee also come into play for longer hitters. Shots to the left of the green will splash in the hazard, and bunkers on the left and right guard an extremely difficult multitiered green.

Naples Grande Golf Club
Designer: Rees Jones
Hole No. 6, par 4, 465 yards
A 200-yard carry off the back tee is required to clear the pond in front of the green, with two fairway bunkers down the right side and a series of bunkers 250 yards down and running all the way to the green. Another bunker guards the left front of a putting surface that leans left to right and slopes from front to back.

Lely Resort Golf & Country
Club, Flamingo Island,
Naples
Designer: Robert Trent Jones Sr.
Hole No. 17, par 4, 422 yards
A narrow 25-yard fairway features bunkers down the right side and trees marked by out-of-bounds stakes down the left. The second shot must clear water to a peninsula green. There are no bunkers in front of the putting surface, and there is a bailout area about 50 yards short of the green on the right side.

Fiddlesticks Country Club,
Long Mean Course,
Fort Myers
Designer: Ron Garl
Hole No. 18, par 5, 549 yards
Standing on the tee, players see a fairway that doglegs to the right. A drive down the middle generally means a three-shot, lay-up approach to the green; bolder players might try to cut the corner and fairway bunkers down the right, leaving a decent drive with a 230- to 250-yard approach over water to the green. A circular waste bunker guards the front of the large, undulating putting surface, and shots struck long can land in sand, leaving a tricky downhill blast.

Wyndemere Country Club,
Gold Course, Naples
Designer: Arthur Hills
Hole No. 5, par 4, 434 yards
A water hazard cuts across the fairway at about 230 yards and a 250-yard drive to a narrow landing area is necessary to clear that watery grave. A mid- to long-iron second shot must carry over a U-shaped bunker that runs from the right front all the way around the back of the putting surface.

Stoneybrook Golf Club,
Estero
Designers: Gordon Lewis and
Jed Azinger
Hole No. 14, par 3, 274 yards
Best to bring out the biggest and straightest bopper off the tee on what may be the longest par 3 from the tips in all of Florida. All you have to do is reach a narrow green between water in the front and a cypress preserve behind. No wonder they call this diabolical hole the "Little Devil."

Naples Lakes Country Club
Designer: Arnold Palmer
Hole No. 17, par 4, 440 yards
A dog leg veering to the left, the corner is protected by a large fairway bunker, and the second shot must clear marshy swamp land to reach a green framed by four difficult bunkers in back of the putting surface. A false front to the green fools many players into not using enough club to get the ball back to the flag.

Riviera Golf Club, Naples
Designer: John Gifford
Hole No. 12, par 5, 481 yards
Another short, straight par 5 hole, unless you happen to hit a sweet drive down the right side that catches an overhanging tree jutting out at about 220 yards off the tee. A fairway bunker down the left side at about the same distance also is very much in play, and bunkers front left and right guard the green.

Cypress Woods Golf &
Country Club, Naples
Designer: Gordon Lewis
Hole No. 18, par 5, 549 yards
Plenty of trouble all the way from tee to green on this straight hole. A series of fairway bunkers run down the right side and farther right are out-of-bounds wetlands. There’s also a water hazard down the left side, and a lay-up second shot is the preferred route to this peninsula green protected by water on three sides.