Cypress Point’s 16th is the most photographed par 3 in golf, and arguably the most intimidating shot on any course in the world. A 231-yard tee shot across an inlet of the Pacific Ocean, played from a cliff to a green pinned against another cliff, with the wind doing whatever it wants. Most amateurs never see this hole in person — Cypress Point is one of the most exclusive clubs on Earth — but understanding how to play it teaches lessons about wind, club selection, and decision-making that transfer to every coastal par 3 you’ll ever face. This is how the hole was designed, why it asks what it asks, and the strategy that survives both the wind and the nerves.
The Hole at a Glance
Cypress Point Club sits on the Monterey Peninsula in California, next door to the more famous (and far more public) Pebble Beach. The course was designed by Alister MacKenzie and opened in 1928, six years before MacKenzie’s masterpiece at Augusta National. The 16th hole has three sets of tees:
- Championship tee: 231 yards, fully across the cove. Hit it short or right and the ball is in the Pacific.
- Member tee: 219 yards, the same line, slightly less carry.
- Forward tee: Around 130 yards, played to a bail-out fairway short and left of the green, designed for golfers who don’t want to attempt the carry.
The green itself is small (roughly 4,500 square feet), sits on a peninsula of rock with the ocean on the right and short, and slopes gently from back to front. The MacKenzie-designed bunkers cluster around the front and left, and a small grove of cypress trees behind the green frames the target and steals shots that fly long.
What Makes the 16th So Difficult
The Wind
Cypress Point sits on a coastal headland exposed to prevailing northwesterly winds off the Pacific. On the 16th tee, the wind almost always comes into the player and from left to right, which means a 231-yard carry can play 250 or 260 yards. The Monterey wind is not the steady trade-wind found in tropical coastal courses — it swirls, gusts, and frequently shifts direction during the swing. Players who watch the flag for ten seconds and decide on a club have lost half the information. Smart players also watch the cypress tree tops behind the green, the ripples on the cove, and the spray off the rocks at impact.
The Carry Penalty
Most difficult par 3s offer a bailout — a fat side of the green, a friendly slope short, a place to miss. The 16th offers almost none. Short is the ocean. Right is the ocean. Long is a dense grove of cypress trees and rock. Long-left is one of MacKenzie’s deepest bunkers. The only honest miss is short-left of the green, where the forward-tee fairway sits — but reaching that bailout from the championship tee requires a deliberate, ego-swallowing shot that most players cannot execute under pressure. The carry is binary: you make it, or you reload.
The Visual Trick
From the championship tee, the player looks down into the cove. The eye registers the ocean as between the player and the green, which inflates the perceived distance and triggers a defensive swing. MacKenzie set the tee deliberately to use this visual deception. The actual carry is shorter than the eye says it is, but the eye wins almost every time. This is why amateur scores on the 16th are dominated not by topped tee shots but by full-club misses — players take one less club than they need, swing harder than they normally would, and finish in the cove.
The Strategic Choice: Carry or Bail
The 16th is one of golf’s purest decision holes. Before the player has swung, they must answer a question: am I trying to make 3, or am I trying to avoid 7? The two strategies are different shots played by different swings.
The Carry Play
The carry play targets the front-left edge of the green, accepting that anything short-left dies in the bunker. For most amateurs, this means a fairway wood or hybrid — not a long iron, despite the temptation. A 3-wood that carries 230 yards with a slight draw will hold the line into the wind. A 4-iron that nominally carries 220 will balloon, drift right on the breeze, and end up in the Pacific. The carry play is the right choice only if the player has a high-launching long-distance club they trust in wind. If not, the bail is the smart play.
The Bail Play
The bail targets the forward-tee fairway short and left of the green, leaving roughly a 60- to 80-yard third shot. This is the play used by most members and by many tour pros in wind. It accepts bogey as the realistic worst case and turns the hole into a wedge-and-putt scoring opportunity. The mistake amateurs make is choosing the bail in their head but swinging the carry shot. The body responds to the green, not the bailout. A committed bail play hits a punched mid-iron at the bail target, not a tentative long iron at the green.
The same kind of strategic discipline shows up on other famously demanding par 3s, including the one we cover in our guide to Pine Valley’s Hole 5, where the right miss is everything.
Club Selection and the Wind
Wind club selection on the 16th follows a simple rule that most amateurs ignore: take more club, swing easier. A controlled three-quarter swing with a hybrid travels through wind far more reliably than a full swing with a long iron. The reason is launch angle — fuller swings produce higher launches, and high shots get pushed around. The pros who play Cypress in wind typically club up two or three from their nominal yardage and swing at 80 percent.
The cross-wind compounds the decision. A left-to-right wind across the 16th’s line of play turns a slightly leaked carry into an ocean ball. Players who naturally fade the ball should aim further left than feels comfortable. Players who naturally draw can use the wind to hold the line, but must guard against over-drawing into the bunker.
Understanding shot trajectory in wind is itself a skill. For the underlying physics of how launch and spin interact, see our breakdown of angle of attack in golf, which explains why steep-attack iron shots balloon in headwinds while shallow-attack fairway-wood shots bore through.
Famous Moments on the 16th
Bing Crosby’s Hole-in-One
Bing Crosby, the singer, actor, and Cypress Point member, made the only recorded hole-in-one on the 16th from the championship tee in a competitive setting, in 1947. He carried the cove with a 2-iron — the equipment of the era — into a quartering wind. The shot is part of the hole’s folklore precisely because, in nearly eight decades since, no other amateur has matched it in competition under the same conditions.
The AT&T Pebble Beach Pro-Am Era
From 1947 to 1990, Cypress Point hosted the AT&T Pebble Beach Pro-Am rotation alongside Pebble Beach and Spyglass Hill. Tour pros spoke about the 16th the way they speak about the 17th at TPC Sawgrass: it was the hole they thought about in bed the night before their tee time. After Cypress Point left the rotation in 1990, the hole returned to the relative privacy of member play, which is partly why its legend has grown. The amateur golfer can no longer watch the world’s best try it on television.
Jack Nicklaus’s Quintuple
Jack Nicklaus, by his own account, once made a 9 on the 16th during a tournament round — dunking a tee shot, dropping, dunking again, dropping again, and finally finding land. The episode is a useful corrective to the idea that elite ball-strikers solve the hole. Wind and a 231-yard forced carry humble even the players capable of stopping a long iron next to any pin in the world. The 16th does not care who you are.
How MacKenzie Designed for the Decision
Alister MacKenzie believed that the best holes presented multiple plausible strategies, each with a clear risk-reward calculation. The 16th is his purest statement of this philosophy. He did not design a hole that required the carry — the forward-tee fairway is a real, playable route to bogey. He designed a hole that tempted the carry, and rewarded players who could match strategy to ability. The hole is not difficult because it is unfair. It is difficult because it asks the player to know themselves under pressure.
This is the same design philosophy at work in Augusta National’s Amen Corner, which MacKenzie designed alongside Bobby Jones six years after Cypress Point. The 11th, 12th, and 13th holes at Augusta similarly reward decision discipline more than they reward raw talent.
What the Amateur Can Take From the 16th
You will probably never play Cypress Point. The 16th is still worth studying. Three transferable lessons:
Match the swing to the strategy. A bail strategy and a carry strategy require different swings. Decide on the tee, commit fully, and never play a hybrid swing at a definite target. This is the single biggest source of unforced errors on any forced-carry par 3.
Watch the wind for ten seconds longer than you think you need to. The flag tells you ground-level wind. Wind aloft, where your ball spends most of its flight, can be different in speed and direction. Trees, cloud movement, and the shape of waves give you altitude information that a flag cannot.
The smart shot is the one you can execute under pressure, not the one you can execute on the range. If your range carry with a 3-wood is 240 yards on a calm day, your tournament-pressure carry into wind is probably 215. Plan for the pressure version of yourself. Many of the same principles apply to managing coastal layouts more broadly, which we cover in our guide to a golf trip to Pebble Beach.
If you ever do get to the 16th tee, the experience is worth the airfare and the favor it took to get on. The cypress trees, the cove, the sound of the surf below the cliffs, the small white-knuckle silence before the swing — there is no hole in golf quite like it. Play it once, well or badly, and you will understand why nearly a century later it still defines what a par 3 can ask of a player.
