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Cypress Point Club

Like most golf fans, I have always been intrigued by Monterey. Having grown up in New York, every February I would find myself watching the PGA tournament held at Pebble Beach and I would be overcome with jealousy. During college, I went on a trip to San Francisco and took a ride down to Monterey, but did not play any golf. Nonetheless, it conjured to mind the scene in Rudy where the father, a lifelong fan of Notre Dame, walks into the stadium for the first time and remarks, "This is the most beautiful sight these eyes have ever seen." I have been fortunate to travel to some remarkably beautiful places, but I do believe that the Monterey peninsula is indeed the most beautiful site these eyes have ever seen. At the time, I made it my goal to play Pebble Beach some day. The thought of playing Cypress Point seemed a bit too ambitious given the notorious near impossibility of getting past the sign reading "Cypress Point Club Members Only."

I wouldn't return to Monterey for five years, but little did I know that when I did it would be to play Cypress Point (and I would not play Pebble Beach until three years after the first time I played Cypress). Without going into much detail, during the next five years I would meet two exceptionally kind and generous people. It is through them that I was able to play Cypress Point three times over the past three years. Each time has been a different experience, but a few things remained constant. First, the sheer excitement of playing there does not dissipate. I think it is something that no matter how often one were to play it, it would never be taken for granted. Second, as difficult as it is to get an invitation to play, once you do the club (and everyone at it) is warm, welcoming, and entirely understated. Third, the caddies are a bottomless pit of entertainment with some of the best golf stories you will ever hear.

Each time I played the course I experienced different weather. The first was overcast and gloomy. You might think such conditions would diminish the experience, but it only made it atmospheric. As long as there is not fog to hide the views and scenery, a cloudy, windy day will only make the Pacific a more formidable backdrop. The second time I played, it was an average day--some clouds, some sun. Most of the below photographs are from my most recent playing when the weather was absolutely perfect with unlimited visibility and the bluest of skies. The few cloudy and overcast ones are from my first playing, but I provide them to demonstrate how the weather can change the feel of the course.

Now for the review. The most striking thing about Cypress is the diversity of its terrain. The first few holes start in the forest, similar to what one would expect at Spyglass (in fact there are points on Cypress where you could hit greens on Spyglass if your caddy told you where to aim). The course then routes through sand dunes before turning to the ocean. It is like playing three majestic courses in one. While many courses feature one of these terrains (e.g. ocean at Pebble, forest at Augusta, or sand at Pine Valley), Cypress combines them all, which, in my opinion, makes it the best course I have ever played (and, though I have many more courses to play, I will be surprised if any course ever tops it). Also noteworthy is the fact that Cypress provides some of the best ocean scenery you will ever encounter on a golf course. But, equally importantly, the course is still playable despite being directly on the ocean. I have recently played Tralee and Old Head in Ireland (reviews forthcoming), both of which rivaled the ocean views of Cypress (I mean Old Head is literally built on a peninsula that is barely connected to the mainland). However, both courses had such strong, sustained winds (approximately 40 mph) that the courses were nearly unplayable. I asked my caddy at Old Head when was the last time there was a clear day without high wind--three years ago. At Tralee and Old Head you either get beautiful views and high wind or fog/overcast and calm conditions. At Cypress you are not faced with that devilish dilemma.

Lastly, before getting to some of the individual holes, Bobby Jones said of Cypress, "Pebble Beach is more difficult, but Cypress is more fun." This assessment cannot be more true. From the championship tees, Cypress plays a little more than 6500 yards and only 6300 yards from the middle tees. Does this make it a bit easier than some of the other great courses? Yes. Does this make it more fun than other great courses? Most definitely. One of the lasting impressions you take away from Cypress is that the round was a lot of fun. Often when you play a top course, you will only get one shot at it, which is unfortunate given it is difficult to play a new course well. When I play a course that I am familiar with, my goal is to shoot in the low 80s (with a great round if I break 80). When I play a course for the first time, my goal is to break 90 and hopefully shoot in the mid-80s with low 80s being a great round. The first time I played Cypress I shot 82--though the expert caddies may be as much responsible for that as anything else.

Below is the notorious "Members Only" sign. Felt pretty good to blow past that.

Stupidly, I did not take a photograph of the clubhouse when I played, so I got this one from the road when I was just biking by.

Adding to the already existing jitters, the first tee box is located directly in front of the clubhouse (though there are not always onlookers as each time I have played there were few other people on the course with us, let alone people lining up to tee off). Moreover, your tee shot has to go over 17 mile drive, so a topped shot may very well hit a car if the timing is right (or wrong, from the perspective of the driver). But, other than playing arguably the best golf course in the world, there is no reason to fear the hole. It is an expansive fairway to a large green with beautiful ocean views running up the left side of the hole. Despite the timid nature of the tee shot, my brother (putting below), who is a better golfer than I, still hit a four iron (oddly, his go to club when he needs a sure fire shot) to ensure he made it off the tee without any embarrassment. The hole serves as a good introduction to the ocean vistas you will encounter later and serves as a good ease into the course.

View down the first fairway as you walk over 17 mile drive.

First green looking back towards the tee. Pictured is my brother and one of our two caddies for the round. The caddy had started caddying here as a teenager, then left to pursue his career. Upon retiring, he returned to caddy. Talk about someone with course knowledge.

The second hole is where you turn away from the ocean and head into the forest. It is a 535 yard slight dogleg left par five. The difficulty on the tee shot is knowing exactly how much of the dogleg to cut. Too little and your drive runs the risk of running through the fairway and going out of bounds. Too much and you may not clear the bunker guarding the fairway. The rest of the hole requires navigating fairway bunkers that require you to think about the placement of each shot.

The third is one of the few underwhelming holes at Cypress. It is a 150 yard par three that, to me, seems oddly fit between the second green and the fourth tee. The green is well-bunkered, but there is little else to the hole. Perhaps it is just that the other par three's on the course are among the best in the world that this one pales in comparison.

View of third green from the tee

The fourth hole is a 370 yard par four, and it is the first time you truly appreciate the forest aspect of the course. The difficulty of the hole arises from the fairly narrow tee shot, many fairway bunkers to navigate, and tiered green that requires penalizes being above the hole.

The fifth hole is a short par five similar in terrain to the fourth hole--surrounded by trees with many fairway bunkers to avoid. Though short, the elevated green makes it difficult to hit in two. Each time I have played, my strategy has been to hit driver and then a club to leave me 100 yards to the hole. This approach makes it such that your drive is critical, but then the next two shots are ones that you should be able execute (likely a seven iron lay up and then a wedge).

View from fifth fairway.

The sixth hole is another par five measuring 509 yards. Yes, back to back par fives, which you rarely see (the other course that immediately comes to mind that has this is Ballybunion). The fifth is a fun hole. There is a fairly significant elevation change on this hole with the tee being above the green. Further, the hole is a dogleg left and is designed such that if you hit the slope on the correct part of the fairway, you will get a lot of run (though if you hit it too far left, trees will foreclose any attempt to go for the green in two). There is not much trouble on the hole, so, with a good drive, you may be able to exploit the terrain of the hole and get close to the green in two.

View from sixth fairway.

The seventh hole is the first of the great par threes. The hole is not great because of its scenery, but because of the elevation change, bunkering, and shallow green. It measures 159 yards and you hit from an elevated tee, over a valley, to a green that is at the same elevation as the tee. So, there is not much elevation change, but it appears as though there is. Making the hole particularly difficult is the narrowness of the green, though there is a bit of a backstop to prevent balls that go long from getting into too much trouble.

The eighth hole is where you move from the forest into the sand dunes. This hole, measuring 342 yards, is among my favorite on the course. It is a blind tee shot over sand dunes with something less than driver, unless you are feeling particularly bold and want to heavily cut the sand dune (though that is unnecessary as the green is not reachable and a 200 yard club off the tee will leave you a comfortable shot into the green). The second shot requires precision to avoid the bunkers on the left and the large sand dune on the right.

Dad hitting approach shot between bunkers and sand dunes. Led to a birdie.

The ninth is a fantastic risk reward hole. A par four measuring 283 yards, the tee shot requires a decision between driver and a lay up shot. The choice is particularly difficult, though, because even if you do not have the ability to hit the green, the second shot becomes considerably easier with a short club given how narrow the green is.

Ninth tee. Going with driver runs the risk of finding sand on the left, but, if done properly, you will leave a much

easier shot into a very narrow green.

Ninth green with my father, my brother, our two caddies, and I. My dad is getting a read.....even he putted well that day.

The tenth is one of my least favorite holes. It is a 476 yard par five. The main obstacle is bunkering in both the fairway and around the green. With a good drive, you are either left with an easy lay up to set up a wedge into the green, or you can go for the green and even a poor shot will only find a green-side bunker, which is not the worst place to be hitting three on a par five.

Still in the sand region of the course, the eleventh is another of my favorite holes. As a 427 yard par four, it is among the longest holes on the course, thus making a good drive essential. The beauty of the hole comes as you approach the green with an enormous sand dune serving as the hole's backdrop. Though it should not come into play (unlike the many bunkers surrounding the green), it makes the hole among the most beautiful on the course.

Sand dune behind the eleventh green.

The twelfth is another hole among the dunes. Measuring 397 yards, it is among the longest par fours on the course. The key to this hole is hitting it far enough to clear the sand dune you are hitting over, but short enough to avoid running into the fairway bunker.

View from twelfth fairway. Clearly my dad did not have enough to clear the dune.

The thirteenth is where you really start to head back towards the ocean. A short par four measuring 344 yards with a tee box that presents a stunning view and an ocean-side green. Like many of the recent holes, the approach to the green requires precision to avoid the many bunkers.

View from thirteenth fairway.

The fourteenth hole is a 384 yard uphill par four and among the best on the course (it was my caddy's favorite). The hole is framed by the ocean on the right and the approach (or drive if you are very long) requires a shot through a shoot of cypress trees. Truly fantastic.

Fourteenth tee.

Cypress shoot leading up to fourteenth green.

What the 16th hole has in fame, the 15th (the first of back-to-back par threes) has in fun. Perhaps a better adjective, which I steal from another golf writer I follow, is that it is the sexiest hole in golf. Have you ever had the feeling standing on the tee that you just want to hit a good shot on this particular hole because it would be such a waste not to? Well, 15 definitely gives that feeling because it is only 120 yards. It's the pitching wedge you have hit perfectly on the range a million times. Now you just want to do it on one of the best par threes in the world over the Pacific Ocean. There is nothing particularly difficult. The green is more than accommodating for a wedge, and the ocean should not come into play unless you truly succumb to the moment. I, unfortunately, hit a shot that should have landed on the fringe about 25 feet from the hole, but it hit a sprinkler head and shot over the green. Alas. If I had to choose one hole to play over and over again, this would be it. It's fun, it's supremely scenic, and it feels like it's in its own secluded part of the golf course. I suggest that you check out Gallery Sur (which has its gallery online) for amazing aerial photographs of the ocean holes at Cypress (including 15 and 16). The aerial view is the best way to appreciate the ocean carries and how the hole sits in relation to the ocean. Below are two videos of tee shots on fifteen.

My brother and I on fifteenth tee. On a good day I beat him. On an average day he beats me by 4 shots.

This photograph is from the first time I played the course in overcast conditions. You can see how it gives the ocean

more of a moody feel.

Fifteenth green.

One of the best parts of the course is the walk from 15 to 16 through the cypress trees knowing that one of (if not the) best holes in golf awaits you. There are holes I may want to play more due to the historic aspects of the holes (e.g. 12 or 13 at Augusta or the Road Hole at St. Andrews), but the beauty presented by the 16th at Cypress and the exceptional golf shot it demands, I cannot imagine a better hole in golf. Measuring 218 yards nearly all of which is carry over the ocean and often into a strong wind, there is no coming up short. Though Alister MacKenzie provided a lay up option, if this is your only shot at this hole, you are going for it. Each of the three times I have played, I hit a 3/4 driver (which is often my go to shot on par threes that require a shot in the range of 210-240 yards). I have hit the green twice and the ocean once. The result- two pars and one double. One of the pars might have been a birdie if pride did not get in the way. I had a ten footer for birdie and told my caddy that I wanted to try to read the putt myself. One of the great things about Cypress is that the caddies know every inch of the course. The caddy tells you where to hit your putt and at what speed. If you do it, it will go in. I made more twenty footers in three rounds at Cypress than I would expect to make in ten normal rounds. Below I provide some photos, but also provide the layout of the hole so you can appreciate the carry that is required and so you can see the potential lay up route (which maybe you take if this is not your first round at Cypress and you need to go bogey bogey to break 80).

Google maps view of 16th hole from

Brother walking up shoot of cypress trees to the sixteenth tee.

The famous (and infamous) sixteenth. Could not ask for a more beautiful day. The 15 mph winds were just enough to get the white water going. As the story goes, caddies were not permitted to play Cypress in the past (I think that has changed such that there are times when they can play). However, on one loop many years ago, a member gave a caddy known to be a great golfer a shot at the sixteenth. The caddy grabbed a club and knocked it in the hole. But, it was not an official hole in one (as he was not supposed to be playing and the USGA recommends--though it is not a formal rule-- that to be official a hole-in-one should occur during a round of at least nine holes). Or so my caddy told me.

Me getting ready to tee off.

We also went in prime seal season. Below are seals that you could see (and hear) from the green.

I feel like the flowers that are all over the ocean holes never get the due they are owed for their contribution to Cypress's beauty.

When you step to the tee at 17, you see the only place that a past Cypress member is memorialized, and it is this image that I have chosen to serve as the banner of this site because I think it is something we should all keep in mind and remember how lucky we are to be able to play golf at all, let alone one of the greatest golf courses on the planet.

The 17th is a 374 yard par four that requires another ocean carry (though it should not come into play, other than for scenic value). Though with their differences to be sure, this hole reminded me of an inverse version the 17th at Ballybunion (as did the 18th--more on that below). Both have the ocean going up the right and both are doglegs (Cypress to the right (further out into the ocean) and Ballybunion to the left (away from the ocean). In the middle of the fairway is a grove of Cypress trees that you have to mind from the tee--get too close and the second shot becomes impossible. Not only does the second shot require you to go over the trees, but it is yet another ocean carry. Below is a video from the 17th tee.

Seventeenth tee.

Cypress grove in the middle of the fairway.

The 18th hole gets a lot of flak. Is it a good hole? No. Does it make true the statement that Cypress is the best 17 holes in golf? Yes. Get over it. You just enjoyed the best golf course in the world (not to mention 14, 15, 16, and 17, which is arguably the best four hole stretch anywhere). It is a weird little 326 yard dogleg left par four with a huge tree in the middle of the fairway that you have to hit under in order to get to an elevated green. Like I said above, it strongly reminds me of 18 at Ballybunion, which, in my opinion, is also a weak closing hole after a phenomenal golf course (as it is also a dogleg left to an elevated green with no particular scenery to note).

Tree that guards the left side of the eighteenth fairway (and often proves an annoyance on your second shot).

Even after having played Cypress three times, if on Friday I was asked to complete a foursome on Saturday morning, I would leave my desk, get on the next flight no matter the cost, and get to Cypress Point. It was simply a transformative experience. As I explain in the introduction to this blog, it is what set me on this quest to play as many great courses as possible (perhaps to discover if anything can top Cypress or if I have already played the best there is). The diversity of the terrain, the stunning ocean views, the warmth the club extends to its visitors, the caddies telling wild stories about the people they caddied all makes for the perfect day. If I had two days left to live and could do anything I wanted, one day would be spent with my family and the other would be spent playing Cypress Point. After playing Cypress, I have made it a subgoal to play as many Alister MacKenzie courses as possible (the only other one I have played is Lahinch). In the near future I hope to play Pasatiempo in Santa Cruz. Obviously Augusta is at the top of everyone's list, though I also find Crystal Downs in Michigan to be particularly intriguing. Also, I suggest that you read The Match, which is a book about a golf match held at Cypress in the 1950s between Ben Hogan and Byron Nelson. Not only does it describe Cypress well, but it is an engaging read about a historic day in golf's past.

As a closing thought after having played the two best courses in California, Cypress is no doubt a better golf course than Pebble Beach. But, more than that, it is simply a different kind of experience. I think the reason is because it is private, and not in a snobbish way that you feel like a hotshot for playing there. That is not it at all (and I think people who want to play the best courses to feel like a part of the "in-crowd" are valuing the wrong thing--see the UK where even the best courses gladly welcome public play). Rather, the whole day feels meant for you. The club knows how special it is that you are getting to experience this masterpiece of a golf course and that comes across from the moment you set foot on the property. There is rarely many other people on the course, so it feels like you are taking a walk in your own personal golf nirvana. I think the main distinguishing feature is that you have the sense that you get to do this once and only once. As my brother described it, he was not nervous hitting his first tee shot at Pebble, but he was certainly shaky at the first on Cypress. If you shoot 105 on Pebble Beach, you can come back the next day and give it another try. By contrast, the evanescent nature of Cypress is always palpable. This may be the last time you hit that first tee shot or go for the green on 16. Once you finish the first hole, it is now a memory that you can relive in your head, but maybe never again in reality. This leads to a sense of urgency to savor every second you have on the course, every shot you hit, and every ocean vista you admire. I hope one day that Augusta, Pine Valley, or some other course proves me wrong, but I think Cypress Point, despite its ranking at fourth in the world, will be the best course I ever play.


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