The Itinerant Golfer

The Itinerant Golfer's Take on Cypress Point Club

Pebble Beach, California | Cypress Point Club

Architect: Dr. Alister Mackenzie & Robert Hunter
Year: 1928

3150 17 Mile Drive, Pebble Beach, California 93953
(831) 624-2333

driving range available to members and accompanied guests
walking only - caddies available
on-site accommodations
long pants required

I’ve just knocked my ball onto the green at perhaps the most famous hole in golf and my caddie has walked ahead while I enjoy the long walk to the green with my putter in hand. As I stroll around the path to the fairway watching the seals play in the inlet below I can’t help but get a little overwhelmed by the moment. The color of the day is yellow – I’m playing a yellow ball and wearing a yellow shirt and hat – in memory of Donna Briley the generous and kind woman who granted me the keys to the kingdom for a day. The original plan had been for her to be there with me, but sadly she passed away unexpectedly 2 weeks earlier. I’ve thought about her all morning, I’m thinking about her now and I will think about here every time I recall my tee shot at the 16th hole. I’m certain that in addition to her help getting me on the course, that she’s had a hand in guiding my ball away from trouble and into the holes that have been cut in this magnificent piece of land known as the Cypress Point Club.

Anyone who is familiar with the great golf clubs of the world knows Cypress Point Club. Bing Crosby was a member and made the club famous by including it in his annual Crosby Clambake (regretfully renamed the AT&T Pebble Beach National Pro-Am) which was a regular tour stop until 1991 when the club elected to withdraw. Another member, Bob Hope, very famously stated in regards to the exclusivity of the club “One year they had a big membership drive at Cypress . . . they drove out 40 members”. The bottom line is that this place is one of the toughest tee times in the world to obtain.

Opened in 1928 Cypress Point is often referred to as Alister Mackenzie’s finest design. Mackenzie also designed Bobby Jones’ beloved Augusta National so that gives you an idea of the gravity of the statement that Cypress Point is Mackenzie’s finest work. The course is laid out in 3 groupings of holes. Holes 1 through 6 are woodland holes set in the midst of the cypress and pine trees. Holes 7 through 13 are dunes holes expertly laid out among the natural sand dunes. Finally holes 14 through 18 are seaside holes that test the mettle of even the best of players lucky enough to tee it up here.

My day at Cypress Point started early. I was keeping myself on East Coast time for this trip so I first woke up at 2:30 AM Pacific time excited and ready to go. I struggled to sleep any more but managed a few more winks before I got up at 4 AM. I’m an excitable person, so once I realized it was Cypress Point day I had a tough time not getting on with things. My mom tells a story about when I was a little kid of 4 or 5 and we were going to the zoo. I woke up at 3 AM that morning and said “Is it time to go the zoo yet?” I guess thats just my way. First thing I did upon waking up was walk out to my car to make sure that I hadn’t been towed during the night. I’d hate to miss my tee time because of something ridiculous like that. Fortunately it was still right where I had left it the night before.

I left my hotel room and headed for Pebble Beach. The range at Cypress Point is reserved for members, so I was hoping to find the Pebble Beach range open early. I was in luck and the range was open at 6:30 AM when I drove by. I hit a bucket of balls in my street shoes and jumped back in my car and headed over to Cypress.

When I arrived at Cypress Point I parked my car and went into the proshop. I had the dew-sweeper tee time of 7:15 AM and I would be playing alone today. I play solo a lot at home so I’m used to playing my match against Old Man Par and often times prefer it. In retrospect, I think playing alone here made the round that much more special.

The guys in the pro shop directed me to the locker room where I could change shoes. It was one of those great old locker rooms where the benches have spike marks from years of shoe tying before the days of soft spikes and ghosts lurk around every corner. Byron Nelson, Ben Hogan, Arnold Palmer, Jack Nicklaus . . . all the greats have laced their shoes up here. In a quick glance around the room I saw Clint Eastwood’s locker and Charles Schwab’s but I didn’t linger too long as I was anxious to get out on the course. The photo below is not real clear, but it shows the unusual locker design.
Cypress Point Club
After hitting a few putts I met my caddy Bob Pegis. Not the same Bob I had at Spyglass and Pebble. The Cypress Point caddies only work Cypress Point. Bob first looped at the club as a youngster starting in 1955. He took many years off to work as a PGA club pro and then came back to CPC five years ago. Having the right caddie makes or breaks a round on a course like this – especially when playing solo. Bob was not a man of many words this morning but I liked him right away. He would prove to be the perfect combination of companion and guide for my stroll around Dr. Mackenzie’s masterpiece.

I teed up my yellow ball on number one and Bob directed me where to hit it . . . I swung and with the sound of my driver striking the ball, the journey began.

I started out with a par on number one which was a nice way to start. The photo below is taken from the 2nd tee looking back up the starting hole. From this angle you want to play right of the Cypress Trees. To the left is the members driving range.
Cypress Point Club
My photos of the 2nd hole and 3rd hole didn’t turn out so great because the sunrise was wreaking havok with my camera. Hole 2 is a nice par 5 with a tough drive over the dunes and the 3rd hole is a really nice par 3 ever so slightly downhill. Photos are below, though they are pretty poor.

The view from the 2nd tee box
Cypress Point Club
The view from the 3rd tee box.
Cypress Point Club
The 4th hole is a great par 4. I ended up in the right rough after my ball miraclously avoided the trees. The cool thing that Bob pointed out to me at the 4th hole was that when you look at it from the tee you can see a multitude of bunkers as shown in the photo below.
Cypress Point Club
When you look back at the hole from the green (as shown below) the bunkers are not visible. Pretty cool trick Dr. Mackenzie!
Cypress Point Club
The 5th hole is a par 5 with a dogleg left. Below is the approach where I played my 3rd shot from.
Cypress Point Club
The 6th hole is another par 5. There are back to back par 5s and par 3s on this course. A bold design move you don’t see much at all. I pulled my drive left here and into the 9th fairway. I got it back to the rough of the 6th hole and played my 3rd shot from the spot in the photo below. I love the bunkering on this course.
Cypress Point Club
The 7th hole is a really interesting par 3. In the photo below you can see the 6th green just below on the right and you have to hit your tee shot from an elevated tee box to an elevated green. I hit 5 iron to the fringe here.
Cypress Point Club
The 8th hole is a par 4 with a 90 degree dogleg right. You have to play your tee shot straight over the dunes pictured below and hope you clear them to make the fairway. I ended up on top of the dune but was able to chip out to the rough for a chance at the up and down.
Cypress Point Club
Below is where I played my 3rd shot from and hit it to the very front fringe. I was a little jerky on the uphill par putt and hammered one that hit the hole and almost dropped in. Luckly it hit the hole because it would have been 20 feet by if I hadn’t. Instead I made the five footer coming back for a bogey.
Cypress Point Club
The photo below is an interesting view of the 9th that day. Its a short par 4 and as you can see the green starts at the upper left and falls all the way to the lower right. The flag is sticking out way up there at the top. With that hole location you have to be careful with a putt that is above the hole. I was not and my ball went wee wee wee all the way down to the bottom of the green. Ugh!
Cypress Point Club
I dont have any photos of the 10th hole but is the only par 5 that was reachable in 2 for me. It was slightly uphill and fairly straight. I went for it and ended up in the greenside bunker in 2. I was on in 3 but 3 putted for a bogey.

The 11th hole is a par 4 that is pretty straight forward. Below is a photo of where I hit my approach from in the left rough. I had a some trouble on this green and had to take a triple.
Cypress Point Club
With the 12th hole you start to head out to sea and the wind really picks up. This hole as pictured below is a dogleg right. I hit great drive, but the wind got me on the approach and I had to chip on.
Cypress Point Club
Below is the 12th green. You can see the wind is really starting to show its teeth.
Cypress Point Club
Below is the 13th hole. What a view. Truly amazing.
Cypress Point Club
Here are two views of the 13th green. Note how the manmade bunkers just blend right into the natural dunes. Great design! I had to hit a utility club into this one to beat the wind. Starting with the 13th hole they had the flags tied down to the flagstick so they won’t get frayed from flapping in the wind. Made a nice par here.
Cypress Point Club
Cypress Point Club
Below is a view from the 14th tee box. This hole runs along 17 Mile Drive and it plays LONG. It is real windy today and all uphill every day.
Cypress Point Club
Below is a photo of the approach shot at 14. Its a narrow shoot and a long shot. It was a utility club for me. I missed a 40 foot birdie putt from the front of the green to a back hole location here by 1 inch. Would have been a great birdie.
Cypress Point Club
After the 14th green you cross over 17 Mile Drive for some of the most famous golf holes in the world. A really cool surprise was that once we crossed the road there was a little inlet where harbor seals were pupping. As Bob pointed out they are VERY protective and those that were able to get into the water with their young swam away and those left on the beach with babies never took their eyes off of us.
Cypress Point Club
Cypress Point Club
After a short walk up the path we come to the 15th hole. One of the most famous holes in golf and the friendly little brother to the menacing 16th hole. Below is a photo from the tee box.
Cypress Point Club
Heres a couple of views of 15 as I’m walking over to the green. In the second photo below take note of my ball about 6 feet behind the hole. I hit a smooth 9 iron and sank the putt for a 2 here.
Cypress Point Club
Cypress Point Club
Below is the path that leads to possibly the most famous hole in golf. It was a bit of an intimidating walk.
Cypress Point Club
Once I broke through the path and saw the hole as you see it below I asked Bob only half jokingly where the appropriate place to throw up was. Notice the white caps in the water. The sea was angry that day my friend.
Cypress Point Club
225 yards over the sea with a stiff wind . . . Par 3. When the hole was built Mackenzie wanted it to be a par 4 because the shot was just too hard. US Women’s Amatuer champion Marion Hollins insisted it be a par 3. When she pulled out a club and struck a ball over the water landing safely on the other side she convinced Mackenzie to make it a par 3. When Cypress Point was on the PGA Tour this hole was routinely voted the toughest hole on tour and many a pro golfer has admitted to losing sleep the night before playing it. The scores here are as low as 1 (Bing Crosby is one of the few to record an Ace here) and there is no limit to upper extremities of scoring on this hole. Porky Oliver carded a 16 here in 1954 at the Crosby Clambake. I’m certain there has been worse.

On the tee Bob and I discuss our game plan. I was playing well and I considered laying up to the left and then trying to drive the green for fun after I had a ball safely in play. I didn’t want a high score here to ruin a good round. Generally speaking I’m a conservative player and that would not be an unusual move for me.

In the book “The Match” (which I had read on my flight) Byron Nelson recalls himself in a similar situation at the 1937 Masters where he was tied for the lead and must decide to lay up short of Rae’s Creek on Augusta National’s 13th hole or go for the green and give himself a chance at a 2 stroke lead. As Nelson stood in that fairway and considered his options, the phrase “The Lord hates a coward” rose up from his Christian roots. I’m not a religious man myself, but that same thought was running through my mind as the wind blew into my face on that seaside tee box. I thought about how the round had gone so far and knew Donna was with me and going to help me out. I decided I had to go for it.

Bob decided I could hit a 16 degree utility, a 3 wood or a driver. I’d been hitting my driver well all day and Bob said “Driver, I like the driver. You may be long, but you’ll be up there.” Bob’s confidence in me, and in his club selection, subsided any nerves I was feeling and I simply took aim, addressed the ball and swung. It was about the most perfect swing I’ve ever made in my life. It was one of those easy ones that just feels effortless where the ball hits the club face true and flies off like a missle headed straight for the target. No fade, no draw, just straight and true cutting through the wind. We watched the ball come down on the green and Bob and I celebrated with a high five and cheers. My moment of elation is captured in the photo below.
Cypress Point Club
Bob pulled out my putter and said “Have a long walk with your putter. I’ll meet you over there.” The walk to the green was a long one and I took my time to soak it all in and capture the moment and everything that lead up to it in my memory. Though Bob probably didn’t notice I was a little shaken from the gravity of the situation by time I got to the green. I was happy to see that my ball had landed hole high 6 feet to the right of the flagstick and run about 30 feet past the hole location. I was feeling a little jerky and my putter was not as sure as it had been on the previous 15 holes. I hit a putt that I left about 3 feet short and then just missed my par. I tapped in for a bogey and was delighted to do it. Below is a look back at the 16th tee box from the green as I say goodbye to an incredible moment.
Cypress Point Club
Hole 17 is another one of the famous Cypress Point seaside holes. Really good players can bite off a big chunk of the hole and play to the right of the cypress trees. That requires a bold carry, so I elected to play to the left of the trees. I had a little trouble here and almost had a lost ball which would have been my first of the day. Luckily, we found it but it was under a bush and I had to take an unplayable lie. Below is a picture of the 17th hole taken from the tee box.
Cypress Point Club
My third shot was not a good one and I ended up virtually in the middle of the Cypress trees and played a fun shot high over the trees and onto the green. I two putted and had to take double bogey. Below is a photo taken from the 17th green. Note the flag that is tied down to the flagstick.
Cypress Point Club
The 18th at Cypress Point takes a lot grief from people, but I dont think its justified. I think the only reason people complain about it is because they’ve just completed 15, 16 and 17 which are possibly the 3 greatest golf holes in the world. The tee shot at 18 must be placed in the right spot to have a good angle at the severely elevated green. Below is a photo of the approach to the green.
Cypress Point Club
Again for me on this hole it was up and over the trees because I hit my tee shot a little too far left. I hit the fringe and had a testy chip from the back right rough to a back hole location.

After I putted out on the 18th green and was finished with my round at Cypress Point I realized I hadn’t added up my score all day. I’d just been so engrossed with the entire experience that I hadn’t bothered. I knew I was playing pretty well and when I did add it up I discovered that I had found the 80s and played several strokes below my handicap. I was perfectly happy with that. Here is one last look at the 16th taken from just outside the clubhouse.
Cypress Point Club
In closing all I can say about my round at Cypress Point is that it was magical and unbelievable. I count myself as one of the lucky few who was able to play what could possibly be the best golf course in the world. I hope to someday be able to return under better circumstances and only time will tell if that will happen. If it never does, and it certainly may not, I have one person to thank for making an ordinary day in April extraordinary for for one person. Thank you Donna.

Donna Briley
In memory of Donna Briley

  • Dan Shafer

    Thanks for a great piece of golf writing in memory of a terrific and compassionate human being who blessed every life she touched.

    Dan Shafer
    Spiritual Teacher in Residence
    Unity of Monterey Bay
    Friend of Donna

  • reader

    “The sea was angry that day . . .” was anyone there a marine biologist? Jealous you got to play Cypress. Thanks for the great writeup . . . hope to set foot on the grounds myself some day.

  • Jim

    Playing Cypress next week and this post has me sleepless already… Quick question: what was the caddy fee?

  • Jim,

    You are going to love Cypress. Everything about the place is spectacular. As far as the caddie fee goes, I don’t remember what it was exactly but I don’t recall it being any different from what is fairly standard for the Monterey Peninsula. Have fun and and take it all in. In my opinion its one of the best golf courses in the world. Enjoy!!!


  • Jim

    Just returned from my trip to Cypress. I read this before the trip and had incredibly high expectations. However, after playing CPC, the experience exceeded my expectations. Re-reading your summary helped me to re-live the day and crystalize the experience because it is overwhelming in the moment –almost religious. It is magical and special. Anybody who gets the opportunity to Play CPC should drop everything, and take advantage of it. I’ve been fortunate to play 7 of the top 10 – according to Golf Digest’s most recent ranking (not including Augusta) and CPC – without any question – is at the top of my list.

  • Glad you had a good day at CPC Jim. I agree about it almost being a religious experience. All of the Top 100 courses are fantastic, but there are a select few that are so far above and beyond the others that they just about warrant being on their own list. CPC is definitely one of them. Thanks for sharing your thoughts.

  • Roberto

    Hello – Thanks for the great story and pictures. I am reading “The Match” by Mark Frost, which happens at CPC and your pictures are the perfect companion to the book. Awesome! Thanks much. I hope to play CPC one day…


  • Nathan

    I am trying so hard to get onto Cypress Point this summer when me and my dad take a vacation to Pebble Beach. It will be my last trip to Pebble with my dad more than likely and to get him on there would be amazing. Do you have any suggestions on how to get on? I would do almost anything.

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  • Brian

    I played Cypress Point a few weeks ago…and i would agree with the statement about it being a semi religous experience. I have played SF Club 4 times and I would have to say it gives me that same feeling as cypress. The first tee jitters at sf club always get me!! Great photos.

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  • Bob

    Just finished playing Cypress something I never thought would happen in my wildest dreams. All the great things you hear about it are true. We had a great day to play sun shine and low wind. I had a great round going (how could it not be great I was playing Cypress) and along came hole 16. It never crossed my mind to go the short route to the hole if you only get one chance and don’t go for it on this hole you don’t deserve to be there. Two swings and two balls into the ocean and we dropped on the other side but as I said you have to go for it.

  • Tod

    Thank you so very much for this wonderful tour around Cypress Point. I had the honor of playing the course this winter with three friends. Your discription is spot on. I am a 16 handicap at Cypress so you can imagine what my score was. However, it did not seem to matter. I too had a bogey on 16 after my driver barely made it over. It was a thrill. I have this site saved in my “favorites” just so I can reminisce from time to time. Thank you!!!

  • John

    Does anyone have any leads on how one can get on to play Cypress Point? I am in the California area for the next few weeks and would love to have a chance to see Cypress Point

  • lbandito1 .

    Most golfers have seen the ocean holes at cypress, #’s 15, 16, and 17, but until you experience the inland holes it’s hard to appreciate how influential the routing of this course is. The quirky short par 4’s, the back to back par three’s, standing on the green after putting out wondering where the next tee box is only to find that it’s behind and above you tucked into a sand dune; all these elements clearly informed the routings at the courses at Bandon, at streamsong, at Ballyneal, etc…Such things might be common in Ireland or Scotland, but it’s pretty unique on this side of the Atlantic.