A T.
Yelp
I was lucky enough to be invited to play Cypress Point by a member (along with two other members of my family). Our plan was to meet for lunch in the clubhouse first, then play golf.
Lunch in the clubhouse is old school. Men must wear a jacket and tie and there are regulars who sit at their "usual" tables. There is a more casual grill now, but we stuck with the full treatment in jacket and tie. The view is incredible, overlooking the ocean with the 16th green visible at the point. There are no menus, your server will tell you what's available. The food was very good. For dessert, again, there is no menu. In fact you don't order. Instead, you walk just outside the dining area to the dessert area where a bunch of daily desserts are set up. The creme brûlée is apparently famous so I tried it and it was very good. Other desserts included a nice looking chocolate cake (just cut yourself a piece) and several other cakes and pies - all self serve - just take what you want.
Next stop is the locker room to change into golf shoes. Again, we are talking old school here. The lockers are from a time in the past. The names on the lockers are handwritten and include the names of prior members. So yes, as you walk in, look to the lockers on the right and you see Bob Hope's.
Now, the real reason to go to Cypress is for the golf. First, it should be noted that the pro shop is tiny yet well staffed. They sell lots of merchandise to guests out of this tiny space. Just outside the pro shop in the 1st tee. There may be a few bags out there depending on if there are any golfers planning to go out (probably not).
The first tee has a drive that goes over 17 mile drive. To the right of the fairway is the driving range. The range is small, but serviceable given the amount of play. It's stocked with ProV1 practice balls indicating an attention to detail.
The first few holes go into the forest winding amongst a handful of nice homes. Your caddy, who is required (no carts and all members must also take caddies) will point out which members own certain homes. The fairways and greens are immaculate as you would expect given the low play and lack of carts.
After several "forest" holes the course turns back toward the ocean. Now, instead of a forest setting we start to see dunes. The dunes (waste areas) are all sand but do not play as bunkers. They make for a new challenge (also present on other courses on the Monterey Peninsula).
Hole 13 starts the transition to the ocean part of the course and the great views. 14 is played next to the ocean but 15 is where the signature parts of Cypress come in to play. The ocean is in full view with seals and sea lions playing on the rocks. 15 is a largely unknown gem, a short, over water par-3.
16, on the other hand, is the world famous over water par 3. The day we played (from the tips) the yardage to the flag (in the middle) was 235. We hit driver as our caddy implored, only to fly over the pin and off the back of the green. It was the only bad call by the caddie all day. Fortunately, I was able to save par.
Similar to 16, the first shot of 17 is also a long over water carry, with the second shot to this par 4 over a menacing tree. 18 finishes off the round with a short, uphill par 4, with 3-wood off the tee. The finish to a great round.
Overall, great golf. The caddies are awesome and really good at reading putts. There are no yardage markers anywhere so you really depend on your caddy to tell you what to hit (and where).