Few golfers know more about each break, dogleg and rough on the Tri-Valley’s 17 golf courses than former Round Hill and Crow Canyon head pro Larry O’Leary. So we asked him to handicap the local links.

1. TOUGHEST COURSE: We used to have a Nationwide Tour event at The Course at Wente Vineyards, and the scores there were the highest on the whole tour. (Wente is 7,181 yards with a 75.8 rating and a 145 slope from the tips.) It’s hard to beat The Course at Wente Vineyards. It’s the only Greg Norman–designed course in Northern California, and it’s on this beautiful property. Just beside the fairway, you’ve got those stunning vineyards.

2. PRETTIEST COURSE: Poppy Ridge in Livermore is our pick here. Rees Jones designed it, and it’s got three nine-hole courses (Chardonnay, Merlot and Zinfandel). Most of the courses here are built so that they have a lot of undulations—they’re not very flat—and that’s very appealing. I’d say we’re lucky in this area to have so many great courses.

3. BEST BANG FOR YOUR BUCK: We have some great nine-hole courses, like the Pleasanton Golf Center and Las Positas Golf Course (which also offers an 18-hole course). There are a few par-4s on both, but they’re great for people who want to work on their short game.

4. SIGNATURE HOLE: One that really sticks out to me is the 18th hole at Crow Canyon Golf Course. You’ve got to drive it right off the tee because of a water hazard to your left and then hit up onto an elevated green. They’ve got this beautiful clubhouse behind the green: It’s striking, and the wind’s always in play.

5. BEST 19TH HOLE:  They’ve all got really good restaurants and bars, but you can’t beat Beeb’s Sports Bar and Grill at Las Positas. It’s a great sports bar— they’ve always got three or four TVs with all the different games on, and you’ve got the local crowd out there just coming in after a round of golf. It’s pretty fun.