Bucket List Golf Trip at Pebble Beach
Mike Preston wanted a special way to ring in his 40th birthday, so he arranged a tight foursome with his brothers, brought the wives along for the after-golf festivities, and did it right at Pebble Beach. Mike shares the stories, tips, and costs that made it a Sick Golf Trip.
- Guest
- Mike Preston
- Destination
- Pebble Beach Golf Links, Pebble Beach, California
- Location
- CA
The Setup
Mike Preston wanted a special way to ring in his 40th birthday — so he booked the bucket-list one: Pebble Beach Golf Links. He pulled together a tight foursome with his brothers, brought the wives along for the after-golf festivities, and did the whole thing right. Mike joins the pod to share the stories, tips, and costs that turned a milestone birthday into a Sick Golf Trip.
The Format
We get into how a trip like this comes together — the rounds, the caddy experience at Pebble, and the gambling formats and side games the crew ran to keep it interesting. Mike also breaks down the lodging side of the trip, including the supporting cast of Spyglass Hill and Spanish Bay, before we walk through the part everyone actually wants to hear: the total cost breakdown.
The Hot Takes
- What it’s really like to play Pebble Beach — and whether it lives up to the hype
- The caddy experience and why it’s worth it
- Gambling formats and side games that kept the foursome honest
- Lodging strategy across Spyglass, Spanish Bay, and the resort
- The full cost breakdown of a bucket-list Pebble Beach trip
The Run-It-Back
We close with the Sick Score course rating and the host FOMO ratings — where Pebble lands as a once-in-a-lifetime play versus something worth building a regular trip around. Mike makes the case, and we put it through the bar-conversation test.