The Captain's Kit
The Pebble Beach Pilgrimage
Pebble Beach / Monterey, CA
Walk holes 6-10 along the cliffs, play the #1 public course in America, and check the box you've been thinking about for years.
4 days · 3 rounds · all-in ~$3,600/pp
- The full day-by-day, course by course
- Lodging pick, line-item costs, booking contacts
- The captain's playbook (insider tips, bonus plays, founder note)
Plus weather codes, caddie strategy, and the airport you should actually fly into.
Checkout opens at launch · one-time purchase · no subscription
Verified May 2026
Top courses
Where you'll play
Pebble Beach Golf Links
Must stay at Pebble Beach Resorts property for guaranteed tee time. Walk-on possible but rare. Caddie recommended ($75 + tip). #7 par-3 is 106 yards of pure adrenaline.
Spyglass Hill
Harder than Pebble. Front 9 is dunes/ocean, back 9 is forest. Robert Trent Jones Sr. Many say it's the better golf course (just not the views).
The Links at Spanish Bay
Scottish links-style on the ocean. Bagpiper plays at sunset from the Inn. The most atmospheric course on the peninsula.
Pacific Grove Golf Links
The 'poor man's Pebble Beach.' Municipal course with ocean views and deer on the fairways. Back 9 along the coast is surprisingly beautiful. Best $55 you'll spend.
From captains who've been
What the captains know
The small things that make or break the trip. Booking windows, weather codes, caddie strategy, the airport you should actually fly into.
7 insider tips · all unlocked in the kit below
The itinerary
What you'll play and when
A captain wrote this. Every tee time has a reason. Here's the first part.
Day 1
The Links at Spanish Bay
Tee time: 1:30 PM
Arrival day with links golf — no pressure, atmospheric, and you'll catch the sunset bagpiper after.
Day 2
Pebble Beach Golf Links
Tee time: 8:00 AM
Morning tee time beats afternoon fog and gives you the best light on holes 7-10. Walk it with a caddie.
What's inside the kit
The rest of the trip
Five sections. Everything a captain needs to run this trip — not just dream about it.
Where you'll stay and why
The lodging pick, the rate, the reason it beats the alternatives.
What it really costs (line by line)
The actual number per person. Not a vague range.
Who to call and what to ask
Phone numbers, emails, the exact booking script.
What to do when you're not on the course
The best meal of the trip. The post-round bar. The sneaky par-3.
From the captain
Why this trip, what to expect, the things that make the difference.
3 more days inside
The full day-by-day — including which course to play when the wind picks up, caddie strategy, and the right tee times to book — is in the kit.
The whole trip · one kit · $29
The Pebble Beach Pilgrimage
4 days · 3 rounds · all-in ~$3,600/pp
Checkout opens at launch · one-time purchase · no subscription
You're the captain. Show up and run the trip.