The Captain's Kit
The Sentry Venue + Island Sweep
Kapalua, Maui, HI
Play where the Tour plays in January, trust the elevation, and split a Montage residence with full kitchen.
4 days · 4 rounds · all-in ~$2100/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.
One-time purchase · 7-day refund · no subscription
Verified June 2026
Top courses
Where you'll play
Kapalua Plantation Course
Host of PGA Tour's Sentry Tournament of Champions. Dramatic elevation changes with ocean views on every hole. The 18th is one of the most iconic finishing holes in golf.
Kapalua Bay Course
More playable than Plantation. Ocean views, Molokai Island backdrop. Recently redesigned.
Royal Ka'anapali Golf Course
In Ka'anapali resort area. Ocean and mountain views. More accessible than Kapalua.
Wailea Gold Course
South side of Maui. Robert Trent Jones Jr. design. Three courses at Wailea — Gold is the championship test.
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.
5 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
Travel + Range
Most mainland flights land OGG after noon. Use afternoon for beach and settling in at Kapalua.
Day 2 (AM)
Kapalua Plantation Course
Tee time: 7:30 AM
First full day on the bucket list course. Morning tee before wind picks up and while legs are fresh for elevation changes.
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 Sentry Venue + Island Sweep
4 days · 4 rounds · all-in ~$2100/pp
One-time purchase · 7-day refund · no subscription
You're the captain. Show up and run the trip.