What They Have in Common
Both are tier-2 GPS devices preloaded with 40,000+ courses, offering full-color hole maps, hazard views, slope mode, and tournament-legal modes. Both charge via USB-C, skip heart rate and fitness tracking entirely, and offer enhanced features (green contours, plays-like distances) behind a paid tier. Neither includes automatic shot tracking out of the box.
Where They Differ
Form Factor — Wrist vs. Cart
This comparison is almost entirely decided by how you get around the course. The S44 is a 42-gram watch you strap on and forget. The Caddie is an 8-inch, 544-gram tablet that Pinned themselves describe as unsuitable for walking. That's not a knock — it's a feature for the right golfer. If you ride every round in a cart, the Caddie's screen real estate is legitimately impressive. If you walk, push a trolley on a tight course, or rotate between riding and walking, the Caddie becomes a logistical problem. This isn't a close call.
Screen Size and Display
Here's where the Caddie is genuinely hard to argue with. That 8-inch color touchscreen is over three inches larger than the biggest handheld GPS in the market, and significantly larger than a 1.2-inch watch face. Hole maps, green views, hazard layouts — they're all dramatically easier to read on a tablet-sized screen. The S44 uses an AMOLED display at 390 x 390 resolution, which is excellent for a watch. It's crisp, readable in sunlight, and easy to navigate with a glove on. But it's still 1.2 inches. If screen readability is your primary concern and you're in a cart, the Caddie wins this category without a fight.
Course Data and Green Views
Both preload 40,000+ courses. Both offer basic front/center/back yardages free. The meaningful difference is in what's locked behind premium tiers and what those tiers cost.
The S44's green contours and plays-like distances require Garmin Golf membership at $9.99/month or $99.99/year. That's real money — $300 over three years just to unlock features on a $299 device. The Caddie's greens heat map and plays-like distances require Pinned Premium, with one year currently free. The catch: Pinned doesn't publish the renewal price. You're committing to a device where a meaningful feature tier has an unknown ongoing cost. My read is that's a real concern — especially compared to Garmin, where you know exactly what you're paying.
That said, if the free year of Premium sticks around and the renewal is reasonable, the Caddie's green heat maps are a strong feature at any price.
Shot Tracking
Neither product is great here out of the box. The S44 does manual shot tracking on-watch and supports Garmin's CT10 club sensors (sold separately — budget $200+ for a full set). The Caddie does manual shot tracking with what it calls "stat precision," but there are no tags or sensors to buy. If you want automatic tracking on the S44, you're adding cost. If you want any tracking at all on the Caddie, you're doing it manually every shot. Neither is the automatic, no-thought-required experience that dedicated shot tracking devices offer.
Battery Life
The S44 gives you 15 hours in GPS mode — that's a full day of golf and then some. The Caddie doesn't publish a runtime in hours; Pinned rates it as "72+ holes" on a 8,000 mAh battery. That's probably two to three days of riding 18 holes. In practice, both will last your round without issue. The S44's 10-day watch battery means you're not hunting for a charger between rounds. The Caddie needs a dedicated charge cycle before a trip.
Who Should Buy Which
Buy the Garmin Approach S44 if:
- You walk any of your rounds, even occasionally
- You want a device that works on and off the course without carrying anything extra
- You prefer known, predictable subscription costs ($99.99/yr if you want green contours, nothing if you don't)
- Lightweight gear matters to you — 42 grams is essentially nothing on your wrist
- You want 15 hours of GPS you can trust without thinking about charging mid-trip
Buy the Pinned The Caddie if:
- You ride in a cart for every round, no exceptions
- You want the biggest, most readable GPS screen available at any price point in the handheld category
- You'd rather have a large course map than a wearable
- You're comfortable with an unknown future subscription cost for premium features — and the free-first-year offer is still active when you're buying
- Green contours and plays-like distances matter to you and you don't want to commit to Garmin's ecosystem pricing
The Bottom Line
The S44 is the right call for most golfers. It works in every context — walking, riding, travel, a quick nine after work — without requiring you to think about it. The Caddie is a niche product with a genuinely impressive execution: that 8-inch screen is legitimately useful for cart golfers who want to see their hole map clearly without squinting. But "cart-only, 544 grams, unknown subscription renewal cost" is a lot of asterisks for a device at $449.99. If every round you play is from a cart, the Caddie deserves serious consideration. If there's any chance you'll want to walk a course, the S44 isn't even a close call.
Get the Garmin Approach S44.