Win the pin! vs Upwind
Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.
Win the pin!
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Pin to Win is the simplest sailing race start timer for Apple Watch. Hit your line with the same 5- and 3-minute countdowns race officers run — with big glanceable digits, every classic audio signal according to Appendix U, and a sync-to-minute button right on your wrist. WHAT IT DOES • 3- or 5-minute countdown, switchable in settings • Sync to snap to the current minute when you're late off the line • +1 to add a minute when the start is postponed • Reset to start over instantly • Flips to count-up after the gun so you can track race elapsed time EVERY SIGNAL YOU EXPECT • N long beeps at every minute mark (5, 4, 3, 2, 1) • Halfway warnings: 2 long + 3 short at 2:30, 1 long + 3 short at 1:30 • 3 short at 0:30, 2 short at 0:20, 1 short at 0:10 • A short beep every second through the final five • A 3-second start tone at zero Every audible signal also fires a haptic so you feel it even when the wind drowns out the watch speaker. DESIGNED FOR THE BOAT High-contrast digits stay readable in the sun. The background fills from bottom to top as the countdown drains, so you always know how much time is left from a glance. The screen flashes red ↔ white through the final five seconds — you can't miss the gun. PHONE COMPANION The iPhone app mirrors the watch live. Start, sync, +1, or reset from either device — they stay in sync. The watch keeps running standalone if your phone drifts out of range during the race. PRIVATE BY DESIGN No accounts, no ads, no data collection. Everything stays on your devices.
Upwind
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Upwind is a sailing tracker for Apple Watch, iPhone and iPad: live speed and course, recorded sessions with speed-colored tracks. Free, with no accounts and no ads. INSTRUMENTS - SOG (speed over ground) in knots, smoothed for reading at a glance - COG (course over ground) on a compass ribbon - Automatic night mode: red instruments after sunset to preserve night vision RECORDING - Explicit Rec button: recording never starts on its own - Speed-colored track, from cyan (slow) to coral (fast), scaled to your session - Distance, average and maximum speed, duration - On Apple Watch, recordings also save as Sailing workouts in Health (with your permission) WATCH, IPHONE OR BOTH - Apple Watch records standalone with its own GPS - iPhone and iPad are full trackers too, with live map and instruments - Sessions sync automatically between your devices through iCloud AFTER THE SAIL - Scrub through the speed chart: speed, time and position at any moment - Standard or satellite map, free of clutter - Share sessions via AirDrop, export GPX, import GPX from other apps - Nautical coordinates (degrees and decimal minutes) PRIVATE BY DESIGN No accounts, no developer servers, no ads, no analytics. Your data stays on your devices and in your private iCloud. TIPS - For sessions longer than a couple of hours, record with an iPhone or iPad connected to onboard power - On iPad, GPS requires a Wi-Fi + Cellular model Continued use of GPS running in the background can dramatically decrease battery life.
Screenshots
Verdict
Win the pin! and Upwind are too close to call on the numbers: across 5 compared parameters — price, ads, in-app purchases and device support among them — neither pulls far enough ahead to decide it. What separates them is feature set and interface, not measurable difference.
Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS
Both are free to download. Neither carries in-app purchases, so what you see is what you pay.
| Parameter | Win the pin! | Upwind |
|---|---|---|
| Price | Free | Free |
| Update frequency | Weekly | — |
| Ads | No | No |
| In-app purchases | No | No |
| Devices | iPhone, Apple Watch | iPhone, iPad, Apple Watch — better |
| Requires iOS | 18.0 | 18.0 |
| Further details — not scored | ||
| Size | 4 MB | 6 MB |
| Age rating | 4+ | 4+ |
| Developer | Arnaud Benahmed | Vincenzo Risi |
In-app purchases
Win the pin!
No in-app purchases
Upwind
No in-app purchases









