Comparison

Win the pin! vs Upwind

Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.

Head to head
About

Win the pin!

Features
Read full description

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.

About

Upwind

Features
Read full description

Upwind is a sailing tracker for Apple Watch, iPhone and iPad: live speed, course and manoeuvres, and every outing recorded with a speed-colored track. Free, with no accounts and no ads. INSTRUMENTS - SOG (speed over ground) in knots, big and readable at a glance - COG (course over ground) written on a compass ribbon - Six live values: COG, distance, average, MAX 10s, manoeuvres and peak - MAX 10s: the best 10-second average, so a wave or a GPS glitch can't inflate it - Tacks and gybes counted while you sail - Speed chart of the whole outing, with time and speed axes - Instruments or Map view on iPhone, portrait and landscape; iPad shows everything on one screen - iPhone Duo support - Automatic night mode: red instruments after sunset to preserve night vision LOCK SCREEN AND DYNAMIC ISLAND While recording on iPhone, speed and course stay on the Lock Screen and in the Dynamic Island, with time, distance and the last 10 minutes of speed. Keep the phone locked: the track keeps recording. RECORDING - Explicit Rec button: recording never starts on its own - Speed-colored track, from cyan (slow) to coral (fast), scaled to your session - Recording keeps going in light air and at anchor with the screen off - Sessions saved to Health as Sailing workouts with their route (with your permission) WATCH, IPHONE OR BOTH - Apple Watch records standalone with its own GPS: big speed, compass with your course, live manoeuvres - iPhone and iPad are full trackers too, with live map and instruments - Sessions sync automatically between your devices through iCloud AFTER THE SAIL - Each session shows distance, duration, average, MAX 10s, manoeuvres and peak - Tacks and gybes marked on the map: tap one and the chart jumps to that moment - Scrub through the speed chart: speed, time and position at any moment - Standard or satellite map - Share sessions via AirDrop, export GPX, import GPX from other apps - Nautical coordinates (degrees and decimal minutes) - A Glossary explains every abbreviation and how values are worked out 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

Win the pin!1 screens
Upwind4 screens

Verdict

The call

The clearest difference is update cadence: Win the pin! at weekly against Upwind's every 3 months. On price, ads, in-app purchases and device support there is nothing between them.

Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS

CostPrice · In-app purchases · Ads · Monetization

Both are free to download. Neither carries in-app purchases, so what you see is what you pay.

UpkeepUpdate frequency

Win the pin! ships an update weekly, Upwind every 3 months. Both last shipped on October 31, 2026.

Scorecard1 real difference · 5 level
Win the pin! versus Upwind: the parameters behind the verdict, then further details
ParameterWin the pin!Upwind
PriceFreeFree
Update frequencyWeekly — betterEvery 3 months
AdsNoNo
In-app purchasesNoNo
DevicesiPhone, Apple WatchiPhone, iPad, Apple Watch — better
Requires iOS18.018.0
Further details — not scored
Size4 MB8 MB
Age rating4+4+
DeveloperArnaud BenahmedVincenzo Risi

In-app purchases

None

Win the pin!

No in-app purchases

None

Upwind

No in-app purchases

Questions

Is Win the pin! free?
Win the pin! is free to download, with no in-app purchases.
Is Upwind free?
Upwind is free to download, with no in-app purchases.
Do Win the pin! or Upwind have ads?
Neither Win the pin! nor Upwind shows ads.
Which is updated more often, Win the pin! or Upwind?
Win the pin! ships an update weekly, and Upwind every 3 months. Most recently, Win the pin! was updated on October 31, 2026 and Upwind on October 31, 2026.

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