Should I Sail

Should I Sail

Planning and Sailing Assistant

0 ratings
Free
In-App Purchases

Rating summary

Details

Released
May 7, 2026
Updated
October 16, 2026

Features

Background Location Access

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About

Should I Sail? answers the question every skipper asks before leaving the dock — and keeps watching the water after you do. Tap anywhere on the sea and get an instant, colour-coded verdict: Yes · Challenging · Requires Safety Gear · Only if You Must · No. The answer is tuned to your boat, so a 50-ft cruiser and a dinghy get different calls in the same conditions — and you can see exactly which factors drove the score. Free to download. Sign in free to unlock the full toolkit for a day at a time with Pro Days, then go Pro when you’re ready. MARINE WEATHER, ANYWHERE Hourly forecasts for any point of sea worldwide: wind and gusts, wave height and direction, swell, current, visibility and rain. Scrub through 24 hours and 9 days with everything updating instantly, and read directions at a glance on the compass-rose overlay. Set a condition alert on a departure and get notified if the forecast turns before you leave. PLAN ROUTE Drop waypoints, pick a departure time, and the app scores every leg, works out arrival times from your cruising speed and warns you if a leg crosses land. Save routes, revisit them, and share any route with a link so the crew can see the plan. DEPARTURE CHECKLIST (new) A skipper-grade pre-departure checklist built for your boat type — weather, documents, safety gear, engine, rig, deck, crew briefing and last look. Tick items off at the dock, add your own, reorder sections, and keep going with no signal: ticks sync when you’re back online. ON THE WATER Your boat pin follows live GPS with heading and real-time speed over ground. The OpenSeaMap nautical overlay adds depth contours, buoys and hazard markers right on the chart. TRACK RECORDING Record your sail in the background — it survives the app being closed or the phone sleeping. Finish to see distance, duration, average and top speed, then turn the track into a saved route in one tap. Recording stops automatically when you reach shore. ANCHOR WATCH Place the anchor, enter your chain length, and rest. The app pulls water depth from the GEBCO global database, calculates your safe swing radius and watches for drag continuously with the screen off. A full-screen alarm fires the moment you stray outside the zone. MY SPOTS Star the anchorages and launch points you return to and check them in a tap. MADE FOR EVERY CREW 16 languages including Hebrew and Arabic with full right-to-left layout. Large text, high-contrast and bold modes. Have a code from your sailing club or partner? Enter it for bonus Pro months. Terms of Use: https://shouldisail.com/terms Privacy Policy: https://shouldisail.com/privacy
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What's New in Should I Sail

1.4.0

October 16, 2026

Pro Days — try every Pro feature for free, one day at a time. Sign in free and start a Pro Day whenever you need the full forecast, routes or trip tools. Departure Checklist — a sailing-ready checklist you can edit, reorder and tick off before you leave the dock. Works offline and syncs when you’re back. Partner codes — got a code from a sailing club or partner? Enter it on your profile for bonus Pro months. The app now opens in your device language on first launch. “Draw Route” is now “Plan Route”. Plus bug fixes and performance improvements.

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Subscriptions & In-App Purchases

Should I Sail Pro

Unlock all Pro sailing features

$49.991 Year
How to cancel Should I Sail subscription ⁉️