Cycling planner that connects to Strava: stop guessing the wind

You've got your favourite loop saved in Strava. You check the weather, see "south-westerly 20 km/h", shrug, and head out anyway. Forty minutes later you're grinding into a headwind you didn't see coming.

Sound familiar? That's the gap. Strava is brilliant for recording rides and building routes, but it doesn't answer the question you actually need answered before you leave the house: should I ride this route today, and if so, when?

A cycling planner that connects to Strava should do more than just pull in your routes. It should take those routes and tell you what conditions will feel like along every kilometre, hour by hour, so you can pick the best departure time and avoid wasting a precious riding window on a route that's fighting you the whole way.

What "Strava-connected cycling route planning" should actually mean

At minimum, a Strava-connected planner should let you authorise your account, import the routes you already ride, and keep that data synced. That bit's table stakes.

What it should add on top of Strava is a route-specific wind and weather forecast tied to departure time. Not a pin on your postcode. Not a generic "windy today" banner. A forecast that tracks where you'll actually be on the route at each hour, accounts for the direction of each segment, and gives you a clear signal about when conditions will be in your favour.

What you need to bring: your routes (via Strava, or a GPX file if you prefer). What you get back: an hourly score and the best time to go.

How to connect Strava to Tailwind GPS (step by step)

Tailwind GPS is a mobile-first web app built specifically around this workflow. Here's how the connection works:

1. Open Tailwind GPS in your browser (no app download needed, it works on your phone, tablet, or desktop).
2. Sign up or sign in, then go to your account settings.
3. Select "Connect Strava" and authorise the connection via Strava's standard OAuth screen. Tailwind only requests the permissions it needs to read your routes.
4. Your Strava routes appear automatically. No rebuilding, no copy-pasting coordinates.
5. Each route immediately gets a Tailwind Score for every departure hour across the forecast window.

If a route lives in Strava as private, the Strava API v3 requires the appropriate scope for private route access, so make sure you grant that during the authorisation step. And if you've got a route that isn't in Strava at all, you can upload a GPX file directly, draw a new route on the map, or snap to roads freehand.

What you get after linking: route-specific scoring, not generic forecasts

Once connected, every route in your list gets a Tailwind Score from 0 to 100 for each departure hour. The scoring works by dividing your route into segments, sampling wind direction and speed along each one, and then calculating whether the wind is working for you or against you at the time you'd actually be riding that section.

The bands are straightforward:

• 80–100: Excellent. Expect favourable tailwinds for most of the ride.
• 55–79: Great riding conditions.
• 40–54: Neutral.
• 20–39: Challenging.
• 0–19: Prepare for a tough one.

The score also factors in your riding speed, so it's personalised to where you'll be on the route at each point in time, not some average rider. Temperature and rain probability are layered in too, giving you a genuinely complete picture without needing to interpret a single wind rose.

This is what separates a cycling weather forecast along your route from a location-based weather app. A southwest wind at 20 km/h can mean a tailwind on your outbound leg and a brutal headwind home, depending on how your route sits. Tailwind GPS accounts for that.

Planning now vs planning 14 days ahead

The free plan gives you up to 3 saved routes and a 3-day forecast window. That's plenty for "should I ride this evening or tomorrow morning?"

Subscribers unlock a 14-day forecast window and up to 40 saved routes, plus weekly ride summary emails and per-route email alerts. At $2.99/month (or $19.99/year, with a 7-day free trial), the paid plan is aimed at riders who want to plan rides 14 days ahead for holidays, training blocks, or club weekends where getting the timing right genuinely matters.

If you're locking in a cycling holiday two weeks out and want to know which days to schedule your big mountain stage, the 14-day window is what you need. For daily commute decisions, the free tier handles it fine.

Choosing your route and departure time

The practical workflow is simple. Open Tailwind GPS, swipe through your saved routes, and compare hourly scores for today or the next few days. Pick the departure time that lands in your preferred riding window with the best score. That's it.

For commuters, this might mean checking whether 7am or 8am gives a better score on your regular loop. For weekend riders, it's comparing Saturday morning versus Sunday afternoon. For training, Tailwind GPS also has a Headwind Training mode that deliberately surfaces routes and times with sustained headwinds, useful for building strength without needing a coach or complicated software.

Subscribers can also set per-route alerts: choose a score threshold (say, 70+) and Tailwind GPS sends you an email when conditions on that route hit your target. Rain alerts during your preferred riding window work the same way. Set it once, let it watch the forecast for you.

How Tailwind GPS fits alongside other tools

It's worth being honest about what different tools actually do, because they serve different needs:

• Strava Routes is brilliant for building routes using the heatmap and community data. It doesn't offer route-specific wind scoring or departure-time recommendations.
• Komoot and Ride with GPS are strong navigation and route-discovery tools, with offline maps and device sync. Neither is built around answering "when should I leave based on wind along my route?"
• Tailwind GPS fills the gap between having a route and knowing when to ride it. It doesn't replace navigation apps; it sits alongside them to answer the timing decision.

A simple way to think about it: use Strava or Komoot to plan and navigate where you're going, and use Tailwind GPS to decide when.

FAQs

What if I update a route in Strava? Routes sync from Strava, so if you modify one and re-import, the scoring updates to reflect the new line.

Can I use GPX if Strava doesn't have the route? Yes. Strava's API supports GPX export (via the getRouteAsGPX endpoint), and Tailwind GPS also accepts direct GPX uploads, so you're not locked into the Strava ecosystem.

Do I need to understand wind to use it? No. The whole point of the Tailwind Score is that you don't need to read wind arrows or pressure charts. One number, clear bands, done.

How do I pick a score threshold for alerts? Most riders find 65–70 a useful starting point for "good ride" alerts. If you're chasing personal bests, set it higher. If you just want to avoid the worst days, set it lower.

Does it work for training as well as easy rides? Yes. The Headwind Training mode flips the logic and highlights rides where sustained headwinds will make you work harder, which is useful for endurance building. See the best cycling apps for forecast-based planning guide for a broader comparison.

Pricing at a glance

There's a 7-day free trial on the paid plan, so you can check whether the 14-day window and alerts are worth it for you before committing.

Connect Strava and find your best ever ride

The free plan is a no-risk starting point. Add your three most-ridden routes, connect Strava, and spend a week checking the scores against what you actually experience on the road. Most riders find the number matches their gut feel pretty quickly, and that's when it becomes genuinely useful for planning.

When you're ready to plan further ahead or want alerts doing the watching for you, the subscriber plan is there. Open the interactive wind map, connect Strava, and see what your routes are scoring this week.

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