7 narrated drives per county
3–5 minute stop stories and midway narration, voiced by Jack.
Narrated road trips & secret walks
FIND YOUR
FREEDOM
Pick a drive, press play, and let Jack tell you the stories of the road: castles, abbeys, smugglers' coves and moorland legends, stop by stop.
iPhone app · 1 month free, then £5.99/month · Coming soon to the App Store
DRIVE. LISTEN. STAY. REPEAT.
Quick guide
How to use Milestones
Jack walks you through the app in under a minute and a half, from choosing where to go to setting off.
Join the waiting listComing soon
Watch the teasers
Tap play and let Jack show you what's on the way.
Yorkshire drives
Narrated road trips through the Dales, Moors and coast.
London walking tours
Secret walks through the streets of London.
Pubs, days out & more
Places to eat, days out with the kids and all the bonus features.
How it works
1
Choose a county
Seven story-led drives per county, starting with Yorkshire.
2
Start the drive
Send the route to Apple Maps, Google Maps or your Tesla.
3
Listen as you go
Jack narrates a 3–5 minute story at every stop, plus a shorter one for the road between.
4
Stop, walk, stay
Pause the drive for a walk, find food nearby, or book a bed for the night.
Everything for the road
Secret Yorkshire walks
Hidden corners on foot, with offline downloads for when the signal drops.
Pause drive & start walk
Park up, explore on foot, then pick the drive up right where you left it.
Pictured: Studley Royal Water Garden · Photo: Martin Dawes, CC BY-SA 2.0
Places to stay
Hotels, B&Bs, hostels and campsites along the routes.
Pictured: The Lister Arms, Malham · Photo: Mark Percy, CC BY-SA 2.0
📍 Near me: eat, drink, things to do🏰 National Trust places🏛️ English Heritage sites🌳 Woodland Trust woods🗺️ Apple Maps, Google Maps & Tesla
Navigation
Works with
Tap a stop and Milestones hands the route straight to your favourite sat nav.
Google Maps, Apple Maps and Tesla are trademarks of their owners. Milestones isn't affiliated with or endorsed by them.
Sample route
Moors & Coast
Route 1 · North York Moors and Coast · 9 stops · about 100 miles, roughly 3 h 05 min of driving.
From the Minster to the sea, through abbeys, moorland villages and a smugglers' bay. Each stop comes with its own story, and Jack keeps you company on the road between.
Get notified at launch- York Minster
- Castle Howard
- Helmsley Castle
- Rievaulx Abbey
- Hutton-le-Hole
- Goathland
- Whitby Abbey
- Robin Hood’s Bay
- Scarborough Castle
Simple pricing
Milestones for iPhone
1 month free
then £5.99/month. Cancel any time in your App Store settings.
- All narrated drives
- Secret walks with offline downloads
- Stays, Near me & heritage places
- New counties as they go live
Coming soon
City walking tours
Narrated walks through the streets, starting with London, with more cities to follow. Leave your email below and we'll tell you when they land.
LONDON
and more cities on the way
and more cities on the way
Reviews
Your adventures
Out on a Milestones drive? Tag your photos #FindYourFreedom and @milestones_roadtrips and we may feature them here.
FAQ
When can I download Milestones?
The iPhone app is with Apple for review now. Join the list below and we'll email you the day it launches.
How much does it cost?
Your first month is free. After that it's £5.99 a month, and you can cancel any time.
Which areas are covered?
Yorkshire is live first, with seven narrated drives. More counties follow as Jack's stories are written, and city walking tours are coming.
Does it work without signal?
Secret walks can be downloaded for offline use, so you can still follow them in the hills.
Can I use my own sat nav?
Yes. Send any route to Apple Maps, Google Maps or your Tesla.
Is it safe to use while driving?
The stories are audio, so you can keep your eyes on the road. Set up your route before you set off.
Try free for a month
Milestones is nearly here. Get notified at launch and start your free month on day one.
This opens your email app to send us a note. We'll only use it to tell you about the launch.
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