Winter Holiday Trip Planning Checklist & Timeline
A simple checklist for booking, packing, and departure day.
Keep flights, lodging, and packing on track. Share the countdown with your travel companions.
Plan this event
Planning timeline
30 days before
- Book flights and lodging
- Request time off
- Check passports or documents
- Start a packing list
14 days before
- Book activities or reservations
- Plan transportation
- Review travel requirements
- Buy travel essentials
7 days before
- Confirm reservations
- Share itinerary with companions
- Set a budget for the trip
- Set packing reminders
1 day before
- Pack essentials
- Charge devices
- Set travel alarms
- Download tickets and confirmations
Home Screen Widgets
Beautiful countdown widgets that sit right on your home screen.
Lock Screen Widgets
See your countdown without even unlocking your phone.
Live Activities
Real-time countdown updates on your Dynamic Island.
See the app in action
Use the same Outside app experience you saw on the homepage to keep your plan, countdown, and reminders in one place.
Related countdowns
Related date pages
Travel without stress
Outside keeps your timeline and reminders in one place.
Share the countdown
Invite travel companions so everyone stays aligned.
Frequently Asked Questions
When should I start planning?
For most trips, start 4-8 weeks out for the best prices and availability.
Can I share my itinerary?
Yes. Share the countdown and key reminders with your group.
How do I avoid last-minute packing?
Use reminders 7 days and 1 day before departure.