Calendar 366
Calendar 366: A capable Apple calendar with natural-language entry, automation, and travel reminders. Ranked #74 of 193 in Calendar Apps by our editors (3.0/10); pricing: Free plan · 7-day trial; best for apple users wanting calendar automation and reminders.
At a glance
- Editor score3.0 / 10
- PricingFree plan · 7-day trial
- Best forApple users wanting calendar automation and reminders
- Free planYes
- Facts checked22 Sep 2026
Where it wins
- Natural-language creation for events and tasks
- Two-way sync across iCloud, Google, Outlook, and other services
- Apple Watch, widgets, Shortcuts, and travel-time reminders
Where it doesn't
- Limited to iOS and macOS platforms
- Paid plan pricing varies by region and purchase option
- Some advanced features require a premium plan
Our verdict on Calendar 366
Calendar 366 is a native calendar and task app for iPhone, iPad, Apple Watch, and Mac. It suits Apple users who want one place for events, tasks, reminders, recurring schedules, invitations, and multiple calendar views. Natural-language entry helps users create events and tasks, while calendar sets organize calendars and lists for different contexts. The app also supports time zones, alerts, location-based reminders, travel-time notifications, and meeting links for Zoom, Google Meet, and Microsoft Teams.
Its freemium structure gives users a free plan alongside a seven-day premium trial. The paid lineup includes Calendar 366 Pro, Calendar 366 Pro for iOS, Calendar 366 Pro Family, and the corresponding iOS family option. Pro plans add premium features, while Family plans are designed for family use. The published offer allows a subscription or one-time purchase, and App Store pricing can vary by region. This makes the app suitable for buyers who want to compare ongoing access with a one-time purchase before committing.
Calendar 366's strongest fit is the Apple ecosystem. It connects with system calendars and reminders, iCloud, Google, Outlook, Microsoft 365, Fastmail, CalDAV, Todoist, Zoom, and .ics calendar subscriptions, with two-way calendar sync. Apple Watch support, widgets, complications, Shortcuts, URL-scheme automation, and selected AI integrations extend it beyond a basic calendar. Choose it if Apple platform support and automation matter more than cross-platform access. Users who need Android, Windows, or a broader device strategy should consider an alternative with wider platform coverage.
Questions about Calendar 366
Is there a free trial of Calendar 366? Yes: a 7-day free trial.
What does Calendar 366 run on? iOS and macOS. It runs as a desktop app and as a mobile app.
What does Calendar 366 integrate with? 10 integrations, including System calendars and reminders, iCloud, Google, Outlook and Microsoft 365.
Who is Calendar 366 built for? Solo users and small businesses (our editorial estimate).
Your product? Our editors can test Calendar 366 in depth and publish a review, labelled as paid · from $149/mo →
Calendar 366 pricing
All 4 Calendar 366 plans and prices →
Calendar 366 fact sheet
| Free plan | Yes |
|---|---|
| Paid from | Not verified |
| Shared calendars | Yes |
| Time blocking | Not verified |
| Scheduling links | Not verified |
| Calendar sync | Two_way |
| Mobile apps | Ios |
| Video meeting support | Yes |
| Free trial | 7 days |
| Deployment | Desktop, Mobile |
| Platforms | iOS, macOS |
| Support | Email, Docs |
| Built for | Solo, Small business (editorial estimate) |
| Integrations | 10 integrations: System calendars and reminders, iCloud, Google, Outlook, Microsoft 365, Todoist … See all → |
| Pricing | Free plan · 7-day trial (source) |
| Website | calendar366.com |
| Facts checked | 22 Sep 2026 |
Calendar 366 integrations
Calendar 366 lists 10 integrations on its own site.
- System calendars and reminders
- iCloud
- Outlook
- Microsoft 365
- Todoist
- Zoom
- Fastmail
- CalDAV
- .ics calendar subscriptions
See all Calendar 366 integrations →
Alternatives to Calendar 366
- Google CalendarA versatile calendar for personal schedules and Google Workspace collaboration.9.4
- Microsoft OutlookA flexible calendar choice for people and teams already working in Microsoft’s ecosystem.9.2
- Zoho CalendarA low-cost calendar with booking, sync, room reservations, and broad integrations.9.1
See all Calendar 366 alternatives →
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The editor score above is our own research. What this page doesn't have yet is a reader's view — what you used Calendar 366 for, what worked and what didn't. No stars are seeded and no review is paid for; an editor reads every one before it appears.
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Reviewed by iTechGuides Editors · Editorial team · Updated Nov 2026
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