Calendar 366 review
A capable Apple calendar with natural-language entry, automation, and travel reminders.
Reviewed by iTechGuides Editors · Editorial team · Updated Nov 2026
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).
Calendar 366 pros and cons
- 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
Calendar 366 fact sheet, pricing and score →
Advertiser disclosure: iTechGuides is reader-supported. Vendors can pay for top positions in our rankings and for a place on other products' pages, and we may earn a commission when you click some links. Bought places stand at the number bought; this page and our disclosure say so. Paying vendors may get a fuller, more detailed review from our editors, and that review can change their score. How we rank.
Last updated · How we research and update