Tilly
Tilly: A cross-calendar assistant that turns schedules, tasks, and focus time into one daily plan. Ranked #26 of 55 in AI Personal Assistants by our editors (6.3/10); pricing: Free plan · 14-day trial; best for cross-calendar personal organization.
At a glance
- Editor score6.3 / 10
- PricingFree plan · 14-day trial
- Best forCross-calendar personal organization
- Free planYes
- Paid from$59.99/yr
- Action automationYes
- Founded2025 · Columbus, Ohio, United States
- Facts checked23 Sep 2026
Where it wins
- Unifies iCloud, Google, Microsoft, and CalDAV calendars
- Combines briefs, tasks, notes, focus blocks, and people context
- Prepares calendar and task changes for user approval
Where it doesn't
- Free plan syncs with up to two calendar accounts
- Deeper planning tools require a paid Pro plan
- Assistant changes still require approval before they are applied
Our verdict on Tilly
Tilly is a calendar-first personal assistant for people coordinating work and personal schedules across multiple providers. It brings together calendar views, tasks, reminders, daily briefs, focus time, notes, people records, goals, and booking links. Available on the web, macOS, and iOS, it is aimed at users who want one planning layer across iCloud, Google Calendar, Outlook and Microsoft 365, CalDAV, subscribed ICS feeds, and Apple Reminders.
Its plan structure gives the product a clear entry point. The Free plan includes Today and calendar views, tasks and reminders, and synchronization for up to two calendar accounts. Tilly Pro adds unlimited calendar connections, a planning assistant, richer briefs, focus tools, and conflict support. The published plans also show Tilly Pro Annual with the same listed highlights. A 14-day trial is available to eligible new subscribers, and the listed starting price is 7.99. This makes Tilly suitable for evaluating a multi-calendar workflow before committing to the paid planning features.
The standout capability is the connection between scheduling and daily organization. Tilly can summarize commitments, conflicts, and open time; schedule tasks with subtasks, priorities, and reminders; protect focus blocks; and create booking links from connected availability. Its assistant can draft calendar events, tasks, and focus-block changes, while consequential changes require approval. That approval step suits people who want assistance without handing over unrestricted calendar control. Choose Tilly if cross-provider calendar management and personal planning are central to your routine. Consider another option if you need a narrower task tool, fully autonomous changes, or a platform outside the web, macOS, and iOS experience.
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Tilly pricing
All 3 Tilly plans and prices →
Tilly fact sheet
| Free plan | Yes |
|---|---|
| Paid from | $59.99/yr |
| Action automation | Yes |
| Calendar management | Yes |
| Task management | Yes |
| Email management | Not verified |
| Connected apps | 5 apps |
| Mobile apps | Yes |
| Browser extension | Not verified |
| Free trial | 14 days |
| Deployment | Cloud, Desktop, Mobile |
| Platforms | Web, macOS, iOS |
| Integrations | 6 integrations: iCloud, Google Calendar, Outlook and Microsoft 365, CalDAV, Subscribed ICS feeds, Apple Reminders |
| Pricing | Free plan · 14-day trial (source) |
| Website | trytilly.com |
| Facts checked | 23 Sep 2026 |
Tilly integrations
Tilly lists 6 integrations on its own site.
- iCloud
- Google Calendar
- Outlook and Microsoft 365
- CalDAV
- Subscribed ICS feeds
- Apple Reminders
Alternatives to Tilly
- ChatGPTA broad AI assistant spanning chat, research, creation, analysis, and teamwork.9.4
- GeminiA broad AI assistant for users who want Google services, research, and creation tools together.9.3
- Microsoft CopilotA broad Copilot experience with especially strong Microsoft 365 integration.9.1
Also Ranked In
Tilly is ranked in 2 of our directories.
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Reviewed by iTechGuides Editors · Editorial team · Updated Oct 2026
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