Compare

Milestones vs Trello

A native Apple project planner with milestones and tasks vs a cross-platform Kanban board. They solve different problems — here's the honest breakdown.

Download on the App Store Free · Works on iPhone, iPad, and Mac.

Trello is the original Kanban-board app. You drag cards across columns — usually Backlog, Doing, Done — and that's the whole model. It's been around since 2011, runs on every platform, and is great for the simplest possible team workflow.

Milestones is a native iOS, iPadOS, and macOS planner built around a different idea: every project has milestones, every milestone has tasks, and progress fills in as you check them off. There's no board. There's no team admin. Your data syncs privately through your own iCloud — no account, no servers.

If you live on Apple devices and you're planning your own work, Milestones is closer to how you already think. If you need a board everyone on your team can share from a browser, Trello still wins.

Feature comparison

Milestones vs Trello

  • Platforms

    Milestones

    iOS, iPadOS, macOS — all native SwiftUI

    Trello

    Web, iOS, Android, Windows, macOS

  • Planning model

    Milestones

    Project → Milestone → Task hierarchy

    Trello

    Kanban board with columns and cards

  • Account required

    Milestones

    No account, no signup

    Trello

    Atlassian account required

  • Sync

    Milestones

    Private iCloud sync (your iCloud, end-to-end)

    Trello

    Atlassian cloud servers

  • Offline

    Milestones

    Local-first; full offline editing

    Trello

    Limited offline; needs sync

  • Team collaboration

    Milestones

    Personal use only

    Trello

    Built for teams from day one

  • Tags

    Milestones

    Custom tags with colors, cross-project filtering

    Trello

    Labels per board

  • Smart lists

    Milestones

    Today, Upcoming, Inbox out of the box

    Trello

    Saved filters / Power-Ups

  • Recurring tasks

    Milestones

    Native recurrence

    Trello

    Power-Up only

  • Pricing

    Milestones

    Free; optional Pro upgrade

    Trello

    Free tier + paid Standard / Premium / Enterprise

  • Integrations

    Milestones

    Apple-native (Shortcuts, Calendar, Reminders import)

    Trello

    Hundreds of Power-Ups (Slack, GitHub, Jira, etc.)

Pick Milestones if

  • You only use Apple devices and want an app that feels like one.
  • You're planning personal projects — a side project, a renovation, a thesis, a launch.
  • You don't want to create yet another account or send your data to another company's servers.
  • You think in deadlines and milestones, not columns.
  • You want the same data on iPhone, iPad, and Mac without configuring anything.

Pick Trello if

  • You're collaborating with a team that includes Windows, Android, or web-only users.
  • Your workflow is genuinely a Kanban board — and the columns mean something to your team.
  • You depend on Power-Ups (Slack notifications, GitHub PR linking, Butler automations).
  • You need to share boards publicly with clients or stakeholders.
  • You're already deep in the Atlassian ecosystem (Jira, Confluence).

Bottom line

Trello is a team Kanban tool first. Milestones is a personal project planner first. If you're a solo person who lives on Apple devices and wants their own projects organized by milestone and deadline, Milestones is the better fit. If you're picking software for a cross-platform team that wants a shared board, stick with Trello.

FAQ

Frequently asked questions

Can Milestones import my Trello boards?

Not currently. Milestones is built around a Project → Milestone → Task hierarchy, which doesn't map cleanly onto a free-form Kanban board. Most people who switch use the move as an excuse to re-plan from the milestone level rather than copy cards 1:1.

Is Milestones really free?

Yes — Milestones is free to download and use for personal projects on iPhone, iPad, and Mac. An optional Pro upgrade unlocks advanced capabilities. There's no per-user pricing like Trello Standard or Premium.

Does Milestones have a Kanban view?

No, but we're planning to add Kanban view soon.

What about Trello's web app — can I open Milestones in a browser?

No. Milestones is intentionally Apple-native. If you need browser access from a Windows or Linux machine, Trello (or Notion, Linear) is a better fit. The trade-off buys you the polish, speed, and privacy of a real native app on Apple devices.

Can I share a project with my partner / collaborator?

Not yet. Milestones is single-user; iCloud sync moves your data between *your* devices, not between people. If you need shared projects, Trello (or Notion) is the right tool.

Plan your next project the way you actually think.

Free, native, private. No account required.

Download on the App Store

Free · No account required · Private iCloud sync