Overview

Made by a company founded in 2011 and now part of Automattic, Day One combines personal journaling with private Shared Journals for families, friends, or small groups. Entries can hold writing, photos, video, audio, drawings, and documents, while search and filters help keep a growing archive navigable. Passcodes, biometric security, end-to-end encryption, and automatic backups address the sensitivity and continuity of that archive.

Day One also supports exporting data at any time. Paid plans add PDF and CSV/JSON export formats, useful for readers who want more than an in-app record. Daily prompts, templates, reminders, a prompt gallery, and streaks give both structured and self-directed writers ways to return to the journal.

Readers comparing options can browse Journal Apps and Journaling Software.

Key features

Entries and organization

The broad media support suits journals that preserve more than prose, but the Basic plan's one-photo-per-entry cap quickly constrains image-heavy records. Silver and Gold raise that ceiling to 30 photos or videos per entry. Search and filters help retrieve entries, and offline access supports writing without a connection.

Privacy, sharing, and integrations

Passcodes and biometric locks add local access protection, while end-to-end encryption and automatic backups cover privacy and continuity. Shared Journals offer a focused option for private group journaling rather than keeping every record individual. Silver and Gold also include Strava, Zapier, and IFTTT integrations, which matter most to users who want journaling connected with those services.

Pricing

Basic is free and includes basic journaling features, one-device access, and one photo per entry. It is a reasonable way to establish whether a private journal suits you, but not for someone who needs cross-device use or richer media in entries.

Silver costs 49.99 USD per year, billed annually. It expands the allowance to 30 media attachments per entry, offers unlimited devices and sync, and includes the named integrations. This is the practical upgrade for multi-device users who want room for photos or video without needing Gold's advanced reflection and AI features.

Gold costs 74.99 USD per year, billed annually, and adds advanced reflection and AI features alongside unlimited-device access. It is aimed at users who specifically want those additions; Silver is the more restrained paid choice for expanded media and integrations.

A free one-month trial is available in the app, subject to App Store eligibility. Cancel before a paid trial ends to avoid a charge. Upgrades and billing changes must be made on the platform where the subscription began. The paid plans are recurring annual subscriptions.

Platforms

Day One is available on iPhone, Android, iPad, Mac, Apple Watch, Windows, browsers, and browser extensions. That breadth is useful for people who move between mobile and desktop devices, though Basic's one-device limit means the free tier does not deliver the full cross-device case.

Who it's for

Day One suits people building a private, multimedia journal, especially those who value encryption, backups, search, and access across different device types. Its prompts and reminders help writers who want structure, while templates and flexible entry formats leave room for personal methods. Shared Journals make it relevant to families and small groups, too. It is less compelling for a free user who wants multiple devices or frequent photo and video entries.

Pros and cons

Pro: Text, photo, video, audio, drawing, and document support accommodates varied records in one journal.
Pro: End-to-end encryption, access locks, and automatic backups address privacy and preservation together.
Pro: Broad platform coverage and search and filters support a journal used over time and across devices.
Con: Basic is restricted to one device and one photo per entry, limiting its usefulness for cross-device or image-heavy journaling.
Con: Silver and Gold are recurring annual subscriptions, so users who need expanded media must pay rather than simply lifting the free photo cap.

Alternatives

Journey is a reasonable alternative for someone who wants a freemium journal spanning Android, iOS, Linux, macOS, web, and Windows; its annual Membership is 50.04 USD per year and includes 10GB cloud storage, 5,000 entries, and a stated media allowance.

Diarium may suit someone who wants a free basic journal and is willing to consider a Pro plan with cloud sync, unlimited attachments per entry, and Word export; its Pro price is custom pricing.

Apple Journal is the simpler choice for someone seeking a free app limited to iPhone and iPad, with some features dependent on language and region.

Diarly is another freemium journaling option.

Penzu is worth considering for someone whose priority is unlimited entries and basic journal covers, fonts, and writing reminders in a free plan; its Pro plan adds encryption features.

Stoic is an alternative for readers interested in guided journals, reflections, exercises, mood tracking, and habits through its paid plans.

Daybook offers a free plan with unlimited entries and sync across multiple devices, which suits readers who prioritize those basics; Pro adds mood analytics and word tracking.

Diaro is another freemium diary and journal option, with a Pro plan that includes Dropbox synchronization and export.

Verdict

Choose Day One if you want a private journal that can grow from text into multimedia, remains protected and backed up, and works across a broad range of platforms. Its strongest case is the combination of privacy, varied entries, and sharing; look elsewhere if a free plan must sync across devices or allow more than one photo per entry.

	Day One	Penso Notes
Free plan	Yes	Yes
Free trial	No	No
Paid from	$4.17/mo	Free
Open source	No	No
Platforms	Android, extension, iOS, macOS, Windows	Android, iOS
Free plan	Yes	Yes
End-to-end encryption	Yes	Yes
Export formats	multiple	basic

Day One vs Penso Notes

Day One

Penso Notes