Here is the second edition of our Weekly Office 2.0 Roundup. Today, we will review 12 calendaring applications, from 30 Boxes to vivapop. We will identify some unique features that might help your own selection process, and you will get a chance to cast your vote for the best online calendaring application.

With the help of many contributors, we completed the Calendar section of the Office 2.0 Database. From the 12 players we identified, 9 are actively developed and qualify as credible alternatives to offline calendaring tools. They offer very similar sets of features, therefore selecting the one that is right for you will strongly depend on your personal preferences at the user interface level.

Functionality
From a functionality standpoint, most online calendaring applications share a common set of features. They allow you to record events and set reminders that can be propagated over email, SMS, or even IM. Many applications provide simple to-do lists, which items can have a due date shown on the calendar. Most applications let you share calendars with colleagues and friend, or publish them on the Web. The most advanced ones also give you the ability to syndicate your calendars through iCal or RSS feeds, as well as subscribe to third-party iCal feeds, in order to display public events such as holidays on your private calendar for example. Some applications, such as 30 Boxes, Kiko, and Spongecell, also let you create events using natural language expressions like “Soccer practice every other Tues at 6.” Some others also provide an API that lets you create, edit, or delete events from another application. This is especially useful if you want to integrate your online calendar with applications such as a CRM system.

Ease of Migration
Migrating from an offline calendaring tool like Microsoft Outlook to an online alternative is a fairly challenging process. While data export and import are supported by most online calendaring applications, many critical features are usually missing, such as integration with your email client. As a result, many early adopters might want to adopt a hybrid approach combining Outlook and an online calendaring application that supports synchronization with Microsoft’s product. The good news is that most of the applications we reviewed support it. The bad news is that they are not created equal in offering transparent synchronization, and several of them require manual export and import of data, which makes it a non starter for me. Also, if you want synchronization of events with your mobile device, using Microsoft Outlook in combination with ActiveSync is usually the only option. There is hope though, for some devices are starting to support iCal natively, such as Apple’s iPhone for example, but customers in the U.S. will have to wait until June 2007 to get it. In the meantime, you will have to be creative, or patient. Last but not least, none of the applications we reviewed require any browser plug-in, making migration a tad easier.

Price
At the exception of Epointment, which is presented as an enterprise calendaring solution, and Trumba, which is more akin to an event management application, all the applications we reviewed are entirely free. As a result, the good news is that you won’t have to open up your wallet, and the bad news is that you will want to be extra careful in selecting your provider, for it might not be around for very long. Same as for bookmarking applications, advertising seems to be the only working business model in this area, and it’s not clear to me that it’s a sustainable one. I personally believe that synchronization with mobile devices could be marketed as an advanced features, and sold through subscriptions to individual users and small business groups.

Alternatives
Events and to-do lists can be managed with other tools than dedicated online calendars. First, most CRM applications such as Salesforce.com or SugarCRM provide very advanced calendars that can link events and tasks to other objects. Second, decent calendars are also found within Group Managers. Third, to-do lists can also be managed with dedidated Task Managers. Also, if you’re a Mac user, you should definitely consider using the calendar provided by .Mac. It’s one of the best solutions out there, and integration with the upcoming iPhone promises to be a blast. And if you’re not, it’s not too late to switch…

Top 10 Players
Several online calendaring applications do make use of HTTPS, therefore the Alexa ranking is not as reliable as we would like it to be. Nevertheless, and according to this ranking, we can extrapolate a Top 10 list of players in the space, which is corroborated by the fact that the first five members (beside Scrybe) show a Google PageRank of 7 or more, on a scale of 0 to 10.

Editor’s note: Alexa only ranks primary domains, not subdomains. Therefore, traffic generated by Google Calendar is lost among the traffic generated by all applications provided by Google. As a result, there is no easy way of evaluating how successful this application really is. Nevertheless, there is enough anecdotal evidence available to tell us that a significant number of Gmail users also use Google Calendar, making it one of the most popular online calendaring applications currently available. For this reason, Google Calendar gets the top spot on our list. vivapop does not have an Alexa rank yet, but it’s one of the most interesting applications out there, so make sure to check it out.

Quick Reviews
There are only 12 applications in our database, so all of them got a review.

30 Boxes: This sweet little gem of an application is the most popular independent calendaring tool out there. It has a truly unique user interface, which is also one of the fastest you can get with AJAX. It provides some very interesting features, such as natural language entry, invitations to events, integrated maps, tagging, blog timeline, RSS and iCal feeds, and mobile phone access. It is under active development, and its authors, Julie Davidson and Narendra Rocherolle, are some of the nicest persons you’ll ever get to meet in the industry.

CalendarHub: This application introduced early on some interesting features, such as display of local events and subscriptions to iCal feeds. Unfortunately, its blog has been inactive since January 28, 2006, making it a risky bet.

Epointment: This one comes from the Netherlands and is targetted at specific businesses and professions, such as beauty parlors or plumbers. It boasts an impressive list of features for the enterprise, but some of them are only described in Dutch, making it a questionable option.

Google Calendar: There is no need to present this one, which is to calendaring what Gmail is to email: streamlined, smart, and fast. Native integration with Google’s email application makes it a sure winner if you’re developing a Google-centric setup. Also, our friend Charlie Wood at Spanning Partners is about to release Spanning Sync, which will open up Google Calendar to the brave new world of iCal, making integration with CRM applications like Salesforce.com a reality. Quite frankly, I cannot wait…

HipCal: Acquired by Plaxo, Inc. in May 2006, this one is no longer in development, but the HipCal team is working on a new calendar for Plaxo, to be released sometime this year. If you’re already using Plaxo to manage your contacts, I would seriously consider using HipCal as a temporary solution, and upgrade to the next one when it becomes available. Hopefully, the good folks at Plaxo will make migration easy, if not transparent.

Jotlet: This application offers a clean user interface, with color-coded events and tasks. To-do lists and SMS reminders are also part of the package. But most importantly, it is available in English, Spanish, French, German, Japanese, Korean, Russian, and Chinese. It also provides integration with Netvibes, and is under active development. A business version is also available upon request, but few details about it are publicly available.

Kiko: This one also provides a natural language interface, and can send reminders via Email, SMS, and IM (an exclusive as far as I could tell). iCal and vCard import are also supported, and the application is under active development.

Planzo: There is not much that sets this one apart from the rest of the pack, beside some funky background images used for the demo account. If you work in a shop as a mechanic, Planzo might be your Office 2.0 alternative to a calendar showing nude models. If not, I would consider something else.

Scrybe: This one is not fully available yet, but promises to be one of the most interesting. It can work offline when using a Web browser that supports offline browsing (Internet Explorer and Firefox do), provides super sexy drill-down capabilities, advanced support for time zones, sophisticated to-do-lists, and an integrated notepad. It also offers the ability to print calendars onto regular letter paper that can be easily folded into pocket-size calendars. Definitely one to keep a close eye on.

Spongecell: Here is another credible player, with natural language interface, iPod synchronization, and support for iCal and RSS feeds. Most interestingly, it also offers integration with email, allowing you to forward any email account to your Spongecell account, and get email invitations recorded as events, much like Google Calendar would do with Gmail. This is a feature that I wish other calendars would support as well.

Trumba: This application is much more than a personal or group calendar, and really falls into the category of event management application, something akin to a professional version of Evite. Its advanced set of features also makes it close to an enterprise calendaring tool, including calendar customization, event registration, and real-time event feedback. If I ever had to organize a conference again, I would use Trumba in combination with eventWax, which would allow me to automate almost everything, in a very cost effective way.

vivapop: This last one is defintely one of my favorites. It offers all the features you’ve come to expect from a good online calendar, plus access from mobile devices, advanced synchronization with Outlook, and user-generated content for public events. And its founder, Elizabeth Souther-Tarbel, is one of the kindest persons I got to meet at the Office 2.0 Conference. Take a look!

Personal Favorite
Because my CRM system (SugarCRM currently) is the hub of My Office 2.0 Setup, I use its embedded calendar for managing most of my events. But quite frankly, it’s not enough, and I wish I could get integration with email for turning invitations into events, as well as integration with public iCal feeds. For this purpose, I am eagerly waiting for the release of Spanning Sync, which would allow me to integrate Gmail and Google Calendar with SugarCRM and my iPhone.

What’s Missing
From all the applications reviewed, one feature is missing: scheduling, as in making it easy for two or more parties to agree on a date, time, and place to meet. This problem is responsible for massive waste of time in the enterprise, and unless you standardize on a proprietery groupware system such as Lotus Notes or Microsoft Exchange, there is very little that can help today. For users of Microsoft Outlook, the recently-released TimeBridge is solving part of the problem, but the world is still waiting for a generic solution that could address such a common need once and for all. TimeToMeet is also interesting, and is already integrated with Google Calendar (Link courtesy of Zoli Erdos). Last but not least, having a free-busy feed that could be published or shared with colleagues and friends would be very useful.

Best Online Calendaring Application
Now that we know what’s out there, it’s time for a vote:

Note: if you cannot see the voting form, please follow this link.

Final results will be announced next week as an update to this post. In the meantime, please help me build next week’s roundup on Contact Managers. You can use this form courtesy of Wufoo for suggesting new applications, or providing additional information about existing ones. I would also welcome ideas for domain-specific criteria that could be used for evaluating the players on our list.

See you next week!

Update 2007-02-05: Diarised can help you schedule meetings as well.