Most email providers limit attachment sizes to around 2-25 megabytes (MB), making sharing any appreciable amount of travel photos, documents, or videos pretty cumbersome without putting them online on sites like YouTube or Flickr. Sometimes though, you don’t want the world to see you dancing around drunk at a full moon party or spend an entire evening crafting multiple emails to send the travel videos of Ecuador you just took to mom.

worlds largest filing cabinet

There are a number of ways to send large files across the Internet – too many in fact – to easily make sense of all the offerings. These are a few bedrock applications that will save you hours from searching online on how to send that file that’s just over your email limit.

squeezing headCompress Files To Squeeze Under The Limit

Email is still our most familiar file transporter and sometimes all those large files need is just some shrinkage. Both Windows and the Mac OS X operating system have compression tools built into them which can significantly reduce the size of many file types. In both cases, the easiest way to start is to move all the files you want to send into a single folder.

  • Windows 7Compressing files and folders on Windows 7 is a easy as a right-click and selecting “Send To > Compressed Folder”.
  • Mac OS X – Just as easy on a Mac; right-click the file or folder to be sent and select “Compress”.

In general when on flaky Internet connections at many a hostel, it’s a good idea to compress any large files you’ll be emailing or otherwise. That will save both you time in uploading and the recipient time in downloading.

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multitaskingMulti-Task With Skype

The versatile travel communication program Skype not only lets you make voice and video calls for free, it also gives you the ability to send files (of any size) to your contacts. Simply click on a contact and select ‘Send File’. Your file will be sent to that other Skype user, even while you’re chatting with them online.

  • Another bonus of using Skype to send large files is that, like Skype chats and calls, the files you send are encrypted as they’re sent over the Internet.

Skype encryption is also notoriously difficult to crack (even by intrusive governments) and the program tends to get around local Internet censorship more often than not.

Sync And Share Files With Dropbox

Dropbox not only lets you share files with others up to 2 gigabytes (GB), it also makes it incredibly easy to sync your files across multiple devices. Documents, photos, and the rest are seamlessly maintained on your laptop, iPhone, and other gadgets by dragging files into the Dropbox folder the program creates on your desktop.

Dropbox also encrypts your data as it floats between you and home for free. (You can increase the 2GB file limit starting at about $10 per month.)

Send Files Up To 5GB With No Registration Required

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The website File Dropper is as simple as a file sharing interface as you can get. Simply upload your files and once the process is complete, you’ll have a download link to email to friends and family. Recipients can then download the files at their convenience from the link that File Drooper provides for 30 days.

file dropper

  • File Dropper doesn’t encrypt files so best not to upload anything you really wouldn’t want in the wrong hands.

On top of the lack of encryption, File Dropper also doesn’t tell you exactly how long an upload has to go before completing; in most cases these deficiencies are worth the generous 5GB file limit.

Even More Ways To Send Annoyingly Large Files

As I mentioned earlier, there are what seems like endless ways to transfer large files when your email account just isn’t enough. Windows Live users can take advantage of 25G of storage on SkyDrive and Sizable Send lets you upload multiple files at once (up to 2GB each). Although sharing large files isn’t a problem most travelers look to solve when planning a trip, it’s worth having a good fallback in mind rather than staying up all night in a hotel lobby searching for ways to send a hefty Photoshop file.

[photos by: heather (world’s largest filing cabinet), PYHOOYAH (squeezed head), ryantron. (multitasking)]