How To Send And Share Large Files With Friends And Family While Traveling

December 14, 2010 by Anil Polat  

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”.
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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.

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.)

The Best Headphones For Travel

Send Files Up To 5GB With No Registration Required

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)]

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  1. Nora says:

    I’ve finally taken the plunge into backing up often-used-and-edited files (like my writing documents) into the cloud (in addition to my other backup methods like external hard drives) by using Dropbox.

    So far, I love the peace of mind I have in knowing that as soon as I edit a file in my Dropbox folder, it’s uploaded to the site. That way the really important stuff I have is constantly up to date and backed up.

    • Anil P. says:

      That relief of knowing your files are being backed up is a great feeling – especially right after a hard drive crash or some other mishap!

  2. ayngelina says:

    I had no idea about Skype, yet another reason it’s amazing.

    • Anil P. says:

      Yes – funny, I just read that it’s completely down the moment and there’s a Twitter uproar of sorts. Guess people don’t like their awesomeness taken away, even for a short bit!

  3. Amazing article Anil. This is one of those posts you bookmark because you know you’re going to need it sometime. Thanks.

    • Anil P. says:

      I appreciate that, I think when people say they’re going to bookmark one of my posts, it’s truly one of the highest compliments I can receive.

  4. bethany says:

    Great list Anil! I have used Skype before but never knew about the encryption! This is a great list. Thanks 🙂

  5. Anil your tech tips are always the best. When traveling to you simply attach you phone to your laptop for internet or are the WiFi connections usually pretty decent?

    • Anil P. says:

      I don’t usually carry or have a phone right now but even still, with a bit of planning, finding wi-fi isn’t too difficult. 🙂 I plan all of my travels around wireless, so I know fairly well when and where I’ll be online just about anywhere.

      Surprisingly enough, many places you wouldn’t expect are fairly well connected 🙂

  6. Mark H says:

    Wow, several new and useful tips here. I wasn’t aware that encrypted files could be sent via Skype.

  7. Sherry Ott says:

    Cool – some great info. I had never considered using skype in that way – thanks! What is the size limit with skype? I do use Drop Box and have been really happy with it.

  8. Frank says:

    Nice article and some good tips and recommendations. Personally, I like to use FilesDIRECT ( to send large files and store them online: you can send 2GB files even with the free plan, storage starts at 30 GB, there’s no software to install AND it includes 128-bit SSL encryption on all transfers. Pretty sweet!

    • Anil P. says:

      Does the free version require registration? Any other caveats?

      • Frank says:

        Registration is needed for all accounts, even the free trial. I think they aim more for business users, instead of folks who want an anonymous file drop like used to provide.

        They also provide a free customizable dropbox that you can use to have other people send you files, which is pretty handy.

        I’m not sure about other caveats – was there anything you have in mind in particular

  9. Dave Brett says:

    got to love DropBox, really easy to expand the free 2GB to 8GB just by inviting friends, saves some money.

    also for movie makers yousendit is good for clients and companys when you need to get your work across on the road.

    file dropper thats new I’ll check it out and I nether though about using Skype as well, awesome cheers mate.

    • Anil P. says:

      YouSendIt is an old favorite but now seems they changed to a pay-service (except that old users are grandfathered in and the site is still free for them).

      These services must be useful often I’d imagine with all the video work 🙂

  10. Great list. Plenty of love for Dropbox from this traveler.

  11. I didn’t know about the Skype option -thanks so much for that tip as it will definitely come in handy. I also use YouSendIt and find it easy to use and convenient, and they till offer a Lite User option that is totally free, with which you can send files of up to 100 Mb.

  12. indespensible!

    I like to use Yousendit…thanks for the info!

  13. Hey, I’m starting to feel quite techy now as I’ve heard of (and use!) Drop Box and a company similar to File Dropper. They’re indispensable for us. Never knew about sending files on Skype though. 🙂