Getting Around
Maps
The first and most obvious tool in your iPhone's travel arsenal comes pre-installed. With the Maps application, not only can you find where you are and get directions to where you want to be, but you can search for different businesses and types of businesses around you.
Mobile Streetmaps
If you're out of service area or roaming and you can't connect to wifi, the Maps application becomes pretty useless. Sometimes even when you are connected, Maps doesn't load at the speed you need. Prepare for this scenario with Mobile Streetmaps ($1.99 per map).
These maps are saved to your phone, so they're viewable even when you're offline. Purchase a map in advance for the city you're visiting, and you'll be able to find your way around no matter what your connection status. You can find these maps in the App Store by searching for the name of the city, or by searching for "Dubbele.com".
Mobile Streetmaps is a must if you're connected but roaming and don't want to deal with massive data charges. Without GPS, all you'll need to do is run a search for nearby streets to find your location. Since all the information is stored on your phone, there's no data charge. With GPS, your coordinates will be matched with your location on the map saved to your phone. Since GPS does not use your phone's data plan, there will again be no data charge.
This excellent user manual walks you through the process of using Mobile Streetmaps, including useful features like searching for amenities and saving locations for later.
Note: The maps in Mobile Streetmaps come from OpenStreetMap, meaning they are community-generated like Wikipedia. This means there may be incomplete areas.
Check out the FAQ for good information on why and how to use Mobile Streetmaps.
Enhancing Your Experience
Audio and video walking tours of some cities are available as iPhone applications. Since these applications are fully installed on your phone, they can give you a location-enhanced experience without using your data plan--like Mobile Streetmaps, all they require is GPS.
Some of the apps have features that do use data; when you're roaming, watch for links to search results, internet content, or the Maps app to be sure you're not incurring extra fees. (You can avoid this problem by accessing these features while connected to wifi, or by turning off Data Roaming in Settings > General > Network.)
Right now it seems that various small companies are building tours of their own cities first, then attempting to branch out; I haven't seen a company with an app for more than one city yet.
These are the cities I've found; doubtless there are more out there.
The London Audio Guide ($5.99) will use your current location to pull up audio, text, pictures, and a map of nearby attractions. The app includes over 150 landmarks, and all of this content is downloaded upon install, so you won't have data charges. For an added bit of fun context, the "More Info" button brings up quick links for Google results, Twitter mentions, Flickr images, and Google News results for the location. These options will, of course, use your data plan (or wifi).
City Slicker: Charleston ($9.99 normally; on sale for $0.99 at time of writing) is a video walking tour. Each stop includes text, images, and a video tour with a qualified guide. This content will not be automatically downloaded when you first install the app; to make sure you have everything pre-loaded, you'll need to tap the "PREFS" button in the upper right and then tap "Download All Content".
Tour Buddy's Savannah Walking Tour ($9.99) is a professionally-recorded audio tour with pictures. You can choose to follow their recommended route, or visit the attractions in your own order. You can navigate through either a menu or a tour map without using your data plan.
The fun thing about these apps is that you can use them anywhere. You can preview the tour from home or from your hotel before you head out. This can help you know what to look for ahead of time. The London Audio Guide is also available for free online, if you'd rather preview that content on your desktop or laptop.
Save and Share Your Experience
Journaling
There are many ways you can chronicle your trip using your iPhone. The native Notes application lets you save text to your phone that can be emailed or copy-and-pasted later. This is a good option if you don't want to use data while you're out and about. You can also simply save memos to be expanded into a full blog post or private journal entry later.
You can also send brief updates to the world using Twitter or Facebook, either through those services' free iPhone apps or via text messaging. When I visited England last year I updated Twitter via text message. I was hit with roaming fees and text message fees, but I didn't incur data fees. You have to make a judgment call based on the charges for each service which one you want to use, or whether you want to use them at all.
If you like the immediacy of Twitter, but don't want to incur data or text message fees, try Birdhouse ($1.99). This app will let you save drafts of tweets to be published later. The pros of using this rather than simply saving your thoughts in Notes are the robust sorting system, the countdown that lets you know how many characters you have left, and the fact that you can easily publish right from the application. One possible con is that your tweets won't indicate the time you first wrote them, but the time you eventually publish them...so if you want to give your followers some context, you may need to include the time of writing in the tweet.
You can also blog from your iPhone--again, this will use data. Most blog systems have a post-by-email feature, which you can use without having to install an app--simply email from Notes or from Mail itself. However, this may result in some formatting oddities such as line breaks, and if you want to add photos, you can only do five at a time.
BlogPress ($2.99) is a robust third-party blogging tool that supports Blogger, WordPress, Movable Type/TypePad, LiveJournal, and others. This app will auto-save your posts as you write them. It has functionality for embedding photos and videos and adding tags and categories. You can tell the app to add location information to your post, and you can also have it send notices to your Twitter and/or Facebook when your posts are published.
WordPress also has its own iPhone application, which is free. This application not only supports posting, but also editing posts and pages and moderating comments.
Photos
Your iPhone comes equipped with a great way to save and share your trip: the Camera/Photos app. You can take pictures all day--or as long as your battery holds out--and then upload them to your favorite photo site from home or your hotel later. If you're on wifi, not roaming, or willing to incur data charges, you can even update on the go.
As mentioned above, most blogging systems have post-by-email options, so a low-tech solution for getting your pictures online would be simply emailing them to your blog. The leading photo hosting sites also have their own mobile pages and applications.
SmugMug, my photo site of choice, has a free app called SmugShot that lets you take photos, caption and tag, and immediately upload in full size. SmugShot also geotags your photos, something the native camera app does not do. By default, SmugShot will upload to a generic gallery that is created automatically. However, you can adjust where photos go in the "Account" area. If you want to change this, be sure to do it before you start taking photos.
The fun thing about automatic geotagging is that you can go back later and see where you were when you took each picture. SmugMug's "Map This" button on galleries is especially nice for this purpose.
Another fun camera application is shoot it! With this app, you can send a regular mail postcard of one of your photos right when you take it. Snap a shot of yourself in front of Big Ben, then use shoot it! to mail that photo to all your friends with a personalized note. The app itself is free; credits for sending postcards have price breaks if you buy in bulk.
Audio or Video Journaling
If words and pictures aren't enough and you want to save and share an audiovisual experience, your iPhone can do that too.
The native Voice Memos application lets you record and trim audio, then either email it or send it via MMS. Similarly, with the Video Recording app, you can record and trim video. Within the native app, video can be sent by email, MMS, or directly to YouTube.
You can post video, audio, text, and more to Tumblr using the free Tumblr iPhone application. Posterous is even easier. Just email whatever the content is--text, photo, audio, or video--to post@posterous.com. In this blog post, Steven Sande describes using Posterous to publish an audio podcast.
The BlogPress app mentioned above can put your videos on YouTube and your blog.
Qik ($0.99) is a video blogging app that lets you record and upload video content. You can keep your videos private or share them with the world; you can choose to add your location or not. Qik can be connected to your existing blog and YouTube accounts. It can also send updates via Twitter and Facebook whenever you upload or stream a video. With the Qik Live app (free), you can even live stream video. Here's more information.
Mapping Your Travels
As I mentioned above, one way to chart where you went on your trip is to take geotagged photos with SmugShot. But if you don't use SmugMug, or if you'd like your tracking experience to be more interactive, you can use a free location-based social media application like Gowalla or Foursquare to share your location. These apps let people know what you're doing geographically in a fun way. You can collect prizes, earn titles, and add friends to see what they're up to.
Gowalla lets you add photos, complete "trips", bookmark locations, and comment on your friends' check-ins. Foursquare lets you add reviews, encouraging you to be specific so your friends will know what to do or try at that location.
Yelp (free) lets you find and write location reviews. You can add friends, find nearby businesses and landmarks, search for certain types of location, bookmark locations, and, like Gowalla and Foursquare, check in at a location. Because it's primarily a review site, Yelp can help you pick what restaurant you want to try or park you want to explore.
Which app you use is really a matter of preference: how do you want to store and share your location? Which interface do you prefer? What features do you want? They're free, so it's not a big deal to try them all out and see which you like best.
Bear in mind that all of these apps integrate GPS functionality with online databases, so you will be pulling data.
Battery Life
If you're using your iPhone intensively on your trip, the battery isn't going to last the day. As many have unhappily noted, you can't just carry spare batteries to swap out, either. Fortunately, there are some things you can do.
Whenever you go out, bring along the USB cord and power adapter that came with your phone. This way, if you stop at a place where you can use a power outlet, you can charge your phone. Apple sells a World Travel Adapter Kit that will allow you to plug in in most countries.
You can also carry external backup batteries. Kensington sells a large portable battery/recharger for the iPhone, a mini rechargeable battery with its own USB charging cable, and a dock that can charge both your phone and a mini battery. If you started out each day with a few fully-charged mini batteries, you'd probably be good to go. (Other companies have similar offerings; I linked to Kensington here because I've used their products before and have been pleased with them.)
If you're driving, several third-party companies have iPhone/iPod car chargers. I have a Kensington car charger/audio adapter that is no longer on the market; while mine cradles the iPhone at the power adapter, this current model mounts to the windshield, plugging into the socket via an unobtrusive cord. (To play your iPhone music through your car's speakers, you would then need a cable like this.)
If you're biking, Make has a tutorial on how to harness that energy to recharge your phone. It looks like many people have built similar devices independently, but I couldn't find a consumer product.
Unfortunately, there doesn't seem to be a solution for recharging using the energy of walking. Perhaps someday we'll have kinetic batteries and battery chargers for our phones. In the meantime, you can always use a hand-crank radio/flashlight/USB cell phone charger in a pinch.
Beyond keeping recharging solutions at hand, you can also follow this advice from Apple to maximize your battery life.
Safety and Privacy
Don't Share Too Much
It can be a lot of fun to post content immediately and check in with a location service everywhere you go, but you should keep in mind that constantly updating your location online can make it simple for strangers to find you. I recommend updating sporadically, and checking in to a location when you're about to leave rather than when you arrive. It's also best not to update your social networking status with a note about where you're headed, unless that particular network is locked so only your friends can see your status.
If you're exploring the area around where you're staying, I suggest trying not to post location information that could possibly lead someone there. Instead of checking in along the way, wait until you arrive at an attraction to post. And if you're alone, try not to make that obvious.
Be careful with photo geotagging. There is no way to turn it off on a per-photo basis in SmugShot. If there's a location you don't want to have on a map, like a friend or relative's house or a place you'll be for a few hours, take that picture with the basic camera app. You can then upload the photo using SmugShot, and no geotagging will occur.
If you accidentally upload a geotagged photo, you can remove the location information using SmugMug's full web interface. Go to the photo in your gallery, tap on "Tools", tap on "More" under "This Photo", and tap "Edit Geography". You will then be able to remove the latitude and longitude coordinates.
If you'd rather not deal with geotagging at all, you can turn it off completely in Settings > SmugShot.
Have a Backup
Don't be utterly dependent on your iPhone. Do research before you go on your trip. Prepare for the possibility of not having the phone at all.
Learn what you need to know to get around and what to look for if you get lost. Try to familiarize yourself with the main streets of the area you're visiting, including the location of where you parked or where you're staying relative to everything else. It would also probably be best to have a hard copy map, just in case.
If you're visiting a country with a different language, learn how to ask for help and how to read and say important words like "police", "embassy", "lost", "sick", and "hospital".
When you're out and about on your trip, pay attention to places where you might go for help if you need it. Also pay attention to where you can get water, food, and money in case of emergencies.
Protect the Information on Your iPhone
Your iPhone has a lot of information about you stored on it. If your phone is lost or stolen, you don't want to be left open to identity theft.
The first thing you should do is set a code for unlocking your phone. Go into Settings > General and tap "Passcode Lock". You will be asked to enter a 4-digit code, then enter it again in order to set the code. Once this feature is enabled, no one will be able to unlock your phone without the code.
You can also protect your iPhone with iHound ($2.99). This application lets you use your phone's GPS to track its location. The best way to use iHound is to turn it on whenever you finish using your phone. Even if you don't do that, though, once you realize your phone is missing, you can send it an alarm via a push notification from the iHound website. The push notification will turn iHound on automatically if someone tries to open the phone to turn off the alarm.
As you can see, the iPhone is an amazing tool for travelers. There are plenty of other options out there that I couldn't get to in this post, like language dictionaries, currency converters, and of course the compass that's available on 3GS iPhones. Do a little digging and you'll probably find a way to do everything you want to do on your next vacation.