The only thing that is further in the past than my last, "real" week-long vacation was the first time I turned to Orbitz as my first and last shopping destination when booking air travel for business and the weekend getaways. According to Orbitz, the first trip I ever booked through the site was in November, 2001 when I flew from Pittsburgh to Philadelphia.

That says a lot about how good Orbitz has been at maintaining my loyalty, but not so much about my savvy shopping skills. With a pair of $1,200+ flights to purchase (based on originall search of Orbitz), I decided it was time to figure out a better way to buy airfare online.

Figure Out When You Want To Travel

One of the reasons for my Orbitz rut is that my travel has been largely for work and holidays. Searching multiple sites when I had specific travel dates meant there wasn't going to be much more than a couple of bucks in price variations from one site to the next.

Planning a vacation, however, meant I have some flexibility in dates. So I turned to the Matrix Airfare Search offered by ITA Software, a unit of Google. By plugging in a single date, I can see the lowest airfares for that date and the following 30 days. Within a few minutes we were able to figure out the cheapest time for our trip involved a mid-June departure.

Buy Now Or Wait?

Another reason why I liked Orbitz is that if someone booked the same flight on the site for less than I had paid, they would send me a check. It's a nice little price guarantee but it doesn't protect me from price fluctuations on other sites, and it doesn't help me figure out whether or not prices are going to go down between now and my trip.

Enter Bing's travel search engine, which tried to predict whether or not flight prices will go up or down. Once we had settled on our travel dates for Paris, we searched for the same flights in Bing and tried to figure out if we should book now or later.

While the price for our Paris search held relatively steady when compared to our initial search on Matrix, note the difference in the sample itinerary I'm using for this article:

Another nice feature about Bing is that it opened the same search in Hotwire, Travelocity, Expeida and Priceline so we could instantly comparison shop.

Track Prices

In both case, the time to buy was when we searched. But had Bing told us to wait, we could have used Yapta to track the price of our flight and even gotten text message alerts sent to our mobile phone when prices dropped.

If we wanted to bid on Priceline to see if we could shave some money off the price of the flight, the Bidding For Travel forum, as well as the Priceline and Hotwire forums on Better Bidding, are good resources for picking up pointers.

Click "Purchase Now"

As it stands, we were ready to purchase. The best possible price on a flight we could get was on Aer Lingus with a stopover in Dublin. We did one last search of the air carrier's Web site (which is often the cheapest place to look). Out of loyalty, and because I am such a big fan of getting checks in the mail, I did one last search on Orbitz.

Ultimately, Expedia had the best price. With just a little extra time we were got the price down to $904 meaning we saved close to $600 on what we would have paid for two flights on our initial search.

Photo courtesy of ShutterStock.

Does technology have a place in a sacred space? It seems as though there might be little choice.

The Saudi government has made considerable changes within the past years to the main ritual sites to accommodate the increasingly large number of faithful who attend the annual pilgrimage. From heat-resistant marble floors to unfathomably large air conditioning units to escalators, the Ministry of Hajj has undertaken many efforts to make the journey easier as the Hajj moves into the summer. This past year, in particular however, technology and the spiritual journey have collided in an unprecedented way and may help change the shape and direction of how many pilgrims interact with the Hajj. The booming popularity of social networks such as Twitter and Facebook as well as the growth of multimedia and citizen journalism as forces of information sharing made easy (both in accessibility and use) have made the collusion inevitable. This has been bolstered by the organic and created growing need to connect with others, both known and unknown, channeled through camera-phones with impressive data plans.

Electronic Pilgrimage

Facebook photo-sharing of solemn or excited faces in front of a backdrop of a thunderous crowd of white garb with specs of color has been one of the oldest expressions of the relationship between the Hajj and social media technology. And it has grown considerably. On Twitter, many Hajjis will tweet brief reports of their experiences. Bilal Aslam, a DC native, went so far as to transcribe daily journal entries from his pilgrimage onto an online forum. According to Aslam after "seeing so many interesting and crazy events, I had to share [them] with others."

Holy Logistics

Yet the intersection of Hajj and the internet has gone beyond just simply sharing images and sentiments of the experience. Such technology has also been used to fulfill the practical needs of pilgrims while other forms have been used to make the burdens of the journey easier. There was a concerted effort by the governor of Mecca to use new media as a means through which would-be pilgrims could gain information about not only what to expect on the pilgrimage and the sort of services provided for them, as well as learn about proper religious legal conduct.

In addition to this, other services have been arisen to help pilgrims learn about what is done during the Hajj, connect with other pilgrims and find appropriate tour groups. This past Hajj, the Saudi government sent out 3.25 million text messages per day to keep pilgrims on their ritualistic toes. Perhaps Saudi Arabia's most emphatic technological approach to Hajj this past year was the live-streaming of the entire pilgrimage on YouTube, allowing millions around the world to click open images of circumambulating pilgrims.

Among young Muslims, the Web has also become the preferred mode of finding information about traveling and booking for Hajj as well as connecting and communicating with service providers. FlyHajj.com, a recent start-up from Pakistan, helps address practical challenges faced by pilgrims, tour operators in multi-billion dollar Hajj marketplace. The online travel portal, which perhaps shows the greatest potential for the market it seeks to fill, caters to both potential pilgrims as well as tour operators who specialize in creating Hajj travel packages. Bringing together otherwise scattered information, tour groups, the website allows travelers to find affordable and appropriate packages, which include accommodation and shopping alongside travel arrangements. Pilgrims can post reviews of their experiences and connect with other pilgrims.

While many lament the new tech-savvy feel of Mecca and experience of the Hajj, they miss that technology, at least the less visually-intrusive part of it, has been, and is increasingly becoming, an integral part of the pilgrimage, both to aid the journey as well as make it more easily accessible to both pilgrims and non-pilgrims alike.

Kaaba photo by Tab59

The high-speed Acela Express trains in the Northeast Corridor already have Wi-Fi service, as well as the Cascades line in the Pacific Northwest. By the end of 2011, Amtrak will expand Wi-Fi service to Amtrak California's state-supported trains, giving 75% of all Amtrak passengers onboard Wi-Fi.

Four other routes - Adirondack (New York - Montreal), Maple Leaf (New York - Toronto), Palmetto (New York - Savannah, Ga.), and Pennsylvanian (New York - Philadelphia - Pittsburgh.) - also get some Wi-Fi service in this expansion, but only select cars will have the equipment for hotspots.

"We are committed to continuing to improve and expand this service as resources and technology allow," says Emmett Fremaux, Amtrak's VP for marketing and product development. Amtrak is in negotiations with cellular companies to expand service and take advantage of 4G speeds.

Photo credit: jpmueller99

Do you travel by train?

Last month in Seattle I met up with TripIt co-founder Scott Hintz and Concur co-founder Michael Hilton (currently Executive VP, Worldwide Marketing). I was most interested to find out how a trendy consumer-focused travel app found its way into the more rigid, paperwork ridden world of corporate travel management - and how it's faring.

Prior to approaching TripIt, Michael Hilton told me, Concur regarded the web 2.0 app as representing a sea change in the business travel industry. Mainly because TripIt was an application that was native to the smartphone. According to Hilton, who has been in the travel solutions industry for well over 15 years now, the smartphone has changed the dynamics of how people travel on business.

The innovation of TripIt, in the eyes of Concur's management, was that it gave travelers power. They felt that the app could be used to manage both personal and business trips. The idea behind the acquisition was that TripIt would enable Concur's customers to consolidate their travel data.

TripIt Was Already Eyeing Business Travel Market

The TripIt team had foreshadowed (or invited) the interest of Concur by launching a business offering in August of last year. Ostensibly this was a move designed to increase its revenue. Although the cynical amongst you might suggest it was to make TripIt an attractive acquisition target for the likes of Concur.

Regardless, it was probably a necessary move from a revenue point of view. Because although the consumer version of TripIt had a premium version for regular travelers, there was stiff competition in the consumer space from the likes of Dopplr, KAYAK and WorldMate.

So other than the obvious motivator of a big pay day, what attracted TripIt to Concur? TripIt co-founder Scott Hintz told me that from day one, TripIt was used by frequent travelers - which he said were mostly small or large business people. He admitted that it took some time for TripIt to recognize that in addition to its popular consumer offering, it could also offer benefits to employers.

In particular, Hintz told me, TripIt had a lot of requests from its users to create small business services. For example enabling office assistants, travel coordinators and others to manage the travel of other people in TripIt.

So while TripIt started out as a way to manage personal trips, the product was eventually extended to organize the trips of other people - typically in a business context.

TripIt is also now extending onto other devices; an an iPad app was launched in May.

Do You Concur With Concur Acquisition?

Much of the work currently happening between TripIt and Concur is in integrating the two services together. In May, it was announced that trips booked in Concur would be automatically copied into TripIt. The reverse data transfer (TripIt Pro to Concur) was announced at the end of June.

Overall, the acquisition by Concur was undeniably a great deal for TripIt. It got cash, stock in a larger, more stable company, and opportunities to flesh out its consumer app into a 'grown up' business one.

For Concur, it remains to be seen whether the bigco can successfully integrate a consumer-focused app into its heavily business-focused solutions. But as we all know, it's a business world increasingly dominated by online - and increasingly mobile - services. Concur couldn't have picked a better web 2.0 app in the consumer travel market, so at the very least it has smart new employees, access to sophisticated TripIt customers, and some very whizzy technology.

What do you think, was the deal a good one for both companies? What about for consumers?

When it comes to traveling, I'm a terrible planner. Figuring out the logistics of going from one place to another leaves me flustered and frustrated to the point that I avoid planning at all costs. For my next trip, however, I'm going to give Plnnr a try.

Plnnr asks you for a couple simple preferences and a location and puts together a full itinerary for a trip to any of 18 cities around the world.

I gave Plnnr a quick test run for San Francisco - a city I recently moved to and still feel a bit like a tourist in - and it put together a great looking itinerary...that I may just follow this weekend!

As you can see, the entire day is plotted both as a schedule and as a Google Maps mashup, taking into account travel time, whether walking or taking a cab, and time at the attraction. Plnnr creates a day-by-day agenda for your trip but, if the itinerary generated doesn't suit you, you can change, add and subtract attractions to customize your trip.

A quick little experiment for you if you haven't tried this before: Go to Google Maps and ask it for directions from San Francisco, CA to Beijing, China. Now, you wouldn't imagine any other way than to hop on a plane, right? Instead, Google figures you'd like to drive, takes you to the beach and then, somewhere around step 32, advises you to make the 3,879 kayak trip across the Pacific Ocean. While the cross-Pacific directions are a perennial joke, they're literally useless for travelers.

Rome2Rio, a site built on top of the much-loved Google maps interface, offers up directions by plane, train and automobile rather than telling you to hoof it to the beach and get to paddling.

The site is launching today and, while it offers a number of flights for each trip, it doesn't appear to have a simple on-site booking functionality, which is a bit of a shame. Nonetheless, it quickly nails down the basic part of directions, letting you handle the rest from there. At least it isn't telling you to take a kayak, right?

The most useful place for Rome2Rio, it would seem, will be where it has train schedules in addition to planes. Knowing the alternatives is always great when traveling and trains can be a great (and sometimes cheaper) alternative to zipping over the landmass in between two spots.

Founders Michael Cameron and Bernie Tschirren explain the site a bit more in the following video and Cameron told us that Amtrak and Greyhound itineraries are in the plans for the future. If you have itchy feet like me, I'd bookmark this site and keep it in mind for future travels.

Kayak is introducing the "Book Now" feature in limited beta, but the simple booking process will be available on its website and mobile apps in the coming weeks. Customers will still have the option to book their hotel rooms elsewhere. But the move will help keep users on the Kayak site, rather than driving them elsewhere to complete their purchases.

When the company filed for its IPO last year, it reported that it had generated revenues of $128 million for the year-to-date, a 48% increase from the previous year. The site also said that it had seen an almost 40% increase in traffic.

But as Kayak prepares for its IPO it needs to continue to grow that revenue and traffic and to fend off competitors in travel search. The most obvious of these is Google, which is in the process of buying the travel information provider ITA Software. In order to defend itself against this, Kayak announced last week that it had partnered with Bing in order to feature Kayak data in Bing search results.

This is the second travel-focused update to Bing in less than two weeks, and is notable in light of Google's attempted acquisition of ITA Software, the system powering travel pricing for dozens of airlines and flight tracking sites. If that deal went through, it would strike a direct blow to Microsoft's attempt to innovate within the travel search vertical.

Improvements to Bing Travel Searches

Last week, Bing introduced a small update that offered airfare information to users who type the phrase "fly to..." followed by a city name into the Bing search box. This now displays the lowest priced ticket to that destination and the dates when that ticket is available in the drop-down box that appears.

The feature is powered by the airfare prediction technology from Farecast, a company Microsoft acquired back in 2008. Farecast will continue to offer airfare suggestions like this, even after the Kayak integrations are complete.

Kayak is only one of Bing's many partnerships to enhance search results with third-party information. Currently, Bing also integrates data from Facebook, Twitter and Wolfram Alpha into its search results. It also recently introduced a feature that offers small "live tiles" to the right of its search results that pull metadata from dozens of partner websites including IMDb, Yahoo Movies, Rotten Tomatoes, OpenTable, Yelp, CitySearch, Urban Spoon, Cheap Flights, YouTube, MTV, Last.fm, Rhapsody, Pandora, MSN and others. These tiles display snippets of information you can read at a glance, without needing to click through on search results. Yesterday, it also added data from deal and coupon tracking site The Dealmap to Bing search results.

Bing, Kayak and Others Position Themselves Against Google

The partnership announcement is also notable as another move that will impact the controversial acquisition attempt by Google to acquire flight data provider ITA Software. ITA provides pricing for around 30 airlines and online travel sites, including Kayak, as well as Orbitz, TripAdvisor, Southwest Airlines, Continental Airlines, United Airlines, US Airways, Virgin Atlantic Airways and others. ITA also provides data to Bing. Because Kayak and Bing source their flight data from ITA, it's unclear why Kayak brings more data to Bing than it had previously. We've reached out to Microsoft for clarification on that point.

Update: A Microsoft spokesperson attempts to explain this like so:

Yes, both Kayak and Bing rely on ITA for key travel search features, and both will continue to do so. The objective of this partnership with Kayak is to complement ITA’s technology. The incorporation of Kayak’s comprehensive search results into Bing Travel helps increase the number of available airlines, airports and cities available to searchers.

Yes, we're still confused, too. We'll attempt to get more specifics on this point.

Update 2: Microsoft clarifies:

Kayak has more partners and thus returns a larger set of itineraries than what is available via ITA alone, providing Bing Travel with expanded coverage of cities, airports and airlines.

That means for consumers, the search results will have the same look-and-feel, but will be more comprehensive, the Microsoft spokesperson explains.

A number of travel sites, including Kayak, Travelocity, Hotwire, Expedia and TripAdvisor, normally in direct competition with each other, have teamed up in a coalition called Fairsearch to fight the proposed Google-ITA acquisition. Seeing Kayak partner with Bing is yet another important move that will impact whether or not that deal becomes a reality.

The move makes sense as airline travel usually necessitates booking a hotel as well. And much like Hipmunk's option to let you search for flights by "agony" - that is, a combination of price, airline and number of spots - you can now look for lodging by "ecstasy." In this case, ecstasy is a combination of price, amenities, Yelp reviews, and location.

Search results include prices, nicely color-coded, which lets you compare them relative to the cost of an average night's stay in the vicinity.

Hipmunk isn't just looking at hotel information either. Its search includes nearby AirBnB rentals, letting you see if there are locals renting out rooms or apartments (great for longer duration stays). When you're ready to book a room, you're taken offsite to HotelsCombined.com.

Like its flight search, the new hotel search features Hipmunk's great eye for design, and pairing flight and search will make Hipmunk even more appealing for users.

Search on Bing for the phrase "fly to..." and the name of a major destination city and you will now see an automatic display of the best dates to fly from where you are to that place, with the lowest price for a round trip ticket and advice about whether the price is likely to go up or down if you waited to buy the ticket later. It's really cool.

Google has a big travel search acquisition of its own in the works of course. It's looking to buy ITA Software, but that deal is super controversial and faces regulatory challenges due to concerns about monopoly power.

Presuming Google can buy ITA, it will be interesting to see what it can come up with to wow users performing travel searches. That is ultimately, after all, what it's all about in the end.

Last month, American pulled its listing from Orbitz over a similar disagreement. And following that move Expedia tweaked its search module, effectively burying American flight listings. Customers could still book flights on American - if they could find them - but after this weekend, no longer. American Airlines flights are gone from the site.

American Airlines is the third largest carrier in the U.S., but as with all the major airlines has faced continued financial losses and sought to cut costs. These savings measures have included attempts to renegotiate booking agents' fees. According to the Journal, American is at "the forefront of an industry effort to reduce the cost of ticket sales that has brought it into confrontation with parts of the travel agent sector, as well as the online sellers."

Whether the move hurts American Airlines or Expedia in the long run, it does serve as a reminder about the struggles for control over flight information and booking services - something that will likely be on the FTC's mind as they weigh Google's acquisition of ITA software, something that will further shake travel search.

In other words, it's your phone talking to your car.

Using the mobile app, owners of SYNC-enabled cars can plan out their trips in advance, and the locations entered into the app are immediately accessible through the SYNC services once in the vehicle, says Ford.

But the app doesn't just serve as an easier way to program your GPS - it also helps you determine when you should take that trip, too. Using traffic forecasting, the app can suggest the best time of day to head to your destination, using color-coded (red, yellow, green) bars on its Fastest Route bar chart to show you the varying traffic patterns. And it estimates when you'll arrive at your end point, too.

The provided traffic maps with real-time speed, accident and incident info are available for highways, interstates, arterials and city streets in 126 metro areas in North America. Traffic information comes from INRIX's Predictive Traffic, which, as mobile blog IntoMobile discovered, actually has its own mobile application in the App Store now.

Up to 25 "Saved Points" (aka destinations) can be accessed through the new app, so you could even plan a cross-country road trip with dozens of stops along the way, if you were so inclined.

An interesting side note about this app: although SYNC is a Microsoft technology, there's no mention of a Windows Phone 7 app from the company. Also, thanks to its partnership with INRIX, the maps displayed come from Google, not Bing.

Ford's Mobile-to-Car Efforts

As handy as this app may be, it's the not the only mobile application that will talk to your car. For example, Ford last week announced SYNC AppLink, a downloadable software upgrade that will connect SYNC-equipped vehicles with mobile applications. The first apps to receive this integration are Pandora's Internet radio, Stitcher (another radio app) and Orangatame's OpenBeak app for Twitter. More apps are coming, Ford said. At the time of the announcement, Ford only mentioned Android and BlackBerry integrations, but the auto maker has since confirmed Apple iPhones will also be compatible with AppLink. More information on this technology is expected to come out during January's Consumer Electronics Show (CES).

The new SYNC Destinations app is available as a free download, but you must have a registered account on www.syncmyride.com in order to use it...and a Ford, Lincoln or Mercury SYNC-equipped vehicle, of course.

Much like Facebook's recent addition of Clicker to its "Instant Personalization" program, today's addition of TripAdvisor brings friends' recommendations and opinions to a realm where friends really do matter - travel.

The addition of TripAdvisor to Facebook's Instant Personalization program means that the site will automatically recommend content according to your Facebook friends. As Facebook points out in its blog, the partnership comes just in time for holiday travel, so if you were planning on taking part of the mayhem that is midtown Manhattan, maybe one of your Facebook friends will be wise enough to direct you to a quieter part of town for an off-Broadway show.

What, you ask, only the second-largest hotel chain? Actually, Choice joins Topguest's previous partners, including IHG, the largest hotel chain worldwide. That means the top two hotel groups are now using Topguest's service for location-based marketing. Maybe it's time you sign up, too?

When Topguest launched this summer, we asked if you were sick of "useless badges and mayorships" and ready for something that really paid off? That sentiment has grown in recent months, it seems. Although Foursquare and sites like it are seeing increased numbers of check-ins (Foursquare is almost at 5 million users now), a backlash from those who don't see the point of these apps is growing as well. For example, this recent diatribe on the blog All Facebook vehemently calls out Foursquare and others for massaging our egos to the extreme, in a very bad way. Of course, that's just one example. Another is TechCrunch writer Sarah Lacy explaining why she wouldn't bother with Foursquare.

In addition, a cavalcade of studies on the actual use of checkin services all report nearly the same data - location-based check-ins are still a very niche activity.That doesn't mean their users aren't passionate (they are) or that the trend won't go mainstream at some point (it probably will), it simply hasn't caught on yet.

But why not? What about the deals? There are plenty of those out there, especially if you live in urban areas like New York or San Francisco, but for the rest of us, there's only the occasional retail discount or free cup of coffee. Good to have, but not ground-breaking.

Topguest's Checkins Lead to "Real" Deals

However, with Topguest, you're getting deals that have a bit more impact on your bank account and lifestyle. You can check into your hotel and earn reward points or you can check into your flight and earn airline miles. And unlike in other "checkin" based applications, those points add up to real perks. Instead of unlocking a badge, you can earn free drinks, spa passes, complementary stay credits, 25% off rooms at top hotels and more.

The best part about Topguest is that it works on top of the check-in services you're already familiar with, including Foursquare and Facebook Places. So if you can't stand to lose your mayorships, or whatever else kitschy stuff they come up with next, you don't have to. Just associate that account in Topguest's smartphone app and checkin. (The app is Android or iPhone only, for now. If you're a BlackBerry user, you can still earn points by signing up online.)

Other Parnters

Since its launch, Topguest has been quickly adding partnerships with major travel brands. In addition to Choice it's now partnered with Standard Hotels, Soho/Tribeca Grand Hotels, Viceroy Hotels, Priority Club (Holiday Inn, InterContinental, Indigo), Select Radisson, Best Western and Leading Hotels of the World properties, Thompson Hotels & Restaurants, Avis Car Rental, Kimpton Hotels & Restaurants, Doubletree, Hilton HHonors, Wingate by Wyndham and Virgin America.

With the new Facebook Places integration, Topguest members will now receive automatic rewards for their check-ins via Facebook.

Rewards for Topguest users include things like 50 Priority Points for check-ins at any Holiday Inn, Crowe Plaza, Intercontinental or Hotel Indigo property, 20% off food, drink or spa at the Viceroy Hotels or room discounts at the Standard Hotels.

With Facebook check-ins, Topguest members will now be able to check-in to a venue via Facebook Places and automatically receive the associated rewards with that location, without any additional effort on their part. (U.S.-only, for now).

Facebook Available, Not Required

But Facebook isn't the only avenue to earning rewards. As noted above, users can add their accounts on other location-based services like Foursquare, Gowalla, Brightkite and Twitter (it supports geo-location), to earn the same benefits.

In fact, forgoing Facebook may even be the preferred course for some who are mistrustful of Facebook's privacy controls, given the network's past transgressions. Thanks to the ACLU's dire warnings about Facebook Places' privacy concerns and the reports of confusing settings that seemingly opt you in before you opt in, using Facebook Places' check-in feature comes with its own set of caveats to contend with. Having a more locked-down account available only to family and very close friends on a location-based service like Foursquare may be better alternative for some geo-location early adopters concerns with security and privacy.

That being said, plenty of mainstream users' first exposure to the idea of check-ins will come via Facebook. Others simply prefer Facebook to Twitter and the other smaller startups because it's the only social network their friends have joined.

Topguest: An Answer to the Question "Why check in?"

By offering real-world benefits for virtual check-ins, Topguest answers the question many users have about using these new sorts of location-based services: Why do this?

For the pragmatic, checking in to a location - thereby potentially exposing yourself to possible privacy issues, geo-stalking, or worse - is not the best idea, especially when the only benefits are the bragging rights of claiming "Mayor" on Foursquare or earning a pretend "passport stamp" in an iPhone app. Topguest provides a more valuable reason for checking-in: real rewards that translate into actual savings or benefits.

Interested users can sign up with Topguest here. The Facebook integration is live now and will require you to authorize Topguest as a Facebook application.