We ask one of Silicon Valley's top technology pros, Adam Goldstein, to peer into his crystal ball and predict how trip planning can be improved in the next five years.

Planning the perfect trip takes a fair amount of work.

Between finding a hotel, flight, rental car, cruise, train or tour, savvy travellers use any number of tools, from online travel agencies like Expedia to meta-search websites like Kayak, to fit all the pieces of the puzzle together.

But those sites are mere half-measures in the effort to snare a dream vacation. What travellers really need is smarter travel search.

The newest player in the flight-and-hotel meta-search market is Hipmunk, a site aimed at de-cluttering travel search results and ranking results by levels of "agony". In its first year, Hipmunk garnered more than $4 million in funding in its quest to rival current search tools (or those that might be established in the future).

Adam Goldstein, the 23-year-old Hipmunk co-founder, has been dabbling in travel search since he became the de facto travel agent for his debate team at the Massachusetts Institute of Technology (MIT). At first, he was planning his own travel to far-flung tournaments. Soon after, he was also booking transportation and accommodations for his teammates and the other teams that would travel to MIT. He became a member of FlyerTalk frequent flyer forums and mastered advanced level booking techniques like hidden-city ticketing. When he graduated school, he launched a start-up website to improve the travel experience; hence, the year-old Hipmunk.

I recently sat down with Goldstein and asked him what practical steps could be taken, using technologies known today, to improve travel search within the next five years.

Ultra-flexible search
Most travel search sites focus on people who know where and when they want to go, but sites should also zero in on the best airfare for travellers who are flexible with their dates. "Imagine a traveller who, sometime in the next year, wants to visit her daughter who's studying abroad in Tokyo,” Goldstein said. “She's willing to travel anytime, but she doesn't want to do 50 searches for various date combinations. She simply wants to know a contour of price trends."

Goldstein predicts that eventually a website will launch a new class of airfare search for travellers with highly flexible itineraries. In the meantime, Kayak's month-by-month fare-comparison tool provides a good estimate of the lowest fares available on a route in a given month, based on fares that customers found in the past 48 hours. When you enter your departure and arrival destinations, a monthly calendar will appear in the right-hand corner. Use the drop-down menu to see prices for the months ahead. If you see a fare you like, run a search for those particular dates for up-to-the-minute fares.

Alternate modes of transportation
Flights are not the only option for putting together an affordable itinerary. Goldstein notes that flying from San Francisco to Chicago used to be expensive for him. But then he found out that flying into Milwaukee and taking a train to Chicago's Union Station was often cheaper. “The train trip from the airport station to downtown Chicago takes an additional 80 minutes, but I was fine with that additional travel time to save money,” Goldstein said. “More sites need to incorporate train and inter-city coaches as travel alternatives, saying when rail or bus travel is relevant and affordable."

Rome2Rio.com suggests itineraries that include train travel whenever a plane isn't the best way to reach a destination. Also BeFrugal.com’s Fly or Drive Calculator helps decide if it’s more efficient to take a road trip or flight on your next US vacation.

Lodging choices beyond hotels
In the future, travel sites will make it as easier to book non-traditional lodging options, such as inns, bed-and-breakfasts and vacation rentals.

"…Hotel booking sites are generally more sophisticated and helpful than vacation rental sites. That gap will close as sites like market leader HomeAway invest in better technology. Two, sites like AirBnB and CouchSurfing.com will increasingly make it easier for individuals to invite travellers to rent out their private homes, increasing the inventory of properties available,” Goldstein said.

Wi-fi search
It doesn't help to know that an airline has installed wi-fi on many of its planes. Travellers need to know if their specific flight has wi-fi. While some sites, such as HasWiFi, list this information, wi-fi availability needs to be integrated into flight search results. Kayak, Mobissimo and Hipmunk note whether individual flights have wi-fi but you can’t filter by that service.

As for hotels, Goldstein points out it can also be exasperating to find out if a particular hotel room — and I mean your hotel room, not some mysterious place in the lobby — will have wi-fi, and whether or not it will be free. Even though we seem to be winning the free wi-fi war, no website effectively covers hotel wi-fi availability. In the meantime, HotelChatter publishes an annual wi-fi report listing coverage at major hotels in popular cities worldwide.