A DIY Solopreneur Longs for the Days of the Corporate Travel Department

Years ago I worked in an office for a medium-size corporation. Looking back, I miss the languor of the midafternoon cafeteria breaks, the carefully crafted Pollyanna prose of the monthly newsletter. Mostly, though, I miss the travel department. Whenever my boss assigned a trip, I'd call down and tell them where and when. Within an hour, a packet would land on my desk. I'd have a plane ticket, a car voucher and a reservation at a perfectly serviceable hotel. It was magical.

I thought of that the other day as I struggled to make arrangements for a visit to Greece. Now that I'm self-employed, I do my own bookings. I rely on the internet, which works just fine for that two-day conference in Minneapolis. I consult Kayak to find the cheapest airfare, TripAdvisor for hotel advice, Chowhound for restaurant recommendations, AccuWeather to know what to pack.

But Greece is harder, especially the hotels. Many of the most highly rated don't even have websites--or if they do, they're only in Greek. E-mails often go unheeded, and when I've called, the person I'm told I need is invariably unavailable. I tried to outsource everything to a travel agent who is a specialist on the region, but the properties she suggested looked like someone's grandmother's apartment. Many didn't have Wi-Fi or other business services I've come to consider essential.

So I'm stuck. As Helen Reddy sang, "I know too much to go back and pretend." I'm so accustomed to being an informed consumer that I don't feel comfortable choosing a hotel solely on a recommendation--not even an expert's. Beyond that, "perfectly serviceable" is no longer good enough. The information is there at my disposal, so why not get the absolute best and most convenient hotel for my money? In the same fashion, I want the most interesting restaurant, the cheapest car and so on. I make better choices now. But I spend hours doing it.

Up late the other night trying to nail down the last few Greek hotels, it occurred to me that if the travel department dropped off a packet at my desk today, I'd scour the internet researching where they had booked me before calling down to request something different. And I'd lose that cafeteria break entirely.

New Tools of the Trip
Travelocity.com: Its new Top Secret Hotels app offers unpublished discounts for same-day booking (the name of the hotel isn't revealed until after booking).

Jetsetter.com: A members-only community, it showcases photos of vacation spots for inspiration, reviews, insider tips and discounts on hotel rooms.

VRBO.com: Users can search more than 150,000 rentals in 100 countries with Vacation Rentals by Owners, booking rental lodging, from cabins to condos to castles.

HotelTonight.com: This app lets users book discounted, same-night reservations in 10 cities, with choices classified by basic, hip and elegant.

Uber.com: Send a text or use Uber's app to call one of more than 100 town cars curbside within minutes. Already in San Francisco, Palo Alto, Calif., and New York City, with plans to expand to several more markets.

Kayak.com: Direct hotel booking from this app lets travelers compare hundreds of travel sites at once and finish their booking in one place.

Hipmunk.com: Here users can streamline their travel plans--even sorting flights by default category "agony" and hotels by "ecstasy."

HotelsByMe.com: Vacationers can browse more than 100,000 hotel choices worldwide based on property type, amenities and price range.

Read more stories about: Travel apps

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This article was originally published in the July 2011 print edition of Entrepreneur with the headline: Flying Solo.