How To Find The Sweet Spot When Booking A Vacation

Conventional wisdom says booking a vacation yourself will save you a lot of money—but conventional wisdom isn't always right. New (and old) methods of booking travel can save money in ways that weren't possible just five years ago, so we decided to find out: In 2012, what's the cheapest, most efficient way to book a vacation.

To get to the bottom of that question, we'll book three different vacations with three different services:

  1. The popular travel aggregation web site Hipmunk: We'll call this our DIY route.
  2. The outsourcing flight search engine Flightfox: You pay a fee and experts track down cheap flights for you. To get the best prices, you should search down cheap tickets first so the Flightfox agents have a price to beat.
  3. Last, we're going old-school, booking with travel agents in each departure city.

All trips are for the week of September 20-27, 2012. Each vacation includes a round-trip flight and a three-star hotel near tourist attractions for two people.

A note on the selection process: I picked each destination city based on places I've never been and know nothing about. This way, the potential benefits of a travel agent would level out with the amount of research I'd have to do personally in order to book a flight and hotel. For the Flightfox hotel booking, we used Hotwire. Finally, the travel agent costs are estimated because we couldn't actually book any of these vacations. The agents told me they would "round up," the price, but could likely get a better deal once I committed (I have no way to validate this claim).

Round 1: Denver, Colorado ✈ Orlando, Florida

How To Find The Sweet Spot When Booking A Vacation

The first vacation has us heading out of Denver, Colorado to Orlando, Florida. Here, I'll be able to play in Disneyworld, check out Universal Studios, visit the Kennedy Space Center, and enjoy a nice stay near the center of the city. Let's get booking!

Hipmunk

  • Total booking time: 13 minutes
  • Flight: $480
  • Hotel: $470
  • Total cost: $950

Picking out a flight and hotel for Orlando was remarkably simple. Since Orlando is relatively condensed with its tourist attractions, finding a hotel that was near everything only took a few minutes. Flights out of Denver were also regular enough that I didn't have any trouble finding a direct flight. Overall, Hipmunk made booking this trip a piece of cake.

Flightfox + Hotwire

  • Total booking time (that I actively participated in): 20 minutes
  • Flight (price includes Flightfox "Finder's Fee" of $34): $416
  • Hotel: $516
  • Total cost: $932

Booking a trip through Flightfox is interesting. First off, you need to start by looking at a web site like Hipmunk in order to get a basis for what a flight will cost so you can give Flightfox a price to beat. Then, you let the Flightfox crew search for a better deal for a few days. When the time limit expires, you hopefully get a cheap flight. In this case, I saved $64 on the tickets. Not a huge discount, but every little bit helps. Likewise, the hotel booking was pretty straightforward with Hotwire, but I somehow ended up spending a little more than I did with Hipmunk.

Travel Agent

  • Total booking time: 14 minutes
  • Total cost (agent didn't provide itemized total): ~$1600

After reading a few Yelp reviews I decided to go with Gold Key Travel as my travel agent for a vacation to Orlando. Since Orlando is filled with tons of tourist attractions, I figured it would be a great place to see how a knowledgeable travel agent could improve on the research I did ahead of time. My agent was very helpful and willing to book tickets for all the resorts and amusement parks, which would have saved a lot of time. Still, I can't help but think a travel agent for a location like Orlando is a little overkill. Orlando just seems very easy to book yourself. Plus, the fact I didn't get an itemized total (none of the travel agents provided this over the phone or email, just a "package total") made me a little wary of where my money was actually going.

Winner, Round 1: Hipmunk

Although Flightfox saved a little money, being able to quickly book an entire trip to Orlando in less than half an hour with Hipmunk made things easier. The travel agent was helpful, but didn't feel necessary for a trip as simple as this. Photo by Jeremy Thompson.

Round 2: Dallas, Texas ✈ Los Angeles, California

How To Find The Sweet Spot When Booking A Vacation

Next up, we're going to fly out of Dallas, Texas and into Los Angeles, California. I've never been to Los Angeles. From what I know from the movies it has enticing attractions like the beach, Hollywood, and Disneyland.

Hipmunk

  • Total booking time: 26 minutes
  • Flight: $499
  • Hotel: $784
  • Total cost: $1283

It only took a couple of minutes to find and book a flight to Los Angeles. However, picking a hotel and finding a good deal was a bit tougher in Los Angeles than I thought it would be. Since such a large part of the city (and its surrounding area) are so enticing to a vacationer, it's hard to find a central spot. In the end, I just picked a hotel that was centrally located in Los Angeles proper as opposed to near a destination like the beach or Disneyland in Anaheim. I'm not incredibly confident in my choice, but it was cheap enough.

Flightfox + Hotwire

  • Total booking time (that I actively participated in): 16 minutes
  • Flight (price includes Flightfox "Finder's Fee" of $34): $442
  • Hotel: $723
  • Total cost: $1165

This time around, Flightfox managed to save me $61 over Hipmunk. Hotwire, too, was able to track down a three-star hotel in the heart of Los Angeles for a little cheaper than Hipmunk.

Travel Agent

  • Total booking time: 8 minutes
  • Total cost (agent didn't provide itemized total): $1507

Digging around for a travel agent in Dallas was a little harder than I expected. A few people didn't call me back, a couple others wanted a $150 deposit. Eventually, I found Custom Family Travel. They were incredibly helpful in getting me into a part of the city where I'd be close enough to the beach and train stations. They did, however, point out that Los Angeles' public transit system isn't great, and it might be in my best interest to either bounce between a couple hotels on different sides of the city, or just pick one area to spend my time in. The conversation itself was about 8 minutes long, then 30 minutes later I received an email with a couple different flight and hotel options.

Winner, Round 2: Flightfox and Hotwire

As far as going into a city blind is concerned, Flightfox managed to save me the most money. The call to the travel agent was helpful, but I imagine I would have found that information eventually. Photo by Ron Reiring.

Round 3: New York, New York ✈ London, United Kingdom

How To Find The Sweet Spot When Booking A Vacation

Since the Olympics are making London look like a fun place to visit, I decided to see what it would take to get out there. I know next to nothing about London, and while I could have hit up a few friends for some intel, I decided to book this as blindly as possible so I'd get an estimate of the time required, as well as track some of the mistakes (and I definitely made some mistakes).

Hipmunk

  • Total booking time: 43 minutes
  • Flight: $1700
  • Hotel: $2077
  • Total cost: $3777

By this point shopping for flights on Hipmunk was pretty second nature and it was easy to find a good set of choices. However, I had absolutely no idea where to even start looking for a hotel in London. At first, I decided to simply book a hotel in the middle of an area with a lot of tourist options, but I realized I had no idea where anything was. So, after some quick research into London's history, where its biggest attractions are, and any destinations I wanted to go, I ended up picking a hotel near the British Museum. The hotel is also close to Buckingham Palace, Piccadilly Circus, and a few other notable landmarks (I think). As it turns out, this was an incredibly over-priced way to book a hotel (more on that in the travel agent section below).

Flightfox + Hotwire

  • Total booking time (that I actively participated in): 40 minutes
  • Flight (price includes Flightfox "Finder's Fee" of $34): $1252
  • Hotel: $2450
  • Total Cost: $3702

Flightfox came up with a pretty massive discount on tickets to London when I let it change the dates around a little. By shifting the vacation over to September 19-25, I saved $448. That's a pretty substantial savings and shows that Flightfox might be best suited for more expensive trips (the higher the ticket cost, the bigger the savings). I did, however, have the same problem with booking a hotel in London as I did with Hipmunk. Even after almost an hour of research, I had no idea what neighborhood I should stay in.

Travel Agent

  • Total booking time: 15 minutes
  • Total cost (agent didn't provide itemized total): $2431

For the London trip I decided to go with STA Travel because none of the smaller travel agents were willing to give me a free quote for overseas travel. STA is known as a student travel service, but they provide travel arrangements for non-students as well (in fact, if you're a student or you use our tricks for a student discount the trip price is dropped to around $2,000 total).

My STA representative was knowledgeable about the city and they were able to pinpoint some of the cooler places in London that were still within an hour's walk from the tourist areas (and saved me money by getting me out of the city center a little). Basically, they saved me a ton of cash by directing me around the city and towards a hotel that was significantly cheaper than I found looking on my own. They also gave me a few pointers on using the Tube to get out of the city for a day or two.

Winner, Round 3: Travel Agent

In the case of international travel, a travel agent was a huge help. Their prices were fair for both the hotel and the flight, but more importantly they had the knowledge to get me into a part of the city I'd enjoy. Another option when planning an international flight might be to check out the options on a budget travel agent like STA, and then actually book the flight with Flightfox. Photo by stephen boisvert.


In the end, it's all about how much you know about and how much time you're willing to spend researching your destination—not how long it takes to book a flight and hotel. As I found with my London trip, a travel agent was a huge help because I had no idea what I was doing. Even Los Angeles, which I thought would be easy enough, turned out a little tougher than I thought it'd be. You can always spend the time tracking down others who have vacationed in your destination, but that all takes a lot of time before you know what you're doing. Which option is best will depend on your willingness to research, and how much of a vacation you like planning out ahead of time.