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Plan Ahead or Do It On the Spot: The Conundrum of Modern Vacations

United Airlines caused a stir two days ago when it announced that travelers could now “subscribe” to its fees. Pay one lump sum in advance—$349, so that’s one big lump sum actually!—and you’ll be able to carry on your luggage “free” for the next year. Oh, wait, no, that amount was just for one bag checked. If you need to check two bags, the fee goes up to $399.  To guarantee a seat in “economy plus”, those seats at the front of economy class that have extra leg room, the yearly fee is even higher, at $499.

Obviously, you’d have to be a frequent traveler—and very good at math—to make these subscriptions pay off. Especially since they only apply to flights in the mainland US and Canada currently, rather than pricier hops to Alaska, Hawaii and other longer hauls (those are available for even more money).  All of the options are detailed at United’s press release.

But this development brings up a bigger question: is it ever worth it to pay in advance travel services and products, or does one do better simply winging it (you’ll excuse the pun), when it comes to travel?

In the case of United’s fees, it’s clear that they make sense for only a miniscule proportion of the flying public (perhaps traveling salesmen, based at a United hub and burdened with sample cases they need to check). Otherwise, you’d be a fool to go for this subscription.

Other pay-ahead deals aren’t as clear cut. Let’s take hotels. On many major booking engines (, Orbitz,, etc), as well as at hotel websites, the best savings are given to those willing to pay up front for a hotel room, rather than simply making a cancelable reservation. The reasons aren’t hard to fathom: it’s much safer for both the hotels and the travel agency sites to lock in a guaranteed reservation in advance.

But does that mean this is the best deal for the traveler? It depends. Often hotel prices will drop the closer to the date of stay, as hoteliers get nervous about moving unsold inventory. Those who use such asps as HotelsTonight can find savings of up to 70% for bookings made on the day of stay. So while you may be locking in the best price on the day of your reservation, it may not be the lowest going rate by the time you get to the hotel. Plus, if you have to cancel, you could incur a substantial fee or even lose the cost of your first night’s stay. 

What’s the solution? Some travelers are now turning to the site, which guarantees that, if the price drops, it will refund the difference. Problem is, Tingo’s prices aren’t always the lowest to begin with (especially on budget properties). Other travelers are monitoring hotel prices themselves as they get closer to their stay, and calling companies to pay up on their “lowest price guarantees” ( has one of these policies as do such hotel brands as Hyatt, Hilton and Starwood) should the price drop

Travelers are also encouraged to save by paying ahead for gasoline at the car rental counter. Here, too, there’s no definitive right or wrong answer. If you’re a heavy pedal sort who always gets to the airport at the last minute before a flight, you may want to pay ahead for gas, as having the rental company refill the cars incurs outrageous fees. For those who know they’ll have time to gas up before returning, and can do so in an area not directly adjacent to the airport (where gas costs are always higher), not pre-paying is probably the best method. To better increase your chances of finding affordable gasoline, I download such apps as (which lists the cheapest gas stations in areas across North America).

A final “buy ahead or on the spot” conundrum: sightseeing. In certain cities, pre-paying for a pass to the major attractions makes a lot of sense. For example, in New York City, the City Pass (, to a total of 9 sights) allows the bearer to skip lines, and can cut by a third the cost of sightseeing. What makes it an especially worthy pass is that it only takes travelers to the places they’d likely go anyway. Similarly, the Paris Museum Pass is well-priced and geared towards the top sights. But I wouldn’t recommend a sightseeing pass for London, since so many of the top sights are already free and the available passes steer people towards sights of dubious interest (unless you have a deep and abiding fascination with methods of torture, that is).

In the end, we all hope our vacations will be carefree, spontaneous adventures. But sometimes, to create that illusion, some amount of advance planning is helpful.