This is part of a broader series that focuses on getting the best prices and routings to Europe. A key part of that strategy is finding the best days to travel, when fares will be lower and you can save money for the rest of your trip.

Previous Installments:

• Coach Getting Too Pricey? Check out Business Class to Europe

It always fascinates me how inflexible some people can be with leisure travel. Yes, I understand that vacation time is limited, the kids have their summer activities, and there may only be a week-long gap before school, but most Americans sprint through their vacation at breakneck speed, spending more money and enduring more stress than is healthy for anyone taking a “vacation.”

Chill out.

It turns out that if you leave midweek, or in shoulder season (May-June and September-October) you’ll enjoy all the charm of European cities and coastal towns with half the people and expense.

As they say in project management, “Good, cheap and ‘when I want,’” — pick two!” Picking a flight often means trying to satisfy incompatible constraints.

There are plenty of apps that will help you plan activities based on seasonality. I’ve come across an app called What’s It Like? recently. Though they’re still in beta, they’ve given me a few ideas of places to check out that I wouldn’t have considered (like the Fringe Festival in Edinburgh).

Depart Midweek If You’re Redeeming Miles

If the shoulder season doesn’t work and you must travel this summer, leaving midweek means you’ll have access to far more award space. Prices will also tend to take a break from “shocking” to “merely high”. Most people looking to use their miles call up the airline, ask to fly out on a Thursday or Friday to minimize the number of vacation days they take (even though most people don’t actually use all of theirs) and get frustrated when the agent tells them that there’s either no availability or seats are only available at double the price.

Observe that availability for European award travel is much better during the middle of the week (blue = business class and yellow = coach).

Just take an extra day off and fly on Wednesday in when business class is available at the saver award price for just 57.5k miles each way, vs. the standard award price for coach of 65k each way. (More miles for far worse seats!) Take that extra day off! Get to Europe in a flat seat, and start your vacation well rested! The example chart above is fairly typical of availability to Europe all summer. Thursday and Friday are bad (and weekends too), but many other days in the week are decent for Athens. Similar for Rome, below.

Award space to Rome is pretty decent …unless you’re departing on a Friday. Most of the business and first class award space is only available mid-week.

Pro Tip: The best days to redeem miles to Europe tend to be earlier in the week (Tuesday and Wednesday) on the outbound. The return doesn’t seem to be as sensitive.

The Story for Paid Tickets Is a Little Different

Because airlines try to do everything in their power to eke out more in fares from business travelers, and business travelers more often than not depart Sunday night or Monday morning, those flights are considerably more expensive than departures later in the week — often 50% to 100% more. So if you’re actually paying for the ticket, time your departure later in the week. Ironically, Thursday and Friday are pretty good here. Again, the return date doesn’t drive price nearly as much, since most fares filed by airlines are governed by when they depart, not their return. Tuesday or Saturdays are likely to work well in your favor.

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As a general rule of strategy, remember that the airlines know that leisure travelers want to depart later in the week and are more price-sensitive than business travelers. This is also why they restrict award space later in the week! They know business passengers won’t use their miles for work trips, but if they can’t sell the seat at a high price, they might as well let someone cash in their miles and take them off the books. But they don’t want to give leisure passengers an easy way out by redeeming miles.

So they restrict award availability, forcing you to pay the sky high award prices if you need to travel on Thursday/Friday — but when paying cash those same flights are cheaper than on Sunday/Monday.

Pro-Tip: Avoid peak business travel times - depart later in the week if you’re buying the ticket. Thursday and Friday are actually the best here (though they won’t be cheap compared to winter prices).

The takeaway is pretty nuanced here, but it’s a great example where viewing miles and cash as tools gives you more options. The cheapest times to depart to Europe are almost countercyclical (Tuesday/Wednesday for Award Tickets, Thursday/Friday for cash tickets). If you’re very determined to travel on a certain day, you might want to pick a different way to pay. If you can pick your day, then check to see if miles or cash offer a better deal.

Conclusion

The most important lesson from this post is to be flexible in your vacation planning. You might need an extra day or two, but it will make the rest of that trip far more enjoyable. If you still think you can’t talk your boss into letting you take your hard-earned vacation, send me an email and I’ll help you craft a narrative.

Pro Tip: Really think hard about taking an extra day of vacation vs. missing a soccer practice or a weekly meeting and leave/return midweek.

P.S — Let me know if you’d like to see more articles on using remote work and “human capital” thinking to actually take time for yourself while still keeping to your obligations. I’m pretty fascinated by it, particularly remote work and virtualized companies.