6 Simple Ways to Enjoy Your Vacations More

This is all advice I’ve shared before but really does bear repeating — we take trips but do we get the most out of them? Or are we traveling, putting too much pressure on our trips, and letting great opportunities go to waste?

The best advice comes down to: spend time planning vacations, take more trips, work while you’re gone, and experience new and unusual things.

  • Planning vacations contributes more to your happiness than actually taking them. Of course you may need to go on vacation to justify all of the planning time, and to convince yourself that the planning is meaningful.

  • You get all of your relaxation benefits on the trip itself, but don’t expect to be relaxed when you get back. We quickly snap back into the stress of daily life, sans any benefit from the vacation. Go in knowing you’ll enjoy yourself while you’re gone, but don’t set the bar for “needing a vacation” that you expect to be reset, relaxed, and in a different place with work upon your return.

  • Being on vacation can actually be stressful. We put pressure on ourselves to enjoy, quickly, in a compressed period of time. After all, unless you travel frequently, you only get one shot per given period of time and you have to make the most of it.

    Take more trips, and take the pressure off of each trip to be perfect. Don’t try to do everything, it’s better to leave some sites un-visited and have some experiences left for the future. Leave yourself longing for more.

  • People actually enjoy trips more when they’re interrupted by real time, as counter-intuitive as it seems. Many short trips mean work punctuates your travels. For longer trips consider staying connected a little bit (with defined times) each day.

  • Look for intense or unusual experiences, things that will stand out in your memory. You’ll get more lingering value out of the trip than just a general sense that you must have been relaxed but where did the relaxation go? You’ll have something to hang onto.

  • Make travel part of the trip. And since planning contributes to happiness spend time working through contingencies so you know how you’ll handle things like missed connections along the way.

How do you approach your travels? What makes you happiest — and leaves you happiest once the trip is done?

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Good advice when you posted it in the past, and good advice now. My two cents? Don’t overdo #1, and focus on #3. I like planning, but there are too many externalities for the execution of even the best-laid plans to come out right 100% of the time. This is particularly true in parts of the world where things might move a little slower or less predictably at times. Plan in flexibility. Go in with some must-do items but ideally be able to reorder them (move this activity back a day if it’s raining, etc.). And in a lot of cases it’s best not to plan anything at all beyond hotels and flights and wait to feel things out once you’re on the ground.

  2. I must be the happiest person in the world since I spend all of my spare time planning more travel!

  3. Gary, I’ve always found that same excitement each morning when I run the Awardwallet update to see what balance has grown!

  4. Greetings from Madrid!! Having toured the Prado today, I’ll remember the intensity of seeing all that world-class artwork in one place forever.

    I much prefer to keep up with work (and personal) EMAIL while traveling. Much less stressful than trying to catch up when I return.

  5. I don’t travel to relax. Just the opposite. Travel is much more difficult that just staying at home.
    Flinging myself half way around the world in a metal tube at 550 mph and then suffering jet lag (which is happening to me now)is not my idea of fun, even if it is in business or first class. I am retired and live in a nice home in a beautiful location. Staying home is much easier and more comfortable that traveling.

    Yet, I travel. I travel a lot. Why? Because it is fascinating. It is worth the stress and discomfort to visit and learn about other cultures.

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