6 Things You Can Do to Enjoy Your Vacations More

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

  1. Planning vacations contributes more to your happiness than actually taking them. You may need to go on vacation to justify all of the planning time.

  2. 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.

  3. 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.

    So take more trips. Don’t make them one-shot deals. Avoid the stress where each trip has to be perfect. Don’t try to do everything, it’s better to leave some sites unvisited and have some experiences left for the future. Leave yourself longing for more.

  4. People actually enjoy trips more when they’re interrupted by real time, as counterintuitive as it seems. Many short trips get interrupted by returning to work in between. For longer trips consider staying connected.

  5. Look for intense or unusual experiences, things you’ll remember specifically. You’ll get more lingering value out of the trip that way than just a general sense that you must have been relaxed but where did the relaxation go?

  6. 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.

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 »

More articles by Gary Leff »


  1. This might be one of your most important posts, but too many people will just skim it and move on to a credit card points post.

  2. best lessons I’ve learned:
    1. Take longer trips.
    The first fews days of any trip are consumed to some extent by jet lag, culture shock, language challenges, general disorientation, and recovering from the physical and mental stress of getting ready to go and the actual travel – especially if the trip is to the other side of the world. And I say this as a veteran traveler who has been to most of the world more than a few times. I’ve decided that it’s a waste of money, time and opportunity to take short trips to far-away places, so I have set “personal minimums” for trip lengths. For me, it’s not worth going to Europe for less than 2 weeks, to Asia for less than 3 weeks – and those numbers are for days there, at the destination, not including actual travel time. Between the “post-arrival recovery” and “pre-departure preparations” its easy to eat up 3, 4 of 5 days of a trip. If your trip is only a couple days longer than that, it’s foolish to go all that way just to say you did it (sorry, bloggers). Stay a couple weeks, or else you haven’t really been there, you just passed through.
    2. Get away from big resorts.
    Sure, 5-star hotels are nice, but when you stay in one, odds are you dont actually experience the place you’ve gone so far to see. The bigger the hotel/resort, the more insulated you are from the real place that you’ve traveled to.
    3. Expect to spend more money than you think you will. You will!

  3. @Evan agreed.

    Gary, this is great. I’ve certainly found all of these to be true. The most counter-intuitive one is #4, but I found it to be true when I went to Asia (on points!) and spent one day a week working. It kept me from being so exhausted and helped me enjoy my trip even more.

  4. Yep totally agree! Always have another holiday planned for when you get back from your current one 🙂 Also lots of short breaks can work really well and feel much longer than one long trip.

Comments are closed.