a woman in a red dress walking on the street

There’s so much focus in travel on the elements which take up the least amount of time. A flight, anywhere in the world, rarely takes over 20 hours, connection included. A hotel, in reality, is just a place you rest your head at the end of the day, even if it can be more. What makes a vacation, or any trip is what you actually do each day, and this is where the real divide occurs.

Are the most relaxing trips all about meticulous advanced planning, or free-flowing, easy going adventure?

From the start, I’m on team both. Growing up, I always found it amusing to see just how different each family approaches “vacation”. Join one family, every hour is scheduled down to the time it takes in transit between each venue. Go with another, each day is a mystery, down until the hour the group will supposedly pick a dinner option. In my life now, I find the “hybrid” works best.

a woman walking under a wooden archDon’t Mistake Research With Scheduling

Perhaps it’s the nature of the job, but I’m on #TeamMeticulous when it comes to pre-trip research. I employ Google Maps, reviews and key landmarks in hopes of picking the hotel best suited for my needs and I do the same with restaurants, bars and anything I might want to do or see during the day. I look at reviews of… everything.

Jumping in and plotting each move and picking the winners feels like an oddly perfect remedy to the sadness of your credit card being charged for the flights! I’ll spend days, weeks and even sometimes months on this step, but don’t mistake this for me being on #TeamScheduled when it comes to the actual trip.

This painstaking planning detail absolutely does not mean that I program every moment of the trip, not even by a long shot. It just means that I can trust in the programmed moments being just about perfect.

San Sebastian city ans La Concha beach from IgueldoI Love Big Gaps And I Cannot Lie

When you’ve put in the work, sometimes months worth, planning your must have meals, or that special hike, tour or adventure, that usually comes with the stipulation of a date. The best restaurants will generally need advanced reservations, and so to an extent, you’re locking yourself in. But for me, for everything I lock myself into, I try to leave an equal gap open.

Figuring out what you want to lock in, or need to (limited space, availability etc), versus what can be free flowing is a useful exercise in itself.

If I’ve got four nights in Melbourne, I’ll schedule two dinners in advance, but leave the other two open for discovery, recovery or calling an audible. If you’re not an American Football fan, an audible means to change the play, right before it’s about to begin. The same tends to go for my days – a mix of fully planned day trips and open adventure days, where I’ll make a plan in the days before.

Close up of lion cubs laying together waiting upon mother.Sticking To Schedules Is Stressful

Tightly wound schedules are for corporate salespeople or dentists. My take on vacation is that it’s supposed to inspire and rejuvenate you, even if it’s a city break. I love going all in, and on shorter trips you often have to, but if afforded the luxury of time, I find trying to stick strictly to what’s planned entirely exhausting.

You may schedule yourself a morning hike in the canyons of LA, only to realise it’s actually fairly tiring, and feel like a failure for not wanting to venture down for a long stroll along Venice beach immediately after. That’s not the idea, in my opinion. It doesn’t mean I can’t aim for both, but I think leaving the time in between is as key as being comfortable enough with yourself to change plans..

a snow covered trees and a lake in a cityStaying Minimalist Brings The Best Up Front

Even on longer trips, I find that over scheduling often means doing things, just because you have the time to do them. Not scheduling them in advance doesn’t mean you won’t get to them in the end, but it makes you focus more on the things you really-really care to schedule.

Read as: if you only schedule two dinners or two day trips out of four days, you’ll do more advanced research to ensure they are “the ones”. It’s no different to seeing 10 pairs of shoes and saying you can only have two.

You’ll probably get to at least one of the others you were considering, but it leaves the opportunity for spontaneity, or to actually listen to an in the know local who is kind enough to suggest an activity, part of town or restaurant that’s exactly what you need. Many of my best ever travel experiences are the ones that began to unfold only hours before, on pure chance.

Ultimately, It’s On You

This may be illuminating to some, but it’s certainly not for everyone, it’s just my take. Ultimately, it’s up to you to decide what makes you happy, and some people just can’t rest a wink without knowing all the little details, down to how many steps it takes to get from the hotel room to breakfast.

My experience in travelling with others on both ends of the planning spectrum has made me see the merits of each solution, and ultimately I think the hybrid is the way to go. Invest the time before you travel to learn as much as possible about all potential things of interest, but then leave things open enough to discover them at a pace that says vacation, not dissertation.

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

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  1. I’m with you on hybrid vacation planning: I want to leave enough time “in between” the pre-scheduled activities. You have to experience the moment you are in with all of its surroundings, and not simply rush place to place. That’s why I’m typically avoiding over-touristy places or visit such ones in shoulder season when crowds are thinner – this way there is less distraction and pace is slower. I remember a day in Machu Picchu – around 3pm most of people left and the place felt amazing. Spend extra 30 minutes just sitting and experiencing the magic of it. Can’t plan for such things in advance.

  2. Now that I’m a little more senior in my years, less is really more. We do have our jam packed trips – but we also have the slow ones. The best ones are with “gaps” to soak up the moments.

  3. Hi Gilbert – Really enjoyed this article. We have a similar philosophy about free-flowing time and generally accomplish it by having just one big activity in mind per day (with the occasional “just hang around the hotel” day if we’re at a resort. I’m like you, I research a ton in advance so I have thoughts about how to pivot depending on how we feel.

    All our best for a happy and healthy baby arrival very soon! ~Craig

  4. Hey Gilbert,
    My wife and I have taken several trips over the past several years, 4-9 days duration, and we do plenty of recon via the internet. I joke that we typically have 10 awesome activities planned, so even if we only do 3-5 of them, we know those will all be satisfying events (this also allows for the substitution of one activity for another, if weather or other uncontrolled event occurs). Add in generous transit time to get from Point A to Point B during our stay, so we can take in local color, points of interest, or just pause for a bit of nature.
    As noted above, we also go where and when the hordes aren’t.
    Both of these strategies have worked to our advantage successfully.

  5. Hi Gilbert. Schools are no longer allowed to give school children time off school for holidays. We used to ask and get up to 10 days to mix with either Easter or the May/June half term. We had a more relaxing time with our sightseeing. Now it is more stressful and I feel we have to work out detailed sightseeing. I think it is exhausting to take heavy luggage. I like to travel with lightweight luggage. Even if we need to putt our luggage in a locker then it would fit.

  6. I like your suggestion to leave an equal gap open in our schedule for every activity we lock ourselves into. My husband and I want to book a rental cabin so we can get away for a week sometime this summer. It’s been a while since I’ve planned a vacation, so the tips you shared here are much appreciated!

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