Planning trips can run the gamut from just showing up at your destination and letting the trip happen to researching and scheduling every last detail. For those fortunate enough to spend more than 2-3 weeks on a trip, the need for detailed planning may be less important. If something you have your heart set on doesn’t work out one day; just do it later. But if you’re like most travelers and have more limited time, there may not be a “later.” Here are seven reasons you should err on the side of planning more, rather than less, for your next trip.

1. Know what you’re seeing.

There can be huge value in doing some pre-trip homework about the history and significance of the places you plan to visit. So many of the things you experience while traveling have amazing back stories. Without planning, I’m sure we’d have driven right by The Quiet Man Bridge on our recent trip to Ireland. Instead, we made a point of finding the quick pull-off and spending some time taking in a bit of classic movie history. If you have a plan, you can read up on the things you’ll see and have a much richer experience when you’re there.

2. Reduce the chance you’ll miss something you really want to do.

Vintage closed signI’ve lost track of the number of times I’ve found myself looking forlornly at a “Closed on Mondays” or “Sold Out” sign for something I would have loved to experience, wondering if I’ll ever make it back to that location again. A little advance research will warn you about activities that are likely to require reservations or that have limited opening hours. Building an itinerary that takes those restrictions into consideration can ensure you don’t miss out on that cool night tour of Alcatraz or attendance at the Ceremony of the Keys.

3. Maximize the limited time you have.

For multi-city trips, there usually will be a best order for your travels. Whether because of geographic proximity or available transportation options, you’ll want to plan your trip in a way that takes maximum advantage of your time and money. And once at a destination, you’ll want to arrange your itinerary in a way that leverages the fact that you’re in a certain area where several of the items on your “to do” wish list are located.

4. Build the excitement.

Travel planning

Perhaps my favorite reason for planning is the resulting pre-trip excitement. Reading through guide books, doing research on potential lodging options, sketching out plans for a given day – it all gets your travel juices flowing. Rather than limiting the joy of travel to the one or two weeks you actually spend on a trip, why not add on several months of anticipatory bliss?


5. Reduce stress.

As liberating as it may sound to simply arrive at a destination and go with the flow, when time is limited you’re likely to feel a bit anxious about how you’re going to see and do all the things you want if you don’t have some sort of plan. This is particularly true if it’s your first time in a city. Who wants to visit Paris for the first (and maybe only) time and not visit Sacre Coeur or Notre Dame? Knowing you’ve built in time to do all the things you want will allow you to enjoy each experience without worrying about having time for the others.

6. Be realistic about how much you can do in the time you have.

As much as we enjoy the actual travel between destinations and within a destination, these components of a trip often are underestimated in terms of how much time they take. Maureen and I recently planned a diving trip to Mexico and knew we wanted to dive in three different areas: Cozumel, Tulum and Isla Mujeres. We started out with the assumption that on travel days we would dive in the mornings, then use the afternoons to get between destinations. But after working through the logistics on Trip30, we realized it would be much more enjoyable – and realistic – to allow for otherwise unscheduled travel days. You can see the itinerary we ended up building here.

7. You don’t have to follow your plan!


And perhaps the most important thing to remember? Hey; just because you plan to the nth degree, doesn’t mean you have to actually travel that way. In fact, it would be pretty unusual if you didn’t make a few on-the-fly decisions to change plans. But, at least, you’ll know what you might be giving up or otherwise need to re-schedule as a result of those decisions.

I’d love to hear where you fall on the travel planning spectrum. Weigh in, below, with what works for you.

Posted by Jim Ball