How I Plan A Stress-Free Vacation Itinerary: Tips to Avoid Overscheduling Yourself on Your Trip

Have you ever come home from a vacation and thought to yourself, ‘I need another vacation to recover from that trip.’ I used to feel that way after almost every trip we took. You see, I love the ‘planning’ stage of trips, where the possibilities are endless. I hoard guidebooks, read blogs, talk to fellow travelers in order to find the ‘best’ itinerary possible. This desire to research everything and plan the ‘perfect’ trip has been my downfall, however, and has often led to trips where our schedule is planned down to the minute, and while we see and do a lot, we end up absolutely exhausted.

Over the years, I’ve tried to learn from my early trip planning mistakes and scale back my travel planning just a bit to leave more room for exploration, relaxation, and general wandering. While aimless wandering sounds like a planner’s worst nightmare, in reality, I’ve found that most of our most memorable travel moments have come from times when we leave our schedule open to just explore our destination.

That said, I’ve also learned that completely ‘winging it’ can be equally as frustrating. Like many of you, I’m not a full-time traveler and have limited vacation time. Sometimes aimless wandering can end up costing time and money to get back to where you need to be.

So, I’m learning to strike a balance in travel planning- plan some things, just not everything. Planning an organized, but not totally structured trip has allowed us more freedom to explore our destination without burning ourselves out.

To keep myself from going overboard when planning a trip, I try to follow these self-imposed guidelines:

How I Balance Under and Overscheduling When Vacation Planning

Limit myself to one ‘scheduled’ activity (may two if they’re complementary) each day

I know, choosing just one activity can be SO hard. But doing so gives some structure to your trip without locking yourself in and feeling like you’re constantly running from activity to activity.

Build the trip itinerary around a handful of ‘ Must Do’ experiences.

I’m a sucker for ‘top things to do lists’ and can easily get sucked into planning a trip as if it’s a mission to check off every ‘can’t miss’ activity off the list. Looking back at the trips where we tried to visit as many top sights as possible, there were really only a handful of experiences or sights on those lists that really appealed to us. In hindsight, I wished I had spent more time focused on those top experiences than chasing down obligatory sights. Now when planning a trip, we make a list of what top 2-3 experiences (more or less depending on the length of the trip) we most want to have, and plan around those.

Leave at least one ‘Chill Day’ where nothing is scheduled.

Even the most comprehensive research can’t uncover all the hidden gems of a new destination, and leaving at least one open day where we don’t have anything that we’re obligated to do gives us flexibility to explore. It’s fine to have a couple of optional activities in mind, but the key is not locking anything in in advance. This tip has come in handy countless times, especially on more active trips where we underestimate how tired/sore we’ll become need some downtime to recover from our adventures. We call this our ‘Chill Day’, and they are crucial to avoiding burning ourselves out. This ‘Chill Day’ can also be a great backup day in case you need to reschedule an outdoor activity that got rained out. While every trip is a little different, our rule of thumb is to plan a Chill Day about once every 3-4 days.

Leave buffer time for transportation.

Flights get delayed, taxis get caught in traffic, GPS sometimes points you in the wrong direction. The moral of the story is that we often find that it takes longer to get places than we think, and there is nothing worse than being stressed out because we’re running late for a tour or connection. Once, on a flight between Paris and Florence, my mom and I got rerouted to Bologna and the entire flight had to be bussed to Florence. Rather than rolling with it, and enjoying the scenery as we drove through Tuscany, I spent the whole time worrying about whether we would arrive in time for the tour I had scheduled that afternoon. While I probably couldn’t have foreseen that detour, I couldn’t avoided unnecessary stress by not scheduling an activity so close to our expected landing time. Now, I try not to schedule any activities on our arrival day if possible to avoid situations like these. Worst case scenario, we don’t need the buffer time and have a little extra padding to get oriented to our destination and explore something unexpected!

Remember that we can always go back.

I’ll admit that most of my desire to overplan trips is driven by underlying anxiety that it’s our ‘one shot’ to visit a destination, so we’d better see and do as much as possible. While that may very well be true, chances are, we’ll have an opportunity to go back at some point, whether it’s next year, 10, or even 20 years from now. We’ve started planning trips with the expectation (whether it’s grounded in reality or not) that we might get to go back someday. You’ll notice that we often include a ‘For the Next Trip’ section in our Destination Guides, so we can get a head start on planning for the next time we get to visit, whenever that may be!

Allow ourselves time to wander.

We always try to leave time to pick a neighborhood that looks interesting and get lost in it for an afternoon, or even just take an indirect route to our next destination rather than hopping in a cab or taking the subway to get there faster. We’ve often found that the path less traveled makes for the best vacation memories can lead to unexpected discoveries that we won’t find in any guidebook.

Pick lodging near experiences we want to have.

This sounds obvious, but I can’t tell you how important it is to pick lodging that is in the right location and has the right ‘vibe’. Traveling to/from your hotel everyday can eat up a lot of valuable time if you don’t plan wisely. It might be tempting to save a few bucks by staying on the outskirts of a city, but want to spend most of your time downtown, that can quickly be offset by spending more on cab fare, car rentals, or having to ‘commute’. Conversely, if you are looking to have a more authentic, immersive experience to experience the culture of your destination, you may want to steer clear of main tourist neighborhoods and pick neighborhoods off the beaten path. On our last trip to Tokyo, we opted to stay in the Asakusa neighborhood, which while still pretty touristy, let us experience a much more laid back area of the city versus bustling Shinjuku or Shibuya.

Avoid one-night hotel stays.

Travel can get stressful if you’re constantly on the move, so we avoid one-night stopovers if our trip includes multiple destinations. Unpacking and repacking bags is a pain, and it’s hard to really experience your destination in 24 hours or less.

Schedule a buffer day at the end of the trip.

It’s tempting to spend as much of our limited vacation time as possible in our destination, but I try to plan our itinerary so we have at least one day at home before heading back to work. This ‘buffer day’ is useful to catch up on sleep, do laundry, and reacclimate to the ‘real world’ after our time away. Buffer days also come in handy in case  your return flight gets delayed so you don’t have to head right back into work after taking a red eye flight!

While these aren’t hard and fast rules, we’ve found these tips to be helpful in ensuring we get the most out of our trip without feeling like we need another vacation by the time we get home. And let’s be honest, I not always great at following my own advice, and some of our trips are still too overscheduled, and we end up paying for it. 🙂

What tips and guidelines do you use to balance under and overscheduling your vacation?

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