Stop overscheduling your vacations and use this easy, flexible guide to planning your travel itinerary to get the most out of your holiday. FREE template, and practical tips and tricks included!

Overscheduled lives, overscheduled vacations: A case for keeping your travel itinerary loose

What overscheduled lives we lead, even in this strange time. Work, social engagements, errands, appointments, we so dearly love our busy day-to-day lives. We’re so good at scheduling that many of us feel like we must schedule our trips to the hilt in order to wring out as much as we can from a location. A detailed travel itinerary is often seen as a triumph of holidaymaking.

Unfortunately, we all to often try to cram too much in, ignore our energy levels and mood, and just charge ahead in the name of keeping our schedule. There’s a better way. By knowing what you want to experience, reserving ahead where you must, and then checking in with yourself each day, you’ll get to do the things you wanted to experience and do them when it works best for you.

Best laid plans can ruin a good time

We’ve all seen them. Beautiful itineraries. Day One, you’ll experience the divine blah blah, and then feast on doodah before an early night. Day Two, you’ll breakfast here, the museum, followed by the gardens, followed by dinner at this amazing restaurant. Day three, you’ll have a little excursion to that place, and then come back in time for sunset at the vista  . . . .

Everything gets reserved and booked in advance, and all you have to do once you’re there is show up at the appointed time. You might have allowed yourself a free afternoon here and there, and a leisurely morning, but basically, from the moment you land until the second you’re off to the airport again, you know what you’re going to do and when.

Detailed travel itineraries are super popular

Detailed itineraries are super popular. I can see why. They do manage to take everything we might want to do on a trip and fit it all in. Voilà! They’re often beautifully laid out, and they can be a load of fun to plan.

But overplanning turns you into a widget, not a traveler

Here’s the thing—they can also ruin your trip if you’re not careful. We’re human beings, not widgets, and our energies ebb and flow, especially on holiday. While we can have a general idea of what to expect for the weather, with greater degrees of accuracy than others (it’s unlikely to rain in the desert), generally we can’t guarantee it.

No room for spontaneity 

Overly planned travel itineraries also leave little room for spontaneity, let alone serendipity. To me, there’s nothing more magical than discovering a little place not mentioned in any of the guidebooks that is the perfect place for you to be in that moment. You won’t find it if you aren’t open to it.

Don’t I need a travel itinerary?

Well, you might be thinking, I’m not just going to wing it. I’ll miss everything.

Oh definitely not. We’re going to plan our travel itineraries! While I have known travelers who truly just wing it—fly someplace and figure it out—I don’t know anyone who does that for just a vacation, and I certainly don’t recommend it.

No, what I mean by keeping a loose travel itinerary is to know what we want to experience, but to keep our actual schedules loose to allow for serendipity, exploration, and to respect our ebbing and flowing energies while we travel.

Keep your travel itinerary flexible and you can pass hours in a café (Santiago, Chile)
Keep your travel itinerary flexible, and while away some incredible time in a café instead of rushing to the next item in the schedule

Keeping your travel itinerary loose—samples from my own travels

Let’s face it, middle ways tend to be very stupid. I always think of Mr. Miyagi or Yoda when I think of third ways. However, hear me out. This one works. Here’s an idea of how a loose travel itinerary works in the form of three typical mornings from my travels.

A glorious morning

Sleepily, I head into the kitchen to make myself a cup of coffee. I drink it slowly, looking at the window of my holiday apartment. Wonder what I’ll do today?

What a dinner last night

Memories of last night’s dinner, those strange and delicious pickled walnuts with the salad, the wine. The people sitting across from me, who I spoke with for a few minutes, the restaurant known as much for its conviviality as for its Michelin Star. I smile. What a life!

Oh, and that park! I’d discovered a little hideaway park in the neighborhood on a wander. I’d stopped there to read and watch the world go by for a while.

I’m feeling up for a little hike

What a glorious day, just as promised. Tomorrow looks like it might rain. I’m happy and energetic today, having had a bit of a leisurely day yesterday. I might be up for that hike up the hill? Yes! Let’s do it. I’ll huff and puff a bit, but the VIEW! So worth it.

I’ll take the tram over there. Maybe have lunch at that café I marked on my map, or someplace else? What else is over that? Oh yeah! That cool little weird museum I wanted to check out, and that building I read about. There’s that restaurant, too, that didn’t require reservations. Would I be there long enough for dinner? Maybe? We’ll see! Let’s get some more coffee at that café first and stop in the park. I liked that park.

Good? Very good! Let’s get ready.

A lazy morning

Another morning, a couple of days later. I sleep in a bit. I’m a bit sore and tired from having gone on a day trip the day before, but what fun I had!

I’m a little bit more leisurely with the coffee. I make a second cup and settle on the sofa for a bit. It’s a bit overcast, but not terrible. Would be a decent day for some photos? I give my list a glance. Oh wait. I got it.

You know what would be awesome? That spa. It’s not so busy midweek, I read, and I could really use it. I have food from the market—remember that old lady with the scarf?—I can make lunch here. Maybe go to the café again, but maybe not. This coffee’s working, and I really like it here.

OK. Booked the spa ticket for the early afternoon. Perfect. We’ll see about the rest of the day after that. Maybe get some photos in, or maybe just wander around a bit before heading back here.

The kind of morning made for exploring

A bright, beautiful morning. I feel amazing. I had so much fun at that little bar last night! Those people were a hoot. SO glad I braved it. Walking around that quarter in the evening was so different from the day. So many people out and about having fun. I’ll have to go back there before I leave.

Drinking coffee and looking out the window, I just decide to hop on the tram and head out to that neighborhood I kept meaning to explore but hadn’t. I’ll walk around and see what I find. It seemed like there was tons to do over there, and it’s really easy to get back for my reservation this evening. Now that’s going to be a feast!

All right, cool. We’ll head out now and get a coffee at a café in that neighborhood. Here’s to a day of wandering!

Flexible Travel Plans: Wonderlust Experience List Checklist to help keep track of what you want to experience while on your trip
Free template to keep track of what you want to experience of your trip! Click on the image to download

Here’s how to keep your travel itinerary loose AND still see what you want to see

In order to try and mitigate against missing something while keeping your travel itinerary loose, here’s how I tend to do it. It involves four steps before you leave on your trip:

  • Make a list
  • Make a map
  • Make a skeleton itinerary
  • The exception that proves the rule: Make a plan for your arrival day

Make a list

While you’re reading up on your destination, start a running list of things that you want to do. Star the ones you absolutely want to go to (don’t worry—you can always pare back, if you’re like me and star everything).

I’ve made a cute free template for you to help with your planning. Subscribe to get it!

Tip!

Keep your list saved where you can access it on your trip

Flexible Travel Itinerary: A Google map with markers of places to visit to help with daily travel planning
The map that my friend and I made for our upcoming Montreal trip

Make a map

 If there’s something that you want to do, mark it on your Google Map. Google Maps has some different markers, and you can customize as you need to. That way, as you’re planning your day, you can see what’s nearby that you’d wanted to check out and add it to your day’s plan.

You could also use a guide like my Wonder & Sundry Guide to Boston, where the map is already made for you (Lisbon coming soon, and more planned!). Subscribe today for access!

Tip!

Make sure that you’ve downloaded your map for offline use in case you don’t have internet access

Make a skeleton travel itinerary

Even the most flexible travel itineraries require some kind of calendar, if for nothing else your transportation and accommodations. However, you can also use your calendar to help ensure that you’ve allotted enough time to do what you want to do and still allow for some serendipity while on your vacation.

Some things just require reservations

As you’re making your list, also mark anything that requires advanced reservations, or where not having an advance ticket would mean that you spend the bulk of one of your precious vacation days standing in line.

Many restaurants, museums, and show-stopping attractions top the list of must-reserves. While Covid restrictions have scaled back, some places still recommend timed tickets. Use your judgement here—maybe check ticket availability for today, a date next week, and the when you’re going to go. If you’re not traveling at a peak time, then maybe you could decide a little later.

Make your skeleton travel itinerary

Get out your calendar (I use Google) and see how you might fit your required reservations. Don’t forget day trips! Edit your list as necessary. Review your calendar and see what you’re planning for yourself. Does it look a bit too hectic? Scale back. Could you maybe fit in another restaurant? Go for it.

Make those reservations. These are now your anchors and you’ll plan the rest of your day around them when the day arrives. Make sure you’ve accounted for the time zone you’ll be in!

Tip!

Go in order of your top choices. You don’t want to miss your #1 pick because you reserved your #4 pick in the same slot

Weiner Risenrad, Vienna, which I rode to shake off jet lag. Gray skies and the iconic red cars.
Even though it was about to pour, I still went to the Prater my first day in Vienna to beat my jetlag

The exception that proves the rule: plan your arrival day itinerary

There is an exception to this loose travel itinerary rule, and that is the day you arrive. Especially if you’re going to be jetlagged (we know not to go to sleep when it’s only 11:00 a.m., right?), you have to get out and do something. This is when you want to have a plan. Really, you don’t want to go to sleep.

I tend to plan for bonkers tourist stuff on my first day in a new place. I’ll ride the Ferris wheel, go on a funicular, run around like the slightly deranged woman I am in a jetlagged state. Throw your stuff down, take a shower, and get out there and do the things! It’s energizing and fun, and a plan will help take the decision making out of it when you really just need to know what to do.

Tip!

Don’t forget to leave time for just wandering on your first day! You’ll get your bearings AND stay awake

How to use your loose travel itinerary while you’re on vacation!

Your loose travel itinerary gives you the best of both worlds. You have reservations for the things you must have them for, and the world is your oyster for the rest. All you have to do is see how you feel.

Either the night before (for early morning experiences) or the morning of, have a check-in with yourself. Consider the following things:

  • Your energy level and mood—How are you feeling? Energized? Exhausted? Up for a challenge? Needing to take it easy? Use your energy levels to help guide your activity for that day. Maybe don’t take that hike on a day when you’re exhausted and a bit cranky. Or, even if you’d planned on taking it easy one day and you wake up feeling on top of the world, rest on another day.
  • Your schedule—Anything reserved for that day? If so, check your map for things around the area that you’d wanted to try and see if you could fit those in, too.
  • Your Must-Dos—How are you doing with your Must Dos? Is there something that you’re going to be really disappointed that you didn’t experience?

Then, take a look at your list. Anything jump out at you? Today’s the day! Do it! Consult your map for things in the area, and you’ll be able to make the most of your time.

Have fun! Don’t forget to just wander!

Hey, wait a minute! Isn’t this just something for solo travelers?

Honestly, this probably does work best for solo travel situations. However, I think that it could prove very useful when traveling with families and/or significant others. We often just march ahead with things, and this allows for a daily discussion and adapting plans to suit everyone’s needs. It could cut down on crankiness and unnecessary fights. I would be very interested to know if you’ve tried this when traveling with your family.

How do you plan your vacation travel itinerary?

I’m really curious to know—how do you plan your time while on vacation? What’s your best tip?

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Flexible Travel Plans: Wonderlust Experience List Checklist to help keep track of what you want to experience while on your trip
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