Tour it OR Wing it

If I took a poll of people who like taking travel tours versus winging it on their own, I bet it would turn out to be about 50/50.  Usually, you’re either a person who loves taking tours or you’re not.  There are pros and cons to each.  First, let’s define what a tour is and what winging it means.  A tour is an organized travel option that can be either short term or long term.  All schedules, locations, itineraries, transportation, lodging, etc. are standardized, structured and usually managed for you.  It’s like the hands off approach to travel.  There are a few types of winging it.  First, just fly somewhere and figure it all out as you go along.  Second, create your itinerary prior to travel (sites, attractions, transportation, lodging, restaurants, etc.), but travel by yourself, without a guide or assistance and take the detours and roads less traveled.  Third, do a little bit of both.  Let’s look at the pros and cons for tours and winging it to see what’s right for your travel needs.

Fort Saint-Andre, Avignon France

Tour Pros:  Everything is organized and planned for you, there’s no need to plan an itinerary, transportation, meals or lodging, etc., in most cases.  Taking a tour is considered a stress and worry free option.  If you want to see a lot in a limited period of time and keep to a specific schedule, this is a great option.  This is also a great option for groups, some solo and first time travelers.  It’s sometimes fun to do a tour to see what you’d like to do when visiting again.  It’s a good way to get bit by the travel bug.

Tour Cons:  Since itineraries are usually packed,  there will be limited time in each location, so you may not be able to see everything on your list.  Usually these tours are structured around specific times, tour schedules and seasons so you need to plan accordingly.  Keep in mind that you may have to compromise on the itinerary based on which tours are being offered.  If on a bus/train tour, there is not a lot of flexibility with itineraries or unscheduled stops.  Even though you may want to see what’s up that mountain road, it’s not on the itinerary, so you won’t see it.  Since most tours are structured in groups (meals, attraction tours and other social activities), there is limited interaction with the locals, and you’ll most likely be hanging out with other people just like you.

Coliseum, Rome Italy

Wing it Pros:  Winging it provides the best flexibility in travel.  With this option you can go up that mountain road or take a back road and find something amazing.  This is a great way to get lost and have blast while doing it.  This option allows you to do pretty much whatever you want, the possibilities are endless.  Winging it it also a good way to mix with the locals and immerse yourself in the culture a little more freely.  The time is all yours, so use it as you will!  This is a great option for seasoned travelers or for those who like a bit of adventure and don’t mind doing a little more homework, not being afraid of the unexpected.

Wing it Cons: This option may seem too open ended or overwhelming.  The planner will either just go with the flow or have to plan every major and minor detail.  On the one hand the planner needs to have an open mind and on the other, be detailed oriented and organized to manage all the schedules, activities, transportation, lodging, etc.  This may not be the best option for group or first time travelers.  If you enjoy the idea of planning as you go for the entire trip, then make sure no one in your travel party is OCD because it will definitely put them on edge.  Not like I have any experience with that or anything….

Whether touring it or winging it, a fair amount of research will be involved.  For instance, decisions need to be made to find out Where to go, Who to travel with, What to do, When to travel, Why or reason for trip.  There are many social media travel group sites now that you can join and find an abundance of tips and information about traveler experience and suggestions about reputable tour groups, rental car agencies, etc.  Also, check out some of my tips for specific locations here.

Marburg, Germany

If you do have some leisure time during your travels, whether on a tour or winging it, take in the local sites and do an individual day or attraction tour.  Research where the tourist centers are, there are usually a bunch of them right next to each other and have similar pricing, though the itineraries may differ.  You can always research reviews for the different centers to see which has the best service for your travel needs.  Just keep in mind there are some tours you’ll need to book well in advance, and others you can just walk up and book for the next day or so.  It’s kind of a trial and error experience.  Another suggestion is asking the locals where they go or what is a must see.  Locals are the best source of information for pretty much anything.  Give it a try and ask, you won’t be disappointed.


My husband and I wing it, but the organized kind.  We create a detailed itinerary ahead of time and leave a few leisure days open at each location so we can either find something cool to do along the way or book an organized tour.  Here are two examples of us actually winging it and touring it:

We were self driving through Southern Ireland along the Copper Coast and it was absolutely stunning.  The coastal road winded around through town after town, continued, dead ended then continued again.  We saw a sign for a particular castle so we veered off the main road to find it.  After walking around the castle grounds we got back in the car and drove on.  My husband was driving and we passed a small road that lead to the sea.  We both saw the road for an instant and I gasped from the gorgeous view.  He literally slammed on the brakes (it was a coastal road in the country, there was no one in sight) and floored it in reverse to go down the road to the sea.  We wound up in a parking lot by the bottom of the deep purple cliffs that met the sea.  The wind and rain were out of control, but we got out of the car and went to the sea’s edge.  It was one of the most fun wing it moments we had!

kylemore abbey
Kylemore Abbey, Connemara Ireland

This past year we visited Naxos, a Greek island in the South Aegean.  It was a large island and we wanted to see as much of it and learn as much about it as we could, but had to rely on public transportation.  Once we disembarked the ferry and arrived at port, there were a select few tourist centers that offered different types of tours.  Our favorite type of tour is by boat, but we really wanted to see the island’s interior, hence the decision to do a bus tour.  We booked a bus tour for the next day and it was a full day of touring different locations.  We saw some amazing sites and learned a great deal about the island, which we wouldn’t have been able to do otherwise.  It was great, don’t get me wrong, but we only had about 25-30 minutes at each location.  We are quite leisurely, and being a bunch of lollygaggers we like to take our time to explore and take it all in.  We’re always the last people in the back of a tour group, and this time the last people running to the bus.  Our bus tour was pretty much packed and quite crowded, so it took a while to get off the bus then go wait in line with other tour groups to see some of the attractions.  We were lucky that our itinerary had a different route than the others because there were some areas where we were the only people at the site.  After the fourth or fifth stop we were in information overload and wished we had more time to sit and have a coffee while viewing the scenery at the more picturesque spots.

Naxos, Greece

So no matter which way you like to travel, try to step outside of your comfort zone and try a little touring it and a little winging it.  I can’t promise you’ll love it all, but I do promise you’ll have an incredible experience that will have you telling stories for years to come.


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