Pre-book Accommodations or Wing-it?


Mister and I use to wing-it for accommodations when traveling, we didn’t like to schedule the exact where and when.

This habit began way back when the kids and I would go along on Mister’s business trips. He didn’t always know how long or how many daily stops he would make so it was easier to wait and choose where to stay each night.

Plus, we preferred to see properties in person, rather than rely on phonebook listings or brochures which usually used out-of-date pictures.

Some may find this next detail hard to imagine and the concept may make some shutter.

The wing-it days I refer to started before the biggest world change I’ve witnessed in my life, so far.

It was back when people didn’t own home computers, laptops, iPads, notebooks, or cell phones with internet. Heck, back then we never heard of Google. A handheld GPS was better known as a, map.

Now, with internet at our fingertips, even-though you can’t believe everything on there, I feel with enough research and weeding through reviews you can get a pretty good idea about a place.

And so, we made a habit change for our last few holidays. I pre-booked accommodations for all or most nights we were away. The main reason was, a couple places were popular enough that if we hadn’t had reservations, we would have been hooped.

Unexpected upsides came with having nightly reservations.

We never pulled into a town or city tired and possibly in the dark and then had to search for a place to stay. We also never stopped too early because uncertain of what the next town would offer. Both these may sound trivial, but believe me, Mister and I have shared many cranky episodes regarding these points in the past.

Do we ever pass places we would like to stay at while on our way to one we’ve booked? Yes, but we’ve also driven through towns that if winging-it we would have been disappointed and moving on down the road.

Another bonus to pre-booking is becoming aware of local events that may mean places are full. I can’t count the number of times while winging-it we would arrive somewhere, towns or cities we had stayed before and knew they had lots of choices, only to find a concert or sport event had everything jammed.

Our trip planning starts with a basic route or a particular destination in mind. Using the internet, I research sights along the way and estimate the time it will take to drive and see the ones that interest us. Considering that information, I’ll check 2-3 towns or cities we would be near at about 2-5pm each day. I like to look for unique Hotels, or Motels but we have some well-known chains we like too. I’ll make my choice after reading reviews on numerous websites.

If the trip isn’t for a while, and it’s required, we always pay the couple dollars extra for, get this, free cancelation. Smiley face.

Pre-booking still causes me occasional trepidation, but there is also the excitement that we could stumble on a hidden treasure of a place, which has happened. By this I mean, an establishment that its curb appeal might have us driving past, but by reading reviews we’ve booked, stayed and have been pleasantly surprised.

Knock on wood, we also haven’t been disappointed to the point where we’ve had to move to a different premise.

For now we’re enjoying this new way of travel, but I’m also sure we’ll do a wing-it trip again. If and when though, I’ll use the internet to research and list possibilities along the route.

I’ve also tried doing reservations a couple days ahead while on the road, but this meant evenings were spent researching and booking, and I felt it took away from the trip.

Do you pre-book trip accommodations or wing-it as you go?

Do you prefer privately owned motels or big hotel chains?

What is the biggest worldly change that has occurred during your life, so far?


18 thoughts on “Pre-book Accommodations or Wing-it?

  1. Pingback: Everyone’s Favorite, Part#2 | kathy knull

  2. If I am going to a city I am familiar, I will book the day before I arrived. For cities I visited the first time, I will pre-booked especially cities that have language barrier. Basically I do not wish to feel stress looking for accommodation while I am on holiday. I would rather spend my time planning what to do and where to visit or to simply relax.

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  3. Ever since our driving trip to Florida, with two kids in the back seat, where we decided to just see how far we could drive and then find a place to spend the night….only to find that there were NO hotel rooms available in the town we were looking in….we have always prebooked accommodations. Sometimes we cancel them and change them if our plans change or we are unhappy with the hotel we booked, but I like knowing for sure there is a place I can lay my head at the end of the day.

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  4. We’re mostly wing it type. We do plan ahead though, to the extent that we have a plan. But plans change. On or current trip with had planned on staying in Dickinson ND but the roads were horrific and nasty and delayed us so we stayed in Minot overnight at Svenson’s. We got to Dickinson at 10:00am and it was cold and snowing and we could see if we drove just four hours more we we be in temperatures above freezing and out of snow. So we did it and it was great. We are back in fall temperatures. We found a great campground in Rapid City open year round and we decided to stay two nights and go see Mount Rushmore again.

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  5. Jon and I like to wing it when we can. Lately, we’ve learned that reservations are needed in advance for popular destinations. When we decided to visit Glacier this past summer, we lucked out by calling ahead and getting the one and only spot when the campground had a last minute cancellation. All the other campgrounds had no spaces. Like you, we have a destination in mind and head out. But we usually make reservations for a few days at a time. Not for the whole trip. I guess we could always park at a Walmart if we really got stuck. Although I prefer staying in an RV site. As for the GPS, I’ll stick with my paper map. It’s more reliable.

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  6. I haven’t winged it since I was young (pre-computer civilization days). I’ve only had one disappointment. I got a great rate on a room at a great ocean front hotel in Key West. I knew the room wasn’t ocean front but that was ok. Not only wasn’t it ocean front but it’s window was on a walkway so we had to keep the curtains closed or people could look in from 6 inches away. There was 3′ around the bed. Banged my legs many a time. Somehow I got snookered. I always regret not asking to upgrade or something. Fortunately it was only a long weekend. Nowadays it’s so much easier to book. There are reviews and better pictures (although still taken at the best angle that doesn’t always reflect what the place looks like).

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