Road Trip Vacation Planning: Cliffs Notes for the Busy and Frazzled

Road trip vacation planning can seem deceptively simple – pick a destination, pack your stuff and go. Right?

Not really!

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In addition to all the more serious stuff like figuring out your budget (check out my road trip budget calculator to figure out yours) and getting your car serviced, you really need to do some planning to make sure that your road trip vacation is a ton of fun – I mean, how much time do you have off? You’ll want to get the most out of it!

These tips are the Cliffs Notes of my website – covering, in a very simplified way, all of the essential things you can do to make sure the good times roll when you’re on the road. These can really help if you don't have time to read all the articles on this website.

Fun Road Trip Vacation Planning Tip – Vacation Destination Agreement:
Want your road trip to be fun for everyone on it? Make sure that all of you agree on your destination. This may seem like a no-brainer, but it’s really something that people blow off – either because they’re the one planning the trip and the destination is one they’re really excited about visiting (and they end up forgetting about the rest of their group in their excitement) or they just don’t take the time to talk it out with their traveling buddies or family because they’re so busy.

Even if they do briefly talk to each other about the trip, a lot of people smile and agree to go to the selected destination just to get along, but they’re really not that interested. Other people suggest different destinations only to have their suggestions shot down. Others come out and say they’re not interested in the destination, but their opinion is ignored or the subject turns into an argument.

There’s a lot of talk about compromise being so essential to relationships, but really it often means that one or more people don’t enjoy or are even unhappy during their vacation. That’s just plain wrong. Everyone on your road trip vacation matters – take the time to select a destination that you’re all excited about.

Fun Road Trip Vacation Planning Tip – Avoid Hauls Like the Plague:
To make your road trip truly great, you’re going to need to plot out a route that includes a lot of stops along the way – for both each stop’s entertainment value and to break up all that time in the car. Long hauls trying to get to your destination as fast as possible with very few stops are not fun – in fact, they suck. Everyone ends up crammed into a car for hours losing feeling in their legs and feeling more murderous by the minute. Sound like fun to you?

How to avoid long hauls:

  • Pick a destination that is closer to home so you have more time to spare on the road.
  • Fly to a location closer to your destination and rent a car for your road trip, giving yourself more time to enjoy the road.
  • Take more time off from work/school/your life if possible – ideally two weeks. I know, I hear you – two weeks? I can’t go away for two weeks! I’m here to tell you: yes, you can. The world will not fall apart at work, school or home without you to hold it together. No one is indispensable; it’s a fantasy that’s a double edged sword. It may make you feel important, but it also makes you a slave to your day-to-day grind. The longer you spend away from it all, the more relaxation you’ll enjoy and perspective you’ll gain.
Need help plotting your route? Check out my article Map It! for tips. Want a Cliff Notes version? It’s all about stopping a lot along your route and seeing everything there is to see. That’s what a road trip is all about. If you wanted to get there as fast as possible, you’d fly!
Fun Road Trip Vacation Planning Tip – Stay Somewhere Fun:
Besides going to a great destination and stopping at every interesting sight along the way, plan to stay at fun hotels. These do not need to be expensive – in fact, some of the coolest places I’ve stayed were mid-range as far as rates go. One option is to stay at older places (and often cheaper) from the 40’s, 50’s and 60’s for that retro feel.

More than the hotel itself – where is it? Try to stay in places that either have great views or are located near sights or interesting towns so you can sightsee where you’re staying. Also, if you can afford it, see if they have a room with a Jacuzzi or some other cool thing that will make your stay unique. You don’t have to spend every night this way, but it will add a lot of flavor to your vacation. This is an important road trip vacation planning tip that people often neglect, but can really make a difference.

Fun Road Trip Vacation Planning Tip – Games and Songs:
Adding road trip games and songs are surefire ways to make your road trip incredibly fun. In addition to all those great places you’re seeing, you’re having fun on the road as well as at the sights and stops along the way. Everyone will get in the spirit of competition and next thing you know, you’re having a blast!

As far as songs go, you may think that you’ll just talk and listen to the radio, but it really won’t be enough. Everyone gets talked out, and on a road trip you’ll be spending hours together with more than enough time to talk.

The radio is not reliable – I’ve been in areas that I could only get three radio stations and all three of them didn’t have anything appealing – one was all-mouth-harp all-the-time, one was a preacher (no offense to the religious out there) and one was basically an hour-long commercial for milk.

Fun Road Trip Vacation Planning Tip – Food Glorious Food:
Make sure when planning your trip to include great and unique restaurants along the way. Some of my fondest memories are the funky little diners and the places offering local cuisine and other products from the area where I was traveling.

For example, I was in Vermont on a skiing road trip, and we went to this place called Maple Sugar and Vermont Spice (Sugar and Spice for short) in Rutland that has huge vats in the middle that are used for making maple syrup and a cute gift shop offering all things maple. The food was delicious – especially the maple syrup (obviously) – but it was also the feel of the place. It’s a rustic wooden house with lots of floors/levels so there are spots all over where you can sit, eat, and watch them make maple syrup. The air smells of bacon and syrup – breakfast itself. To top it off, it’s a local favorite that’s packed with people who live in Vermont, not just visit it.

Eating out in places that offer the cuisine of the area that you’re visiting makes your trip that much more special and will forever stand out in your memory. Get out of your usual rut and try something new! Even if you’re on a budget, there are ways to make sure your meals are memorable – just try these frugal road trip tips for dining.

Use these road trip vacation planning tips (even better, check out all the resources on this site to help you plan) and you’ll have the best road trip ever!


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