Baby Boomer Travel, Over 50 Travel, Travel Tips

DIY Travel Plans

We like DIY travel plans. We really appreciate doing exactly what we want, when we want. Just showing up and flying by the seat of your pants often ends up with a lot of confusion and wasted time. Especially if you are a baby boomer, that kind of a vacation sounds miserable. Then having a travel agent make your plans or going with a tour can be a little to restrictive. Making your own travel plans is perfectly in the middle and much easier than you think, especially when you have the right tools.

We start making our travel plans about 4-5 months ahead of our departure. I’m going to share with you step by step how easy it is to do. Get your bucket list out and let’s get organized.

Organizing Travel Plans

I like to print myself up several blank calendar pages off the internet. You can find them for free and they will have the month and year. Look for ones with individual big day spaces. This really helps me to see the trip as a whole. I can make notes about what we plan to do on each day, tours, driving, stuff like that.

A notebook is really important too. I scratch out all sorts of ideas as I build our plans.

One of my very favorite  tools is an app is called Tripit. I love it! As we finalize all of our plans, we simply forward the details to Tripit and everything is organized into a neat little itinerary. Tripit will notify me if there are any problem areas, like a layover that might be to short. It keeps all details in one place, including flight #, seat assignment, train tickets, hotels, check-in and if there are any changes to any of these.

diy travel planner

You can also manually add details and make changes. Then when you are traveling, as you complete each portion of your journey, they are removed from the schedule. Neat and tidy.

Vacation Destination

Choosing your destination is the first step. Your bucket list is probably filled with dream vacations. Once you have a couple of options, research the best time of year to visit your desired destinations. This is an important factor in making your final choice. You will want to consider crowds, temperature, rainfall, etc. Everyone’s choice in this regard will vary so there is no right or wrong here.

Travel Route

Now that you know where you want to go, begin doing research on what there is to do in the vicinity of the country and cities that interest you. I like to use my notebook and make notes that include interesting cities and what there is to do there. This helps me to narrow down locations that are most interesting to us. Tour ideas are good to make a note of now.

Doing this step really helps to narrow down what places are highest on our agenda. We can’t see everything, so look for locations that give you the most bang for your buck.

Once you have some sort of rough idea of what you want to see, begin making a rough draft of the route you will take. Do research on whether you should drive, fly, take the train or use some other form of transportation between your various cities and countries. Again, scratch this down on paper  in your notebook. At this point you should still be several months out, so you can mull things around, and really research all the cool things there are to do and see.

Primary International Flights

Once you know the where and approximately when, start looking for your flights. I like an app called Hopper. It’s really easy to use and I can set it up to monitor prices as they change. It will tell you when is the best time to buy. I don’t particularly use Hopper to purchase our tickets, but it pays attention to pricing when I am not.

For international flight you want to start looking for your tickets beginning about 120 days out in order to catch the best airfares. Hopper will tell you if you should wait or buy now. Tuesdays, late is a good time to find the lowest fares, but in my experience, there is not any hard and fast rule. I let the Hopper guide me. You might have another favorite way of monitoring airfare prices.


Once I have booked my international flights, our plans are really taking shape and I begin looking for our accomadations. Occasionally we fly in and out from different cities, but more often than not it’s a round trip. The inside plans from here can still be somewhat fluid, but by now you should have a pretty good idea of where you will be and when.

Once you know how many days you would like to stay in each location, you can begin moving forward with your bookings. What kind of accomadations do you like? Lot’s of choices, depending on your taste and budget. There are hotels, vacation homes, bed and breakfasts, and hostels.

I use several options for booking accomadations., Expedia, VRBO and I’ve used AirBnb quite a bit and we have never been dissappointed with any of our accomadations. I try as often as I can to find accomadations that have FREE cancellations just in case we change our minds about wanting to go here, rather than there, etc.

Fun Details

Once we know where we will be staying, we start filling in all the fun details. Unless you plan on tours, most of this is very fluid. So as an example, on my little calendar print out I will start piecing in the sites that are must sees. When we were in Rome, Italy, it was The Vatican Museum, the Colloseum, Trevi Fountain, and the like. Whatever your must sees area, put them on your schedule but don’t pack to much into one day.

All along the way, feel free to add them to Tripit, because you can easily make adjustments if you change your mind,

Then little things like shopping, dinning, smaller sites, they can just be slipped in here and there as you have time.

6-8 Weeks Out

Getting really close now. Destination -> done, Route -> done, International Plane Hlights -> done, Accomadations -> done, Tours -> done.

Are you going to get travel health insurance? We recommend it. No one plans on getting sick or injured, but it does happen. Now is the time to shop around.

Now, how are you going to get around? If you are going to fly, take the train or rent a car and drive yourself, you want to finalized those plans. Don’t forget to consider how you will get to and from the airport, both from home and while abroad. Once these details are completed you are pretty much done. All you have to do from here is plan on what you will pack.

travel luggage


Once you are blissfully on your vacation, where to eat becomes very important. Really simple too. Use Yelp! It has worked great in every country we have been in to date. You can even be standing on a corner somewhere in France and it will tell you what restaurants are near you, how far away, all while meeting your criteria and Yelp even gives you real customer review ratings. They have pictures of the food too in most cases.

So, there you have it! You are going on an amazing vacation all done your way because you did it yourself. Have a wonderful time and come back and let us know how you did!


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