Practical Tips for Planning a Trip with a Senior

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I have often wondered about the expression “the devil is in the details”.  Instead, I have always said, “God is in the details” because, at the end of the day, you want trip plans to fall into place beautifully. Seamlessly. Effortlessly.  It is NEVER perfect but if you pay attention to the details you will find planning a road trip with a senior will always turn out better.

I found myself obsessing over flights. Fly into Barcelona or Madrid? Start in London and then fly down to Madrid? Should we even go to London? Where do we go when we finish up in Madrid?  As it turns out, we are flying into Barcelona, taking a train flying to Madrid and at the end of our bus tour, flying from Madrid to Porto.  The bottom line, is I have a beginning/middle/end but I don’t have all the details ironed out.  Not yet.  But I will very, very soon because I am a planner.

Travel Planning for a trip with a senior to Europe @DownshiftingPRO

I have been accused of micro-managing.  It is a badge I wear both proudly and with shame.  When I was a full-time professional organizer, having planning skills, and being able to look at the bigger picture was a bonus.  But it also means that I like things to happen in a particular (some would say, systematic way).  Why? Because I view every possible ‘worst-case scenario’ and weighed out the pros and cons of it all.  I have a few strategies I use to plan an epic trip.

Tools for a Trip with a Senior:

Pinterest Board

Trip with a senior - Intergenerational Travel

Mine tends to involve creating a Pinterest board which holds all of the pins to blog posts that I may want to read.  Here is my Road Trip to Portugal and Spain board which I created for this trip.  On it are suggested itineraries, travel tips, must-see locations, foods to try, and cheap ways to get around.  You name it and it’s likely on my board.  This is my digital note vision board for my trip with a senior.

Google Maps

If you are unsure how to get from point A to point B, there are two very helpful tools: Google Maps and Rome2Rio. The first is your standard lookup on the internet giving you various route options, time traveling and suggested hotels and attractions. If you use the street view, you will see what the street should look like (including buildings, and landmarks) to help guide you.

If you are looking for a particular address for AirBnB or VBRO, you can see what the house looks like. You can also create Google Maps for your journey with added attractions or restaurants along the way. In this travel itinerary post (10 Best Things to do in the Saguenay Fjord Region of Quebec) you can see how I used Google Maps to plot a route.


Rome2Rio is a website and app that helps you find the best way of getting to a particular spot. For example, if you wanted to get from Madrid to Barcelona, it will give you options for car rental, public transit, buses, planes and trains. The variety of options can help you narrow down the options quickly.


I also have an actual notebook where I write down all the things I have to see (a summary of places, restaurants, and events).  I find it easier to just write it down, use tabs to keep things separated, different colours to highlight important notes.  I also hand it over freely for friends to write notes about their past trips, travel tips and suggestions.  I refer back to it when trying to remember the hot chocolate and churros bistro – did they say it was in Madrid or Barcelona?

The notebook may also have important information about reservations, addresses or info that I made need should I drop my phone and break it (It could happen and I’ve planned a 3-week trip).

Guide Books

As much as I love apps and having a guide in my pocket, for me there is nothing like having a guidebook to look at.  I read it better, I can look at the table of contents and I can also place little sticky bookmarks for my reference later on.

I am a fan of the DK Eyewitness To 10 Series.  As this is a very quick trip which covers many destinations, it is great to have a professional reference for what I need to see or do.  What is THE MOST IMPORTANT?   I love the Top 10 Andalucia and the Costa del Sol.  I will likely carry at least one or two guidebooks to read on the long bus rides from point A to point B.  An added bonus if you are a visual learner, like I am, seeing the picture of the building I am looking for or the street reference is gold.

Travel Guides @DKCanada @RoughGuides @DownshiftingPRO

Paper Maps

I am fully aware that paper maps are old school but there is something beautiful about being able to lay out a map and see the bigger picture.  I do that well.  I like to see which road leads where and how I’m going to get there.  It is also helpful when you are searching for villages or cities to stay in so you don’t have to keep moving around.  A map can also help the family when you are away.  I plan on marking one up so they can follow along with where we are.  My husband is not on social media so getting updates on Facebook, Instagram or even Twitter is not really an option for him.  I know my girls will be showing him my updates but this is a better way for him (and I to keep track).  If it’s Tuesday they must be in Sevilla, right?


When traveling with a senior, it is always advisable to get travel insurance.  Even if you are not a senior, it is best to always have travel insurance. Period. I am covered both through my credit card and my husband’s benefits.  Make sure and check out your options before your travel.

My mother, on the other hand, is not, so coverage for her is mandatory. It can be both reasonable and expensive depending on your age and ailments but there is no doubt that it is a necessity.  You can get insurance through various carriers so be sure and shop around.  You can get insurance through the tour operator you are using.  It was less expensive than going with a bank policy.  Check out CAA or Alliance.  Take out trip delay, trip cancellation and of course medical.


Both my mom, sister and I take meds at some point in time during the day.  Getting a scrip with all of the meds and a letter from your doctor is a very good idea.  If for any reason we need to get meds refilled, we have the English name at the very least and can then get the translation done if need be.

We will also have my mom’s meds in a blister pack so everything is measured out evenly. The blister packs that we receive from the pharmacist have both a picture of what the medications looks like as well as the dosage.  So it is clearly illustrated.  I am considering bringing a few in containers so that we can show those also.

Don’t forget the over-the-counter meds: Tylenol and/or Advil, Immodium, antacid, Robaxacet (for back pain) and maybe even a topical muscle relaxant cream.  All of the OTC meds are likely available wherever you are traveling but it is better to carry what you are used to.

Clothing and Footwear

I cannot stress enough how important it is to wear comfortable shoes when you are traveling.  Your body takes a toll when you walk on cobblestone streets.  As I’m with my mother, the importance of having a good pair of shoes that provides stability in order to prevent a fall is utmost in my mind.  We have purchased a few pairs that she found stylish enough but a good travel shoe is not just about style, it’s about being lightweight and can be worn for hours! I have seen a few of my travel friends with Skechers and have decided to try them out for myself. So far I love them.

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You always need to bring at least one pair of ‘fancy’ shoes for those nights when you want to go to dinner and be a bit more dressed up.  I purchased a lovely pair of sandals with good support in a neutral colour.  Now, I just have to schedule a pedicure.

Your choices of clothes when you travel for 21 days should be limited.  Work with a specific colour palette and build from there.  You can search for a capsule wardrobe and see tons of ideas on how to build your outfits out of a handful of basic pieces and accessories to dress them up or dress them down.

I have based most of my wardrobe on two colour choices grey/white and tan/black.  This gives me a variety of outfits without caring to much.  Be sure to leave space in your suitcase because you will find a way to bring back one or two pieces for your wardrobe.

Planning a 3 WEEK trip

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Travel Documents

First things first, take a picture of your passport and send it to someone you trust.  You may need to have that information should your passport go missing.  Secondly, write the information down in your notebook.  You will be asked by the travel agent, airline and hotel for your information.

Print out confirmations for hotels, car rentals and tours which you have booked.  You may not have data or WIFI available when you need confirmation numbers.

Have the itinerary of your tour available so you can review where you will be and when.  You tend to lose track of what day of the week it is when you travel.  When taking a taxi ride it is nice to have the address written on the reservation so there is no confusion on where you are going to end up.

The best advice I can give you is to read a lot of travel blogs.  They are full of great advice and can help you find gems you never knew you had to see.  Ask your friends if they have been and if so, when did they go, what did they do, and what are their best takeaways from the trip.

I look forward to sharing a few pictures from my trip to Spain and Portugal to show you what I have put together.

Bon Voyage!

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Margarita Ibbott is a travel and lifestyle blogger. She blogs about travel in Canada, the United States and Europe giving practical advice through restaurant, hotel and attraction reviews. She writes for and other online media outlets.