Traveling as a family has given us the incredible gift of adventure, lasting memories, time to bond in new ways, and seeing the world together with fresh eyes. While shorter trips are relatively straightforward to plan, embarking on an extended journey requires a little more thoughtfulness and preparation. We recently returned from a five week trip in Italy as a family and here are some of the biggest tips I have to share.


Pack Light

Pack half of what you think you will need. We were gone for five weeks and I should have brought clothes for two weeks and then just wash them. I really wore the same things over and over. What I wear at home is what I wore in Italy.  This may not be true for you but I tend to have ideas of travel Jeanne but what I wear is pretty much my same style that I wear at home. The whole family agrees with this and we all will pack less next adventure. Packing examples: 1 jeans, 2 skirts, 3 dresses, 3 shorts, 7 shirts, hiking clothes, pajamas, 1 lounge outfit, swimsuit and cover-up, trench coat, 2 sweaters, umbrella, vans, flip flops, nice tennis shoes. It is also fun to pick up a few things while traveling if you really find that you are missing something.


Have Realistic Expectations

Unless I am on an art retreat (and not teaching), I go off to create art by myself or once the kids are not on a trip with us…I will not make a lot of art while traveling and that is because I want to be with them. I brought a suitcase full of supplies with ridiculous ideas of how much art I was going to make. That amount of art would have only happened if I ignored everyone the whole time. My regular creative process is to create alone so that would have been counter intuitive to my environment. When I did create it was me doing quick studies, contour sketches, quick captures with watercolors etc. Next time I will only take one art journal, pencils and watercolors. If it fits into a makeup sized bag it is allowed to come along, otherwise it needs to stay home. It added physical weight, took up space and then emotional weight because I felt guilty because I wasn’t using everything I brought. And if I really, really, really want something I don’t have I can probably find it.


Don’t Forget Your Books

I bring one book for each week I am traveling. I brought more than that on this trip but that was because I was traveling in Italy and knew I wouldn’t have access to the English books I would want while along Lake Como. Three of the five of us are big readers and I recommend everyone have a book on them when we are out and about because we will have opportunities to rest at a park, have a cappuccino in a cafe or even those little moments here and there when we are waiting for the ferry/train/bus etc. It is a really good habit to get into to not reach for your phone during those moments and to reach for your book instead. Part of the joy of travel for me is getting to read more so on this five week trip I was able to read six books. Some of you may read more, some of you less…the point is that if you love to read make sure you bring them along and a little here and there means finished books. Even if you are not a big reader I think you will love having one on hand for all of those little moments throughout a trip when you have rest or waiting.


Everyone’s Voice Counts

Fight for everyone on the trip to do something they really want to do and then when when we are doing those things (even if you hate it) you shut your mouth and show up for each other. We travel well together because we fight for the things that others want and may not be saying. I am very vocal about what I want to do. Others in my family not so much so I have to make sure they are heard and we create experiences for them too. It is the showing up part that really matters. Doing it but complaining the whole time is not a gift. Show up and love them well by participating with a smile on your face. Whether we were visiting an art museum, singing along at a Harry Style’s concert, at a car show, checking off special places in Harry Potter or a million other things…we did it together and with a good attitude.


Have Breaks From Each Other

Give people the freedom and permission to go off by themselves. No strings attached. Once a week we had a whatever you want to do day. We all ended up coming back and being together but knowing we could go off and not feel guilty was really important. Some went to lay out in the sun, some to the cafe to read,  to the park and make art, others would nap, workout, take photos etc.


Create Routines

I am a very routined person at home and I need it while traveling an extended time too. We walk so much while we are in Italy that I don’t need to make sure that gets included each day but things like my morning routine, flowers in the house, getting our work done in the morning, keeping our space picked up, meals at home for some of the week, what days we will walk to the markets (we got a cart this year), what we expect and need from others in the family etc. Get everyone’s input on what is important to them and what helps them to feel settled. I have found that all five of us have different routines and how we go about our day and honoring that has a lot to do with how we take care of ourselves and each other. A routine helps create stability and a sense of familiarity, reducing stress and making the adventure more enjoyable for everyone.


Space For Everyone

This may seem like a no brainer but it can be hard to find spaces for a family of five here in the US and it gets even trickier in Europe.   Most places are made for four at the max, so Benjamin (being our youngest) was often on pallets on the floor, couches etc. when he was littler. Now that everyone is grown we work harder to find a place with space for everyone. We had airbnbs in Italy and then a family hotel room while we were in London (one full and three twins all smooshed in a room but everyone had a bed!). Separate spaces with doors is a true luxury but get them if you can. The longer the trip the more you will appreciate a space that fits your family.


Everyone Carries Their Own Gear

Whether you are at an airport, traveling from city to city, on and off a train or a million other examples…everyone should be able to EASILY travel with what they bring. You may want to pack lighter than this but we have found that each person having a medium to large suitcase and backpack needs to be the max. This is especially true if you are changing apartments/cities etc. When we travel with more than this we truly look like the circus has come to town as we are getting on and off trains. Don’t be the Olivers and look like a circus:-).


Ebb and Flow Between Activities and Rest

When we travel do we want to get back from our vacation and need a vacation? No! You will never see it all anyways, so be ok with not trying to. Every person in our family has a different idea of what a vacation is, so we really try to schedule things around those that want to read at the cafe, see museums, layout at the pool, workout etc. Maintain a loose itinerary that allows for spontaneous discoveries and adjustments along the way. Be open to unexpected experiences and take advantage of opportunities that arise. Remember that the journey itself is often as rewarding as the destination.It is finding the balance between go, go, go and also just sitting in the sun all day. At the end of the trip do we each have beautiful highlights that include a kaleidoscope of the personalities that we traveled with? That is our heart and goal each time we travel!


Traveling well for an extended time with your family requires careful planning, adaptability, and a willingness to embrace new experiences. With a little bit of thoughtfulness, you can ensure a beautiful and memorable journey for everyone involved. Celebrate the joys of being together, and make the most of the opportunity to explore the world as a family. Happy travels!