Traveling With Your Parents, Successfully

Every year, for the last five, I have taken an annual trip with my parents. These trips will likely be the most lasting memories that we all have together, but it took years to understand how to do it right. We primarily travel with our parents as kids and then somewhere between college and adulthood, family trips get disjointed or dismantled. There may be a family gathering at a resort here and there or a weekend get-together but actually traveling, on a cultural, adventurous trip as adults is an endeavor that you have to put real effort into. Trips with grandchildren often take precedence, or just simply not traveling at all, as that becomes the easier way to spend time together within busy schedules. But leaving the daily grind behind for a few days away with your aging parents is quite possibly the only chance at concentrated, real time together, that I highly recommend. As you get more trips under your belt everyone’s comfort levels increase and the fun begins. The first year, and even the second, can be bumpy. Each year gets smoother. In our family, I do all of the planning, it works best for us that way, but I always love hearing how others trip plan, so share your wisdom!

We decided out of the gate that we wanted to visit a large European city every year. That became our format. We go for a week and often times stay in one singular city the entire time. Sometimes we add one excursion like the Costa Brava from Barcelona or Hydra from Athens but we try not to hop around too much. A key to a successful trip for us is staying put. Given the age of my parents, the long haul flights are hard enough to recover from so everyone is usually happiest if we don’t have to unpack, repack and move multiple times. On a few of our earlier trips, I was the driver between stops. It was stressful. We soon opted for a local driver when moving between destinations. It alleviates the pressure of navigating it all in a foreign place, and having the old family dynamics flare up. Pay attention to logistical pain points while traveling and correct them on the next go around. Most travelers these days want to pack as many places in as possible while seeing a region. Our most successful trips have been to Paris and Rome, for both we stayed in a single, large hotel room (two rooms works too) for a full week, never moving (Relais Christine and Martius). This gave everyone a comfortable home base that we all knew how to get to. Which brings me to another takeaway from the early trips we took…all parties need to know how to get back to the hotel on their own.

I can now pinpoint the qualities in my parents that I find challenging and know how to (mostly) curb the friction that causes our less-favored selves to appear. My dad wants to know that our airplane seats lay flat and that we have the largest room in the hotel. Those are always his two greatest concerns. He knows that I will find the versions of those at the best value so doesn’t worry too much about cost. This is not the way we traveled when I was growing up and it’s a treat for everyone now. My dad wants to comfortably wake up hours before everyone, have his coffee, and move around without concern. He usually has one request for a place he wants to go and see, be it a museum, ruins, somewhere he stayed or remembers from childhood, and that one thing cannot be missed. My mom’s anxiety builds and builds leading up to a trip. She starts obsessing over a small thing or two months in advance and then goes ham just days before the trip. It always blows over by the time we actually leave for the trip and she is a pleasant traveler who is always up to go or do anything once on the ground. My mom also wants to know that we have dinner reservations at the restaurants her tennis buddies have been to and that we can stay at the hotel that one of the morning show talking heads stayed at recently. I try to honor the tennis buddies, less so the talk show hosts.

We keep the itinerary of the trips fairly loose. There are certain “musts” to book prior to departure. I book dinner reservations for the majority of the nights, usually leaving two nights free. I block out our days based on neighborhoods and loosely plan a few things within that neighborhood to see or do. In our case, we all like to shop, even my dad, especially my dad, and it’s a neutralizing activity for us. Everyone can meander within a small radius and it’s a way to be together but not all that together and then we reconvene at a nearby cafe. I usually plan the daily jaunts between 10 am (after everyone spends time on their own early morning) and 3pm, after which my father usually goes back to nap, and my mom and I carry on. By 5ish we are all typically back at the hotel for a relax and refresh and then dinner about 7.

On the first few trips, every item on the itinerary, every meal we had, felt like it had to be the BEST. Now that everyone is more used to the cadence and has a broader swath of memories from each trip, there’s less pressure for every bite to be amazing or every day to be monumental. Great meals, mediocre meals, the most memorable days, horrific travel days, things start to feel less dramatic and all part of the experience. The more you travel, especially later in life, the more comfortable you are stepping into the foreign and unknown. For me personally, I have also learned to carve out windows of time to myself on the annual trip. I schedule blocks of time for all of us to go and do our own things, as I know that my own happiness and enjoyment hinges on some independent wandering and exploration. Also do not be fooled, I would say that we are bickering, still, for a good 30% of the trip. Because what would a trip with your parents be without it? But I can actually say now that in the memories from the last five years of the annual parents trip, I cannot remember a single disagreement we got into but I do remember every walk we took, site we saw and bite we ate. Call your parents! Ask them if they want to take a trip!