How to nail a dream trip with senior parents

Growing up, my family rarely traveled for fun. My parents immigrated to Canada from Korea when I was 5 years old and, like many immigrant families, spent most of their time working to provide a better life for my brother and me. Vacations weren’t a priority.

But in the summer of 2021, after a too-long time apart because of Covid, my parents and I decided that it was finally time to take a trip that we’d talked about half-seriously for years: a 14-day tour of Italy and Portugal to soak up rich history and culture (we wanted to give my dad the chance to practice his self-taught Italian).

But we needed to lay out our plans carefully to ensure the trip accommodated widely varying sets of needs: While I am a spontaneous 40-year-old solo traveler, my parents are both over 65 and have underlying health conditions. What we do have in common, however, is a love for Renaissance art and a deep commitment to prioritizing local spots.

With a bit of extra care and patience, our multi-generational family trip became one of my most cherished experiences. Here’s how we made it work:

Long-haul flights can be a hurdle for older travelers who aren't as mobile as they once were or who aren't as comfortable sitting for for long stretches. Before diving into flight research, my parents and I had a frank discussion about how long felt like too long for them—a convo that helped bring potential destinations into focus and helped narrow our choices.

My parents are both early risers: A 7:30 a.m. flight from Toronto to Lisbon worked for us because it was not only a direct flight, but the early departure time meant minimal traffic en route to the airport and fewer crowds at check-in.

With an almost-10-hour flight home from Rome looming as a cap to the trip, we know we'd have to splash out on more legroom: The $100 more per ticket was a real boon, allowing my parents to stretch their legs. But the upgrade also came with other perks: priority boarding, first dibs on in-flight meals, and (best of all, perhaps) unlimited snacks.

Tip: Your standard travel insurance may not cover all pre-existing medical conditions, so be sure to read the fine print and consider purchasing supplemental medical insurance. We didn’t have to use ours—no emergencies, thankfully—but just having it offered us major peace of mind.

Both my parents suffer from chronic knee pain, and neither is comfortable walking long distances. Anticipating that we might need to do more walking at the airport than we’d anticipated, I requested two wheelchairs through our airline at check-in, just as a precaution.

Travelers have the legal right to wheelchair assistance at airports, so if that's you or your folks, pipe up and don't be shy about it. And if you think your group might need a wheelchair at any point after landing, be sure to contact tour guides, hotels, and other vendors before finalizing your reservations.

My parents were exhausted from the flight when we landed, but luckily we didn't have anything planned on Day No. 1—a golden rule for me when I travel. That means no scheduled activities; just time to rest and recover. Don’t overbook outings, either—one activity a day was the sweet spot for us, allowing some room for spontaneity without overwhelming my parents.

A flexible itinerary is also key. Throughout our trip, our plans were constantly changing depending on how my parents were feeling. We had to cancel a couple of excursions like climbing to the rooftop of the Duomo in Milan and a hiking tour in Portugal. I ended up doing some of that solo while they rested. Other tips: Book tours with lenient cancellation policies, and nab early-morning time-slots if you can, when most major sites are usually the emptiest.

We reserved a private transfer for the roughly three-hour drive between Florence and Rome, and our driver carried our luggage, made restroom stops along the way, and dropped us off directly at our hotel. We napped peacefully in the car—a much-needed vacation indulgence that felt well worth the expense.

We found the same sort of comfort and flexibility in private guided tours. In Cascais, Portugal, we put ourselves in the capable hands of André of Shortcuts Tourism Portugal, who picked us up at our hotel, built a custom itinerary that was specifically designed to minimize walking, and nimbly adapted his tour for the comfy confines of the car when it became unpleasantly windy outside.

A hybrid apartment-hotel designed for large groups, Martinhal Lisbon Chiado felt like plush home base, with an oven, a fridge, and the vacation Holy Grail: a washing machine. We also had access to typical hotel perks like a concierge and room service. In Florence, the connecting rooms at Irene Firenze - Hotel Savoy, a Rocco Forte Hotels allowed us to form a de facto suite while still maintaining some much-needed privacy (and sanity). The rooms were also large (hotel rooms in Italy can often feel small, and not in the charming way) and there were plenty of dining options that catered to my parents’ specific dietary restrictions.

Tip: For older travelers with limited mobility, a convenient location is a must. Irene Firenze was a five-minutes walk from the Uffizi and other key Florence sights, meaning my parents didn’t need to exert unnecessary energy on foot.

When I lost sight of my parents as we were walking around the dense, crowded St. Mark's Square in Venice, my heart skipped a few beats. Then I spotted my dad, with his light-pink T-shirt and bright-white hat. I'm not saying you need to walk around in matching neon tank tops—that is, unless you want to—but eye-catching clothes can be an easy way to keep everyone together. Plus: style points.

Tip: The app Life360 is also helpful with things like this, allowing you to track your parents with real-time-location mapping.

My dad is a published photographer, but it’s been some time since he last wielded a camera (let alone a digital one). To make sure we had frame-worthy prints—beyond the smudged selfies—I booked a private session in Rome through a service called Flytographer, which connects travelers with professional photogs in more than 350 destinations. Five days later, like magic, we got a batch of edited photos—perfect for blasting out to friends and family as a not-so-humble vacation humblebrag.