Expert Tips from GoTravelDaily for Planning Multi-Generational Family Vacations

Inspiring Family Holidays Around the World

Family holidays are an amazing way to bond and spend quality time with your nearest and dearest. Planning a trip to accommodate multiple generations can be tricky, so we gathered insights about memorable trips taken with families, sharing experiences that highlight what worked and what didn’t.

San Miguel, Mexico

Sheeka Sanahori, Director of Video

My parents used to live in San Miguel de Allende before they had me. They had always dreamed of revisiting but had not in about 40 years, so I took them along with my 3-year-old son. I frequently travel with my husband (who had to work during this trip) and son, but I had to plan some things differently for this trip. Transportation was a big change; normally my family takes public transport on trips, but since my parents are in their 70s and my dad (77) has mobility issues, we opted to rent a car.

We flew into Mexico City (CDMX) and drove to San Miguel. I researched this trip extensively to ensure the hotels didn’t have steps, which are challenging for my dad. I still ended up having to ask the hotel in CDMX to change his room because there was a significant step up to their bathroom. My parents were amazed at all the technology I used to make the trip possible (Uber, Airbnb, and other phone apps like maps.me).

I ensured we took a slower pace on this trip to avoid wearing out my parents. They had to adjust to vacationing with a toddler, meaning stopping for naps and the occasional temper tantrum. My parents enjoyed showcasing their Spanish skills (they still remembered!) and sharing with my son and me their nostalgic memories. They had numerous wonderful stories about their time living in Mexico, and it was fulfilling for me to learn more about their lives.

Morzine, France

Jess Cole, Commissioning Editor

It was my dad’s 70th birthday wish to gather the entire family for a week-long ski trip: him, my stepmum, two of their friends, five sets of grown-up offspring with their partners, and four children – including our own son, then a mere 9-week-old. I’ll admit to a degree of new-parent anxiety as the trip approached; however, it ultimately helped break us out of our comfort zone. A few years earlier, my dad had become an amputee; there’s nothing quite like witnessing a septuagenarian parent learning to paraski, which shifted my ‘world-revolves-around-the-baby’ mindset.

Amtrak Tour, the US

Meghan O’Dea, Digital Editor

My grandmother was an irrepressible traveler and train enthusiast. It was her dream to take each of her grandkids on a special trip. As the oldest grandchild, I received the inaugural and most ambitious outing – an Amtrak tour around the perimeter of the United States (one of the world’s most amazing train journeys).

I was twelve years old, and it was my first time traveling without my parents. The trip was manageable for my grandmother in that the train was a contained space where we could sometimes do our own thing. Meals were handled in the dining car, we had our sleeping compartment that converted to a living room by day, and the observation car where we could meet fellow passengers.

During city breaks of a day or two in New Orleans, LA, San Francisco, and Denver, we stayed in hostels and enjoyed inexpensive meals like ramen, oatmeal, and instant soup heated up on a communal stove. My grandmother provided me a wonderful gift through this experience. She not only instilled her love of exploring new places but also taught me the art of thrifty travel she had practiced since she was a teenager. We walked everywhere, did our laundry in the sink, and carried everything we needed in our backpacks. To this day, I travel much the same way, whether going solo, showing my parents around Portland, or introducing my aunt to Greece on her first trip to Europe.

Disney World, Florida

Amy Lundeen, Senior Editor, Video

My sister and I organized our first family trip to Disney World last year for our families and my mom. Our group ranged in ages from 6 to 76, with some teenagers included. Knowing that Disney offers fun for everyone, we also understood my mom’s concerns about walking and food. Therefore, extensive planning took place before our visit to minimize worries upon arrival. Key smart moves included:

  • Choosing a hotel with a pool
  • Avoiding overplanning
  • Researching food options in advance, particularly considering food allergies, which Disney was very accommodating for.

During our free time, my husband could venture off with the teenagers to the thrill-seeking rollercoasters while my mom found a shaded spot for a snack, and I took whoever was left on another Star Wars ride (my favorite). The only hiccup we encountered was my family of four catching a stomach bug; however, we made lasting memories from the trip overall.

Ireland

Matt Phillips, Digital Editor

My father lost his dad to cancer at the age of one, and he and his two older brothers were raised by my grandmother (known endearingly to me as Nanny Phillips) in a poor neighborhood of Belfast. In his early 20s, he followed his middle brother to live in Canada during the Troubles in Northern Ireland, where he met my mother (who emigrated from England). I was born in Mississauga, but grew up in Vancouver.

A poet, storyteller, and romanticist, he dedicated countless hours of my childhood sharing tall tales of his adventures along the Antrim Coast, through the Mourne Mountains, and around the bogs of Belfast. He also recounted the many hardships he faced in the city. Understanding his creative nature, I’m unsure if I fully merited many of his fantastical tales. Yet everything came to life in 1997 when I traveled to Ireland with him. We explored his old street, revisited his stomping grounds across Northern Ireland, and ventured south into the Republic. It was a magical three-week experience. I not only discovered my father’s homeland but also gained deeper insight into his character.

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