Family Holiday Experiences

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 asked iBestTravel staff about the trips they’ve taken with their families, how they planned, 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 dreamed of revisiting but hadn’t in about 40 years, so I took them along with my 3-year-old son. Traveling frequently with my husband (who had to work during this trip) and son, I had to adjust my planning for this trip. Transportation was a significant change; while my family typically uses public transportation, we opted to rent a car because my parents are in their 70s, and my dad (77) has mobility issues.

We flew into Mexico City (CDMX) and drove to San Miguel. I thoroughly researched our stay, ensuring the hotels were accessible without steps, which proved challenging. I still had to ask the hotel in CDMX to change his room due to an inconvenient step. My parents were amazed at the technology I employed to facilitate the trip (Uber, Airbnb, and other useful apps like maps.me).

We maintained a slow pace to avoid exhausting my parents. They adjusted to the vacation rhythm, which included stopping for naps and occasional toddler meltdowns. It was a joy to witness my parents showcasing their Spanish skills and reminiscing about their old stomping grounds. They shared countless delightful stories from their time living in Mexico, enriching my understanding of their lives.

Morzine, France

Jess Cole, Commissioning Editor

It was my dad’s 70th birthday wish to gather his whole family for a week’s ski trip: him, my stepmum, friends, grown-up children and their partners, plus four children—including our own son, a mere 9-week-old at the time. While I felt anxiety as a new parent leading up to this trip, it ultimately broke us out of our comfort zones. A few years prior, my dad had become an amputee; witnessing him learn to paraski truly shifted my perspective from focusing solely on the baby.

Amtrak Tour, the US

Meghan O’Dea, Digital Editor

My grandmother was an irrepressible traveler and train enthusiast, dreaming of taking each grandchild on a special trip. As the oldest, I experienced the inaugural and most ambitious outing—a scenic Amtrak tour around the perimeter of the United States (one of the world’s amazing train journeys).

I was twelve, traveling alone with my grandmother for the first time. The train provided a contained space, facilitating independent activities. Meals were prepared in the dining car, and we had a sleeping compartment that transformed into a living room during the day. The observation car allowed interaction with fellow passengers.

During city breaks in New Orleans, LA, San Francisco, and Denver, we stayed at hostels and enjoyed affordable meals. My grandmother not only shared her passion for exploring new places but also instilled the practice of thrifty travel. We walked everywhere, did laundry in the sink, and carried our necessities in backpacks. This approach has influenced my travel style, regardless of whether I’m going solo, guiding my parents in Portland, or introducing my aunt to Greece on her first European trip.

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 included ages ranging from 6 to 76, with teenagers in the mix. While we anticipated fun at Disney, my mom expressed concerns about walking and food options. Consequently, we meticulously planned to minimize decision-making during our visit. Here are a few effective strategies we applied:

• Secured a hotel with a pool.
• Avoided overplanning to maintain flexibility.
• Investigated food options in advance, taking into account possible dietary restrictions.

During our scheduled free time, my husband entertained the teenagers on the thrill rides, while my mom relaxed in the shade with a snack, and I took care of whoever wanted to experience another Star Wars ride, which is my favorite. The only minor hiccup we encountered was our family of four catching a stomach bug. Nevertheless, we all cherish wonderful memories of the trip.

Ireland

Matt Phillips, Digital Editor

My father experienced significant life challenges; he lost his dad to cancer at just one year old and was raised by my grandmother in a humble neighborhood of Belfast. In his twenties, he moved to Canada amidst the Troubles in Northern Ireland and met my mother, who emigrated from England. Although I was born in Mississauga, my upbringing was in Vancouver.

My dad, a poet and storyteller, filled my childhood with riveting tales of his adventures along the stunning Antrim Coast, the enchanting Mourne Mountains, and the bogs surrounding Belfast. While skeptical about some tales, my skepticism faded when, in 1997, I traveled to Ireland with him. We explored his childhood streets and stomping grounds across Northern Ireland and the Republic, resulting in a magical three-week experience. I not only discovered my father’s homeland but also gained deeper insights into the person he is.