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I usually plan every family trip meticulously. Letting my father-in-law take over was the best thing I’ve ever done.

By Eric November 20, 2025

In a recent article, Janine Clements shares her transformative experience of relinquishing control over family vacation planning to her father-in-law, resulting in one of the most enjoyable trips of her life. As a travel writer and self-proclaimed vacation expert, Clements typically takes charge of organizing family outings, a role that often brings with it a hefty dose of pressure to create the perfect itinerary. However, during a family trip to Alvor, Portugal, she decided to step back and allow her father-in-law, a seasoned traveler to the area, to lead the planning. This choice not only eased her stress but also opened the door to unexpected delights in a destination she initially wouldn’t have chosen.

Alvor, a quaint former fishing village on Portugal’s southern coast, proved to be a hidden gem, offering a charming atmosphere with its whitewashed buildings and picturesque cobbled streets. Clements was initially concerned about the limited activities for her children, as she would typically opt for a livelier spot like Lagos. Yet, she was pleasantly surprised by the town’s offerings, which included delightful seafood restaurants and a selection of shops and ice cream parlors that kept her kids entertained. The family stayed at Pestana Alvor Praia, a large resort that provided ample amenities for all ages, from tennis courts to a mini-golf course, making it an ideal base for their vacation. Although the resort’s distance from the town center was a minor inconvenience, it also helped keep her kids’ shopping desires in check, ultimately benefiting the family budget.

Clements reflects on how her father-in-law’s relaxed planning style allowed for a more enjoyable and flexible vacation. With an itinerary that included both group activities, such as visiting local historical sites and enjoying water sports, and ample downtime for relaxation, the trip struck a perfect balance. This newfound freedom enabled Clements to bond with her oldest daughter before she left for college, creating cherished memories during a boat cruise to see dolphins and explore the stunning Benagil Cave. Through this experience, Clements learned the importance of stepping back and trusting others with the planning process, recognizing that it can lead to a more fulfilling and stress-free family vacation. Moving forward, she plans to embrace this approach more often, allowing herself the space to relax and connect with her family without the burden of meticulous planning.

I always plan our family trips, but I was happier when I let my father-in-law take over.
Janine Clements
I typically plan all our
family vacations
, but recently, I let my father-in-law take charge.
Although it was hard for me to let go of the reins, it turned out to be one of my favorite trips.
He did things a little differently than I would have, but it was nice to be able to relax.
As a travel writer, I consider myself a
vacation expert
— which means I like to be in control when planning family trips.
However, as the self-appointed trip director, I find the self-inflicted pressure to curate the perfect trip can get overwhelming.
For a recent family vacation, though, my father-in-law did the planning, including choosing the destination: Alvor, Portugal. It made perfect sense, as he’d been there several times with my mother-in-law, so he was familiar with the destination. Plus, he’s retired, so he had more time to plan.
Although I struggled to let go of the reins, it turned out to be one of the most enjoyable and
relaxing family vacations
I’ve been on.
Alvor wasn’t a destination I would’ve chosen, but I was pleasantly surprised by how much I loved it
Alvor is located on the southern coast of Portugal.
Janine Clements
Alvor is a small, former
fishing village
on the southern coast of Portugal. Although it’s gorgeous, I was worried there wouldn’t be enough for my kids to do.
If I were planning the trip myself, I probably would’ve chosen somewhere like Lagos, which is bigger and more lively. However, I knew I had to relinquish control and trust that my father-in-law would lead us in the right direction.
During the trip, though, I ended up loving the laidback locale. It felt authentically Portuguese, with whitewashed buildings lining its narrow, cobbled streets, and an estuary below, dotted with colorful boats.
We also ate at some great seafood restaurants, and I thought the prices were reasonable compared to what I’m used to back home in
New York
.
Surprisingly, despite its small size, the town center had some great shops and
places to get ice cream
, so my kids were happy, too. The experience definitely reminded me of the importance of not judging a book by its cover.
I usually book smaller hotels, but I really enjoyed staying at a larger chain resort
We stayed at Pestana Alvor Praia in Alvor.
Janine Clements
When traveling, I typically book smaller, independent hotels because I prefer a low-key atmosphere. For this trip, however, my father-in-law booked Pestana Alvor Praia, a large chain resort situated on a cliff overlooking a golden sand beach.
And as it turns out, it was perfect for traveling with a large group. The resort had great facilities with tennis courts, a gym, and a mini-golf course, which made it ideal for our family, especially my teens.
The only downside was that it was a bit of a trek to get to the town center. The positive, though? Although I would have loved to have been closer to the action, it was good for my wallet — because it limited my kids’ opportunities to shop.
My father-in-law created the perfect relaxed agenda
When I’m in charge of
planning a vacation
, finding activities that appeal to everyone is what I find most stressful. I can sometimes spend hours researching the perfect activities and restaurants, even when we’re away, which takes away from the enjoyment of the actual trip.
Other than
prebooking restaurant reservations
, I was thankful that my father-in-law kept our days wide open — a smart move, given the big age range (7 to 75) to accommodate.
It meant we could relax by the pool whenever we wanted, but also mix in group outings like visiting the Fortaleza de Santa Catarina in nearby Portimão, or trips to the waterpark and tubing for our thrill-seeking kids. Meanwhile, my in-laws opted for more relaxing pursuits, like going for long walks.
That balance gave everyone the space they needed. Plus, we weren’t together 24/7, which, as any family knows, can be a bit much.
I also got to bond with my oldest daughter before she left for college
My daughter and I got to visit sea caves together.
Janine Clements
My daughter left for college a few weeks after we returned home, so the trip also provided the perfect opportunity for the two of us to do something special together.
Having someone else in charge meant I didn’t have to constantly worry about everyone else all the time. Instead, I had time to do what I wanted.
While my in-laws hung out with my younger daughter, we went on a boat cruise to see dolphins and sea caves, including the famous Benagil Cave. Being able to spend one-on-one time with her on a magical trip like this was unforgettable.
Unlike most family vacations, I didn’t have to worry about a thing on this trip, thanks to my father-in-law’s impeccable planning

it was bliss.
Through this experience, I’ve learned that my need to plan everything often holds me back from truly relaxing and being present with my kids. My plan for the future is to let someone else take over the planning — occasionally, anyway.
Read the original article on
Business Insider

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