Ask an Expert: A Bespoke Travel Planner answers all our top questions

2 days ago
5 min read

Smiling family of five poses at a turquoise lake with snowy mountains and clouds; one shirt reads Michigan.

It seems only fitting that Jen answered all of our top travel questions just before taking off for the most complex trip she's ever planned - Japan! While Jen's love of traveling with her own family runs deep, her and her team of travel planners have guided and planned some truly special trips for hundreds of families. Passionate about exploring the world, helping families make memories and really experience other cultures, she graciously shares her tips and insights below. Whether it is figuring out where to go in the first place, taking the leap to a first international trip with kids, or planning just enough that a trip feels full AND relaxing, she breaks down how she approaches planning a trip with some incredible guidance.

Ali, Book Aficionado from @The BookClubCart

Ali asked:

Three smiling children hold ice cream by London’s Tower Bridge under a bright blue sky with clouds.

We are hoping to plan our families first international trip this next year. Our kids are 7-11 years old. Where would you recommend going first? They can handle long flights well so distance is not a deterrent.

Jen answered:

Ages 7 and 11 are great ages to start exploring the world! It does depend a bit on your kids interests, how adventurous they want to be and their overall stamina. But, Switzerland is a giant playground for families! There are playgrounds at the top of mountains, tobogan rides down to small villages and the trains make it very easy to get around! London is another good starter trip, especially if you have Harry Potter fans. You can go to the actual studios where the movies were filmed! And, with English being the spoken lanuguage and the tube to get around, it doens't get any easier than that!

Kim, Home Connoisseur from @Reverie.and.Root & Founder of Spilling Goodness

Kim asked:

Volcanic eruption with a tall lava fountain and thick smoke over a gray cratered landscape and distant mountains

How do you decide where to travel to each year?

Jen answered:

I tend to choose our travel destinations based on my kids' ages and interests. When they were younger, our trips centered around beaches, cruises, and theme parks, where fun and convenience were the priority.

Most of our trips actually begin with a conversation. One of the kids will mention something they're curious about, a place they want to see, or an activity they want to try, and that simple comment often sparks the next stage of planning. Their individual interests help shape where we go. When my youngest became fascinated with volcanoes, we planned trips to Hawaii and later to Pompeii, where he could see the power of volcanic history from two very different perspectives. When my oldest wanted to see PSG play and visit their stadium, Paris became an easy choice. I love finding ways to connect what they're naturally curious about with places that bring those interests to life.

As they've gotten older, I've shifted our travel in two ways. First, I've added more adventure. Second, I've started introducing history by working backward through time. We began in London because it felt like a natural starting point. The language was familiar, making international travel a little less intimidating, and there were plenty of historical connections they already recognized from growing up in the U.S. From there, they could begin to understand Roman Britain before we moved on to Rome and then Greece. Next on our list is Egypt, where they'll be able to connect what they've learned about the ancient Mediterranean world with one of its most influential civilizations. Experiencing these places in sequence has helped create a narrative that makes the complex history between cultures and civilizations much more meaningful and easier to understand.

Smiling boy in gray Nike shirt carries a sandboard atop golden desert dunes under a clear sky.

On the adventure side, Dubai was the perfect introduction because it offered exciting yet accessible experiences while exposing them to a very different culture. From there, we expanded to destinations like Alaska and Norway, where cruises make it easy to access incredible outdoor activities directly from port, and Hawaii, with its beautiful but manageable hikes. Our next step has been places like Belize, Costa Rica, and Iceland. These trips often involve longer transfers, moving between multiple locations, and activities with age or height requirements. They are experiences that are much better suited for older kids than younger ones.

Rebecca, Woman's Leadership Coach from @PleasantlyAggressive

Rebecca asked:

Four smiling children lean over the camera in an ornate gilded cathedral with painted vaulted ceiling.

I always get nervous traveling. I make pretty detailed itineraries in order to make the most of our time, especially on big (expensive) trips. But desperately want to go with the flow of unexpected opportunity. How do you balance both?

Jen answered:

You are absolutely right. Building in some flexible time is key! I like to plan for up to 2 activities in a day. One in the morning, and one after lunch. Even with that, some days will have no pre-booked activities at all, but just a framework in my mind of what might work well depending on the mood and energy level of the family. I also like to have the kids each pick out one activity they are most excited for. I am sure we fit in their picks and then consider anything beyond that a bonus, which helps with not feeling too overwhelmed and that we have to pack it all in.

Ashley, Millennial Mom Nutrition Coach from @AshleyBreaksTheCycle

Ashley asked:

Three silhouetted people stand on a wet beach at sunset, facing the waves with orange sky and reflections on the sand.

Where do you suggest to take a family of 5 that wants/needs things to do with 13, 11 and 9 year olds without it being Disney World? What do you think is best when traveling as a family, AirBNB or hotel? Is there anywhere you don't recommend to go as a family that's super hyped up? Someday I'd like to take our kids to Beaches in Turks and Caicos but I've heard it's gross now and people get sick when they leave there.

Jen answered:

Ha-well, I don't think I would call Beaches Turks and Caicos gross and I have never gotten sick there, but is does come with a hefty price tag! People love Beaches Turks and Caicos since it is one of the few all-inclusive resorts on crystal clear waters, with direct flights from the US, easy transfer from the airport and overall on a very safe island. But, I would not consider it the gold standard or a "must do" especially as your kids get older. I find it most beneficial for the toddler/elementary age group as it is also one of the only all-inclusives that has childcare provided for those under three year of age.

For a family of 5, with kids ages 9-13- the truth is you can really start to do just about anything! Perhaps not quite the time for Patagonia or Antartica, but otherwise, the world is your oyster! Those are great ages for Alaska, Costa Rica, or cruises to name a few options. When it comes to AirBNB versus hotel, I am team hotel ALL the way! There are way too many horror stories with AirBNBs being cancelled last minute without any recourse. And, who wants to cook and clean on vacation anyways?

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Ask an Expert: A Bespoke Travel Planner answers all our top questions

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