Do’s and don’ts for planning great family vacations – from 6 travel advisors who’ve been there

TORONTO — Just a few years ago, a six-figure booking for a multi-generational family vacation would have been the stuff of travel industry urban legend.

These days, it’s far from unheard of. For Brenda Goodby, CTM – Certified Virtuoso Cruise & Travel Advisor based in Lethbridge, AB, it was a $110,000 booking, and it was the real deal.

She’s not the only one seeing big dollar numbers for family getaways. Demand for customized and more complex family vacations continues to soar, long after the initial post-pandemic surge, and many travel advisors tell Travelweek that family vacation budgets have soared too.

For Goodby, the booking started with a core of four family members, and soon multiplied into a multi-gen mega-trip complete with in-laws, brothers, sisters and grandkids.

“The booking grew from a family vacation of one week to two weeks, and from 4 people to 22, within a week of my suggesting they share the idea with other family members. It was a sales increase from $10k to $110k within a week,” she says.

Goodby and other family travel specialists contacted by Travelweek say that while Mexico and the Caribbean and their ever-expanding portfolios of all-inclusive resorts are still very popular, demand for more bespoke family vacations – the type of bookings travellers most often need an agent’s help with – is strong and growing.

Curated family trips come at a cost, plus the price of just about everything, including travel, is up. What about inflation concerns, and the economy?

“Although family vacations have gone up in price over the last few years, I’m not seeing a decrease when it comes to family travel bookings,” says Ellison Travel & Tours’ Beth Baskey in London, ON. “Families are continuing to travel, and many are comfortable with the cost to do so. I’m finding that families that have always travelled, are making it priority to continue to do so.”

While there’s more competition now than ever for family travel dollars, the value of all-inclusive vacations means this travel style will always have staying power. Goodby says she’s seeing clients focus on vacations with food, drinks and entertainment to manage economic concerns. Families pooling resources to share large vacation rentals or cabins on cruises are also on the rise, she adds.

COSTA RICA, ASIA & EUROPE: THE NEW FAMILY TRAVEL FAVOURITES

Costa Rica, the Galapagos Islands, Japan and Thailand, Europe, cruises and African safaris: these are just a few of bucket list dream destinations that have become go-to vacation spots for many families.

It’s all part of the changing nature of family travel vacations. Well-travelled Millennial parents are eager for their kids to see the world, and at a young, impressionable age.

“Travel really is the best classroom. Adding hands-on educational experiences into family trips, like cooking with locals, visiting conservation centres or exploring ancient ruins, creates opportunities for families to engage meaningfully with the world,” says Jane Patrick with North South Travel in Vancouver.

Patrick says she’s seeing families and multi-gen families “looking to slow down when they travel, requesting more nights in one city or destination before moving onto the next and to travel with intention.”

Boomer grandparents, often footing the bill, are typically along for the ride.

“Multi-generational travel just keeps growing, with families putting more focus on spending meaningful time together. I’m especially seeing grandparents investing their time and money into family experiences now, while they can truly enjoy them, rather than waiting for ‘someday’,” says Lauri Walters with Direct Travel in Calgary.

Walters adds that family vacation budgets “are definitely higher today. Rising hotel, flight, and dining costs, combined with more families traveling internationally, mean trips are more expensive. On top of that, extras like excursions, tips, and unexpected expenses can easily add 20 – 40% more, so planning ahead is key.”

Part of the rise in family travel vacation costs is coming from the temporary shift away from the U.S., catapulting long-haul international destinations to the top of family travel wish lists.

Agents tell Travelweek that their family clients are continuing to book away from the U.S. One agent pegs the drop in her agency’s U.S. bookings at 95%; another says that less than 5% of her family clients are booking U.S. destinations right now.

Authentic experiences that emphasize togetherness, meanwhile, are big business for family clients. Private villas, family-friendly resorts, and custom itineraries that mix relaxation with adventure are seeing big demand, says Clara Power with Power Travel in Vaughan, ON.

“Experiences that appeal across generations are especially popular,” says Power. “Families also want convenience through seamless planning and easy transfers, while still enjoying touches of luxury.”

A recent stand-out booking for Power was one that incorporated accessibility for the family at every step: “I planned a multi-week, multi-country itinerary for a family in Europe, with a key focus on accessibility. This included arranging a fully wheelchair-accessible cruise, coordinating hotels, tours, and transportation to ensure every experience was seamless and comfortable.”

THE DO’S AND DON’TS OF FAMILY TRAVEL

Anyone who’s seen a young traveller wilt under the hot summer sun on yet another hours-long tour of an ancient ruin will understand that when it comes to planning successful multi-gen family trips, flexibility is key.

“The do’s: Plan early, build in flexibility, and create a mix of shared and independent experiences,” says Power. “The don’ts: Try not to overschedule, avoid assuming everyone has the same interests or energy levels, and do not leave important details like room configurations or dining reservations to chance. Families often underestimate how early they need to book, especially for peak seasons, or assume every resort can easily accommodate large groups with connecting rooms.”

Lisa Dunne with Treasured Moments Travel in Dunnville, ON recommends agents have a group conversation with one head person from each room, “to iron out all of the details in advance to help create good, open communication and start off on the right foot.”

Patrick says a schedule of meetings with multi-gen family trip clients can be a big help. “This allows advisors to ensure every-one is on the same page. Children are also invited to the meeting – and I usually ask them a few questions about what they are interested in, what they like to do. Children travel at a slower pace and generally have a slower attention span. You need to account for these differences in the itinerary planning. It’s impossible to expect a 6-year-old to spend five hours walking around the Roman Colosseum.”

Patrick also emphasizes the importance of everyone in the family getting some alone time on the trip too. “Clients often feel they should do everything together as it’s a family vacation. In reality, even the most loving families need space and alone time.”

Baskey points out that organizing a group vacation can be difficult for the group leader. “It’s unrealistic for everyone to agree when presented with too many options. I advise the group leader to get a sense of everyone’s interests and ideas, then we can chat and narrow down options. I recommend presenting no more than two options to the family to decide on. Family members are usually grateful for the opportunity to travel together and agreeable to what the group leader ultimately decides.”

Walters notes the importance of not overlooking “small comforts and hidden costs that make a big difference for kids and seniors.”

Establish a clear budget early on in the process, says Patrick, and communicate with the group and give updates on a regular basis.

Most importantly? “Be sure to charge a planning or professional fee to cover your time and expertise.”

This article appears in the Sept. 11, 2025 edition of Travelweek; click here.






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