The Traveling Family Reunion

From when and where to who’s coming and what you’ll do, here’s a step-by-step guide to planning a memorable group trip.

By Jessica Wynne Lockhart - Illustrations by Kelsey Davis

When Beverley Arduini sat down to plan her first family reunion, she knew she wanted to bring three generations together. But rather than hosting it at home in Vancouver, she chose Fort Worden — a historic state park in Washington — as the destination. The location meant everyone wouldn’t just sit in a room and reminisce about the past. Instead, they’d create new memories, playing on the beach and biking through the towering evergreen forest.

That was more than 40 years ago — and it was such a success that her family has returned nearly every year since.

It doesn’t matter whether you’re planning a one-off event or hoping to establish a new tradition: Destination family reunions are an unparalleled opportunity for your loved ones to reconnect. If you’ve got your guest list in hand, follow this step-by-step guide to make your destination family reunion one for the scrapbooks.

To have a travel advisor — an unbiased person — saying, ‘this is the best option’ is very powerful. It will help you offload the bigger decisions.

1. Get buy-in and set your budget

It’s fun to fantasize about jetting off to a private Caribbean island or booking out a dude ranch in the High Sierra. But unless there’s just one person or family footing the bill, you’ll need to know how far everyone is willing to go — literally and financially.

Dropping the question in your family WhatsApp chat might seem like the easiest solution, but Seattle-based travel advisor David Hawkraven cautions against this tactic, even if your extended family is tight-knit or small.

“If you’re on a call together or an email thread, you’ll never get the real answers,” says Hawkraven. “The more information you can get individually, the better.”

He recommends starting the planning process at least 12 months in advance by sending out a survey to your guest list. This can help determine the style of trip, budgets and timing, as well as gauge what your family members want to get out of the experience. Working with a travel advisor from the beginning can also help.

“The primary planner is going to have multiple opinions coming at them,” says Hawkraven. This can include everything from your chosen destination to the accommodation you stay in. “To have an advisor — an unbiased person — saying, ‘this is the best option’ is very powerful. It will help you offload some of the bigger decisions that might be contentious.”

2. Choose your style of accommodation

Accommodation isn’t just about a place to sleep at night. It can also influence the format the reunion takes and what the daily agenda might look like — and vice versa.

“It all comes back to one central question: Do you want to be very close together? Or are you all happy to opt into select activities during the reunion, like a signature meal or two?” says Hawkraven.

All-inclusive resorts and cruise ships are well equipped to deal with family groups, with rooms and activities that cater to a broad age range. But they’re not the only solution. Other options include renting out a large house or villa, booking an exclusive lodge or blocking out rooms in hotels.

3. Create an itinerary

The biggest challenge of a multi-generation trip is just that: You’re planning for a group that likely has a range of needs. In addition to considering accessibility — including for young parents of babies or toddlers, and grandparents with limited mobility — you also need to think about what activities will appeal to different age groups.

This is particularly true if traveling to an ancestral destination. While amateur genealogists might delight in visiting gravesites and archival libraries to see original documents, consider activities that will appeal to a broader range of attendees, like cultural performances, walking tours with a historian, or learning to cook a traditional meal with a local family.

Hawkraven suggests soliciting opinions from the youngest, middle and oldest members of your group, which will allow you to plan activities that everyone can get excited about.

“You can’t please everybody completely, but you can please everyone just a little bit,” says Hawkraven.

Most importantly, remember that your hard work and planning will be worth it.

For Arduini, helping to plan her annual family reunion is a labor of love — but it’s one that pays dividends. “It’s very rewarding to look around the table and see everyone’s smiling faces,” she says.