How to Plan an Unforgettable Trip With Your Adult Siblings

No noogies allowed.

Devorah Lev-Tov and sister drinking at sunset in Shaharut, Israel

Courtesy of Devorah Lev-Tov

Family travel — whether multi-gen, nuclear, or extended — can be fraught even within the best (read: least-dramatic) family dynamics. When siblings are involved, old rivalries rear their heads, long after you've grown up and stopped living under the same roof. All of a sudden, you may find yourself calling shotgun or arguing over who has to share a room with the younger sister who snores. Your squabbles will likely also be about the larger issues that come up on any group trip, like where you want to travel to, budgets, and who is in charge of dinner reservations.

When I traveled to the Six Senses Shaharut in Israel with my sister, who lives in a small town between Jerusalem and Be'er Sheva, we disagreed plenty. We squabbled over how many nights to spend (we both have children we'd left with our husbands); where to eat (she has dietary restrictions and I like to try everything); and how much time should be devoted to relaxing by the pool versus hiking and camel riding.

That said, we also bonded in a way we hadn’t since we were kids, sharing secrets and stories like we used to when we shared a bunk bed as tweens. As much as a sibling trip can be stressful, it also has the potential to be truly magical, reigniting a connection that has faded over time.

After that trip, plus a Napa vacation with my youngest brother and an upcoming Amsterdam jaunt with my older brother (yes, I'm one of four), I’ve learned a few things about traveling with adult siblings. I also spoke with some travel experts to get even more tips. Here, five things to keep in mind when planning a trip and traveling with your adult siblings.

The pool and entry of Six Senses Shaharut in Israel

Courtesy of Devorah Lev-Tov

Determine the Purpose of the Trip

Is this a long-awaited safari trip or a repeat visit to one of the places you went to as kids? As you start to plan, make sure everyone is on the same page about where you’re going and why, and what each of you hopes to get out of the trip. If one of you wants to relax by the pool and the other is hoping for nonstop bonding time, that might create some friction. To avoid any conflict, talk beforehand to determine everyone’s goals. “Consider the places you have traveled in the past (individually or together), and if you want to revisit a nostalgic destination for your family or try something new together,” says Bridget Lackie, general manager of Scott Dunn US. “Some siblings may be up for a once-in-a-lifetime adventure, some may be yearning for cultural exploration through a historically significant destination, while others would prefer a relaxing, off-the-grid beach destination.”

Make the Trip Accessible for Everyone

Similar to other group trips, it’s important to keep everyone’s needs in mind, even if they are extremely varied. This applies to budgets, mobilities and physical differences, time frames, and more. Lackie says, “You may all be at different stages in life and budgets are different for everyone, so we have found having the conversation early around budget can help mitigate the stress to ensure everyone agrees on an amount to make the planning more enjoyable for all."

Beyond monetary considerations, be sure to check in about expectations around things like modes of transportation and activities — and how active those activities will be. “When planning the itinerary for a group like this, you need to offer engaging activities that everyone can enjoy together, as well as ones that are more tailored for individual interests,” says Stephanie Papaioannou, Abercrombie & Kent's vice president of Tailor Made and Private Travel. Also, think about how long everyone has to get away — your single sibling who works remotely can probably do a longer trip than your sib who has three kids at home. Find the middle ground that works for everyone — I promise, there is one.

Have One Decision Maker

After you discuss everyone’s needs and desires, you should select a point person. You probably already know who this should be among your siblings — the person who typically takes charge anyway and probably planned your parents' 25th-anniversary party. Having one person take the lead helps avoid a lot of back and forth and long text chains about trivial things, like what time dinner should be. “The biggest tip for planning a family trip like this would be to have one decision maker who will collect and distribute information,” Papaioannou says. “A&K’s Tailor Made team finds it helpful to do an initial conference call with everyone in order to get a good idea of what each guest wants to have out of the journey, but afterward there ultimately needs to be just one point of contact.”

Person enjoying sunset and a group of three camels sitting in the shade in Shaharut, Israel

Courtesy of Devorah Lev-Tov

Keep the Past in the Past

When you find yourself with family, and especially with siblings you know too well, you may be tempted to bring up an old argument or embarrassing story from when you were kids. Don’t. Instead of rehashing childhood pain points, like who mom favored or why the baby of the family never had to do the dishes, just enjoy the new memories you’re creating in the present. Of course, nostalgic stories from growing up together that won’t make anyone feel hurt are welcome.

Nobody Is the Parent

Although there should be a point person, that person is NOT the parent. Neither is the oldest sibling. While it may be tempting to fall into old patterns, you’re all adults — even the youngest sibling — and nobody is responsible for anyone else. With that in mind, everyone should respect each other and their opinions and needs. Treat one another more like friends in this regard, and things will go much more smoothly. For example, when I went to Napa with my younger brother, it took some time for me to accept that he had opinions on wine and where we should drink it. In my mind, he’s stuck at 12, his age when I left home for college, but in reality, he’s 32 and just as much a grown-up as I am.

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