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Traveling With Siblings: What You Need to Know

The basic lessons I've learned after years of vacations.

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3 siblings on a bike, traveling and having fun.
Jared Oriel
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I love my two brothers and adore my sisters-in-law. We speak frequently, but getting all of us together in person is a rare treat. Of course, we’ve stayed in each other’s homes over the years, but some of our most enjoyable get-togethers have involved group travel. After several trips together, I know what it takes to vacation in harmony, allowing for periods of togetherness and solitude.

Our ages span 12 years, and I’m the senior member of the family. Now that I’ve entered my 80s, and we’ve lost a sister, getting together with family means more to me than ever — especially when it’s trouble-free for everyone. No one has to be burdened "hosting" the family visit, providing meals for everyone or planning activities.

More importantly, when we travel somewhere together, we’re removed from our own daily activities and responsibilities, free to devote ourselves entirely to just being together. Some of our best trips have included a Caribbean cruise, a family reunion in Norway and a Christmas visit to New York City. This year we chose Key West for a winter getaway.

We lead diverse lives in different parts of the country, but we haven’t grown apart. We’re of retirement age, and have all worked hard in long careers to afford these group adventures together. (My longtime partner and I are writers). While we all lead active lives, we’re flexible enough that we can plan well ahead and take advantage of special off-peak travel rates. With our shared family history, and varied lifestyles and interests, we have plenty to catch up on when we’re together.

The fact that we can all get along for a period of concentrated togetherness is reason enough to celebrate. We weathered the passing of our parents and navigated through other periods of crisis and emotional upheaval that can test the bonds of sibling relationships, and stayed close. Our social and political views are compatible, and we haven’t allowed any festering resentments or rivalries to destroy our good times together — so far.

I value these relationships too much to let anything spoil our treasured get-togethers. For me, that means heeding some basic lessons learned from our previous travels, and being mindful not to throw my weight around as “big sister.”

Nobody wants a sibling to parent.

I heard my younger brother loud and clear when he said, “I don’t need a mother.” When he was born, I became “junior mom.” By the time I went off to college, he was still a “kid.” It’s easy to fall into old patterns — which is especially grating for him. He’s been blind since his early 30s and is entirely self-sufficient.

A man who can do his own electrical wiring and work with power tools doesn’t need a solicitous big sister hovering to do things for him. Nor does my other brother need sisterly advice on running his life, (tempting as it is).

Everyone has a voice in planning.

It didn’t require much discussion to agree on our destination. None of us had been to Key West, and we were all eager to visit the southernmost city in the continental United States. According to an online travel brochure, Key West is “famed for its sunsets, turquoise waters and wooden gingerbread houses painted in the pastel pinks and greens of the Caribbean.”

The charms of the quirky, laid-back island, which has lured the likes of Ernest Hemingway, Jimmy Buffett, Judy Blume and President Harry S. Truman, did not disappoint — nor did its key lime pie.

Where to stay is key.

Togetherness goes just so far. We need our private time to recharge. Instead of a hotel, for comfort, cost and privacy, we chose an Airbnb that had three bedrooms, each with its own bathroom. No couple wanted to be stuck sleeping on a pull-out in the living room or sharing a bathroom. Our reasonably priced dream rental came with a pool, a sunny porch, a veranda wide enough for dining and a cozy living room where we congregated for wine, cheese and conversation.

Make room for spontaneity.

Instead of an SUV, my brothers rented a six-passenger electric golf cart, perfect for cruising around the island. We had a fresh, open-air view of tourist sites, and stopped whenever something caught our interest. We visited Truman’s “Winter White House,” toured Hemingway’s home, bought ice cream cones, enjoyed drinks at sunset on the beach, posed for pictures on a pier and had delightful encounters with cats and roosters everywhere we went.

Have patience — there’s no rush.

I listened when one of my sisters-in-law reminded me that, “there’s no need to hurry.” Like my father, I’m generally first out the door and quick to finish a meal. We all have vivid memories of Dad sitting behind the wheel of the Studebaker, beeping the horn as the rest of us straggled out of the house. Though on vacation, I was gently admonished that, “We didn’t have to be anywhere.”


Our tastes, interests and energy levels all vary — and none of us run on the same clock. Breakfast was not a shared meal and it was understood that not everyone would want to shop, take a guided tour or stroll on the beach. We took turns choosing restaurants and split the check by couples — and always ordered key lime pie for dessert.

It all paid off. Home again, with another batch of family photos and memories, we’re looking ahead to our next sibling trip.

Have YOU ever traveled anywhere with your siblings? How did it go? Let us know in the comments below.

Follow Article Topics: Relationships
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