A Trusted Friend in a Complicated World

The Best 8 Trips to Take with Your Sister

Updated: Jan. 13, 2023

Traveling from Chile to Colorado and beyond, these sibling pairs discovered new dynamics as adults—and learned that they could be friends as well as siblings.

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Marlisse Cepeda
Courtesy Marlisse Cepeda

For making memories: Travel the world together

For RD.com editor Marlisse Cepeda and her sister Massiel, travel is part of the way they bond together. They’ve been all over—from Washington, D.C., Las Vegas, and Puerto Rico to Amsterdam, Copenhagen, Prague, and Berlin. When they pick a place to get out of town together, they try to embark on new adventures where they’re both experiencing a destination for the first time. They also tend to lean toward touristy spots for a few reasons. “This means there will always be a lot of things to do, and that it’s safe,” she shares. To make it a memorable experience for both, Cepeda says it’s ideal to have some plans, but leave room for wandering. “Some of our best memories came from events, activities, etc., that weren’t planned,” she adds.

If you don’t happen to have a sister to travel with, these are the 10 best places for women to travel solo.

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Air Skydive Pucon
Courtesy Air Skydive Pucon

For bucket list adventures: Pucon, Chile

As the oldest brother of three siblings, software developer Rob Dugas had very few opportunities to travel with his baby sister, Katherine, who is nine years his junior. But thanks to an opening in their travel schedules, they were able to make a trek to South America. In addition to navigating language barriers with broken Spanglish, they explored this new-to-them region of the world—with its beautiful volcanoes and scenery—and had quite the adventure.

After many hikes and heart-to-hearts, Katherine suggested skydiving. And not just parachuting out of an airplane on her own, but specifically, she wanted to skydive with her eldest brother.

“I watched as my little baby sister jumped out of a plane in tandem with a strange man behind her. I couldn’t believe it: she was not even flinching. She was determined to go first, which meant I watched her plummet down first. Usually, I was the leader, but this time she led the way,” he shares. “I couldn’t help but be proud of her and her sense of adventure and risk, which I had no idea about prior. A few minutes later, down on the ground, I was in shock and she was all smiles, ready to go at it again. I’m sure that will not be our last skydive.”

You’ll want to add these amazing beaches to your bucket list ASAP.

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Traveling in Rome
Courtesy Arestia Rosenberg

For a milestone birthday: Rome, Italy

Though Italy might be deemed among the most romantic of all of the European countries, for freelance filmmaker and writer Arestia Rosenberg and her sister Thayer, it was the perfect way for two sisters to ring in a big birthday. For this trip, as her sister blew out 30 candles marking the start of a new decade, the duo toured around this ancient city, trying as much of the local fare as they could. Because both are seasoned travelers and independent, the trip was an eye-opener in that it showed them how well they could jet set together, having that shared common ground of having grown up together. “We could be honest about what we wanted to do. She even ditched me for one afternoon to go see something I wasn’t interested in while I worked in a café. Everyone got to do what they wanted, and no one was mad,” she recalls.

Get inspired for your next vacation with these photos of the world’s most luxurious and expensive trips. Hey, it’s fun to dream!

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Courtesy Katherine Conaway

For reconnecting: Munich and Berlin, Germany

Up until 13 years ago when she went away for college, writer, producer, and consultant Katherine Conaway and her sister Elizabeth spent nearly every single day together. Since then, they bonded over the holidays and visited each other, but never really had time to truly get out of town, just the two of them. With a goal of checking Oktoberfest off their bucket lists, they decided to prost their way through Germany. The experience gave Katherine a renewed connection to her sister, as they stepped away from their “real lives” and experienced a new time and place together. “We spent hours at the German Historical Museum because we’re both nerds, went out to a fancy brunch and dinner for her birthday, and also almost peed ourselves giggling on the metro home one night. It was really fun and special to spend a week together, learning more about each other’s lives now and falling back into our playful, snuggly childhood dynamics,” she explains.

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Courtesy Jessica Tatham

For navigating the roads—and life—together: England and Scotland

Web developer Jessica Tatham and her sister Sabrina are lifelong travelers, having spent their childhood collecting passport stamps with their parents and older brother. But once they reached the age where they could afford to—and stand to—travel together, just the two of ’em, they decided to hit the road… literally. For two weeks, they drove through England and Scotland with an open-ended itinerary, giving them room to figure it out as they went. For Jessica, the trip, with its many ebbs and flows, changed the dynamic of her relationship with her baby sis. “The time in the car was really great for us to bond. It was the first trip we had taken together, both as adults, and it really cemented that we could be friends as well as sisters. We also both love high tea, so every town we drove into, we would visit the castles and then immediately find the best spot for tea,” she shares.

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Courtesy Veronica Silva

For returning to your roots: Oaxaca, México

Though both were born in Oaxaca, graphic designer Veronica Silva‘s little sister Daniela was only two months old when they moved to Mexico City. When an impromptu opportunity to see their hometown presented itself, Veronica was excited to introduce her sister to the culture and the region that defined their family. As they explored the area together—seeing memorable sites and eating their way through the local cuisine—they grew even closer, bonding together over their shared history. “After the trip, my sister said she finally understood why I love our hometown. We actually went back the next year because she enjoyed it so much,” she shares. “I think that when you travel with your sister, you get to bond a lot, and if you have a good relationship, it can be an amazing time.” For Silva, traveling with her sister taught her to treat her like she would a best friend: “Have fun, get to know each other better, do things that both of you enjoy, and if it’s necessary, give each other some space to avoid conflict.”

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Courtesy AnnRagan and Cooper Kearns

For the best mix-it-up vacation: Barcelona, Spain

For the ideal mix of culture, leisure, and nightlife, publicist AnnRagan Kearns couldn’t have picked a better spot to explore with her sister Cooper than the heart of Spain. Together, they lounged away at countless beaches, stood in awe of must-see historical architecture and ate their way through many top-tier restaurants and bars. Though they both always enjoy getting away, it is the way they approach their trips together that makes it a successful undertaking: always packing snacks for when hunger strikes, each making a list of necessary experiences, keeping one another safe, and setting a budget that works for both.

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Courtesy Jenn Sinrich

For closing the gap on an age difference: Madrid, Spain

Since freelance journalist Jenn Sinrich and her younger sister Sammi are eight years apart, they didn’t have a lot of mature bonding experiences when they were living under the same roof. Though they grew closer as Sammi collected birthday candles, it wasn’t until she studied abroad in Prague that the chance to travel together became a reality. Given the opportunity, Jenn caught a flight to meet her sister, and together they sampled beers in Munich before heading to Madrid to savor Spanish wines. “It taught us a great deal about each other in terms of who we have become, not the children we once were,” Jenn shared. Just pack your own clothes, she warns—since sister bickering happens no matter where you roam. “I made the mistake of packing light, with the assumption that I could borrow from her since we wear the same size clothing, but that quickly turned into the same arguments we used to have when living together,” she recalls.

Find out the best vacation for you—and your sister—based on your personality type.