From teenage best friends to lifelong companions, families are making room for the people who matter most—and creating more meaningful travel memories together
By Abby Shelton
The sun is setting, two best friends are still swimming, and the grandparents are watching from the terrace. It's one of those vacation moments everyone will remember, especially the two friends who got to share it together.
Families are increasingly inviting their children's friends and close family friends on vacation. For some, that means letting a teenager bring her bestie along for one last summer before college. For others, it means inviting an old friend to join a 70th birthday celebration or a family anniversary trip.
It might mean an extra plane ticket, another bedroom and a little more planning. But having the right people along can make a special trip even better.
After all, family vacations can be a chance to spend time with relatives and the friends who have become part of the family, too.
Why Family Vacations Are Making Room for Friends
According to Hilton’s 2026 Trends Report, more travelers are encouraging their children to bring friends along. Hilton’s research, conducted with Ipsos, surveyed more than 14,000 travelers across 14 countries. While the report does not assign a specific percentage to the bring-a-friend trend, it points to a broader desire for more engaging, shared family experiences.
Seventy-four percent of travelers said travel strengthened family bonds by participating in activities related to their interests. Among people traveling with children or grandchildren, 73% expected to encourage the younger generation to help shape vacation plans. And 84% of travelers said they would seek opportunities for the whole family to play together.
Inviting a friend fits naturally into that picture. Instead of planning a trip around what adults think everyone should enjoy, families can make room for the relationships that matter to their children, too.
Teenagers, especially, may welcome the chance to share their adventures with someone their own age. A beach afternoon becomes more exciting, a long drive feels shorter, and even a family dinner can become more relaxed when a familiar friend is at the table.
Parents may find the arrangement benefits everyone. In a Fox News report on vacation etiquette, etiquette expert Diane Gottsman noted that parents often invite a friend so their own child can have a more enjoyable trip. It's a reasonable motivation, particularly when siblings have different interests or struggle to share the same space for an extended period.
Of course, bringing a friend doesn't mean every moment will be perfect. Talk to your child beforehand about what to expect. Make it clear that the friend is joining a family vacation, not a trip where every activity will revolve around the two of them. That little conversation can make a big difference.
Chosen Family: Celebrating the People Who Belong
Sometimes, the person you most want beside you at a celebration isn't a relative. It might be the godparent who has been there since your child was born, the neighbor who has joined every holiday dinner for years, or the college friend who has shared four decades of birthdays, weddings and family milestones.
For a 70th birthday or a 50th wedding anniversary, inviting those people along can feel just as natural as gathering immediate relatives. Their presence adds another layer of meaning to the milestone. They remember the early years, understand the family jokes and can tell stories that even the younger generations have never heard.
Imagine a family gathering at a countryside estate for a grandmother's 70th birthday. Her children and grandchildren are there, but so is the lifelong friend who stood beside her through new parenthood, career changes and every major turning point. Over dinner, that friend shares a story from decades ago, and suddenly the celebration becomes a living history of the person everyone has gathered to honor.
Graduations offer equally meaningful opportunities. A senior's last summer before college is an especially memorable time to bring a best friend along, celebrating their friendship before new responsibilities and distance change everyday life.
The destination doesn't need to be elaborate. What matters is choosing a setting that suits the group, whether that means a coastal retreat, a mountain escape, a private countryside home or a memorable rail journey.
For inspiration, explore TOGETHER's 12 Great U.S. Resorts for Celebration Vacations and its guide to milestone train journeys. Both offer starting points for planning a trip around the occasion rather than choosing a destination simply because it's popular.
Whatever you choose, leave some room in the schedule. Plan a few special meals or activities, but don't feel the need to keep everyone busy from morning until night. Some of the best moments happen when nobody has anywhere else to be.
Finding the Right Place for Everyone
Choose a place where everyone has room to relax but can still gather for meals and activities.
A private villa or estate rental can work beautifully for a larger family gathering, especially when the group wants shared meals, outdoor space and the freedom to follow its own schedule. Resorts offer a different kind of convenience, with connecting rooms, multi-bedroom suites, and amenities that let different generations enjoy the same property in their own way.
When you're bringing your child's friend, think about sleeping arrangements before you book. Two teenagers might be happy sharing a room, but they'll still appreciate having space to themselves. Adult friends joining a family celebration may prefer separate bedrooms.
Consider the number of bathrooms, common areas, dining arrangements and sleeping spaces. Check the property's occupancy rules and make sure the additional guest is included in the reservation.
TOGETHER's Family Stays collection is a useful place to begin exploring accommodations suited to different group sizes and travel styles.
Who Pays When a Friend Comes Along?
No single rule works for every family. Some hosts cover the entire trip, while others ask the guest's family to pay for certain expenses. Either approach can work as long as everyone understands the arrangement.
One common option is for the host to cover accommodations, meals and planned activities while the guest's family pays for flights, transportation to the departure airport and spending money. The details depend on the trip, the family's budget and what everyone is comfortable with.
The key is to have the conversation before booking. In the Fox News report, Gottsman emphasized that hosts should communicate costs upfront rather than asking guests to reimburse them afterward. The same principle applies to adult family friends: a warm invitation should never leave someone guessing about the financial commitment.
A simple conversation can settle the matter easily: "We would love to have Maddie join us. We're planning to cover the house, meals and activities, but we'd ask your family to arrange her flights and send some spending money. Would that work for you?"
Discuss expensive excursions, restaurant choices, transportation and cancellation costs, too. Once everyone agrees, there's no need to revisit the issue throughout the vacation.
A Little Preparation Goes a Long Way
Before bringing someone else's child on vacation, talk with their parents about health needs, routines, rules and anything else that will help the trip go smoothly.
Even if you know the child well, ask about allergies, medications, dietary restrictions and any medical concerns. Find out about phone use, curfews and how often the parents expect their child to check in.
Share your own family's expectations in return. Explain how meals work, whether everyone is expected to help tidy shared spaces, how much independence the teenagers will have and what happens if the group splits up for an activity. These details are easier to discuss at home than in the middle of a busy vacation.
For international travel, paperwork deserves particular attention. U.S. Customs and Border Protection explains that some countries require a consent letter when a minor travels without both parents or a legal guardian, and some require the letter to be notarized. Requirements vary by destination, so check with the relevant embassy or consulate before departure.
It's also wise to carry a signed medical authorization from the child's parent or legal guardian, along with emergency contacts, relevant medical information, and insurance details. Confirm what documentation is necessary for your trip.
Finally, make sure the friend knows how to reach their parents and understands the basic plan. A little preparation gives the adults peace of mind and allows the children to enjoy the experience.
A Bigger Guest List, a Richer Family Story
As the sun sets, the two girls finally climb out of the water and reach for their towels. Their grandparents are still on the terrace, ready to hear all about the swim. Years from now, the family may remember the house, the warm evenings and the time they spent together. The girls may remember it as the summer they shared before heading off to college.
Whether it's your teenager's best friend or someone who's known your family for decades, inviting them along can make a special trip even more memorable.
You don't need to invite a crowd or plan an elaborate trip. Sometimes, all it takes is making room for one more person.
So when your teenager asks, "Can Maddie come?" take a moment to consider it. With a little planning and an honest conversation about expectations, that extra guest might become part of a family memory everyone treasures.
Because the people who make a trip special aren't always the ones who share your last name.
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