Are you thinking of taking a trip with your extended family? Whether you want to reunite with relatives after a long time apart or simply enjoy some quality time with your loved ones, a multi-generational family vacation can be a great way to create lasting memories. However, it can also be challenging to plan a trip that suits everyone’s needs, preferences, and budgets. Here are some tips to help you plan (and enjoy) a fun and stress-free multi-generational family vacation.

Understand expectations in advance

Before you book anything, have a conversation with the potential travelers about what they want from the vacation. Is this a “relax” vacation or an “adventure” vacation — or a little bit of both? Everyone has a different vacation style, and the best way to avoid disappointment or frustration is to manage expectations ahead of time. Some family members might want to relax on the beach, while others might want to explore a museum or go hiking. Try to find a destination that offers something for everyone, or at least allows for some flexibility and choice.

Also, consider how everyone will get to the destination — is it centrally located, or might the distance be a hardship for some members of the group?

You should also discuss how much time you want to spend together as a group and how much time you want to have for yourself or your immediate family. This will also help to determine your travel arrangements. Consider a large vacation rental home with lots of common spaces and a big backyard if you’re looking to maximize your big-group time. Or perhaps a block of hotel rooms or condos in the same complex is a better fit for families who want to have their own spaces. Some people might enjoy being with the whole group all the time, while others might need some space and privacy. You may even consider booking adjacent campsites or cabins at a campground or RV park!

Know how you’ll manage the finances

Money can be a sensitive topic when it comes to family vacations. Some grandparents or parents might want to treat the whole family to a trip; others might not be able to afford it or might simply prefer to split the costs. You should have an honest and respectful conversation about who pays for what before you book anything. You can also look for ways to save money by sharing accommodations, using a car instead of flying, or choosing off-season dates.

Consider each person’s budget and comfort level when choosing where to stay and what to do. Some people might prefer a luxury hotel; others are happy with a budget-friendly Airbnb. Some people might want to splurge on fine dining; others prefer casual eateries or a homemade meal. Try to find a balance that works for everyone, and never pressure anyone to spend more than they can afford.

It can help to have a designated person manage receipts and coordinate the settle-up at the end of the trip using Venmo.

If playing accountant doesn’t fit the culture of your family, you’ll need to be OK with things not being perfectly even. Ensure that this is an acceptable arrangement for the group. Maybe you rotate who pays for grocery or restaurant trips, or leave it to each individual household to pay for their own activities. Alternatively, you could have everyone pool funds ahead of the trip based on their budget.

Find ways to split “chores” — and childcare

One of the benefits of traveling with multiple generations is sharing the work and cost. This way, no one feels overwhelmed or burdened by the responsibilities of travel.

Meals are an easy place to start. Maybe you arrange for each adult or family unit to be responsible for cooking one group dinner during the trip. Maybe you rotate planning, cooking, and cleanup. You could even task the kids with packing picnic lunches! No matter which method you choose, planning ahead is key to a successful trip.

Other chores might also benefit from a rotation or designated “captain” for each task. If you’re in a vacation house, maybe one person handles laundry for the group and another is responsible for taking out trash and recyclables according to the house rules.

You also may be able to eliminate some chores altogether by doing things like ordering groceries to be delivered shortly after you arrive or utilizing a local linen service as part of your rental booking to manage bedding and towels.

A big advantage of traveling with grandparents or other relatives is that they can help with child care. If you have young children, you might appreciate having some adult-only time with your spouse or partner, or just some time for yourself. You can arrange with your parents or in-laws to watch the kids for an evening or a day while you enjoy some alone time. Try rotating childcare so that each adult couple gets a night out without kids.

Choose flexible and varied activities — or leave things unstructured!

One of the challenges of planning a multi-generational family vacation is finding activities everyone can enjoy. You don’t want anyone to feel bored or left out, but you also don’t want anyone to feel forced or uncomfortable. The key is to choose activities that appeal to different ages and interests and that allow for different levels of participation.

For example, you can visit a theme park that has rides and attractions for both kids and adults, and let each person choose what they want to do. You can go on a scenic drive or a boat tour that lets everyone admire the views and take pictures. You can visit a historical site or a cultural attraction that has interactive exhibits and guided tours. You can also plan some free time for each person or family to explore in their preferred small groups. Be respectful of each other’s wishes and boundaries, and don’t take it personally if someone wants to do something on their own.

If that sounds stressful, it’s because it is — and that’s OK. Sometimes vacation isn’t about planning action-packed days every day. Don’t feel pressure to plan everything, and consider only choosing one activity to do together as a group. The beauty of this kind of vacation is in the time spent together, even if you’re just lounging on the patio.

Leave time to just be together

With a large group, everything takes longer than you think. Resist the urge to build an itinerary; instead, approach the trip with as much flexibility as possible. The most important thing to remember when planning a multi-generational family vacation or family reunion is to have fun and cherish the moments. Don’t let minor disagreements or inconveniences ruin your mood or your relationship with your family members. Be flexible, adaptable, and respectful of each other’s needs and preferences. Focus on the positive aspects of traveling with your loved ones, such as sharing stories, laughter, and experiences.

Hannah DeLisle-Stall
Hannah grew up in rural central Massachusetts and now lives in a teeny tiny town in the Berkshires. Hannah has BS and MS degrees in engineering and has spent most of her career working as a manager in the manufacturing industry — where there are few women, and even fewer moms. She is currently a Senior Manager in the Aerospace Manufacturing industry, working on parts that go into Commercial and Military Airplanes. Hannah and her husband met during college, when they were both volunteering at a local food bank. After graduating, building their careers, traveling, and even living on opposite coasts for a few years, they were married in 2015 and welcomed a son in 2019. Together, they love to camp, travel, and hone their DIY skills. In 2023, they completed a 3-year project to design and build their family's forever home. Hannah loves to volunteer, especially with organizations that help women and mothers advance their careers.