Tips for Organizing a Multigenerational Family Vacation

In the wake of recent travel restrictions and family separations, discovering ways to travel while reuniting with loved ones offers a wonderful dual benefit. Multigenerational trips are becoming an increasingly popular option for extended families.

While multigenerational travel can be incredibly fulfilling, these journeys often require more intricate planning. With a larger group, there are diverse interests to accommodate and various constraints to keep in mind.

If you're contemplating a vacation that includes multiple generations, you'll likely need to plan and prepare more meticulously than for a trip with just your immediate family. Here are some tips to help you make it a success.

What are the benefits of traveling with multiple generations?

Before embarking on planning a multigenerational trip, it's essential to evaluate whether this travel style suits you. Not everyone enjoys a harmonious relationship with their extended family. Spending a significant amount on a vacation can lead to disappointment if you're not enjoying the company of your travel mates.

However, if you do get along with your prospective travel companions, multigenerational travel offers several benefits.

Many families opt for multigenerational trips to make the most of their limited vacation time. For instance, my family of four, which includes my husband, our 13-year-old daughter, and our 8-year-old son, started traveling with my parents who live across the country for this very reason.

We aimed to visit my parents regularly but didn’t want to spend every holiday stuck at my childhood home. Instead, we chose to take our family bonding on the road to more exciting destinations.

Together with my parents, we've road-tripped through Utah's national parks, enjoyed vibrant times in Las Vegas and Cabo San Lucas, and unwound in the mountains of North Carolina's High Country.

With my in-laws, who live nearby in California, we often vacation in Hawaii, Palm Springs, and Lake Tahoe. Occasionally, aunts, uncles, and even a cousin or two have joined the adventure. Disney parks and resorts have been regular destinations with various family combinations over the years.

We've certainly made our share of mistakes along the way, but the priceless memories my kids have created with their grandparents, aunts, uncles, and cousins are invaluable. In the process, we've checked several destinations off our travel bucket list while saving money by sharing larger accommodations.

Moreover, my husband and I have been able to explore more on our own, thanks to the extra help from grandparents and other family members, especially when our children were babies and toddlers.

If your family seems like a good fit for a multigenerational vacation, here are some essential planning tips to consider.

10 essential tips for organizing the ideal multigenerational getaway

Organize and book your trip well ahead of time

One of the biggest challenges of a multigenerational vacation is often agreeing on a suitable date. With more travelers involved, coordinating schedules can become complex.

When school-age children are part of the group, many families opt to plan their multigenerational trips around school breaks. However, these holiday periods are typically when popular destinations fill up quickly. It's crucial to plan early if your travel dates coincide with peak seasons.

How far in advance should you begin planning?

For a family reunion involving multiple households, it's wise to start planning more than a year ahead. Some destinations and accommodations allow bookings a full year in advance, so having your trip's basic details in place is crucial by that time.

For smaller multigenerational gatherings, you might not need as much lead time. When inviting just the grandparents, we've successfully arranged trips just a few months prior.

Sometimes, the dates naturally align. My family often organizes travel plans for Thanksgiving week, as my husband's extended family consistently has that week off, and we all prefer celebrating somewhere other than home.

Openly communicate about the budget and who will cover which expenses

One of the biggest challenges when planning a trip with extended family is addressing the financial aspect.

Different households are likely to have varying budgets. Even if everyone is in a similar financial position, priorities can differ significantly. One family might want to indulge in a luxurious resort, while another may opt for simpler accommodations to allocate more funds for experiences.

To prevent awkward moments that could dampen the vacation spirit, it's essential to discuss budget considerations early and frequently during the planning stages. Consider all expenses, including flights, rental cars, gas, activities, dining, groceries, and other incidental costs.

On some multigenerational trips, one individual or household may wish to treat others to all or part of the vacation. If certain attendees will be receiving a gift of this nature, it's important to clarify the details beforehand. Ensure that everyone involved feels comfortable with this arrangement, as while many appreciate someone else covering expenses, it can also lead to feelings of embarrassment or discomfort for others.

Choose a designated planner to oversee the trip preparations

Too many planners can complicate things, much like too many cooks spoil a meal.

When traveling with a larger group, it's essential to appoint one person as the lead planner. This individual will handle deadlines, manage communications, make reservations, and coordinate expenses—or delegate these tasks to others who are willing to help.

Given that you're reading this article, it's likely that you may be the one taking on this role. Families often rely on those with travel planning experience to manage the logistics of group trips.

If you're not keen on this responsibility or lack the time, think about hiring a travel agent for assistance. While there will still need to be a primary contact for the agent, a good travel professional can save the planner a significant amount of research and effort.

Choose a destination that appeals to everyone

Selecting a location for a multigenerational trip demands considerable time and effort. Many places can work well, so don’t worry too much about finding the perfect spot. The main goal is to ensure the destination offers activities for all ages and types of travelers in your group.

Which destinations are ideal for multigenerational travel?

Beach vacations are a popular choice and have been the go-to for my family over the years. National parks are also excellent, blending adventure with education and history. Cruises can be a fantastic option, as they provide entertainment and activities suitable for all ages—just make sure no one in the family is prone to motion sickness.

Disney locations are incredibly popular choices for multigenerational travel groups. We’ve visited both Disneyland and Walt Disney World with grandparents, but a week of walking over 20,000 steps daily in a theme park might not be feasible for everyone.

If the allure of Mickey Mouse is strong, consider Disney's alternatives like the Aulani Resort in Hawaii, Disney resorts in Vero Beach, Florida, or Hilton Head, South Carolina, or even Disney Cruise Line.

Don’t hesitate to think creatively when choosing a destination.

When I brought my parents and my young kids to Las Vegas, many friends found it an unusual choice — but we had a wonderful experience. The city offers numerous family-friendly shows and activities that cater to both kids and grandparents.

Sometimes, certain family members may have already picked a destination and then invite others to join them. If you receive such an invitation, think carefully about whether the location suits your immediate family. Don’t feel pressured to go on a vacation that doesn’t fit your needs. If it doesn’t work out, you could suggest planning the next extended family trip instead.

Choose a destination that everyone can easily access

The destination should also be reachable. If family members are traveling from various locations, ensure that getting there is convenient. You don’t have to meet in the exact middle or agree on the same travel times, but the chosen place shouldn’t be too far or prohibitively expensive to reach.

When I organized a large family reunion a few years back, we chose Alabama's Gulf Coast beaches primarily for its accessibility for everyone involved.

It was a manageable drive for family members from the Southern states, and it was conveniently located near two airports in Mobile, Alabama, and Pensacola, Florida, providing distant attendees with multiple flight options. A bonus was that one of those airports is served by Southwest Airlines, allowing many flying family members who live in Southwest focus cities to use Rapid Rewards points for affordable travel to the reunion.

Take mobility and other limitations into account

When traveling with a multigenerational group, it's crucial to consider any potential limitations within the party. Discuss these issues early in the planning stage to avoid complications later.

For instance, are there family members with mobility challenges that you'll need to consider when selecting suitable accommodations and activities? Even active grandparents or toddlers might struggle with navigating multiple flights of stairs in a multi-level condo on a daily basis.

Is there a baby or toddler among your travelers? Planning around nap times and early bedtimes is essential. If your destination has a vibrant nightlife, it may not be ideal if someone always has to head back to the hotel early to put a little one to bed.

Choose your accommodations

After finalizing your dates and destination, the next crucial step is to secure your lodging.

It's essential to explore the available lodging options while comparing different destinations. At a minimum, ensure that all chosen locations have suitable options for your group and that there's availability for your travel dates. Then, you can narrow it down to specific accommodations in your chosen area.

There's no universal solution for accommodations during a multigenerational trip.

The ideal lodging will largely depend on your destination. In areas with a wide selection of vacation rentals, securing a house or large unit through platforms like VRBO or Airbnb often proves to be the best choice. This way, family members can enjoy their own rooms and bathrooms while sharing communal spaces for quality time together.

Splitting the cost of a vacation rental can often make it a more budget-friendly option for everyone involved.

However, a rental house or condo might not be suitable for every destination. Some families may prefer the amenities offered by a large resort instead of the solitude and limited services of a home rental.

In certain locations, vacation rentals may not be the most practical choice based on your planned activities. For instance, when my family visited Zion National Park with my parents, a vacation rental would have placed us too far from the park's attractions. Instead, we opted for adjoining hotel rooms at the historic lodge inside the park, providing us with convenient access to the Zion shuttle, which made getting around easier for my parents.

No matter what you decide to book, it's crucial to carefully review the cancellation policies.

With a larger group, the likelihood increases that someone might be unable to attend the trip due to injury, illness, or emergencies. It’s wise to opt for flexible bookings when significant funds are involved. Before committing to any shared, non-refundable reservations, ensure everyone agrees on how costs will be divided if someone has to drop out.

Establish clear expectations regarding babysitting responsibilities from extended family members.

One of the advantages parents with young children enjoy in multigenerational travel is the access to built-in babysitters. Over the years, my husband and I have greatly benefited from the generous babysitting offers from family members during our trips.

However, it’s likely that grandparents or other relatives didn’t travel to a distant destination just to stay in a hotel room caring for someone else's children, even if they adore them.

If you anticipate taking on the babysitting role during a multigenerational trip, communicate clearly with your family about how much support you're willing to provide for the kids.

Offering a single date night or taking a younger sibling out for a few hours so parents can enjoy an activity with an older child is a fair compromise and likely to be appreciated. However, ensure that being on duty isn’t your default role for the entire trip. If you’re the one benefiting from babysitting help, consider doing something special in return for those who assist you.

Share responsibilities — or hire help when necessary.

While vacations should ideally focus on rest and relaxation, many still require a considerable amount of effort. This is particularly true for vacation rentals, which often involve daily chores like cooking and cleaning, just as at home.

Don’t assume that others will take on these tasks or let one person unintentionally carry more than their share of the load. Delegate tasks in advance and determine what you’re willing to handle (and what you’d prefer to outsource).

In recent years, my daughter has taken the initiative to create a meal calendar for our extended family trips to Lake Tahoe and Palm Springs. She assigns each family the task of preparing dinner for one night during our weeklong stay in a vacation rental.

On the other nights, we either dine out or order takeout. This shared approach and the clear expectations set before our trip have been effective in preventing anyone from feeling overwhelmed — plus, we all enjoy several nights off during our vacation thanks to her planning.

Avoid the urge to plan every moment together and steer clear of micromanaging others.

With a multigenerational travel group, you'll encounter varying interests and travel speeds. While it’s enjoyable to partake in activities together during the day, too much time together can sometimes lead to disagreements.

Avoid the temptation to tightly schedule every moment or micromanage the entire trip. It’s important to allow some free time for individuals or smaller family units to explore their own interests or simply relax.

As the designated travel planner in my family, I’ve discovered that the best approach is to share activity options without planning every detail. I typically compile a list of local attractions at our destination. Family members can then review the list and create smaller groups based on shared interests. I organize a couple of major group events (like a dinner at a local restaurant) while letting the rest of the itinerary unfold naturally.

In summary

While they may require a bit more organization, multigenerational vacations can be incredibly fulfilling. These trips provide an opportunity for family reunions, allow you to share the expenses and responsibilities of travel, and enable exploration of new places together.

For additional multigenerational travel tips, check out these related articles:

• Advice for visiting grandparents while traveling
• Suggestions for a successful multigenerational ski holiday
• Skip-generation travel trends: top getaways for grandparents and grandchildren