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How to Survive Your Multi Generational Holiday

Start with Communication

In even the most easy going families, planning and surviving a multigenerational family holiday can disintegrate into chaos if communication is not clear and all-inclusive. That means there should be lots of talking — more specifically, lots of questions asked of each other up-front.

In large or diverse groups, it may be wise to establish chains of communication. Where a handful of people are responsible for communicating with a string of people by whatever means those group members usually communicate through. That way if Grandad talks on his mobile but can’t text, email or chat, he still has someone assigned to keep him in the loop. This also works well for busy 20- and 30-somethings who can be difficult to reach. Make sure they fall into someone’s communication circle, especially regarding important details like payment deadlines or online check-in.

Addressing the hard questions in the early planning stages helps avoid late-stage meltdowns. You most likely know your own family’s trigger points. Here are a few specifics that may need to be discussed initially when planning a multigenerational holiday.

Who are the decision makers?

Is there a committee? Is it a specific generation? It is often easier to begin with a small group making the big decisions, then later opening the discussion of minor details to more of the group.

Is the holiday exclusive to a specific family group?

Or may friends or significant others join? This is a bit more complicated for cruises than for land-based family reunions simply because a cruise is more attractive, meaning more people want to join the fun. It is always best to have an open discussion about this early rather than risk hurt feelings later.

How will financial matters be handled?

Who is paying for whom or what? For example, if the family patriarch generously offers to pay for everyone, perhaps a more luxurious option could be considered than if young families had to pay their own way. It also impacts the question of whether non-family members can join in on the fun.

Who is in charge of bookings?

Some families designate the occupants of each room be responsible for their own booking, while others put one person in charge of all bookings. There are pros and cons both ways, so the question should definitely be discussed before the booking begins.

What is the child care situation?

Groups with children should have this conversation pre-holiday. Will (or can) everyone’s children participate in available youth programs? Who is watching babies and toddlers too young for the onboard kids’ clubs? Will different family members take turns staying in the room with children with early bedtimes, or will kids be allowed to stay up past their bedtime in group babysitting? There will be much disappointment if cousins of similar ages have different rules about activities, and if parents of young children are always forced to stay in at night or entertain the kids, while their relatives get to relax by day and enjoy the entertainment and nightlife in the evening. Planning well ahead of the holiday takes the stress out of the situation.

Who is taking care of elderly family members?

If there are older members of the group who need assistance, discuss how the duties of hanging out with them will be handled. Perhaps several responsible adults divide up the days, or maybe there’s one family member who is comfortable taking all responsibility. And don’t assume that just because someone is advanced in years that they don’t want to explore new places; let the older generation weigh in on their own needs for adventure versus relaxation.

Spread the Workload

Usually nobody wants to feel obligated to oversee every aspect of planning the holiday; establishing a roster of who oversees which details makes the workload lighter for everyone and prevents unnecessary confusion. Several people can divide up researching cruise lines, hotels, itineraries and travel agents, but you might want just one person to be the main point of contact with the agent you choose.

Once the holiday is booked, other “jobs” might include coordinating group dining reservations, researching group excursions or planning games and activities. If young adult children or elderly relatives need assistance with booking-related tasks, ask for volunteers or your travel agent to help them.

Pick the Right Holiday

Pick the wrong holiday and you dramatically reduce the odds of everyone enjoying the trip, but choose wisely and everything should fall into place smoothly. If you have previously travelled extensively with the people in your group, the choice for a particular holiday may be a simple one, but quite often that is not the case. Here are the top things to consider when choosing a holiday for a multigenerational group.


How long do you really want to holiday with this particular group of people? Even the largest resorts start to feel confining if there is any friction at all among group members. Elderly family members, young children and couples travelling with new babies all need consideration when the group chooses the length of the holiday.


If school-aged children or school teachers are part of your posse, timing of the trip will most likely be dictated by their schedules. To add an element of celebration to the trip, consider timing your multigenerational holiday near a significant date like a wedding anniversary of the senior family members. Birthdays, graduations and anniversaries are all great reasons to get everyone onboard a cruise.

The larger the group, the more difficult it will be to find dates that work for everyone. With a large family reunion, it may need to be stated up-front that there is a “majority rules” policy when it comes to selecting the date. Planning a year or more in advance can help eliminate some conflicts, but there will always be the possibility that someone might be left out.


It is easy for couples with no children to overlook the budget restrictions of larger family groupings. Or wealthier siblings to forget that certain expenses might be hardships for less well-off family members. Unless the group has a benefactor that will be paying for everyone, approach financial topics openly early in the planning phases to ensure that everyone is comfortable with the result.

Cruises are an excellent choice for large families with a range of spending abilities. Family clusters can adjust their individual costs up or down with budget-appropriate cabin categories, add-on packages that suit their needs and shore excursions that fit within their budgets. The goal should be to find a cruise that works for both the top and bottom of the financial spectrum.


A multigenerational family holiday, by its very nature, is supposed to be more about being together than the destination, but the choice of where to holiday should still be part of the initial discussions.

Keep mobility issues in mind — in the form of baby strollers, walkers, canes, scooters or wheelchairs. Ports where tenders are required to go between ship and shore present challenges, as do a predominance of activities involving busses or extensive walking.

Communicate openly about the types of activities everyone enjoys. Food and wine lovers might prefer a European holiday over one to the Caribbean. Water sports enthusiasts and beach lovers may have no desire to don jackets for a mid-summer Alaska cruise. Families with young children might prefer a holiday that’s close to home rather than one with a long flight.


While choosing a resort or cruise line that suits all ages and temperaments is critical to the success of a multigenerational holiday, the choice should come only after the previous four things have been considered. This is the point at which an experienced travel agent may be a good idea if there is not already a consensus.

In general, mainstream cruise lines like Carnival, Royal Caribbean, Princess, Norwegian and MSC Cruises offer the largest variety of staterooms, dining options, entertainment and activities to keep everyone in a large group happy. They have activities for kids and adults, and offer an array of price points on the same sailing, with everything from inside cabins to suites and family-specific accommodations. Smaller or more luxurious ships are better suited to multigenerational groups with large budgets, older children and less of a need for a broad range of activities.

Ground Rules

Once you have the holiday booked and the itinerary planned, it may be time to lay out some ground rules that keep things running smoothly. This is where your early conversations about babysitting (the young, the old and goofy Uncle Bill) and financial matters really come into play. Here are some possible rules to consider:

No add-on costs that affect everyone once the holiday starts
Things like last-minute plans to dine at the specialty restaurants can be budget busters for some, causing hard feelings for those that were not prepared for the extra expense. Address additional expenses in advance, and make spur-of-the-moment purchases optional for group members.

Everyone comes to dinner together X number of nights

Family resorts and cruise ships are crazy fun places with so many unexpected things to enjoy. With everyone doing different activities by day, you might never spend some time with certain members of your family. If there is a plan in place — such as big group dinners every other night — you balance together time with letting people be spontaneous with evening plans.

Everybody is entitled to some free time

On the flip side, some members of the group might expect the entire family will spend every available moment together. Stating free time expectations up-front in the form of a rule helps with those moments when parents must excuse themselves from a card game because it’s a toddler’s nap time, when the teens are tired of hanging out with the adults or when people disagree about the best tour to take.

Rooms are for privacy

There are obvious exceptions to this — like teens or tweens in a cabin of their own, or when someone in the group has booked a large suite specifically for entertaining. But overall, having an expectation that your room is your refuge is a wise peacekeeping choice.

Parents are responsible for parenting their own children

There is nothing worse than having your every parenting decision questioned by the whole family group. It’s best to make sure everyone has the comfort to parent as they see fit without group pressure. Having said that, it is also wise for everyone to be vigilant about keeping an eye on the safety of all the children in the group and to volunteer to entertain the kids from time to time so parents get a break.

Communicating is a must

Because Wi-Fi can be spotty and expensive, communication can get tricky, and it’s easy to lose track of people and not see them again until dinner. Agree on a communication method for all members of your multigenerational holiday. On cruises, some groups put magnetic whiteboards on cabin doors to notify others of their whereabouts; others arrange morning coffee gatherings at a set time each day to outline where people will be throughout the day.

Plan the Fun

Holidays and parties are enhanced by planned activities. A few pre-planned moments of fun go a long way toward the success of the entire holiday. Once again, dividing the workload for the activities prevents an undue burden on any one person. Here’s a list to get you going.

Breaking the ice

Because families expand through generations and marriages, there may be members of your multigenerational group who have either never met, or are not normally in close contact. Increase the comfort level of diverse groups with a quick meet-up after everyone has arrived. But keep it brief for those that want to explore the resort. You can keep it simple with a hugs and handshakes gathering on the promenade, but this is also a great time to hand out lists of room numbers and discuss any scheduled activities.

Group photo ops and matching outfits

Cruises offer plenty of opportunities for group photos. Formal nights when everyone is already dressed work well. The large cruise lines offer a wide range of photography options onboard. Check with the photo shop early for ideas and scheduling appointments. And don’t forget impromptu moments for photos with people you rarely spend time with.


While it is usually best to allow each family cluster or individual to make their own plans for excursions, there may be times when there is enough consensus among group members that a particular excursion for all is a viable option. The key to success is to never assume that a group member wants to participate without asking.


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About the Author
I've worked in travel for 13 years. As a marketer I've worked for Thomas Cook, Going Places, Direct Holidays, Gill's Cruises, Virgin Holidays and cruise brands,, and Strawberry Holidays was born because I LOVE TRAVEL. In the last 5 years my family and I have been to 39 places and 17 countries.