How to Plan a Multi-Generational Family Vacation

For a lot of people, getting the entire family together -- we’re talking grandma and grandpa, parents, and children -- for a few major holidays each year at home is more than enough. For others (let’s call them Clark Griswold types), it is the ultimate fantasy to wrangle in the troops for an epic trip that everyone will remember for the rest of their lives. (No pressure.) But pulling off a trip involving different generations can be much more challenging than expected, leading to a lot of unnecessary stress for the organizer. 

To gain professional advice, we interviewed Susan Farewell, founder and owner of Farewell Travels LLC, a Westport, Connecticut-based travel design firm. Farewell and her staff manage the travel portfolio for several clients and their families year after year. At least 25 percent of her clients will take one multi-generational family trip annually. Read on for the best tips and tricks to start the family trip planning process.

Start planning early (and make it fun).

Beach at Marriott's Aruba Surf Club/Oyster

As is the case for many things in life, the sooner, the better. Preparedness is key, especially for trip planning and budgeting. Susan says, “Start planning very early -- you’ll find more availability and the best prices. Allow an enormous amount of time to do this. It is not a part-time job. You are basically planning an event and I can’t stress enough the number of challenges one encounters -- in the planning, during the trip, and sometimes even after travel.” 

Susan also makes the point that the hardest part is pinpointing dates for different ages and stages of life. Confirming dates may make it difficult for everyone to commit early, especially college-age kids, but persistence is key. The earlier they can lock down dates, the more they can work around their schedules. Plant the seed with your family early by starting a conversation when everyone is together. If it can’t be in person, start an e-mail chain and make the tone easygoing and fun so that everyone wants to respond. 

Get everyone involved.

Horseback Riding at the White Stallion Ranch/Oyster

While it’s imperative to have someone take the lead, nobody likes a bossy dictator who thinks they know best. Of course, the person or people who are footing the bill will likely have more say in the decisions. That said, the organizer should start gathering input from all sides, so that everyone can help decide on a destination together. Travel preferences vary from family to family, but Farewell says she is seeing a clear change in how multi-generational families travel. In the past, it was all about just being together and relaxing. Now, she says, families are much more motivated to have a balance between leisure time and experiences that are educational and cultural. 

Active outdoor adventure vacations are also gaining popularity. “We have several multi-generational families going to western resorts and ranches,” she says. “What’s so great about these is that different members of the family can do whatever they want to do, whether it’s white-water rafting, horseback riding, or fishing, but the whole family comes together for meals and other family activities.” 

Avoid hard-to-reach places.

Pool Bar at the Pompano Beach Club/Oyster

In the early planning stages, it may be enticing to consider a faraway, exotic destination in order to maximize adventure and memorability factor. While this might be right for certain families, it’s usually better to stick to a simpler route to avoid travel complications, delays, and cancellations. Farewell says, “When it comes to big multi-generational families, the fewer moving parts the better. We do our best to avoid destinations that are hard to reach (and have multiple connecting flights). This can be very challenging because family members are coming from all over the place.”

Consider all accommodation options.

Three Bedroom Villa at The Landings St. Lucia/Oyster

All have their pros and cons. A family-friendly hotel or resort may be the easiest option, as it offers everyone their own space (and escape route), plus allows adults to meet up and split off when they want. It also helps when there are on-site restaurant options, as well as a range of on-site amenities and activities to keep everyone busy. This is a vacation after all, and the objective should be to relax and spend quality time together.

But in many cases, renting one big villa makes more sense, especially if you’re traveling to a remote area, or if your family prefers a more authentic local experience. Kitchens are a huge draw but can also take away from the hospitality experience. Farewell says, “Houses (or villas) can make great bases for families to be together. That said, on these family trips, my clients don’t necessarily want to be cooking and cleaning (or fighting over who should do those things). With some villa rentals, though, you can hire a staff, including a cook.”

Trip insurance is a good idea.

The Sultan Pool Villa at the Kuredu Island Resort & Spa/Oyster

This extra cost is always a good idea, but even more so when planning a trip involving lots of people. Trip insurance offers financial recovery for medical expenses that are incurred because of accidents and illnesses, as well as protection against trip cancellation and interruption. Farewell says, “Trip insurance is key. If you have non-refundable parts of the trip -- air, deposits -- you stand to lose them should someone get sick or injured.”

Consider hiring a travel professional.

Concierge Desk at The Pierre, a Taj Hotel/Oyster

Don’t beat yourself up if you need to enlist the services of a travel professional. It’s important to know your own limits. While you may be a whiz at putting together your own family vacations, a multi-generational trip is labor intensive. Having a professional, like Farewell Travels or another similar company, orchestrate all the details of a major trip can free you up to deal with all the other family details that might come up (think: sisters who don’t want to share a room or kids who don’t want to go). A good travel professional also has many connections and strong bonds with hotels and villa rentals, and can often score you all sorts of perks (upgrades, preferred rooms, spa credits, free breakfasts, and more). 

At the very least, seek planning assistance and advice from your hotel or resort concierge team, which is another plus of going this route versus booking a private house. Contact your concierge a few weeks before arriving for assistance -- they are considered local travel experts and are eager to help make your trip special. If you’re renting a villa, the owner or management company you book through will likely be kind enough to provide some local tips. 

Make it a tradition, but mix it up.

Entrance at the Hotel Nacional de Cuba/Oyster

If your first multi-generational trip is a success, why not give it a whirl every year? Start the planning process as early as at the end of the current trip to see what your family members would like to see and do for future adventures. And each trip can be vastly different. You might rent a villa in Europe for a week the first time around, while the next trip is all about getting together in a historic hotel in Havana, Cuba. Even if you decide to repeat the same destination, try new activities each year so that you can enrich the experience and distinguish this vacation from others. 

You’ll Also Like: