How to Plan the Best Multigenerational Trip Ever

Multigenerational Travel

If you aren’t including more than two generations on your family vacations this year, you’re in the minority. According to a 2019 Virtuoso Luxe Report, multigenerational travel is the No. 1 travel trend for 2019. Yup, more and more often, family travel can refer to everything from just bringing your kids along, to including everyone from your parents to your grandkids.

As someone who has been taking as many members of my family who would come, with me on trips for more than 17 years, I can vouch for the fact that family travel only gets better when you include more family.

The reasons for the popularity also mirror my own experience. We are increasingly aware of how little time we get to spend with the ones we love the most. travelling together helps to ensure that we all get a little more of that time. A 2015 survey carried out by AARP found that most multigenerational trips stem from that desire for quality time. That doesn’t mean it is easy.

The more people you include in the trip, the more people you’ll need to try to keep happy. And, if you happen to fall in the generation in the middle, you’re likely the one shouldering a lot of the burden – financial and otherwise, even in situations (Hello, Skip-generation travel) when you’re not invited along for the ride.

The more people you include in the trip, the more people you’ll need to try to keep happy. In this piece, we’ll try to cover some of the most asked questions on Multigenerational Travel and offer some tips on how to do it better.

Should We Travel Together:

1. The Trip Won’t Solve Your Problems

The one thing Multigenerational travel is a solution for the problems you have at home. If your husband snores at home, he’ll snore on vacation. And it’s going to irk you a lot more in paradise. Be realistic in your expectations. If you have trouble spending more than a few hours with your partners’ parents, inviting them on a 5-day trip where you spend most of your time together is going to be a mistake.

2. Have you Travelled together before?

Don’t test out the idea of a multigenerational trip on a vacation that you desperately need. This is what an overnight or weekend getaway is made for. Stay close to home on that first trip. The less money and time you’ve invested, the less you’ll feel the need to “make it work.” This is no time to force a square peg into a round hole. Some people simply aren’t meant to travel together.

3. Is everyone on board with the idea?

You’ll want to make sure you have a clear plan in place about what the vacation will and won’t be. What you will or won’t do, who’s paying for what, etc. If your wife really wants to spend time with the kids and bringing the grandparents along will interfere with that, rethink your plan.

4. You don’t have to bring everyone, every time.

I don’t always bring the entire family on a family trip. I’ve done trips with just one of my parents and one of my kids. We aren’t all keen on doing the same things, so we pick and choose who will go where and when, based on where the best fit lies.

What Kind of Vacation will this be?

1. What do your travel partners expect?

Take stock at the outset of your multigenerational vacation about what the expectations are. A vacation doesn’t look the same to everyone. If your parents think touring is important and your kids are hoping to laze around on a beach, you’re asking for trouble if you haven’t had a conversation about it in advance.

2. Encourage the Compromise

In discussions ahead of the trip talk to all involved about where and when compromise will be required. Maybe breakfasts together are optional (so that early risers and those that like to sleep in, don’t have to shift gears on vacation), but dinners together are non-negotiable. If everyone feels like they’re getting something out of a destination, there will be less bitterness about giving something up. The last thing you want is that someone feels surprised by the itinerary and leaves the trip feeling like they didn’t get what they came for.

3. Is your itinerary accessible to everyone?

All well and good that you and the kids are excited to jump off the cliffs and climb through the canyons, but is it too much for your folks? Make sure you’re keeping everyone’s abilities in mind while doing the planning. Elderly parents or kids recovering from a sports injury may want to go on a long hike, but that doesn’t mean they can or should. Similarly, check any tours your book for participant requirement notes. And be realistic about what everyone will want to / be able to do. If the kids don’t get up early at home, asking them to participate in a pre-sunrise hike is only going to upset everyone.

4. Consider getting help.

Whether it’s a multigenerational tour planning specialist, calling ahead to the resort concierge or booking a vacation where everything is taken care of for you, getting help can alleviate some (or all) of the burden of responsibility that can weigh heavy on the vacation planner in the family. Keep in mind that a tour that has other families on it (vs. a charter) can have pros and cons. With other families, you’ll have to be mindful of how long you stay in any given place, be on time for meetups and it will introduce people you don’t know (and may not like) into the mix. On a charter or private tour, you’ll have more control over your time and itinerary including bailing if the group consensus is that they’d rather hang by the pool for the afternoon. Of course, that freedom may come with a heftier price tag.

5. Don’t Forget You

As the party planner, chances are high that you’re taking into account everyone’s needs but your own.

Where should we stay on our Multigenerational Trip?

You want a laid-back trip

All-Inclusive Resort: Choosing a property that has activities that cater to all ends of the age spectrum will mean less worrying about where you’ll eat, sleep or how you’ll fill your day. All-Inclusives run the gamut from affordable (Think: Chain options) to exclusive (Think: Villa options). Gather intel from the trip participants about what they’d hope to get out of a stay including price ranges. Then, visit the websites and once you’ve got a few narrowed down for options, run it by the group.

Cruises: The great thing about cruise vacations is that they allow you the flexibility of an all-inclusive and a plethora of destinations to choose from. Members of your family can choose between participating in ports of call or hanging back on the boat to rest up for the evening dance parties. Larger ships will have more options and you can let staff know on booking, the number of people in your group so that things like rooms and evening meals can be booked together. Often groups get better deals and incentives as well. On Norwegian Cruiseline ships, “Freestyle Dining” means you can eat at a time that’s convenient to your group as opposed to a set schedule.

You want an Adventure

Outfitters: Work with a small group adventure company that has special tours for families. Two examples are GAdventures and Intrepid Travel. Both will work to make sure your tour group has similarly aged and interested participants. The mix of other families can be a great thing, especially for families where the level of adventure varies between the ages, or the adults don’t want to be entertaining the kids at all times.

Small Ship Cruises: The smaller the ship, the easier it is to get closer to the ports and active adventures in far-flung destinations. Consider lines like UnCruise where children as young as 8 are welcome (younger ones require special approval) on cruises that offer specific activities for children, ranging from tide pool treasure hunts to snorkelling with sea lions. River cruises like AmaWaterways where family sailings are frequent and great tour options make sure everyone is enjoying their trip. Andando Tours offers the opportunity to charter an entire yacht to explore the Galapagos, complete with a crew that will cater to all of your needs.

You’ve got an Independent Spirit

Boutique hotel: If you’re intent on planning it yourself, opt for properties where you’ll still be able to maintain the intimate feel of the family trip. Villas work well here, and if you get one that is staffed there’s no fighting over who will do the dishes or cook dinner. Smaller hotels where you take over all of the rooms, will also allow you a higher level of service and attention. Martinhal Family Hotels & Resorts in Portugal are great because they offer both 5-star luxury and family-focused fun. The Baby Concierge program means parents can pre-order baby products, cribs, safety gates, and other necessary items for the room ahead of time.

You want an Immersive Experience:

Dude Ranch: From horseback riding to family style meals, dude ranches are a great way to work together as a family while experiencing nature. Activities, accommodations and meals are all taken care of for the week, devices are kept to a minimum (often there’s no cell service or Wi-Fi), so everyone can focus on having a great vacation together. Plus, many ranches also offer kids-only activity options, so that older family members can get some adult time in as well. There are plenty of options to choose from. Check the Dude Rancher’s Association for more.

RV Road Trip: RVs have been a popular family vacation activity for decades, but new planning services are making it easier than ever to take generations with you on the road. Caravan type trips mean that you can have more than one vehicle, but everyone has a shared itinerary. It’s perfect for families who want some time together but also need privacy at night. Recently, I shared some great destinations for different types of families on TV. Here’s a link.

Things to Avoid on a Multigenerational Trip

All About Me Activities: Remember that this trip is supposed to be fun for everyone. Itineraries that focus too squarely on one person (or age group) will ultimately mean that someone loses out on having a great time.

Too much time together: Yes, family time is important, but it can be hard to be with people ALL the time. Make sure you build in breaks for naps, independent activities or free time. You might even build in separate activities for different groups. Maybe your parents will have a card game while the kids take in kids’ camp.

Overscheduling: Remember that vacations are best when there’s room for spontaneity and change. Having a loose itinerary is great, but if you find your stress level rising because you’re three minutes late for the scheduled relaxation time, you’ve probably overpacked it.

Too little space: Make sure you get as much space (accommodation-wise) as you can afford. Tripping over each other to use the one bathroom or having no space to sip your coffee in calm before facing your in-laws will get old quickly.

Layovers: The least fun part of the trip is always going to be getting there and getting home again. Minimize the grief by picking routes that are direct whenever possible.

Things to Remember to pack on a Multigenerational Trip

1. Flexibility: Murphy’s Law dictates that just when you think you’ve planned for every possibility; a wrinkle will be thrown your way. Try to remain flexible enough so that those tiny bumps don’t ruin the trip. Encourage your family members to do the same.

2. Travel Insurance: We don’t leave home without it. We always make sure to doublecheck our coverage before heading off on a trip. And, we keep the emergency numbers in our passport holder so that we’ll know exactly where to find it if we need it. Having a list of any prescription medications you’re carrying and numbers for local clinics, hospitals and pharmacies on hand will also make sure that you’re prepared in case something is lost or someone is hurt. When travelling with parents and/or grandparents, be sure to confirm with them that they also have adequate travel medical coverage in place before you go, and keep the assistance phone numbers for their travel insurance plans in your contacts for easy access in an emergency.

3. A Good Attitude: You’ve put so much work into this vacation. Don’t ruin it by going in grumpy or tired. Make sure you’re well-rested before the trip so that you can make the most of your time together.

This post is sponsored by Allianz Global Assistance (AZGA Service Company) and I have received financial compensation.