My family and I have somewhat recently embarked on a number of incredible multigenerational family trips that have been absolute successes. We’re in a slightly different situation than many typical ‘multigen’ trip seekers as we don’t have children ourselves. While our age range is vast (my younger sister is 26, my grandma is going to be 91), we’re all adults which makes finding great options a bit easier. That being said, I don’t plan to change our annual family getaways when we add our own children to the mix. It’ll be a new layer to consider but for the most part, we’ve figured out the formula to help craft successful multigenerational family trips with tons of great memories.
Have a Point Person
This may be partially a personal preference but I find having a group leader makes multigenerational family trip planning much more simple. As the one who typically is the group leader I can attest to the fact that it’s generally a fair bit of work and takes a lot of good communication (and can occasionally be frustrating), but I’ve found that our trips move along much more smoothly with good planning and having one person that truly has a grasp of the entire itinerary, as stringent or as loose as that may be. Many families have one person that falls into the leadership role or a couple of people who can collaborate on this. For people who like planning, it’s a great opportunity to craft fun itineraries that will make everyone’s getaway special.
In the past, this has meant that I’ve talked with my family members about destinations that are on our short lists to get an idea of places that intrigue us individually and collectively. I’ve also mapped out flights from our individual starting points to make sure that we’ll either merge during a layover or arrive at our final destination around the same time. For logistics, this means coordinating a rental car or a private driver if need be, plus finding accommodations that work for everyone. If the itinerary involves moving around a fair bit (like with our road trip in Ireland), it means having a rough day-to-day outline of where you’re going to be each day and a few things that may be on the agenda. It seems anal to have so much mapped out, but in a group setting I find that it actually makes things go much more smoothly. The alternative tends to be a lot of wasted time trying to figure out what to do, and a lot of back and forth with everyone wanting to make sure it appeals to the masses. I enjoy the planning process a lot and have made some executive decisions occasionally when the rest of the group doesn’t have a strong preference. Despite having an itinerary (I literally send PDF itineraries to the group before we leave so they can make sure everything looks good to them), I leave room for flexibility. If something else comes up that intrigues everyone, we don’t need to stick to our ‘plan’. At the end of the day, the plan is to have fun together and make memories.
After you’ve established who’s interested in joining on your family excursion, the first element to consider to begin the discussion is budget. It seems simple enough but the reality is that many families have members in different income brackets and/or different spending styles. What may be an average expense for someone else, could be a splurge for me and vice versa. Budget is a touchy subject but don’t think of it as asking about their income; talk instead about what they’d like to allocate for the trip and what they feel comfortable spending. Alternatively, if your super close with your family members, you may already have a rough idea of what people are comfortable with. Err on the side of being conservative.
If you’re in the exploratory phase and aren’t married to a particular trip, you probably haven’t settled on a destination as of yet. Knowing what you have to spend can allow you come up with options that will make everyone happy. The key thing to remember is that you’re working off the lowest common denominator. You don’t want to have someone feeling stretched thin at upscale dinners and with expensive events and activities. Remember that the world is vast so just because your budget is limited doesn’t mean you’ll have a lesser experience. That may mean opting for a less luxe hotel or renting a home instead; or it may mean looking at reasonable alternative destinations. Perhaps that means opting for Eastern Europe over Western Europe or choosing Southeast Asia over French Polynesia. Also keep in mind that a good exchange rate may open a window for a cool opportunity that you didn’t think possible (e.g. the Euro at $1.10 is a lot different than dealing with the Euro at $1.50).
If your budget isn’t limited or if someone (or the group) is okay with subsidizing someone else’s expenses that can be a workable option, too, as long as the recipient feels comfortable with that arrangement. I think this works best in a ‘gifted’ format vs. blatantly subsidizing someone’s trip. Have a parent who can’t fork over the money for a plane ticket? Get together with other family members and make it a Christmas or birthday gift so they can be involved.
Know Your Audience (and Their Interests!)
Now that you know your relative budget (an important component), a second equally important component for smooth sailing is gauging people’s interests. If you’re like my family, the chances are that your interests will be quite varied but there is probably some overlap and many destinations will offer different facets that cater to different interests. If your group is particularly interested in history and cultural immersion, a luxe beach break may not be in the cards. And conversely, if you have a group that is more interested in a relaxing getaway with pool time and fruity cocktails, an on-the-go Eurotrip may not fit the bill.
The likelihood is that in many destinations there will be something that interests everyone, even if it’s on a smaller scale. Making time to indulge everyone’s individual, sometimes disparate, interests is important though. You don’t want to leave having someone feeling as though they missed their personal highlights in a destination. For example, during our trip to Ireland, we mixed in horseback riding in Killarney National Park, visiting a number of gorgeous and historic castles, going on pub crawls and listening to live music, and simply relaxing and taking in the scenery.
Evaluate the Terrain
The importance of landscape and terrain will be more important when traveling with elderly people and family members with disabilities. In our case, my 90-year-old grandmother is actually fairly mobile but has a difficult time walking long distances without getting tired. We opt to bring a wheelchair for her to easily get her around and allow her to take in the sights and sounds of a destination. In these circumstances though, doing a bit of research into the terrain can make your experience better overall.
In Las Vegas for example, life was a breeze. Everything is ADA compliant, the roads are easy to navigate with a wheelchair, and we had absolutely zero issues getting her around comfortably. Guatemala was a different story. Antigua was a bumpy ride that practically threw my dad’s back out after hours of pushing a wheelchair. Lake Atitlan, best navigated by boat, was possible only because Scott and my dad lifted my grandmother in and out of the boat so she could explore.
For those looking at European excursions, be sure to explore Sage Traveling as a point of reference. They’ve done a great job of providing an overview of some of Europe’s major destinations including ratings on a 1 – 5 scale on things like flatness vs. hilly terrain, cobblestones, accessible public transportation, etc.
Look at All Accommodation Options
The accommodations sector is evolving in a massive way and has made group trips so much more feasible. While some families prefer hotels for the ease and amenities, they’re not the only option. Depending on the destination, a villa rental may be a better fit. During my grandmother’s 90th birthday in Vegas, we stayed in a two-bedroom suite for a few nights since that was what helped make the experience. In Ireland and Guatemala, we used a mix of hotels and villas: villas for longer stretches and hotels for the occasional night or two here and there. Beyond being more cost-effective for us, renting villas has made our experience as a family even better. Having common spaces to hang out is a great bonus, and there’s when it’s just family around in the evenings, it means you can be 100% real: PJs, no make-up, running around barefoot. It’s hard to do that when you’re common space is a lobby bar.
It also means that you can have your morning coffee together and enjoy a few meals (or more) using your facilities. One of the other major things in terms of multigenerational family trips is having a place to call ‘home’ in case someone doesn’t want to go out on a given day. During our trip to Guatemala this happened twice: Scott got violently ill for about 36 hours and had to stay in to recover. Having a comfy bed within the confines of a home was a much more comforting circumstance than being in a hotel bed afraid to leave your room. Secondly, my grandmother was too tired one afternoon to join us for shopping in a nearby town (we were gone for about 4 hours). She opted to stay at home, reading on the patio and chatting with the chef at the house. We felt far more comfortable leaving her home than we would have if we had to leave her alone at a hotel.
AirBnb has been a great source for us for renting apartments or villas, and they have some unique options (e.g. trailers, tents and manor houses) if you want something out of the ordinary. Platforms like this have really changed the way we travel and have made the prospect of researching so much easier. I typically will narrow it down to a list of properties that I’ve shortlisted (e.g. 3 – 5), and email a bullet pointed list of each property, pricing, and what I find to be the pros and cons of each. From there, we can narrow it down and take feedback into consideration. For families that are okay with a lot of together time, an RV trip or doing a catamaran charter in the Caribbean or Mediterranean may be a good fit.
Even without kids in tow, we like to have an idea of which attractions, sites, restaurants and activities are on our must-see list. Our road trip in Ireland for my dad’s 60th birthday was a highlight of 2015 and we all collaborated on building an itinerary. As I mentioned above, I think it’s important to gauge people’s interests and try to find activities that will make everyone feel excited about traveling together.
Meals typically take a bit of planning for me as we like to enjoy a few special meals out but don’t want to blow the budget on food and drinks. Restaurants may hate me for this, but I try to make some key reservations in advance knowing that we can cancel if we have to. Making decisions as a group can be difficult so I find that having ‘defaults’ is key. Unless something else comes up that appeals to everyone, we know we have a great option that awaits.
Bring Your Own Entertainment
Whether you have kids or elderly travelers in tow (or both!), entertainment options help! When renting a house (vs. staying at a hotel), we bring speakers to listen to music, a pack of cards and a couple of games (e.g. Guesstures and Scattergories) for those late-night gaming sessions.
At our resort, we see families do this with kids regularly when it comes to toting beach toys and floaties for entertainment. In some destinations it’s worth looking into whether there’s a local vendor that rents toys as well. On Anguilla, for example, Travel Lite Anguilla rents beach toys, rafts, cribs, etc. which saves a lot of luggage space.
Anywhere in the world can be a potential destination for a multigenerational family trip, though some destinations are clearly more conducive than others. Whether you’re looking at adventures in Costa Rica, a relaxing escape in Mexico, a Eurotrip, or an African safari, many options can be doable with a good support team and with the right spirit. Traveling isn’t always glamorous and often times there are obstacles and stressful moments involved. In my experience, as long as we’ve focused on our time as a family and the memories we’re making, we’ve managed to forget those little travel headaches pretty quickly!