One year, in the throes of single-handedly cooking a Thanksgiving feast, I said enough. Spending so many hours to create a meal that lasted 30 minutes, being too tired to even eat after the meal was ready – this was not how I wanted to connect with my friends and family.
I reached out to my extended family that afternoon. Next year, I said, let’s take a cruise. All of us.
And so we did.
I invested my time and energy into the delicate dance that was planning a multi-generational trip, and as a result, we had an amazing experience. People tried new things, connected with each other in a deep and meaningful way, and we had tremendous fun!
While you don’t have to throw out your holiday or seasonal traditions to enjoy a multi-generational vacation, I strongly encourage you to take on the challenge. The rewards are vast, and the memories are life-long.
In this post, I’ll walk you through some reasons to consider expanding your idea of a “family vacation, considerations you’ll need to incorporate in your planning, and how to make the most of your trip.
To read about our specific trip, check out my post that describes all the highlights and lessons learned!
Why take a multi-generational trip?
Any time you can cross generations in a shared experience, it’s somewhat magical. The memories you’ll take home from this type of vacation will transcend the location and the destination. A multi-generational vacation is a priceless way to connect younger kids with grandparents, and for adult children to see family members in a way they likely haven’t in some time. I found our multi-generational trip to be immensely rewarding for me as a travel planner, but also to remind myself of the true value of family and the excitement of adventure with unexpected partners.
Special considerations for a multi-generational vacation
One of the things I wasn’t quite prepared for in planning our multi-generational cruise was the specific needs of family members I wasn’t around regularly. I had forgotten the long, tiresome days with toddlers and preschoolers. I hadn’t quite thought through all the logistics of traveling with a walker or with someone who was ill. If you end up planning your trip, be sure to consider the wide range of needs and considerations that might affect members of your party, and how the vacation might impact those needs. Consider things like mobility – does someone in your party need a handicapped room? A wheelchair? A new walker? Consider securing lodging and transportation to match those needs.
What about individual habits or needs? Does someone in your party have dietary restrictions, a medication schedule, oxygen, or a CPAP machine? Being aware and talking with your travel partners about these details can help them imagine themselves on your trip, better prepared to meet health and safety needs.
Talk too about the impact of younger kids on a trip. How will we try to accommodate naps? Or a stroller? Or how about, we wanted to climb this mountain, which you can’t easily do with two small children, what then? We learned two things on our trip, the hard way. First, in a small cruise cabin, there’s little to no room for a pack and play, even if they provide one. Second, if your little one is in swim diapers, you’re not going to have a ton of fun at the tiny pool, separated from the rest of your family.
While you can’t anticipate everything, talking through some of these special needs can help make the entire trip more amazing for everyone in your party.
Tips for an amazing multi-generational vacation
Planning any trip requires a strategic approach, but a multi-generational vacation will need even more attention and care. But the rewards are invaluable – don’t be afraid to take on the challenge!
With the tips I’ve shared below, you can craft an itinerary that offers everyone a trip of their dreams, together.
1. Start with clear goals.
As with any trip you plan, you’ll have more success when you start with clear travel goals. When planning a multi-generational trip, or even just a trip with a large group, the goals of the trip for all in the party will serve as the foundation for your planning. Ask lots of questions and be sure to get input from all of the parties and individuals who will be traveling with you. For more on how to use travel goals as the basis for planning, click here.
2. Solicit ideas.
Beyond just goals and values, be sure to ask your traveling partners about their dream destinations (and why) and what types of activities they’d enjoy. Do they long for a European vacation? Or something warm and exotic? Urban or rural? Would they prefer lounging by a pool? Or finally seeing the Cistine Chapel? Ideas will be important as they guide you along.
3. Make deliberate choices.
It is going to be important to recognize, before you even start planning, that you will not make everyone happy with the trip you are planning. To help make these moments of discomfort more tolerable, deliberately make choices that will overall fit everyone’s needs, goals, and dreams. If you’re planning this activity for one group, plan that activity for someone else. If you choose this place for dinner because of someone’s needs, choose that place for watching the sunset for someone else. Then, make these compromises apparent so everyone feels seen and heard. This attention and care will help everyone feel better about making compromises. And with a multi-generational group, everyone will be making compromises.
4. Be flexible.
There are two main ways you need to be ready to be flexible. At the planning stage and during the trip itself. Even if you plan the perfect itinerary that fits everyone’s expectations, something will need to change. Someone will have a preference or an objection that will require you to pivot, be creative, and look for alternatives. That’s ok! If people have input on the plan, that means they’re invested. On the trip, things are going to pop up, too. Someone won’t be into the activity they selected months ago. Someone might be tired or feeling under the weather. Someone won’t have brought the right shoes, or have forgotten their swimsuit. This is normal. It doesn’t mean your trip won’t be as special or wonderful. Either before you leave for your trip or in the moment, something about your plan will need to change. That’s ok. Be flexible and be ready to think on your feet as the unexpected pops up.
5. Get buy-in.
You’ll be asking your family to make a significant time and financial investment in this trip. These decisions and committments become a lot easier when they feel involved in the planning process, that their needs were respected and represented in the final plan, and that they’re excited about the trip! If you’re the planner, you’re also the marketing team championing the idea. Sell it vividly! To be successful here, be prepared to answer key questions about the trip – flexibility on dates, cost considerations, specific preferences or needs. Look for ways to get all the travel groups interested and happy about the idea of traveling together.
6. Build a detailed itinerary.
When planning any trip, but especially one for those outside your immediate circle, clarity is essential. People want to know where they are sleeping, what the accommodations are like. They need to know how the logistics of transportation will come together and what types of activities are available.
One of the key reasons we chose a cruise was that a lot of these decisions were made for us. Once people were on board with the cruise itinerary, we just had to fill in some of the gaps. Make this itinerary easy to share and abundantly clear. I created a two-page day-by-day document that outlined flights, lodging, transportation decisions, cruise ship stops, and more. I also worked with each person to talk about shared activities on and off the ship to make arrangements in advance (no risk of tickets selling out) and to inspire them to try something new.
7. Capture the trip.
Once your vacation starts, remember to capture it! Take lots of photos, collect souvenirs, and keepsakes. Talk to the others in your group about their day – what did they like, love, or wish had been different? Use these conversations to expand your memories of the trip, but also, to help you refine the upcoming days’ itineraries or even a future trip! Pro Tip: If you are taking a cruise, be sure to purchase any photos you want before you hit the gangplank on disembarking day. I learned this mistake the very, very hard way. Dozens of lovely vacation photos were lost.
When you return, consider thoughtful ways not only to capture your experience, but also of the entire group. Consider photo books or other keepsakes you can share. Click here for more ideas on how to capture the memories and vibe of your vacation even after you’re home.
8. Enjoy yourself!
If you need a reminder, which I sometimes do, remember to enjoy yourself! Take each moment as it comes, and let go of what isn’t helping or making your experience positive. There will be ups and downs on any vacation, but for this one, you’ve worked especially hard to navigate all the choices, preferences, and needs. Enjoy the rewards!
Wrapping Up
A multi-generational vacation will likely be one of your most memorable. There is something incredible about watching the different layers of your friends and family meld together in a new environment, trying new things. While the upfront planning can be a challenge, armed with the right perspective, a focus on what truly matters, and some smart planning tools, you’ll have your family off on their next adventure in no time.
Inspired but not sure where to propose as a destination? Check out my travel style quiz to inspire your next vacation!
Cheers!
Andrea
