124. Multigenerational Travel Tips in Honor of National Step Family Day (From This Bonus Mom)

Planning a vacation for three generations isn’t easy. In this episode, I’m sharing what’s worked (and what hasn’t) on our family trips, from cruises to theme parks, and how we make luxury travel feel good for everyone. You’ll learn how to keep the peace (and the minibar under control) on cruises, how to avoid vacation drama with smart planning, and the key rules that make blended family travel actually fun.

Previous Episodes Mentioned:

• Episode: 23. All About Virgin Voyages
• Episode 123: 5 Things to Know About Visiting Finland and Sweden on Our 2026 Group Trip Above the Arctic Circle (Encore)  
• Episode 107: Bridgerton’s World - Exclusive BTS Stories and 2026 Luxury Travel Adventure

Join a Group Trip:

• Dominican Daze with Virgin Voyages
• Nordic Wonders
• Bridgerton Spring Soiree

Connect with Michele on IG: @jetsettingwithmichele or on Facebook: www.facebook.com/groups/MMTinsiders

Contact Michele to plan your next vacation: www.makinmemoriestravel.co/contact or michele@makinmemoriestravel.co.

This episode was produced by The Podcast Teacher: www.ThePodcastTeacher.com.

Transcript

Hello, jetsetters, and welcome back to another episode of Jet Setting with Me. It is I,  Michele, the voice behind Jet Setting with me. And today I am coming to you as a proud bonus mom, AKA stepmother, and my normal travel obsessive self. Today I am gonna get personal. It's in honor of National Step Family Day, which is coming this week. And I'm sharing the messy, the magical, the travel moments that helped turn my blended family into a real family. So if you have ever wondered how to travel across generations without losing your sanity, this episode is for you. I'm going to take you behind the scenes of being a bonus mom on the road.

I'm going to give you practical tips for multigenerational vacations. Things like room pairings, budgets, quiet time, strategies that will save your sanity. And to spotlight the trips that we keep coming back to when we go on our own multi generational trips. I'll give you a hint. It's cruises and the Orlando theme parks. By the end of this episode, you will have clear, doable planning steps for every generation, ideas for where to get those unforgettable family moments, and of course, you get to travel vicariously with me on my favorite trip highlights that perhaps you want to steal when we plan your next reunion. Now, before I do all that, I have to get into some housekeeping. I am actively booking for three group trips right now.

So coming up in November. Yes, this November, the 7th through the 12th, I have a group going on the Dominican days that is a Virgin Voyages trip on board the Scarlet lady have an excellent group rate for you. If you want to hear what it's like to cruise on Virgin Voyages, I refer you to episode number 23. In February of 2026, we are booking for the Nordic Dreams Escape the Northern Lights. Yes, and magical, wonderful Winterland Journey. And you just heard about that last week on episode number 123. I only have two cabins or two rooms, so I really encourage you to let me know about that asap. And then finally, the Bridgerton Spring soiree.

Say that three times fast. Which is being led by Cass Moran, a Bridgerton influencer from Instagram, that was detailed in episode number 107. And we have had so much interest, we may have to get a bigger bus. So if that is something that speaks to your Bridgerton heart, then please, please let us know about that as as possible. Now back to that multi generational family trips. So the first one was a Baltics cruise and it was pre pandemic, so we actually did get to go to Russia. A quick reminder that putting off the trip of your dreams might not be able to take in the future because now cruise ships don't go into Russia because of the war with Ukraine. So I am still moved when I think about that night in St.

Petersburg where we were sitting in a gilded theater watching a Russian ballet. The audience, you could feel the hush of them and I felt like I had been handed a private moment in history. It had. This trip had the perfect blend of grown up magic like that ballet and youthful chaos, like someone in their 20s. My stepson was 20, couldn't drink at home, but was able to enjoy drinks in international waters and in most of the ports we visited. So he met lots of friends on board in his same age group and they basically cleaned out our minibar. I have embarrassing karaoke video of him singing with his new friends. Yes, that is footage I fully intend to play at his rehearsal dinner when and if he gets married.

So for this trip we were in a suite with a split bathroom and he had his own sleeping arrangements instead of, you know, sharing a room with us. It made those big multi generational moments feel more comfortable instead of starting off in a cramped cabin. So a few important reminders about your own multi generational cruise trip like this. Select the right room configuration. So we were in a suite, but you can do interconnecting rooms so that you get privacy and the young adults have their own space. Like I said, we had a split bath and a separate sleeping area so that evenings and early mornings were infinitely more relaxed. Especially because I am an early to bed person and an early morning riser and my stepson, who again was 20, was a night owl. So that's another thing.

Build in late night activities. Make sure that the cruise ship has nightlife so that you know your 18 to 25 year old can socialize safely and you don't have to be there. Check the alcohol and the age rules in advance. Will your child be able to drink abroad when they can't drink at home? And maybe go over some alcohol safety tips? If it's going to be something new for your child, manage those minibar and those incidental costs. Are you going to do a prepaid bar package or are you going to share an incidentals fund? Or are you going to give your young adult an agreed upon budget so that there are no surprises when you balance your shipboard account later? And of course use those onboard activities to bridge those generations? Ours is trivia. Everyone in my family loves the shipboard trivia and everybody of every Age meets up for that trivia. I usually watch because I'm not as smart as the other people in my family when it comes to useless knowledge. Chalk logistics and expectations before you go.

Our rule is you can go and do on a shipboard day whatever you want, but we always get together for dinner. Every night we have dinner together and on excursions. I'll talk about that on that next trip, which is another one Panama Canal cruise. And this one talks a lot about teen freedom because we were with my daughter, who was still, I think she was a senior in high school, so definitely still pushing the boundaries. And I can still feel the spray from Dunn's River Falls in Jamaica, even though this was a Panama Canal cruise. Actually, Dunn's River Falls is my favorite memory. It's a very tourist, touristy thing to do, but I can still feel the spray standing on those limestone steps. And as I climbed, thinking I was doing something I didn't think I could do.

So I was outside of my own comfort zone. But I watched my daughter laugh as she stood under a curtain of water, soaked, triumphant. So we took this cruise, the Panama Canal Transit, over her winter break and my son could not join us. So we let her invite a friend. Because cabins were double occupancy, we didn't want to pay a single person for two spaces. So we decided to let her invite a friend for a minimal fee, a decision that hadn't been fully vetted ahead of time. So my husband and I stayed in a normal mini suite and the girls, we put them in an inside cabin. The girls also made instant friends with people their own age.

It was winter break, so there were a lot of multigenerational families on this cruise. It was great. But it also meant that they chose late night ship activities over our family plans more often than I would have hoped for. And she definitely pushed the rule that we have about always meeting up for dinner, which created stress for everyone. The other families that their kids were allowed to go to dinner by themselves, my husband and I, and of course when we required her to eat dinner with us and not her friends, it created stress for everyone. I loved the shared adventures. Again, waterfall photo is one of my all time favorites and watching my daughter grow bolder. But what I learned is you have to set the rules before you set sail.

So designate a daily family anchor event, whether that's going to be an excursion on a day, a dinner, or a photo moment that everyone commits to. Schedule a daily family anchor event and then allow flexible free time around it. So your teens or anyone without fully developed frontal lobes still get some independence. Cabin strategy equals your sanity. Reserve a mix of suites or interconnecting rooms or an inside cabin that's close by. Parents get, you know, that quiet retreat and their own circadian rhythms. And teens get their social space making them feel more independent. Agree on guest rules in writing.

So even a short group text that confirms our cost and expectation of her friend would have prevented a lot of awkwardness post trip when we were like trying to decide how much she owed us and then asking for the money. We should have done all that in advance. And also we wouldn't have had to foot any surprise incidentals. They could have, you know, put their own car down on their own cabin. I always pre book our shore excursions with trusted local providers. I never use the ship run tours. So smaller groups equals a better experience, a lower cost. And we are supporting local businesses.

I do this every time and it consistently beats the big best option. So that Dunn's River Falls trip I mentioned, we were in a smaller group and we did our own thing and we had to make sure that the girls knew what time we were leaving in our van as opposed to what time the ship's excursion to the same place was leading. We should have planned for incidental costs up front. I mentioned that earlier, but for incidentals on the ship, for example, some beverages were we fitting the bill for that, like minibars, souvenirs, any specialty dining? Or should the teens have had a prepaid card or put their own debit cards or credit cards down for their extras? We really, really strive to protect our family dinners. And perhaps we should have pre booked a few key meals in specialty dining or special tables so that we could guarantee those nights together without any negotiation. Use tech to check in. Hello, everyone has a cell phone. Create a family group chat on WhatsApp.

Set quick check in times after late nights so you know everyone's safe without being a helicopter. Bonus mom. Build in parent time. Yes, yes, yes. Schedule that adults only evening that you can get to recharge without your under fully developed frontal lobes, children, and respect the balance. I could have done a better job of encouraging the teens to meet their peers and setting the expectation that they were still to return for that family anchor time. It keeps the trip inclusive and restorative for everyone. Third, my third most favorite multi generational trip.

Actually this is probably my first, but it's the third one I'm talking about. I celebrated my major milestone 55th birthday, which my birthday's on Halloween. I'm sure you all know that because I talk about it every chance I get in Orlando, my happy place. So we had the glow sticks, I had my birthday button. We had that perfect family photo with Mickey and friends. And it felt like the kind of milestone trip you plan for months, which I probably plan for a year, but that's just because I love, love, love planning family trips to Disney. Now this time we used our Marriott Vacation Club points, so we stayed off the site and we used a rental car. And that meant there was paid parking at the parks, but it also gave everyone private sleeping space.

This time we had our kids and my mother, so literally three generations. So it gave everyone private sleeping space. And one big win is that we ate several meals together in the condo. It saved money so that we could splurge on my extravagant birthday dinner and not have any guilt about it at Universal. We only had one day there, so we purchased the Express Pass. I've mentioned that before that I don't really let my clients go to Universal without the Express Pass. It makes for one spectacular single day and it's a total game changer for maximizing time. My mom, my husband and I actually left early while the kids who were in their late 20s at this point, well, one was in his late 20s, stayed to chase the thrill rides and then we allowed them to grab an Uber back.

So we trusted them to be independent and it worked really beautifully. So the things that I learned from this trip, your actionable planning checklist, what I did, what I recommend, budget trade offs. So way parking and the rental car costs against the condo savings. If you cook a few dinners in or order in, there's great Chinese food restaurant that's around the corner from our Marriott Vacation Club that I have to get at least once every trip. But that means you can reallocate some of those savings toward a special night or that express lightning lane upgrade or you can really plus it up with VIP tours. Highly recommend pre book. In other words, when you buy your Universal tickets, get the Express Pass. That way you already know what it's going to cost you.

And especially when you have limited part time, it's going to save you time and therefore it reduces your stress. You feel like you get more done so you feel like it pays for itself. It doesn't, but it feels like it. Plus it's already been paid for. It's like, you know, sunk cost. So set those independent parameters. So if your older teens or your adult kids want to be on their own for some part of the trip, agree on Those basic rules, are you going to require them to have a curfew so they don't wake people up when they come back into the condo? Are you going to let them use ride sharing apps by themselves or ride the monorail alone? I remember one time my daughter went to Disney World with her biological mother and her grandmother and they let her ride the monorail by herself and she was like seven And I was like, I would never ever do that and have those pre assigned meeting points so that trust doesn't become anxiety. Another example of a multi generational trip we did on a Disney cruise.

My daughter decided to hook up with another family the whole day we were at Atlantis in the Bahamas, so our cell phones were off and she missed that prearranged meeting point. And I spent all day, instead of enjoying the excursion with my mother, I spent all day running around the Atlantis water park looking for her and thinking that she had been kidnapped and horrible things might have happened to her. And then she strolled up to the van, on the very last van, going back to the ship that day as if nothing had happened. Frontal lobe development. Need I say that? Monitor those incidental fees. For example, I turned on my cell phone at that day in Atlantis. The parking, the resort shuttles, the express product costs, they add up. So decide who's covering what.

Is there one big pot of funds that everybody contributes to and then it's a family pot. Are you doing per person or is it going to be billed to the sandwich generation? Hmm, that would be you that I'm talking to. Avoid those surprises. Prioritize sleep and pacing. So for us, a condo made midday naps realistic. It's hot in Orlando even at the end of October. We built them into the plan for my mom so that she wouldn't get exhausted and she could be up for the evening events like the Halloween party. Book accessibility and seating ahead.

So we made sure to have a scooter so we could get accessible parade and firework viewing for my mom, who had really bad knees at that time. It makes staying longer, more enjoyable for the elders. And then of course, capture the story, take the photo, grab the memory. But I never post photos of my kids, ever. That's for them to post. They have their own social accounts. And while traveling, I only usually post photos of me. And that's for home safety and security.

I don't want people to know if my husband and I are traveling together and that means our house is empty. And the same thing for my mom who lives in her own place. I didn't want people to know that she was out of town or traveling with me and that her home was empty and easy to break into. So capture the story, but be careful what you post while you're in transit and in travel. So all right jetsetters, let's wrap this up. If you remember nothing else from today, these are my three biggest takeaways, rooming and privacy matters. Pick suites, interconnecting rooms or a condo so every generation has a place to to breathe. Set the rules before you go.

Written guest policies in a group text, chain a daily activity and clear incidental budgets. Prevent awkward moments and they keep the joy front and center. Pace is everything. Build in the midday rest if needed. Use smart park products like Extension Express, Lightning lanes, VIP tours, especially when time is limited. And of course have that one intentional surprise that is the memory that everyone's going to talk about for years. Next week I'm going to break down the real differences between traveling to Europe in winter versus the summer. If you have enjoyed this episode, I beg you to subscribe and leave a review.

It will help other bonus moms and dads and blended families find this episode. You can share a screenshot and tag me at jetsettingwith Michele on Instagram.  Michele is with 1L. I love seeing your family trips and reading your stories. And finally, if you really have a moment, you can save an audiogram moment from today, send it to a friend who needs that multi generational win. And until next week, jet setters happy safe travels.