Trish and Brooke Harwood have cruised all over the world, but their most recent voyage — a two week sailing from Lisbon to Rouen (and several added days at each end) — stood out. This time they brought along their two sons and their partners, continuing a family travel tradition that started with Trish’s own parents and her siblings when she was just eleven. The Harwoods and their sons/families have just five cruises together under their belts, but are looking forward to more.
“One of the reasons we keep this tradition going is that we’ve learned that our kids, who range in age from 55 to 64, are such a treat to share destinations and experiences with,” Trish says. “And yet it’s a very different experience, even on a familiar ship, from our usual travel as a couple. On those trips, we’re more likely to seek out other guests and participate in more onboard activities. Here the focus is family.”
The biggest difference this time around? “I certainly put more work into the pre- and post-cruise planning,” she says.
The Harwoods are hardly alone in prioritizing trips with their adult kids and, down the road, a post-graduation trip with a grandchild, is already on the horizon. Multi-generational travel is having a moment: in the 2026 Virtuoso Luxe Report, the two strongest motivations to travel were spending time with immediate family and going on multigenerational trips.
It’s easy to see why cruising is such a natural fit for family travel, Trish adds. “Once you’ve identified your ship and itinerary, the heavy lifting is already handled. There’s no worrying about dinner reservations or where you’re going to stay, and the ship’s shore excursion department handles activities in port.”
This is the fifth trip the Harwoods have planned with one or both of their sons, and Trish has picked up plenty of wisdom along the way. Her first rule: “We’re talking vacations, not family reunions, which have different needs and protocols. These are trips with our adult children, not kids — and they’re our guests.”
Here are her top tips for planning a multi-generational cruise of your own:
Trip planning
- Start with a low-pressure suggestion: “We’re going to the Caribbean — would you be interested in joining as our guests?” Or “we’re thinking of visiting the Baltic; is this something you’d be interested in?”
- Be clear about financials from the start — who’s paying for what? Major expenses include airfare, the cruise itself, pre- and post-cruise transfers, and accommodations and meals on land.
- Air travel can be the trickiest piece, especially with limited seats and choices lately. I coordinate with the family and usually book everyone’s flights. But on one trip a couple couldn’t decide when to fly and it became frustrating. I finally said, “Here’s what our flights cost. I’ll send that amount to your bank account and you decide how to get there and book it yourself.
- Whichever approach you take, make sure everyone is treated equally. If one couple can’t join a trip, we make sure a similar trip is offered another time.
- Think carefully about timing. In our family, one couple is retired, and one still works — how much vacation time does the working couple have? If it’s limited, they might only join for part of the trip. Is the destination “good” (weather, crowds, etc.) during the window your kids can get away? If not, are you willing to adjust your own plans?
Setting expectations
- Talk through goals and expectations before you leave. What do you, as host, expect? What do your kids — or teenage grandkids — want from the trip? The couple still working will likely be exhausted just getting to the airport on day one, while the retired among you can’t wait to start sightseeing.
- This goes beyond schedules, too. On a trip to London, your teenage granddaughter might decide shorts, a tee shirt, and flip-flops are perfectly appropriate; you may see it differently. She might think hotel room service is the height of luxury, while you’re yearning for a good pub meal. Setting expectations on both sides upfront can save friction later.
On vacation together
- Let everyone keep their own daytime schedule and meet up for cocktails and dinner. Some like to sleep late, some want to sightsee early or sunbathe. Some like bike tours, others prefer museums, gardens or stately homes. It’s not a hard rule — on a small ship like Windstar, you’ll often end up at breakfast together, or a couple gets invited to dine with new friends — but daytime freedom gives everyone flexibility while keeping evenings as family time.
- Expect dining preferences to shift across generations. We’ve noticed the younger generation tends to prefer more casual restaurants, so we adjust accordingly.
- Stay easily reachable when you’re apart. A family WhatsApp thread keeps everyone in the loop — “A great table just opened up at Star Grill, anyone interested?” or “Just caught an Uber, back on board in 15 minutes” — so plans (like dinnertime) can shift in real time.
- As host, decide how much responsibility you’re taking on for everyone’s comfort. With just the two of us, it’s easy — if something goes sideways, Brooke and I sort it out together. With six people, even agreeing on a restaurant and getting a reservation can get complicated. And where two of us would normally grab a train, taxi, or Uber from airport to hotel, with six I add van transfers to the plan.
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A good example of our different interests is a review of the hundreds of photos we as a group posted on Google Photos during our three-week trip. Some were cathedrals and architectural while others were botanical gardens; some were landscapes while others were monuments or battlefields. All of us posted shots taken in fresh markets and of food! In viewing them it quickly became apparent whose interest was reflected in our growing album — and it got so we could identify the photographer by the subject.
And last, but by no means least:
- Don’t hesitate to ask a fellow passenger to take photos of you as a group … otherwise someone is always left out (unless you like selfies).
Have you traveled as a multi-generational family? Care to share any tips? And if you’re planning a trip like this and have questions, leave them in the comments below (scroll way down!) and we’ll get you answers.
