How to plan a multigenerational cruise that works

My father-in-law Bob broke the news about our honeymoon like this: "Great news, we got you a cruise. Bad news, we're coming with."

That was Royal Caribbean's Freedom of the Seas in 2011, and it was my very first trip. I remember the ice carvings, the cheese sculptures, the folded towel animals, and a nightclub called the Crypt. Sarah went to bed early because she was a little seasick, so I stayed up until 3 am. (I've been forgiven. Mostly.)

In less than a month, we're boarding that same ship again with Bob and my mother-in-law Mary Ann, who were both on the honeymoon. Aiden and Addison are coming this time, and the route is new: the ABC Islands and CocoCay.

Back then, Sarah and I were young, love-struck, and along for the ride. Now we plan cruises for other families, and we take the trips ourselves so we can tell clients what we saw instead of what a brochure says. A trip with 3 generations on board is a good test of everything I've learned.

Pick the itinerary first, then the ship

Most people start by asking which ship. I start with where the ship is going, because the itinerary makes half the decision for you.

Alaska is the clearest example. The ships there are smaller and have fewer things to do onboard, and that's fine, because you're barely on them. You're at the port doing what you came for: the boat tour, the glacier, the fishing charter. The ship is where you eat dinner and get ready for tomorrow. The Galapagos works the same way. Both are itinerary first, ship second.

The Caribbean flips that around. I live in Florida, I've cruised down there for years, and I've been to just about every port. Some days the ship is the destination. Nassau isn't my favorite, and I never get off there. I count it as a sea day, and that's an easy call on a ship like Icon of the Seas, Utopia of the Seas, or Star of the Seas, because there's so much to do onboard.

So before you compare ships, answer one question. Will your family spend its days in port or on the ship?

Match the ship to the family you are

Here's how I think about the 2 ends of the spectrum.

Mega ships (Icon, Utopia, Star, MSC World, Norwegian Prima) make sense when you have younger kids and plenty of sea days. They have water slides, a lot of activities, and neighborhoods that split the ship into zones. That's why they don't feel as crowded as you'd expect. They're still crowded, though, and I won't pretend otherwise.

Small, high-end ships are a different experience. Scenic, Regent, and Crystal compete on space per passenger, and they aim for staff ratios close to 1 to 1. When I'm traveling on my own, that's what I want: a slower pace, a higher level of service, and zero interest in a rock climbing wall.

For a multigenerational trip in the Caribbean, I think Royal Caribbean's big ships are much better than the small-ship options. Everyone finds something. For a multigenerational trip to Alaska or the Galapagos, you won't find those same ships, so you plan around the itinerary and let the ship be what it is.

If I had to put my whole opinion on ship size in one sentence, it would be this: pair the right ship with the right adventure and the type of family you are.

Give everyone a different day

The best thing about a multigenerational cruise is that nobody has to do the same thing at the same time. A cruise gives you the experience you want, and it isn't one size fits all.

Our family is adventurous. We do side-by-sides, snorkeling, zip lines, and off-road tours. Grandma and Grandpa might walk around town and do a little shopping. Or they stay on the ship and enjoy the spa, play cards, win at bingo, or sit with a cup of coffee at the café.

Both versions are a good day. We split up in the morning, and at dinner everybody has a story. The people who went snorkeling tell the people who didn't what they missed. The people who stayed aboard get to say they didn't miss a thing.

That's why I think a multigenerational cruise beats a multigenerational land trip. On land, you either all go or somebody sits out and feels left behind. On a ship, there's always a place for each person to be.

Cabins: what I book and when

I've stayed in inside staterooms, oceanview rooms, balconies, and suites. I'm a value person at heart, and I love having a balcony, but the itinerary decides it. This is how I decide:

• Balcony when the price is close. Sometimes a balcony costs about the same as an inside room, or even less. Take it.
• Inside when it's thousands cheaper. If the savings are that big, I'm happy with an inside stateroom. Spring break sailings are a good example, because inside rooms can be much cheaper then.
• Balcony, always, on scenery itineraries. In Alaska you want to see everything you're sailing past. I feel the same about Norway and Iceland, so I'm booking a balcony for our hosted group sailing on Norwegian Prima next June.
• 2 rooms beat 1 for a family of 4. On this trip, Sarah, Aiden, Addison, and I are in 2 inside staterooms instead of 1. That's what the pricing and the itinerary called for.
• Check what's above and below you. A cabin under a pool deck or next to a nightclub is a bad neighbor.

On this Freedom of the Seas trip, the ports are the draw and the ship is the base. That's a good reason to save money on the room and spend it on excursions.

Board with the right mindset

I think a bad cruise usually comes down to the wrong ship, the wrong people, or the wrong mindset.

The first 2 are the planner's job. You match the ship and itinerary to the group, and you build in the splits so nobody gets stuck doing something they hate. That's the work Sarah and I do for clients.

The third is on the person boarding. Walk up the gangway expecting to have fun, and the trip tends to follow. Walk up hoping it won't be awful, and you'll spend 7 days looking for proof.

Frequently asked questions

What's the best cruise line for a multigenerational trip?

For the Caribbean, I like Royal Caribbean's largest ships because they have something for a 6-year-old and a 66-year-old. For Alaska or the Galapagos, the itinerary matters more than the cruise line, and the ships are smaller by design.

Do grandparents need a balcony?

It depends on the itinerary and how much time they'll spend onboard. On a scenery route like Alaska, I'd say yes. In the Caribbean, where the ship is more of a base, an inside room can be fine if the savings are real. Grandparents who spend more time aboard get more out of a balcony.

Should a family share 1 cabin or book 2?

Price both. Sometimes 2 rooms cost less than you'd think, and everyone sleeps better. For our family of 4 on this trip, we went with 2 inside staterooms.

How do I keep a big family from feeling stuck together?

Plan the splits before you board. Let the adventurous ones book the excursions, and let the others enjoy the ship, the spa, or the town at their own pace. Then meet for dinner.

Are mega ships too crowded for older travelers?

They're crowded, but the ships are divided into zones, so they feel less packed than the numbers suggest. If an older traveler wants space and quiet, a smaller luxury ship is a better match, though it won't have the same things for kids.

If you're planning a trip with 3 generations, send me the ages, the itineraries you're considering, and what each person would do with a free day. I'll tell you which ship and cabin setup I'd book. You can reach me through Travel Squad Vacations at travelsquadvacations.com.

We're also hosting a group on Norwegian Prima, June 6 to 17, 2027. It sails from Southampton to Reykjavik, with stops in Bruges, Amsterdam, Bergen, Geiranger, Ålesund, Akureyri, and Ísafjörður. If you want to sail with us, message me.