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Booking a family holiday abroad is one of those jobs that feels enormous right up until you break it into pieces.
A cruise adds a layer, because you are not just choosing a destination. You are choosing a ship, a season, an itinerary and a set of assumptions about what your children can cope with.
I have put together the questions worth answering before you hand over a deposit. Some of these are obvious and get skipped anyway. A couple I only learned about from friends who wish they had asked sooner.
*This is a collaborative post. For more details, please see my Disclosure Policy.
1. What Time of Year Are You Actually Going?
This is the first question because it changes everything else.
European travel piles into a very narrow window. Eurostat data shows EU residents spent 15.7 per cent of their tourism nights in July and 16.5 per cent in August during 2024, with the busiest month running 3.7 times higher than the quietest.
School holidays are what they are, obviously. But if you have any flexibility at all, late May, early June and September are meaningfully quieter and cheaper.
They are also cooler, which matters more than people expect when you are walking around a Greek archaeological site with a five year old.
2. Have You Checked the Passports Yet?
Everybody thinks they have. Not everybody has.
Post Brexit rules mean passport requirements for travel to most of Europe now involve validity conditions that catch people out, and children’s passports expire faster than adults’ because they are issued for five years.
Check the issue date as well as the expiry date. Check every single passport in the house, not just the ones you can find quickly.
Do this today if you are even thinking about booking. Renewals take time and holiday season is the worst time to need one urgently.
3. What Size Is the Ship?
This is the question I would put at the top if I were being ruthless about it.
Ship size determines almost everything about the experience. Bigger ships have more facilities and more people. Smaller ships have fewer of both.
Silversea, for example, groups its smaller ship sailings into itineraries running from 392 to 728 guests, and luxury Mediterranean cruises at that scale reach small harbours that the very large vessels physically cannot enter.
That matters practically as well as aesthetically. On a smaller ship you get off quickly, the town is usually right there, and you are not queuing for a shuttle bus with a pushchair.
The trade off is honest and worth knowing. Smaller ships generally have less dedicated children’s programming. If your children are used to a supervised club all day, that is a genuine consideration.
4. What Does the Cabin Configuration Look Like?
Families rarely fit neatly into standard cabins.
Ask specifically about connecting rooms, whether a sofa bed counts towards occupancy, and whether there is any separation between sleeping areas.
If your children go to bed at seven and you do not, a single room with no divider is a long fortnight of sitting in the dark on your phone.
5. What Is Included and What Is Not?
The headline fare and the final bill can be very different numbers.
Ask about drinks, gratuities, wifi, shore excursions and speciality dining. Ask whether children’s meals are included and whether there is a supplement for a third or fourth person in a cabin.
Then ask what a typical family spends on board beyond the fare. A straight answer to that question tells you a lot about the operator.
6. Which Ports Suit the Ages You Have?
Not every stop works for every child, and a beautiful itinerary on paper can be exhausting in practice.
The pattern that works is alternating. One demanding port, then one easy one. A morning of history followed by an afternoon somewhere they can run about.
It is also worth thinking about crowding. A Parliament study on overtourism found that the most common measures destinations use involve spreading visitors across time and space, prolonging the season and dispersing arrivals across more sites.
Translated into family terms, the famous port on the busiest day is where a good trip goes wrong.
7. How Are You Handling the Sun?
Mediterranean sun is not British sun and children burn faster than adults.
The UV Index guidance includes a rule that works without checking a forecast: if your shadow is shorter than you are, UV levels are high. That is exactly the window when families tend to be out walking between sights.
Plan around it rather than through it. Out early, back for the middle of the day, out again late afternoon.
Long sleeve swim tops for the younger ones, hats for everyone, and sunscreen reapplied on a schedule rather than when somebody remembers.
8. What Happens If Somebody Is Ill?
The least fun question and the one worth answering properly.
Check what medical facilities are on board and what they cost. Check that your travel insurance covers cruises specifically, because some policies exclude them or require an add on.
Take a small kit of the things you always end up needing. Calpol, plasters, something for tummy upsets, and any prescription medication in its original packaging.
What I Would Do First
If you only act on one of these today, make it the passports. Everything else can be researched at leisure. That one has a queue attached to it.
After that, decide your season and your ship size before you fall in love with an itinerary. Those two choices shape the holiday more than the list of ports does.
And be honest about which version of this trip your family will actually enjoy, rather than the one that photographs well.
Have you cruised with children? I would love to hear what you would add to this list, because I am fairly sure there are at least two questions I have not thought of.