Almost every multi-generational trip I help with begins the same way: one person quietly becomes the family travel coordinator and inherits three group chats plus a spreadsheet nobody else asked for. The grandparents want to know about the walking, the parents want to know about naps, and the cousins want to know whether anyone else has booked flights yet. The answers below are the ones I give most often, and they tend to travel further than the long advice threads, because they assume a group whose ages may span forty years.
Can you find one hotel that suits the whole group?
Yes, and settling on a single property is usually what turns a chaotic reunion into an actual holiday. I look for room types that cover a spread of needs at once: connecting rooms so parents stay close to small children, step-free bathrooms for anyone with mobility limits, and a suite or two for the people who want their own door to close. A shared lounge, a proper kitchen, or a shaded garden often matters more than the star rating, because that is where everyone ends up gathering.
How do you keep activities interesting for every age?
By building choices into each day instead of insisting that the whole party do the same thing at the same hour. Mornings tend to work best together, when energy is high and the sun is kind: a market, a short boat ride, an easy walk. Afternoons can split, so the teenagers go kayaking while the grandparents settle somewhere shaded with a long lunch. I flag the pace of every activity, note where the toilets and benches are, and leave empty space for the nap someone will always need.
What does this planning cost us?
Nothing beyond what you would pay for the trip itself, because the hotels and partners I book with pay me, not you. That is a different model from the advisors who want a fee before they begin, and it means the perks, such as a room upgrade, breakfast for two, or a credit to spend at the spa, are aimed at you rather than subtracted from the value. If a direct booking ever came in lower than my rate, I would say so.
How far ahead should we start?
Six to nine months is comfortable for school breaks and holiday weeks, and longer for a large reunion that needs many rooms in one place. Peak summer, spring break, and the days around New Year fill first, and grandparents often prefer certain dates for reasons of weather or health. Planning early also spreads the payments out, so one household is not carrying the whole bill in a single month.
How do you handle mobility needs and small children?
I ask about both in the first conversation, before any property is suggested, and then match every hotel and transfer to what you told me. That covers step-free entrances, lifts, ground-floor rooms, cribs, high chairs, and streets that work with a stroller, plus realistic walking distances so nobody is stranded at the far end of a resort. If a place looks perfect online but fails on access, it does not reach my shortlist.
What kinds of family trips can you plan?
The shape of the trip matters as much as the destination. I usually start by sorting your group into one of these directions:
- A resort stay with enough room and shade for everyone to spread out.
- A city or cultural break built around food, museums, and hands-on workshops.
- A heritage journey that follows the family's own history.
- A reunion in a shared villa with long tables and plenty of group time.
- A multi-stop route paced so that no generation feels rushed.
If none of those fit, I will help you narrow it down using your ages, budgets, and the kind of time you want together. A few short questions are usually enough to find the right shape.
Who should be the main contact for the group?
One person on your side and me on mine, with room to make small calls without a vote every time. A single contact keeps decisions from stalling while everyone waits on a cousin to reply, and it stops the same request arriving from four directions. That person does not need to know every answer; they just need to be reachable when I have a question.
The question families rarely ask until it is too late is the simplest one: what happens if a household has to drop out? Trips are booked months ahead, and jobs, health, and school schedules change. I arrange terms and travel cover so a cancellation becomes a managed event rather than a lost deposit, and I keep the rest of the group's plans standing if one branch of the family can no longer come.