Luxury travel
Three generations, one trip, and a set of constraints that do not overlap. Grandparents who cannot walk far, teenagers who need something to do, a toddler on a nap schedule and at least two people who will not eat what the hotel is serving. This is the trip we are asked to plan most often, and it is entirely solvable.
Every good multigenerational itinerary is built around whoever has the least flexibility, and it is almost never the person you expect. It is not the toddler, who will sleep anywhere. It is the grandparent with a knee, or the aunt who needs a lift rather than four flights of stairs, or the family member whose diet cannot be improvised.
Identify that person first and build outward. Everything else bends. If the plan works for them, it works for everyone.
Moving a party of twelve costs a full day each time: packing, transfers, check in queues, rediscovering where everything is. Two bases across two weeks is the maximum that works. Day trips out of a base are far easier than relocating.
A villa gives you a kitchen, a shared living space and a place for elders to sit while children swim, and it is often cheaper per head. A hotel gives you daily service, restaurants and a kids club. Many families do a villa for the middle week and a hotel at each end.
Connecting and adjoining rooms are almost never guaranteed by an online booking. They have to be requested, noted and reconfirmed, and on some properties they need to be contracted. This is worth doing properly.
Beautiful resorts are often built up hillsides with steps between every level. We check the actual walking distance from room to restaurant to pool, and ask for buggy service in writing where it matters.
Trying to keep twelve people together for every meal produces friction by day three. One shared dinner, everything else optional, is the pattern that keeps families happy.
Vegetarian, Jain, no onion no garlic, halal, allergies and the grandparent who wants dal at least every other day. Briefed to the kitchen before arrival, not negotiated at the table each evening.
| Destination | Best for | Watch out for |
|---|---|---|
| Riviera Maya, Mexico | Short flights from most North American hubs, large all inclusive resorts, easy for elders | Sargassum season on some beaches, June to September storm risk |
| Costa Rica | Nature everyone enjoys, excellent private guiding, teenagers stay interested | Long ground transfers, uneven terrain at some lodges |
| Italy, Puglia or Tuscany | Villa living, extraordinary food, short drives between everything | Historic properties with stairs and no lift, August heat and crowds |
| Hawaii | No passport needed for US families, excellent accessibility, medical care nearby | Long flight from the east coast, high peak season pricing |
| Dubai and the UAE | Superb accessibility, excellent Indian and vegetarian food, easy stopover from India | Summer heat is genuinely prohibitive, plan November to March |
| Kerala and Rajasthan | Meaningful for families with roots there, elders often travel more happily here | Domestic connections, road time, medical access outside cities |
Twelve months for a summer or December trip with more than eight people. Villas, connecting rooms and large blocks of premium cabin seats all disappear early, and they disappear in that order. Nine months is workable. Under six months, the destination list narrows considerably.
