By Gabriel Eronmosele, Erons Travel, Fargo, ND · Last verified September 28, 2026
Quick answer:
- Start with the people, not the destination.
- List ages, mobility needs, departure airports, room arrangements and each household’s budget, then choose one destination that works for the least flexible traveler.
- One resort or one villa with a single transfer is usually the best default.
The hard trip is three generations, two airports, one week, and a hotel picked because the photos had a slide. We build these for families spread across Fargo, Grand Forks, Minneapolis, Sioux Falls and the Chicago suburbs.
Image courtesy of Lawrence Crayton on Unsplash
What the hotel has to do
- Sleep grandparents without a long walk to the room
- Give kids a place that isn’t the restaurant
- Give adults a bar that isn’t inside the kids’ club soundtrack
- Offer truly connecting rooms, adjoining rooms, or a real villa
Ask hotels to confirm whether rooms connect internally, sit next to each other, or simply share a category. Those terms are not interchangeable.
Image courtesy of Ekaterina Shakharova on Unsplash
Trip structures that work
- One resort, one transfer: Mexico, Costa Rica, Hawaii, or a Caribbean island with good medical care.
- A villa with a cook and a driver: best at eight or more people, when dinner would otherwise be a nightly negotiation.
- A cruise: strong when nobody wants to pack twice and grandparents want a doctor on board. Compare cabin size, accessibility and embarkation logistics.
- Europe: one base with day trips, private transfers on luggage days, and fewer metro stairs.
Image courtesy of Alberto Casetta on Unsplash
Pace
One main outing a day and a pool afternoon that counts as the plan. A private guide serves a stroller and a cane in the same van far better than a 40-person bus.
What changes for a Midwest family
Half the family books FAR, half books MSP, and someone drives.
- Set a shared arrival window, or day one is spent in a lobby waiting for the Grand Forks connection.
- If grandparents leave from GFK and everyone else from MSP, you may need different travel dates.
- A winter delay can strand only part of the family, so put the first group dinner on the second evening and choose transfers that can adjust.
- For early departures, we book a night-before hotel.
Image courtesy of Zoshua Colah on Unsplash
Cost
In our recent planning, trips built through our network often start around $5,000 total and rise with the number of rooms and the space you need. Ask for a dated quote.
Image courtesy of Fernando Jorge on Unsplash
FAQ
Is all-inclusive a good idea for a large family?
Yes, when it saves 21 separate checks and everyone likes the food. Compare what the rate excludes.
Do we need travel insurance?
Review each household’s medical, cancellation and interruption needs with a licensed provider, and consider medical evacuation for older travelers or remote destinations.
What do you need to start?
Everyone’s ages and who can’t manage stairs. We can build from those two facts faster than from a mood board.
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