How to Travel With Grandkids Without Losing Your Mind (or Your Points)
Multigenerational trips are among the most meaningful vacations you'll ever take. They're also logistically complex, emotionally charged, and capable of burning through a points balance faster than you'd expect. Here's how to do it right.
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Category: Educational (Multigenerational Travel)
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Let me tell you about Jim's trip to Hawaii.
Jim — who lives in Minnesota, golfs three times a week, and is constitutionally opposed to paying full price for anything — decided to take his wife Diane and their three grandchildren (ages 8, 11, and 14) to Maui for a week. The trip was Diane's idea. Jim's initial reaction, when he saw the price for five plane tickets and a week in a hotel during spring break, was exactly what you'd expect from a man who once drove 20 minutes to save $4 on a case of golf balls.
"That can't be right," he said, looking at the total.
It was right. Five round-trip flights from Minneapolis to Maui, plus a week in a hotel with enough space for five people, was going to cost north of $12,000 — before meals, activities, or the inevitable souvenir purchases that grandchildren seem to believe are a constitutional right.
Then Jim did something he wished he'd done years ago. He sat down, looked at his points balances across three credit cards, and made a plan. He didn't cover every dollar — that's not how this works, and I want to be straightforward about that. But he covered both flights and four of the seven hotel nights with points, bringing his out-of-pocket cost down to just under $5,000 for the entire trip.
"We've earned some sun," Jim told me afterward. Which is the most emotional thing Jim has ever said.
Here's how to plan a trip like Jim's — one that creates memories without creating financial regret.
Start with the right expectations
Traveling with grandchildren is not the same as traveling as a couple. It's louder, slower, more unpredictable, and infinitely more rewarding — but only if you plan for the reality of it rather than the fantasy.
A few things to know going in:
- You will spend more than you planned. Not because you're bad at planning, but because children generate expenses the way clouds generate rain — naturally and without apparent effort. Budget an extra 20% beyond what you'd spend on an adults-only trip.
- Everyone will need downtime. Including you. Especially you. Build rest into every day. A trip that exhausts everyone by day three doesn't get better by day seven.
- Ages matter enormously. A 6-year-old and a 16-year-old have almost nothing in common when it comes to travel. Plan activities with specific ages in mind, not "kids" as a generic category.
- Communication with the parents is essential. Dietary restrictions, screen time rules, bedtime expectations, medical needs, who's paying for what — sort all of this out before you book anything. An uncomfortable 10-minute conversation now prevents an uncomfortable 10-day trip later.
How to use points for a multigenerational trip
Booking flights for grandchildren with your points
The most common question grandparents ask: Can I use my credit card points to book flights for my grandchildren?
The answer is yes — and it's simpler than most people expect.
Through a credit card travel portal (Chase, Amex, Capital One): You can book flights for anyone through your travel portal. The reservation doesn't need to be in your name. Search for the flights, enter your grandchild's name as the passenger, and pay with your points. That's it. No forms, no approval process, no restrictions on who you're booking for.
Through an airline transfer partner: If you transfer your points to an airline loyalty program (like transferring Chase points to United, or Amex points to Delta), you can book award flights for other people — but the process varies by airline:
- Most US airlines let you book award flights for anyone without additional fees
- Some international airlines require the passenger to be a household member or charge a nominal booking fee for non-members
- Children under 2 who sit on a parent's lap typically fly free on domestic flights and at a reduced award rate on international flights
For a family of five, the portal approach is usually the simplest. You do one search, book all five seats at once, and pay with points. No need to create loyalty accounts for each grandchild or navigate separate booking systems.
The math on a multigenerational trip
Let's look at the numbers for a realistic trip — five travelers, domestic destination, one week:
| Expense | Cash Price (Estimated) | Points Approach |
|---|---|---|
| 5 round-trip flights (domestic) | $2,500–$4,000 | 75,000–150,000 points via portal (at 1.25–1.5¢/point) |
| Hotel: 7 nights (2 rooms or 1 suite) | $2,100–$3,500 | 70,000–175,000 hotel points OR 140,000–230,000 flexible points via portal |
| Rental car: 7 days | $500–$800 | Pay cash on a rewards card (earn points) |
| Meals and activities | $1,500–$2,500 | Pay cash on a rewards card (earn points) |
| Total cash cost | $6,600–$10,800 | |
| With points covering flights and hotel | $2,000–$3,300 | + 145,000–380,000 points |
The range is wide because it depends on where you're going, when, and how you book. But the pattern is consistent: points can cover 50% to 70% of the big-ticket items on a multigenerational trip, leaving you to pay cash only for meals, activities, and the rental car.
Hotel strategies for groups
Hotels are where multigenerational travel gets tricky. Two adults traveling together need one room. Two adults and three grandchildren need substantially more space — and the standard hotel room wasn't designed for five people.
Options that work well:
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Adjoining rooms. Book two rooms side by side. Grandparents in one, grandchildren in the other, with a connecting door between them. This uses more points than a single room, but everyone has their own space — and you can close that connecting door at 9 p.m. when you need quiet.
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Suites. Many hotel loyalty programs have suite options that accommodate larger groups. Hyatt, in particular, has properties with suite-style rooms that sleep four to six people comfortably. The points cost is higher, but you're booking one room instead of two.
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Vacation rentals. For groups of five or more, a vacation rental (through Airbnb or VRBO) often costs less than two hotel rooms and provides a kitchen, a living room, and the ability to do laundry — all of which matter enormously on a week-long trip with children. Some credit card portals now include vacation rentals, and you can also book them on a rewards card to earn points.
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All-inclusive resorts. This is the path of least resistance for multigenerational travel. One price covers accommodations, meals, and many activities. The stress reduction alone is worth considering. Some all-inclusive properties — particularly Hyatt Ziva and Hyatt Zilara in Mexico and the Caribbean — can be booked entirely with hotel points.
Destinations that work for every age
Not every destination is suited to a group that includes both a 72-year-old and an 8-year-old. The best multigenerational destinations share a few qualities: plenty to do across age ranges, manageable logistics, and a pace that doesn't exhaust anyone.
Destinations that consistently work well:
| Destination | Why It Works | Points-Friendly? |
|---|---|---|
| Orlando | Theme parks for the kids, nearby nature for the adults, and enough hotel options to fill a phone book | Yes — excellent availability on Hyatt, Marriott, and airline points |
| Hawaii | Beaches, snorkeling, easy hiking, whale watching. Something for everyone, and the pace is naturally slow. | Yes — strong hotel and flight award availability |
| San Diego | Zoo, beaches, Legoland, Balboa Park. Compact, warm, and easy to navigate. | Yes — good hotel point options, direct flights from most cities |
| National Parks (Yellowstone, Grand Canyon, Acadia) | Awe-inspiring for every age. Teaches kids about nature in a way no classroom can. | Moderate — limited hotel point options near parks, but flights and rental cars work well on points |
| All-inclusive Mexico/Caribbean | Swimming, beach, kids' clubs, and adults can relax by the pool. Everyone wins. | Yes — Hyatt all-inclusives are excellent point redemptions |
| European cities (London, Rome, Paris) | For older grandchildren (12+) — history, culture, and food combine for unforgettable shared experiences. | Yes — excellent flight and hotel availability on points |
Practical tips from grandparents who've done it
These aren't theoretical suggestions. They come from WanderWise members who've traveled with grandchildren and lived to tell the tale — happily.
1. Give each grandchild a "choice day." Let each child pick one activity or restaurant during the trip. It gives them ownership of the experience and dramatically reduces complaints. The 8-year-old wants a day at the water park? That's Tuesday. The 14-year-old wants to try a sushi restaurant? Wednesday night. Everyone gets a turn.
2. Build in solo time — for you and for them. The grandchildren don't need to be with you every moment, and you don't need to be with them every moment. If there's a kids' club or a parent can take them for an afternoon, take the time. Go to a quiet café. Read a book by the pool. Recharge. You'll be a better grandparent for it.
3. Pack a small first-aid and comfort kit. Band-Aids, children's pain reliever, sunscreen, anti-itch cream, a few favorite snacks, and a portable charger for devices. The trip where you don't need any of it is the exception.
4. Manage screen time expectations before the trip. Agree with the parents in advance: how much screen time is acceptable? When is it okay (long flights, yes; dinner table, no)? Having the rule pre-established means you're not the one saying no — the plan is.
5. Take photos of documents. Photograph each grandchild's passport, health insurance card, and any medical information. Store the photos in your phone and in a shared family album. If anything gets lost, you have the information instantly.
6. Don't over-schedule. This is the single most common mistake. The best multigenerational trip days have one planned activity and one unstructured block. A morning at the aquarium followed by an afternoon at the hotel pool is a perfect day. A museum at 9, a boat tour at noon, a cooking class at 3, and dinner reservations at 6:30 is a recipe for meltdowns — from the adults as much as the children.
The points strategy that keeps giving
Here's one more thing Jim figured out, and it's worth noting: a multigenerational trip isn't just a way to spend points. It's a way to earn them.
That $5,000 in cash expenses Jim put on his Chase Sapphire Preferred — meals, the rental car, activities, a few souvenir purchases — earned him roughly 10,000 to 15,000 points. Not enough for another Hawaii trip, but a real start toward the next one.
If you're planning to make multigenerational travel a regular tradition — and many grandparents do — each trip partially funds the next. The points cycle becomes self-reinforcing over time.
Frequently asked questions
Can I use my credit card points to book flights for my grandchildren?
Yes. Through most credit card travel portals (Chase, Amex, Capital One), you can book flights for anyone — grandchildren, adult children, friends. Just enter the passenger's name when booking and pay with your points. No special forms or permissions are needed.
How many points do I need for a family trip?
It depends heavily on the destination and time of year. As a rough guide: a domestic trip for five people (flights and hotel for one week) typically requires 150,000 to 350,000 flexible points if booked through a travel portal. Using transfer partners and hotel loyalty programs can reduce that significantly.
Should I book the hotel or a vacation rental for a multigenerational trip?
For five or more people, a vacation rental often provides better value and more practical space — bedrooms, a kitchen, laundry access. For smaller groups or shorter stays, hotel rooms (especially suites or adjoining rooms) can work well and can be booked with hotel loyalty points. Many WanderWise members use points for the hotel in the departure city, then a vacation rental at the destination.
What's the best age to start taking grandkids on trips?
There's no universal answer, but most grandparents find that children 6 and older are the sweet spot for travel — old enough to remember the experience, manage long days, and express what they want. That said, a beach trip with a 3-year-old can be wonderful; you're just planning differently than you would with a 12-year-old.
Do children need their own loyalty accounts?
For airline loyalty programs, yes — children can usually have their own accounts, and any miles they earn stay in their account for future use. For hotel programs, it's generally not necessary because the room is booked under the adult's account. For credit card portals, you're booking with your points regardless of who's traveling.
The real return on investment
The financial math of a multigenerational trip matters. But the real return — the one that doesn't show up on a credit card statement — is harder to quantify and far more valuable.
Your grandchildren won't remember the points you used. They'll remember the morning you went tide pooling and found a starfish. They'll remember the funny thing that happened at dinner. They'll remember that you were there — not on a phone screen, but right there, in the same place, sharing the same week.
That's the trip worth planning for. The points just make it easier to say yes.
WanderWise helps experienced travelers plan meaningful trips using credit card points — including the multigenerational adventures that become family stories for decades. Take the free Travel Score quiz to see what your points could make possible for the people you love most.