The WanderWise Monthly — March 2026

Subject line: The WanderWise Monthly — March: The Trip Your Grandkids Will Talk About Forever Preview text: Multigenerational travel on points — how to make memories without breaking the bank.

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Hi Friend,

Here's something I hear from WanderWise members almost every week:

"I don't need another thing. I want to give my grandkids an experience."

That impulse — to share the world with the people you love most — is one of the best reasons to travel. And it's one of the best reasons to use your points.

Because multigenerational trips can get expensive fast. Four flights. Multiple hotel rooms. Theme park tickets. Meals for six or eight people. The numbers add up before you've packed a suitcase.

But points change the equation entirely. The flights? Covered. The hotel? Covered. That leaves you free to spend on the things that matter — the ice cream, the souvenirs, the moments.

This month, let's plan a trip the whole family will remember.

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✈️ DESTINATION OF THE MONTH: Orlando, Florida

Orlando isn't glamorous. It isn't exotic. But if you have grandchildren between the ages of 4 and 14, it's magic. And I don't mean that metaphorically.

The look on a grandchild's face when they see Cinderella's castle for the first time? That's the trip. Everything else is logistics. And the logistics, we can handle.

Here's the points math for a family trip:

Round-trip flights for 4 (grandparents + 2 grandkids, from most US cities): ~100,000 Southwest Rapid Rewards points total (no blackout dates, bags fly free) 5 nights at a family suite near the parks: ~125,000 Marriott Bonvoy points (SpringHill Suites or Residence Inn — both excellent for families) Cash equivalent for the group: $4,500+ Points cost: ~$90 in taxes and fees

Southwest is the multigenerational traveler's best friend. No blackout dates, no change fees, and — this is the big one — two free checked bags per person. When you're traveling with kids, that matters more than business class.

Book spring break or early summer now. Availability is thinning, but it's still there.

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💳 CARD OF THE MONTH: Amex Gold Card

Annual fee: $250 Current sign-up bonus: 90,000 Membership Rewards points (after spending $6,000 in the first 6 months)

This card earns 4x points at restaurants and 4x at U.S. supermarkets (up to $25,000/year). If you're the kind of person who feeds a family — and let's be honest, grandparents always are — this card earns points faster than almost anything else.

The 90,000-point sign-up bonus is worth $1,200–$1,800 in travel when transferred to partners like Delta, British Airways, or Hilton. That's real travel, earned from groceries and dinners you were going to buy anyway.

The $250 annual fee is offset by $120 in Uber Cash credits and $120 in dining credits each year. Do the math, and the effective fee is close to $10.

For families that spend heavily on food (and what family doesn't?), this card is remarkably productive.

👉 [Read our full Amex Gold review →] # (Affiliate link — supports WanderWise at no cost to you.)

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💡 POINTS STRATEGY OF THE MONTH: Booking Family Rooms with Points

Here's something most people don't realize: you don't need to book two hotel rooms for a multigenerational trip. You need the right kind of room.

Many hotel loyalty programs offer suite and family-room redemptions at the same point cost — or only slightly more — than standard rooms. The key is knowing where to look.

Hyatt Place and Hyatt House: Family-friendly properties with suites that sleep 4–6 people. Often bookable at 8,000–15,000 points per night.

Marriott Residence Inn: Full kitchens and separate living areas. Usually 25,000–35,000 points per night. Perfect when you need to heat up chicken nuggets at 10 PM.

Hilton Home2 Suites: Similar to Residence Inn — spacious, affordable on points, and designed for longer stays.

The strategy: search for these extended-stay brands on each hotel program's website. Filter by "suites" or "family." You'll often find a suite for the same points as a cramped standard room at a fancier property nearby.

More space. Same points. Happier grandkids. Happier you.

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🗣️ COMMUNITY SPOTLIGHT

[This month's spotlight comes from the WanderWise community.]

"I took my daughter and her two kids — ages 7 and 9 — to Disney World last spring. Four flights on Southwest, five nights at the Marriott. I used 180,000 points total. My daughter cried at the gate when I told her the whole trip was covered. My grandson says it was the best week of his life. He's not wrong." — Carol P., Philadelphia

Planning a multigenerational trip? Reply to this email and tell me about it. I love helping with these.

Not in the community yet? → [Join WanderWise Travelers →]

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📅 UPCOMING DATES & DEALS

• Now: Last call for spring break bookings on points. If you haven't booked April travel, do it this week.
• March 15: Many Amex cardholders receive elevated spending bonus offers mid-month. Check your app for targeted promotions.
• Late March: Summer schedule pricing settles on most airlines. This is when award seat availability becomes clearest.
• April 1: Our next newsletter covers shoulder season Europe — the smartest travel window of the year.

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❓ ASK MICHAEL

"I want to take my three grandkids (ages 5, 8, and 11) somewhere for a week this summer, but I'm not sure my points are enough for five people. I have about 200,000 points total across Chase and Marriott. Is that realistic?" — Margaret W., New Jersey

Margaret, absolutely realistic. Here's one approach: use your Chase points for five Southwest flights (Southwest is the most flexible for families), which would cost roughly 100,000–125,000 points depending on your route. Then use your Marriott points for 4–5 nights at a family-friendly suite property. That leaves you paying cash only for meals and activities. You're in excellent shape. Reply if you'd like me to sketch out a specific plan — I'd love to help with this one.

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The trips your grandkids remember aren't the expensive ones. They're the ones where someone they love showed them something new.

Your points can make that happen. And you've already earned them.

👉 [Book a Free Family Trip Consultation →] /concierge

Until next month — travel well.

Michael

P.S. — One more thought on multigenerational travel: let the grandkids help plan. Show them a map. Let them pick between two destinations. When they feel ownership of the trip, the excitement doubles. Trust me on this one.