The WanderWise Monthly — May 2026

Subject line: The WanderWise Monthly — May: The Best of America, on Points Preview text: Memorial Day trips, domestic destinations worth your points, and a card that makes home travel shine.

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Hi Friend,

Not every great trip requires a passport.

I spend a lot of time talking about European cities and far-flung destinations. But some of the best points redemptions in the world are right here — domestic flights that cost a fraction of international awards, hotels that punch well above their point value, and destinations that remind you why you live in a remarkable country.

Memorial Day weekend is the unofficial start of summer travel. And it's also one of the best times to see the United States — before the full summer crowds arrive, before the heat becomes oppressive, before every hotel in the country raises its rates.

This month, let's stay home. In the best possible way.

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✈️ DESTINATION OF THE MONTH: Charleston, South Carolina

If you've never been to Charleston, this is your year. If you have, you already know why it's on this list.

Late May in Charleston is warm but not yet sweltering. The gardens are in full bloom — azaleas, jasmine, magnolias. The restaurants are among the finest in the country, and many of them are housed in buildings older than the republic.

Walk the cobblestone streets of the French Quarter. Tour a plantation. Take a sunset sail in the harbor. Eat shrimp and grits at a place where the recipe hasn't changed in 80 years.

Here's the points math:

Round-trip flights (from most US cities): ~12,000–25,000 Southwest points per person 3 nights at a historic hotel: ~75,000 Marriott Bonvoy points (The Spectator Hotel or similar) Cash equivalent for two: $2,800+ Points cost: ~$45 in taxes and fees

Domestic travel on points is where the math gets almost absurd. A $2,800 trip for $45. That's the kind of number that makes people check it twice.

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💳 CARD OF THE MONTH: Southwest Rapid Rewards® Priority Card

Annual fee: $149 Current sign-up bonus: 65,000 points (after spending $3,000 in the first 3 months)

For domestic travel — especially if you fly several times a year — Southwest is in a category of its own.

No blackout dates. No change fees. No bag fees (two free checked bags per person). And their points are genuinely easy to use — you search, you book, you go. No transfer partners to navigate, no award charts to decode.

The Priority card's 65,000-point sign-up bonus is enough for 2–4 round-trip domestic flights, depending on your route. You also get a $75 annual travel credit and 4 upgraded boardings per year.

For anyone who travels domestically — visiting kids, seeing grandkids, taking long weekends — this card pays for itself multiple times over.

And here's the thing about Southwest that most people overlook: their Companion Pass. Earn 135,000 qualifying points in a calendar year and a designated companion flies free with you for the rest of that year and all of the next. Two years of free flights for your partner. From one card and regular spending.

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

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💡 POINTS STRATEGY OF THE MONTH: The Long Weekend Multiplier

Here's a strategy that domestic travelers overlook: the long weekend multiplier.

Instead of saving all your points for one big annual trip, consider using a portion for three or four long weekends throughout the year. Three-night trips. Friday through Monday. Close to home or a short flight away.

Why this works:

Lower point costs. Domestic flights on points are a bargain — often 8,000–15,000 points each way on Southwest. A hotel for three nights might run 30,000–50,000 points.

More trips, more memories. One annual trip gives you one set of memories. Four long weekends give you four. The research is clear: frequent shorter trips contribute more to sustained happiness than one big vacation.

Easier to plan. A three-night trip doesn't require weeks of research. Pick a city, book the flights and hotel, and go. Total planning time: 30 minutes.

Savannah for a weekend. Sedona in the fall. A long weekend on Cape Cod. Nashville for the music and the food. Each one costs 25,000–50,000 points total. Most WanderWise members have enough for several.

Think of it as a subscription to happiness — funded by points you've already earned.

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🗣️ COMMUNITY SPOTLIGHT

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

"Since joining WanderWise, I've taken four long weekends on points — Savannah, Asheville, Napa, and Santa Fe. Total out-of-pocket for all four: under $300. I used to save points for a 'big trip someday.' Now I use them every quarter. I'm happier." — Tom R., Connecticut

What's your favorite domestic points trip? Reply and tell me — I'm always looking for new recommendations.

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

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📅 UPCOMING DATES & DEALS

• Memorial Day Weekend (May 25): If you haven't booked yet, check Southwest and JetBlue — both still have point availability for many routes.
• Late May: Airlines often release discounted award tickets for summer Tuesday and Wednesday travel. Flexible dates pay off.
• Now: Summer hotel bookings on points are still available at most domestic destinations. By June, the best properties will be full.
• June 1: Our next newsletter covers summer adventure planning — how to make the most of peak season on points.

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❓ ASK MICHAEL

"Are domestic flights even worth using points for? Shouldn't I save my points for expensive international trips?" — Howard G., Arizona

Howard, this is one of the most common questions I get — and the conventional wisdom is wrong. Yes, international business-class redemptions offer high "cents per point" value. But a flight you never book has zero value. If domestic travel is what you do most, use your points for domestic travel. The goal isn't to maximize a spreadsheet formula. The goal is to travel. Use the points. Take the trip. You'll earn more.

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This country is extraordinary. And getting to see it — on points, over long weekends, without checking your bank account — is one of the great pleasures of being a smart traveler.

Your Memorial Day weekend awaits.

👉 [Join the WanderWise Community →] #

Until next month — travel well.

Michael

P.S. — If you're looking for one domestic destination that consistently surprises people, it's Savannah, Georgia. The architecture. The food. The squares draped in Spanish moss. And it books beautifully on points — usually under 40,000 total for flights and two nights. Just a thought.