The WanderWise Monthly — August 2026

Subject line: The WanderWise Monthly — August: Fall Is Coming. Smart Travelers Are Already Booking. Preview text: September through November is the points traveler's paradise. Here's how to claim your spot.

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Hi Friend,

August has a certain feeling to it. The summer crowds start thinning. The light shifts a little earlier each evening. And something in the air says: what's next?

What's next, for smart travelers, is the best season of the year.

Fall travel — September, October, and into November — is when everything aligns. The weather in most of the world's best destinations is glorious. The crowds thin dramatically. Award availability opens wide. And the experiences? Harvest season in Tuscany. Foliage in Vermont. Wine country in Bordeaux. Temple gardens in Kyoto.

If summer is when everyone travels, fall is when the best travelers travel.

And August is when they book.

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✈️ DESTINATION OF THE MONTH: Tuscany, Italy (September–October)

Tuscany in September is a different country than Tuscany in July. The tour buses are gone. The vineyards are heavy with grapes. The air smells like rosemary and woodsmoke. And the long, unhurried lunches under the pergola — the ones you've seen in photos — are actually possible because there's a table available.

Truffle hunting in the hills near San Gimignano. Wine tasting at family estates where they know your name by the second visit. Driving through landscapes that look exactly like Renaissance paintings because, of course, they inspired them.

Here's the points math:

Round-trip in business class (East Coast): ~70,000 Aeroplan miles per person (transferred from Chase or Amex) 6 nights in a converted Tuscan farmhouse: ~120,000 Hyatt points (through the Small Luxury Hotels partnership) Cash equivalent for two: $8,400+ Points cost: ~$340 in taxes and fees

September availability is excellent right now. But it won't be for long. Book this month.

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💳 CARD OF THE MONTH: Citi Premier® Card

Annual fee: $95 Current sign-up bonus: 60,000 ThankYou Points (after spending $4,000 in the first 3 months)

The Citi Premier doesn't get the attention of Chase or Amex cards, and that's a shame — because for certain travelers, it's exceptional.

It earns 3x points on air travel, hotels, restaurants, supermarkets, and gas stations. That's an unusually broad set of bonus categories. Most of your daily spending falls into at least one of them.

The 60,000 ThankYou Points can be transferred to a solid roster of partners, including Turkish Airlines (outstanding for business class to Europe), JetBlue, and several international programs. Turkish Miles & Smiles, in particular, offers some of the best-value business class redemptions to Europe — often 45,000 miles each way, compared to 60,000+ on other programs.

If you already have Chase and Amex cards, Citi is the natural third card in your portfolio. It diversifies your transfer partner options and opens doors that the other two can't.

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

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💡 POINTS STRATEGY OF THE MONTH: Book the Hotel First, Then the Flight

Here's a counterintuitive strategy that experienced points travelers swear by: book your hotel on points before your flights.

Why? Three reasons.

1. Hotels have better cancellation policies. Most hotel award bookings can be cancelled up to 24–48 hours before check-in with no penalty and full points refunded. Flights are less forgiving.

2. Hotels lock in your dates. Once you've committed to a hotel, your trip dates are real. This focuses your flight search and eliminates the "I'll book when I find the perfect everything" paralysis.

3. Hotel availability disappears faster than flights. In popular destinations during fall shoulder season, the best hotel redemptions vanish quickly. Flights, by contrast, tend to have sporadic availability that pops up through the booking window.

The sequence: Book the hotel now (cancellable). Set flight alerts. Book the flights when they appear. If flights never materialize at a price you like, cancel the hotel — no harm done.

It's a risk-free approach that puts you ahead of the crowd.

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🗣️ COMMUNITY SPOTLIGHT

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

"I almost skipped Italy this year because August flights on points were crazy expensive. Then I remembered the WanderWise newsletter about shoulder season. Moved the trip to October. The flights were half the points. The hotel was available. And the weather in Tuscany was absolutely perfect. I'll never travel in high season again." — Susan and Bill T., Michigan

Planning a fall trip? Reply and tell me where you're headed. I love hearing about these.

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

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📅 UPCOMING DATES & DEALS

• Now through mid-September: Peak window for booking October and November travel on points. Act this month for the best selection.
• Late August: Several hotel programs run "buy points" promotions before fall travel season. If you're short on hotel points for a specific booking, buying the difference can make sense. Watch for 40–50% bonuses.
• Labor Day Weekend (September 1): Last hurrah of summer. Book now if you haven't — domestic availability is still reasonable.
• September 1: Our next newsletter is all about shoulder season gold — why September and October deliver the highest value per point of any months.

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❓ ASK MICHAEL

"My husband and I want to do a fall foliage trip in New England, but we're not sure if points are worth using for a domestic driving trip. Should we just pay cash?" — Ellen R., Pennsylvania

Ellen, great question. For a driving trip, the main points opportunity is hotels — and in New England during foliage season, hotel prices spike dramatically. A $180/night inn in Stowe, Vermont becomes $350/night in October. That's where points shine. A five-night stay at a Marriott or Hyatt property in the foliage belt could save you $1,500–$2,000 versus cash rates. The drive is free. The scenery is free. Let your points handle the roof over your head.

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Fall is coming. And for points travelers, it's the season where everything you've earned — every swipe, every bonus, every carefully accumulated point — reaches its peak value.

The world is quieter, cheaper, and more beautiful in the fall. All it takes is the foresight to book now.

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

Until next month — travel well.

Michael

P.S. — If you only take one international trip this year, make it fall. Make it Europe. And make it September or October. I've been doing this for years, and I can tell you without hesitation: there is no better time to be somewhere beautiful. The light alone is worth the flight.