The WanderWise Monthly — October 2026

Subject line: The WanderWise Monthly — October: Holiday Travel Without the Holiday Stress Preview text: Thanksgiving flights, Christmas getaways, and the booking window that closes faster than you think.

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Hi Friend,

Here's a sentence that makes most people anxious:

"We need to figure out holiday travel."

The logistics. The costs. The coordination. Flying to the kids' place for Thanksgiving, hosting everyone for Christmas, or — here's a thought — escaping to somewhere warm while the rest of the country battles airport crowds and freezing rain.

Whatever your holiday plan, one thing is true: the booking window is closing. Not slowly. Not eventually. Now.

Award seats for Thanksgiving are already 70% booked. Christmas flights are filling. And hotel availability at popular winter destinations narrows every day.

This month, let's handle holiday travel — calmly, strategically, and with your points doing the heavy lifting.

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✈️ DESTINATION OF THE MONTH: Turks & Caicos (December–January)

If your holiday plan involves escaping rather than hosting, let me paint a picture:

December 26th. You wake up. The morning light is warm — not the gray, filtered light of winter back home, but actual, honest sunlight. You walk to the beach. The sand is powder-white and squeaks under your feet. The water is clear enough to see the bottom at 20 feet. You have a novel, a cold drink, and absolutely nothing on the calendar.

That's Turks & Caicos in winter. And on points, it's remarkably accessible.

Here's the math:

Round-trip flights (from East Coast): ~35,000 JetBlue points per person (transferred from Chase) or ~25,000 Aeroplan miles 5 nights at The Ritz-Carlton, Turks & Caicos: ~250,000 Marriott Bonvoy points Cash equivalent for two: $9,200+ Points cost: ~$380 in taxes and fees

The post-Christmas window (December 26–January 5) is prime season for Turks & Caicos, but award availability is still reasonable if you book in October. By November, it's much harder. This is the month.

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💳 CARD OF THE MONTH: Capital One Venture X

Annual fee: $395 Current sign-up bonus: 75,000 miles (after spending $4,000 in the first 3 months)

Think of the Venture X as the premium version of Capital One's travel card — with perks that rival cards costing nearly twice as much.

The $395 annual fee comes with a $300 annual travel credit (automatically applied to bookings through Capital One Travel), effectively reducing the fee to $95. You also get 10,000 bonus miles on every card anniversary — worth another $100 in travel.

Lounge access is excellent: Capital One Lounges (beautiful, growing network) plus Priority Pass membership. For holiday travel — when airports are at their most chaotic — having a quiet lounge to retreat to is worth more than you'd think.

The card earns 2x miles on everything and 10x miles on hotels and rental cars booked through Capital One Travel. Miles transfer to a growing list of partners including Air Canada, Turkish Airlines, British Airways, and Air France.

For the traveler who wants premium perks without a $695 annual fee, the Venture X hits an appealing sweet spot.

👉 [Read our full Capital One Venture X review →] # (Affiliate link — supports WanderWise at no cost to you.)

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💡 POINTS STRATEGY OF THE MONTH: The Holiday Two-Card Approach

Holiday spending is coming whether you plan for it or not. Gifts, dinners, decorations, travel. The average American household spends an additional $1,500–$2,000 between November and December.

Here's how to make that spending work for you:

Step 1: If you're considering a new travel card, apply now — in October. This gives you November and December to meet the spending requirement using holiday purchases you were making anyway. Gifts, groceries for Thanksgiving dinner, holiday party supplies — all of it counts.

Step 2: Use your new card for the bulk of holiday spending, and your existing card for its bonus categories (dining, groceries, etc.).

Step 3: By January, you'll have earned a sign-up bonus of 60,000–80,000 points without spending a single extra dollar. That's enough for flights to Europe or a week at a resort — funded entirely by spending you were already planning.

The timing is strategic. The spending is normal. The result is extraordinary.

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🗣️ COMMUNITY SPOTLIGHT

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

"Last October, I panicked when I realized I hadn't booked Thanksgiving flights to see my daughter in California. Everything was expensive. Then I remembered I had 80,000 Southwest points. Booked two round-trip tickets for my husband and me — $0 out of pocket. No change fees, so when our plans shifted by a day, I just moved the flights online. Southwest is a holiday lifesaver." — Nancy D., Georgia

How do you handle holiday travel? Reply with your approach — I'm always collecting strategies.

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

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📅 UPCOMING DATES & DEALS

• Now — critical window: Book Thanksgiving flights on points this week. Award availability drops sharply after mid-October.
• Late October: Christmas and New Year's Eve hotel bookings should be locked in by month's end. Popular destinations sell out of award nights by early November.
• October 31: Halloween, of course. But also the last day before many airlines adjust award pricing for the winter season.
• November 1: Our next newsletter is our annual Black Friday Card Deals edition — the biggest card bonuses of the year, all in one place.

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❓ ASK MICHAEL

"My whole family (12 people) is coming to our house for Thanksgiving. I don't need flights — but is there a way to use points to make hosting easier?" — Barbara L., Connecticut

Barbara, absolutely. First, if you have Amex Gold, your 4x earning on groceries means your Thanksgiving dinner is earning significant points — a $400 grocery haul earns 1,600 points. But here's the creative move: if you're hosting out-of-town family, book their hotel rooms on your points. Nearby Hyatt Place or Marriott properties often run 8,000–15,000 points per night. You give your guests a comfortable place to stay (that isn't your guest room), you use your points generously, and everyone sleeps better. Hosting doesn't have to mean fitting 12 people under one roof.

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The holidays are supposed to be about connection, not logistics. About presence, not stress.

Your points can handle the logistics so you can focus on the people. But only if you act now. The window is open. Book the flights. Reserve the hotel. Handle it today so you can enjoy it in November and December.

👉 [Book a Free Holiday Travel Consultation →] /concierge

Until next month — travel well.

Michael

P.S. — One of my favorite holiday travel strategies: give travel as a gift. Instead of another sweater or kitchen gadget, give your spouse (or your kids, or your best friend) a printed itinerary. "We're going to Portugal in April. I already booked it." That's a gift that doesn't fit in a box — and it's the one they'll remember.