Itinerary Boss Insider

Hey Reader,

(⏱️ 100‑sec read)

This past weekend was packed with family, friends, and points‑and‑miles conversations. 🏡

We spent time with some commercial real estate and real estate service business owners, talking through how to turn their everyday spend into free flights & hotels.

The weekend ended with a quick trip through Dulles, where we enjoyed Etihad’s Priority Pass Lounge (also a Sapphire Lounge) a nice perk for Sapphire cardholders passing through IAD.

🎉 A Special Milestone: Our 100th Podcast Episode

Today we officially hit 100 episodes of the World Travel Made Easy podcast!

I want to thank you our guests, subscribers and listeners for helping us get here.

Many of you have joined me on the show to share your business insights, travel wins, and points strategies that have helped countless others.

We couldn’t have done this without you!

🎉 Community Win of the Week

We’ve been helping several business owners save thousands of dollars on travel by:

Paying general contractors with credit cards (even when they don’t normally take cards)
Aligning ad spend to maximize points multipliers
Optimizing shipping expenses to earn free travel faster

Each of these tweaks means more points, more savings, and more trips booked on the house.

Actionable Tip of the Week:

Turn Lyft Rides into Flights

Lyft just boosted its Alaska Mileage Plan rewards and stacking this with your credit card strategy is an easy win.

Here’s how it works:

2 Alaska miles per $1 on everyday Lyft rides
3 miles per $1 on airport rides or premium Lyft (Black, Black SUV, Extra Comfort)

💡 Stack this with your credit cards:

Use this card = 5x UR points on Lyft
That’s points + miles for rides you’re already taking

Why it matters:

Alaska awards start at 4,500 miles including American Airlines flights
A handful of airport rides could earn you a one‑way trip to New York, Miami, or Chicago

✅ Action Step:

Link your Lyft and Alaska accounts
Link your card for rides
Watch your points and miles pile up

🎧 This Week on the Podcast

1️⃣ Transfer Partners 101
Learn to move points to airlines and hotels for max value.

Transfer Partners 101: How t...

Aug 5 · World Travel Made Easy W...

12:39

2️⃣ How Credit Cards Can Pay for Family Vacations
Turn everyday spending into free trips plus, tips for teaching your kids the value of points and miles while benefitting .

How Credit Cards can Pay for...

Jul 30 · World Travel Made Easy W...

52:32

3️⃣ The Ultimate 2‑Player Mode
Combine strategies with your spouse or travel partner for faster free travel.

Ultimate Credit Card Strateg...

Jul 29 · World Travel Made Easy W...

17:22

If you think we did the 100 better than Wilt Chamberlain reply to this email.

Because you didn't ask....

We recently binged The Hunting Wives and watched it in 2 days.. Realizing some of it was filmed in Charlotte at Coyote Joes a country bar was great to see. We saw Darius Rucker & Dierks Bentley there last year and then saw on Instagram it was filmed in Charlotte.

Talk soon,
Ross
Founder, Itinerary Boss

P.S. Huge thanks again for helping us reach 100 podcast episodes!

Your stories, feedback, and support keep this community growing.
Here’s to the next 100! 🎙️✈️

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