16: Your Vacation Is Overpriced: Use These Tools to Pay Less and Travel Better

Dreaming of a luxury vacation without the luxury price tag? In this episode of Your Money on Easy Mode, I walk you through how my family is heading to Kauai during peak holiday season—without blowing our budget. From scoring flights using the Southwest Companion Pass and Chase Ultimate Rewards, to booking a luxury resort with Costco Travel perks, I’m sharing every tip, trick, and tool we used to stretch our dollars without sacrificing the view.

Whether you're planning your first big family vacation or just looking to travel smarter, this episode is packed with actionable advice. Learn how to use the Southwest Low Fare Calendar, find honest hotel reviews on TripAdvisor, and even scout out allergy-friendly restaurants with Yelp and Google Reviews. We’ll cover flights, hotels, food, rental cars, and activities—plus how to stack points, perks, and cashback to make every dollar work harder for your trip. Let’s get you out of town the easy way.

Chapters

00:00 Introduction to Affordable Luxury Travel

01:59 Finding the Best Flight Deals

03:11 Southwest Low Fare Calendar

08:45 Paying for Flights with Points

11:20 Tips for Finding Hotels

20:30 Maximizing Hotel Stays with Points

22:22 Costco Travel: A Smart Choice

24:20 Navigating Rental Car Options

25:44 Planning Meals and Dining Experiences

31:24 Choosing Activities and Entertainment

32:34 Conclusion and Key Takeaways

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