Should You Buy Travel Insurance at Checkout?

This week, we’re exploring how to travel for less. We dive into the best tried-and-true strategies for stretching your travel budget.

Elaine Glusac, a longtime travel journalist andThe Frugal Traveler columnist at The New York Times, joins us to share her best money-saving hacks, from timing your flight purchases just right, to negotiating directly with Airbnb hosts. 

She also explains how to leverage under-the-radar resources like Going.com for finding cheap flights and Costco Travel for car rentals.  Plus she shares how to navigate Black Friday travel deals for cruises, flights, and hotels. 

This episode covers:

• When to book flights for the best prices: Elaine breaks down the “sweet spots” for booking both domestic and international travel, plus why holidays require a different strategy.
• Why flexibility matters more than loyalty: Shifting your departure by just a day or two can save you money and stress—and sometimes matters more than which airline you fly.
• How to spot true airfare deals: Tools like Google Flights and Kayak alerts can help you track fares and avoid misleading “fake sales.”
• Why you should negotiate directly with hosts: Reaching out to Airbnb or Vrbo owners can unlock discounts you won’t find through the platform.
• When Black Friday travel sales are worth it: Some cruise lines and hotels run genuine deep discounts—but Elaine shares how to separate the hype from the real bargains.

The Frugal Traveler Columns We Discussed: 

• The Secret to Finding the Best Travel Bargains
• How to Avoid Paying Vacation Rental Fees
• Driving the Alaska Highway
• Credit Card Swipe Fees Are Going Down. Are Points Going With Them?
• Traveling Abroad? If You’re Paying With Dollars, Your Trip Is on Sale.
• Cheap Flights, Half-Price Cruises: This Travel Tuesday, Deals Abound
• Getting the Most Bang for Your Buck While Traveling Overseas
• Join the Club, Save Some Money

Additional reading:

• How The New York Times’s Frugal Traveler Packs for Any Trip Imaginable
• The 3 Best Travel Backpacks of 2025 
• The 6 Best Carry-On Luggage of 2025
• The Best Suitcases for Checking 
• Soft-Sided vs. Hard-Sided Suitcases: The Final Showdown

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The Wirecutter Show is executive produced by Rosie Guerin and produced by Abigail Keel.Engineering support from Maddy Masiello and Nick Pitman. Episodes are mixed by Catherine Anderson, Efim Shapiro, Rowan Niemisto, Sophia Lanman, and Sonia Herrero. Original music by Dan Powell, Marion Lozano, Elisheba Ittoop, and Diane Wong. Wirecutter’s deputy publisher and general manager is Cliff Levy. Ben Frumin is Wirecutter’s editor-in-chief. Hosted by Rosie Guerin, Caira Blackwell and Christine Cyr Clisset.

Find edited transcripts for each episode here: The Wirecutter Show Podcast