Does Holding a Southwest Card Still Offset Fees via Baggage Perks?

Earn the Southwest Companion Pass in 2026 In this Hurdy Gurdy Travel Podcast episode, Justin sits down with Max Craig from Points to the Max to break down exactly how to earn and maximize the Southwest Companion Pass for 2026. We cover the best timing for points, which cards to open (and when), stacking strategies, and what recent program tweaks mean for your plan. Whether you’re brand-new to points or already flying regularly, you’ll get a practical, step-by-step gameplan to secure the companion pass and squeeze maximum value from it, plus intel on routes, hubs, and event meetups to level up your travel. What you’ll learn The cleanest timeline to lock the 2026 Southwest Companion Pass Which credit cards to consider and how to sequence them Points vs. flights: the math to qualify efficiently Recent Southwest program changes (and what still works) Hubs, routes, and positioning strategies Opportunity cost: when not to chase it Chapters 00:00 Intro 00:45 Meet Max Craig (Points to the Max) 02:50 Companion Pass, explained (eligibility & value) 04:49 Credit-card strategy & timing for 2026 06:10 What changed at Southwest (and what didn’t) 07:49 Qualifying: points vs. flight segments 11:22 App strategy: rules, pacing, and denials 23:35 Events, meetups, and community resources 28:47 Music City Miles & Points shoutouts 29:37 Frequent Traveler University notes 30:33 Fine print of the Companion Pass 32:55 Hubs, routes, positioning flights 34:53 Opportunity cost & alternative plays 43:10 Program benefits recap & pitfalls to avoid 43:36 Where to find Max (site & socials) 45:31 Trip planning tips & closing thoughts 51:31 Outro — 🎙️ 📢 Listen to the Hurdy Gurdy Travel Podcast: 👉 SoundCloud → https://soundcloud.com/hurdygurdytravelpodcast 👉 Apple Podcasts / iTunes → https://podcasts.apple.com/us/podcast/hurdy-gurdy-travel-podcast/id1489093490 👉 Spotify → https://open.spotify.com/show/0PRUx83Z4XKHengsgOoLWg 👉 TuneIn → https://tunein.com/podcasts/Podcasts/Hurdy-Gurdy-Travel-Podcast-p1275539/ 👉 iHeartRadio → https://www.iheart.com/podcast/269-hurdy-gurdy-travel-podcast-51807405/ 👉 Podbean → https://www.podbean.com/podcast-detail/vvdph-a3425/Hurdy-Gurdy-Travel-Podcast 👉 Pocket Casts → https://pocketcasts.com/podcasts/1a722d50-2d0a-0138-96d6-0acc26574db2?_prerender=true 👉 …and many other podcast platforms worldwide! 🌍🎧 📡 Prefer using your favorite app? Simply copy & paste my podcast RSS feed: http://feeds.soundcloud.com/users/soundcloud:users:706382626/sounds.rss — 💜 Support My Work & Unlock Special Perks: 👉 Support me through helpful referral links on my site: https://hurdygurdytravel.com/donate-referral-links/ 👉 Use my CardPointers affiliate link to save on annual and lifetime memberships → https://www.cardpointers.com/hurdygurdytravel CardPointers helps you activate card-linked offers and take advantage of other powerful credit card features. 👉 Become a Frequent Traveler University member and sign up for events. https://ftuniversity.com/?aff=24 👉 Earn 500 miles when signing up for Rove Miles using my referral link: www.rovemiles.com/?signup&referralCode=8AS1JSG9 — 👉 Visit the Support Tab on my website to contribute via SubscribeStar → https://www.subscribestar.com/hurdygurdytravel 🎁 Subscriber & Supporter Perks Include: ✨ One-on-one calls ✨ Advance notice of upcoming podcast guests (submit your questions!) ✨ A custom podcast episode recorded just for you 🎙️💬 ✨ Bonus content 🎁 — 🌐 Stay Connected With Me: 🔔 Subscribe on YouTube → https://www.youtube.com/@HurdyGurdyTravelPodcast 👍 Like on Facebook → https://www.facebook.com/HurdyGurdyTravelPodcast 🐦 Follow on Twitter / X → https://x.com/HurdyGurdyTravl 📸 Follow on Instagram → https://www.instagram.com/justinvacula/ — ✨ Thank You for Listening & Supporting the Hurdy Gurdy Travel Podcast! Stay tuned for more tips, strategies, and stories to help you optimize your travel, rewards, and lifestyle. 🚀🌍💳