Points, Cards and Travel

Ross Alcorn

World Travel Made Easy with Itinerary Boss is your weekly guide for busy professionals to travel smarter, stress less, and maximize every trip. Through expert interviews and solo tutorials, learn step-by-step strategies: from best points and miles tips to leveraging AI tools. Hear from experienced travelers, points-and-miles pros, and authors on how purposeful travel help boost health, wellness, and personal growth. While balancing hectic schedules, you’ll discover easy ways to save on flights, streamline planning, and explore more without burning out your budget or your sanity. Tune in now!

  1. 1D AGO

    BILT 2.0 Rewards Explained: How to use Rent and Mortgage Payments to fund free travel with Henah Velez

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 137 of Points, Cards, and Travel, join us as Ross Alcorn sits down with Henah Velez to make the BILT Card feel simple again. If you have rent or a mortgage and you want travel rewards without adding more complexity, this episode breaks down what matters, what changed, and how to think through it without getting stuck in the math. Henah shares how she originally got the Built Card as a renter paying around $4,000 in rent, why earning something beats earning nothing, and how she uses BILT points to book trips like Atlanta to Europe on Flying Blue promos, plus a 4.5K Alaska redemption that replaced a $400 cash ticket. They also unpack housing only vs BILT cash, how transaction fees really work, and why using a calculator can save you from guessing. If you want a cleaner credit card strategy that matches your real spending, this is your roadmap. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Henah’s Social Media: Instagram Newsletter Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    26 min
  2. FEB 11

    How Home Renovations With 0% APR Cards Funded a $6,000 Hawaii Trip on Points with Chris Reichenbach

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as⁠ YourBestCreditCards.com⁠. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 136 of Points, Cards, and Travel, join us as Ross sits down with real estate investor Chris Reichenbach to show how points and miles can fund real travel while helping you move faster in business. If you are paying renovation costs by check or ACH, you might be missing a safer, more flexible way to pay, earn rewards, and keep projects moving. Chris shares how he went from fearing credit cards to using 0% APR business credit cards to cover materials, float expenses between hard money draws, and rack up points and miles without chasing random offers. You will hear how he handled a nightmare renovation that jumped to $140,000, why contractor payment methods matter, and how credit cards can protect you when work is not delivered. He also breaks down how he used points and miles to book a Hawaii trip that saved over $6,000 and created a life moment he will never forget. Credit Card Resources: ⁠5 Step Roadmap⁠ to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Melio: Pay vendors who don't take card with credit card to earn more points Chris’s Social Media: Instagram YouTube Spotify Itinerary Boss Socials: ⁠LinkedIn⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    33 min
  3. FEB 4

    How to Earn Maximum Credit Card Points, Hotel Room Block Rewards, and Plan a Stress-Free Destination Wedding with Kerry Krull (The Wedding App)

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 135 of World Travel Made Easy With Itinerary Boss, Ross sits down with Kerry Krull, founder of The Wedding App, to break down what actually makes destination weddings stressful and how couples can avoid it. Most destination weddings don’t fall apart because of travel costs or venues. They fail because guests don’t know what’s going on. Join us as Kerry shares insights from her background in corporate events and wedding planning, explaining why destination weddings should be treated like multi-day experiences, not just a single ceremony. From missed welcome parties to flight cancellations and last-minute schedule changes, Kerry explains how lack of communication creates chaos and how real-time updates can completely change the guest experience. Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com Credit Card Resources: ⁠⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠ ⁠⁠Best Credit Cards for Travel⁠⁠ ⁠⁠Bonus Offer Notifications⁠⁠ ⁠⁠Transfer Bonus Notifications⁠⁠ ⁠⁠Melio⁠⁠: Pay vendors who don't take card with credit card to earn more points   Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily   Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects Function Health: Optimize your health, explore the world! Kerry’s Social Media: Instagram Itinerary Boss Socials: LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    28 min
  4. JAN 28

    Why 40–50% of Flights Drop After Booking and How SkyKey Automatically Gets You the Difference Back with Jacob Goldberg, Co-Founder SkyKey

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 134 of World Travel Made Easy With Itinerary Boss, Ross sits down with Jacob Goldberg, co-founder of SkyKey, to break down one of the biggest hidden problems in airfare pricing and the simplest solution most travelers are missing. Airlines constantly change prices, and most travelers never check their ticket again after booking. Jacob explains why 40–50% of flights drop in price after purchase and how SkyKey monitors flights 24/7 to automatically secure refunds or flight credits when prices fall. With average savings of $130 per flight, SkyKey removes the stress of timing airfare purchases, deal alerts, and mental gymnastics especially for families, business travelers, and anyone booking peak travel dates. Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com Credit Card Resources: ⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠ ⁠Best Credit Cards for Travel⁠ ⁠Bonus Offer Notifications⁠ ⁠Transfer Bonus Notifications⁠ ⁠Melio⁠: Pay vendors who don't take card with credit card to earn more points   Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily   Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects Function Health: Optimize your health, explore the world! Jacob’s Social Media: Instagram Itinerary Boss Socials: LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    31 min
  5. JAN 21

    Positioning Flights Explained: How to Unlock Business Class Awards From Any Airport with Hunter Threadgill from Professor of Points & Frequent Traveler University

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 133 of World Travel Made Easy With Itinerary Boss, Discover how positioning flights can turn “I don’t live near a hub” into real business-class options. Hunter Threadgill aka the Professor of Points breaks down what positioning flights are, why they work, and how to use them without blowing up your trip when delays happen. You’ll learn how to spot the best airports to position through (think Chicago, Boston, Seattle, Vancouver, and more), how to protect the long-haul seat you actually care about, and how to plan stress-free buffers especially when you’re on separate tickets or switching airports. Hunter also shares how he uses hotel points (like Hyatt and free-night certificates) to turn an overnight into a bonus vacation day, plus a simple way to think about fuel surcharges and smarter Europe gateways like Paris and Amsterdam. We also touch award availability patterns and why competition at “someone else’s hub” can create opportunities. Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com Credit Card Resources: ⁠ The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠ ⁠Best Credit Cards for Travel⁠ ⁠Bonus Offer Notifications⁠ ⁠Transfer Bonus Notifications⁠ ⁠Melio⁠: Pay vendors who don't take card with credit card to earn more points   Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily   Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects Function Health: Optimize your health, explore the world! Hunter’s Social Media: Instagram Itinerary Boss Socials: LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    37 min
  6. JAN 14

    Simplify Tracking Your Points with AwardWallet: Reprice Flights & Avoiding Costly Mistakes With JT Genter of AwardWallet

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 132 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with JT Genter, Editor-in-Chief at AwardWallet, to break down how travelers can finally get organized with points and miles without spreadsheets, stress, or lost rewards. If you’ve ever forgotten expiration dates, redeemed points poorly, or felt overwhelmed managing multiple loyalty programs, this episode delivers clarity. Join us as JT shares how AwardWallet helps track credit card points, airline miles, hotel rewards, expiration alerts, and even flight repricing opportunities, all in one dashboard. You’ll hear how beginners can avoid analysis paralysis, how advanced travelers spot better redemptions, and why flexibility across programs leads to stronger value. JT also reveals common mistakes he sees, including why redeeming points for gift cards quietly destroys value. Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com Credit Card Resources: ⁠The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There⁠ ⁠Best Credit Cards for Travel⁠ ⁠Bonus Offer Notifications⁠ ⁠Transfer Bonus Notifications⁠ ⁠Melio⁠: Pay vendors who don't take card with credit card to earn more points   Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily   Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects Function Health: Optimize your health, explore the world! JT’s Social Media: Instagram Itinerary Boss Socials: LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    40 min
  7. JAN 7

    Credit Card Roadmapping Made Simple: Starter Cards, Premium Card Annual Fees, and Smarter Point Redemptions with Spencer Johnson

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 131 of World Travel Made Easy With Itinerary Boss, Ross Alcorn sits down with Spencer Johnson to break down how to build a simple, sustainable credit card strategy that actually leads to travel. Instead of chasing every shiny offer, Spencer explains how to start with the right foundation, choose cards that fit your real spending, and use transferable points to unlock better flights and hotels. This conversation covers annual fee math, welcome bonus timing, and why most people overcomplicate points and miles far too early. Spencer also explains how “cash back” cards can quietly become powerful travel tools, when diversification across banks actually helps, and how to avoid getting stuck with points you can’t use. If you want a clear roadmap whether you’re brand new or trying to clean up a messy setup, this episode delivers practical advice you can apply immediately. Subscribe to make sure you don’t miss future expert breakdowns. Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com Credit Card Resources: The 5-Step Roadmap to Your Next Free 5-Star Luxury Vacation + the 1 Card That Gets You There Best Credit Cards for Travel Bonus Offer Notifications Transfer Bonus Notifications Melio: Pay vendors who don't take card with credit card to earn more points Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily   Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects Function Health: Optimize your health, explore the world! Spencer’s Social Media: Instagram Tiktok Website Itinerary Boss Socials: LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    53 min
  8. 12/31/2025

    Southwest Companion Pass Explained: 135K Points Strategy, Companion Swap Rules, and Post-Change Reality with Max Craig (Points to the Max)

    (Disclaimer: Click 'more' to see add disclosure) Itinerary Boss is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as YourBestCreditCards.com. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers.   Opinions expressed here are the author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post. The content on this page is accurate as of the posting date; however, some of the offers mentioned may have expired. In episode 130 of World Travel Made Easy With Itinerary Boss, Ross sits down with Max Craig (“Points to the Max”) for a practical Southwest Companion Pass playbook that works in 2025 and 2026 without the timing mistakes that kill your value. Discover how the Southwest Companion Pass really works (true buy-one-get-one for just taxes and fees), why earning it early in the year can unlock up to 21+ months of upside, and how to approach the two-card method using P1/P2 strategy and the 24-month rules.  Max also breaks down the recent Southwest changes, basic fare limits, fare multipliers, assigned seating, and bag fees and the simple math that can make a card’s annual fee pay for itself fast. You’ll also hear a smart repositioning flight framework (like Nashville → Chicago) to reach better international award deals, plus the most common Companion Pass pitfalls, spend tracker surprises, returns, and companion-change headaches (and why calling is often better). Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com Credit Card Resources: Points and Miles Cheat Sheet Best Credit Cards for Travel Bonus Offer Notifications Transfer Bonus Notifications   Favorite Travel & Points Tools: TravelPayouts: Turn your trips into income and earn! Gondola AI: Find better hotels, earn more points, travel for free! Rakuten: Earn cash back/rewards on every purchase! Seats.aero: Discover the best flights for your points SaveWise: Maximize Cashback, Miles, & Points AwardWallet: Organize & track your points and miles RoveMiles: Earn and redeem miles on flights/hotels without a credit card CardPointers: Earn more from your credit cards daily   Our Favorite Daily Personal & Business Tools: Kit: Grow and monetize your email list ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects Function Health: Optimize your health, explore the world! Max’s Social Media: Instagram Facebook Page Website Itinerary Boss Socials: LinkedIn ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Itinerary Boss LLC has affiliate partners and some of these are affiliate links. This means that if you click on the link and purchase the item, we will receive an affiliate commission at no extra cost to you. We only recommend products or services we believe will add value to our listeners.   Disclaimer: The information provided by Itinerary Boss is for informational purposes only. We are not responsible for any outcomes, including injuries, damages, or losses, related to your travel plans. All travel is undertaken at your own risk, and Itinerary Boss assumes no liability for third-party services or actions.

    49 min
5
out of 5
18 Ratings

About

World Travel Made Easy with Itinerary Boss is your weekly guide for busy professionals to travel smarter, stress less, and maximize every trip. Through expert interviews and solo tutorials, learn step-by-step strategies: from best points and miles tips to leveraging AI tools. Hear from experienced travelers, points-and-miles pros, and authors on how purposeful travel help boost health, wellness, and personal growth. While balancing hectic schedules, you’ll discover easy ways to save on flights, streamline planning, and explore more without burning out your budget or your sanity. Tune in now!

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