(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 106 of World Travel Made Easy with Itinerary Boss, we dive into how everyday online shopping can turn into free flights and hotel stays using Rakuten and SaveWise. These two free Chrome extensions make it effortless to earn cashback, credit card points, and airline miles while shopping at your favorite stores. Imagine booking a $500 Viator tour and stacking over 6,000 points toward your next trip without spending anything extra.

Rakuten allows you to choose between cashback or American Express Membership Rewards points, letting you maximize every purchase. SaveWise takes things further by comparing portals and showing you which option Amex, Chase, Citi, or even airline-specific programs like American AAdvantage—gives you the most value. Together, these tools create a powerful system that helps you double dip on rewards while planning travel or just doing everyday shopping.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

itineraryboss.com

Credit Card Resources:

Points and Miles Cheat Sheet

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Mesa HomeOwners Card: Use code KWHDBY to earn 5,000 bonus 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

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!

Itinerary Boss Socials:

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⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 105 of “World Travel Made Easy with Itinerary Boss,” relationship capital, Thr Technologies, and AI relationship intelligence take center stage in this conversation with Eric Creekmore. We dive into how an AI-powered personal strategist can turn missed connections into measurable opportunities, solve the timing-and-trust problem in today’s networking, and transform how business travelers connect.

Eric reveals how verifiable introductions, local-only data, and a future “relationship capital” score could make conference follow-ups faster, warmer, and more effective. If you want fewer cold pitches and more trusted referrals, this episode is your blueprint for smarter, more strategic networking.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Eric Creekmore’s Social Media:

Instagram

THR.APP

Itinerary Boss Socials:

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⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

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⁠⁠⁠⁠⁠⁠⁠YouTube

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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.

(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 104 of World Travel Made Easy with Itinerary Boss, Ross breaks down exactly how to use credit card points and miles to book flights to Munich and Berlin, plus how to redeem hotel points for free nights during your stay. From Lufthansa sweet spots through Aeroplan to Turkish Miles & Smiles redemptions on United, you’ll hear step-by-step strategies to save thousands on your next trip.

You’ll also get a ready-made 3-day itinerary for Munich and Berlin. From Oktoberfest beer tents and the Hofbräuhaus to the BMW Museum, English Garden, Brandenburg Gate, and the Berlin Wall, this trip combines must-see highlights with local experiences. Learn how to maximize Hyatt, Hilton, and Marriott hotel stays, plus discover travel tools like Seats.Aero, Gondola AI, and Points Path to compare cash vs. points.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 103 of World Travel Made Easy with Itinerary Boss, Ross sits down with Jaime Jay, founder of Bottleneck Distant Assistance, to explore the power of hiring virtual assistants, documenting systems, and building a business that runs smoothly—even while you travel. Jaime shares his Delegation Intelligence Framework and how it’s helped countless entrepreneurs regain their time and focus.

From leveraging high-limit business credit cards to pay $75K+ in monthly expenses, to exploring tools like Zil Money, Melio, and custom AI solutions, this episode dives into the real strategies modern entrepreneurs need. Whether you're just thinking about your first hire or ready to systematize your team, you’ll walk away with actionable steps to grow your business and earn rewards at the same time.

Jaime's Social Media Link:

Instagram

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 102 of World Travel Made Easy with Itinerary Boss, Learn how to maximize every point you’ve earned in this episode of World Travel Made Easy with Itinerary Boss. Ross breaks down the exact strategies he uses to transfer points from credit cards like Chase and Capital One to travel partners like British Airways, Qatar, and Hyatt. He explains the value behind each airline alliance, the mechanics of transfer timing, and why being an Executive Club member is key for some redemptions.

You’ll also get actionable next steps: from checking availability before transfers to creating loyalty accounts with airline and hotel partners for faster redemptions. Whether you’re a business owner with hundreds of thousands of points or a beginner planning your first trip, this episode gives you the tools to book smarter and travel further. Don’t forget to subscribe and share—it’s the best way to level up your travel game.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 101 of “World Travel Made Easy with Itinerary Boss,” Ross shares insider strategies for visiting Prague and Budapest using credit card points and AI-powered tools. Learn how to leverage Aeroplan, TAP Portugal, and ANA stopovers to add bonus destinations, find top hotels using Gondola AI, and map out unforgettable European itineraries with ChatGPT’s Plus/Terminal mode.

Ross also shares must-do activities like the Hungarian Parliament tour and Danube River cruises, along with specific lodging tips for both cities. Whether you’re planning a trip this fall or already dreaming about Europe 2025, this episode is packed with tools, apps, and Award Travel insights that will help you save money, travel smarter, and enjoy the journey.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 100 of World Travel Made Easy with Itinerary Boss, Ross and Leslie for a deep-dive into how business owners, parents, and sales leaders can unlock smarter travel using points, systems, and savings strategies. From automating finances to maximizing loyalty programs, they unpack practical tactics that support both career growth and family adventures.

Leslie shares her parenting travel toolkit, including must-pack items and routines that help kids feel grounded even on the go. Ross opens up about recent wins with credit card automation tools and previews a special guest appearance by the CEO of CardPointers. Whether you’re a busy entrepreneur or a parent trying to build memories on a budget, this milestone episode offers inspiration and actionable tips for the road ahead.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Leslie’s Social Media:

LinkedIn

Instagram

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 99 of World Travel Made Easy with Itinerary Boss, Learn how to maximize every point you’ve earned in this episode of World Travel Made Easy with Itinerary Boss. Ross breaks down the exact strategies he uses to transfer points from credit cards like Chase and Capital One to travel partners like British Airways, Qatar, and Hyatt. He explains the value behind each airline alliance, the mechanics of transfer timing, and why being an Executive Club member is key for some redemptions.

You’ll also get actionable next steps: from checking availability before transfers to creating loyalty accounts with airline and hotel partners for faster redemptions. Whether you’re a business owner with hundreds of thousands of points or a beginner planning your first trip, this episode gives you the tools to book smarter and travel further. Don’t forget to subscribe and share—it’s the best way to level up your travel game.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 98 of World Travel Made Easy with Itinerary Boss, Ross chats with Cindy, aka “The Points Mom,” about her journey from crunching numbers to maximizing miles. Learn how she saved over $5,000 on an Aspen ski trip using hotel points, helped her kids build credit starting at age 18, and why she swears by flexible rewards cards over co-branded options.

This episode breaks down real-world strategies for managing multiple credit cards, avoiding interest traps, timing applications around high-spend periods, and making the most of business expenses. Whether you're planning a safari with points or just trying to raise credit-smart kids, Cindy’s advice offers both big wins and peace of mind for families navigating the world of travel rewards.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Cindy's Social Media:

Instagram

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠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.

(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 97, Discover the best travel credit card strategies for couples in this episode of World Travel Made Easy with Itinerary Boss. Ross breaks down “2 Player Mode,” a game-changing approach that helped him and his wife open 9 cards, save $25,000, and rack up 660,000 points. Learn how to check your 5/24 status, evaluate your current cards, and pick the right anchor travel card to start your journey.

Ross also shares tactical tips for aligning card applications with upcoming trips, using no-fee and 0% APR cards strategically, and making the most of quarterly promos. Whether you’re just getting started or ready to level up, this episode gives you the map to travel smarter as a team.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

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Points and Miles Cheat Sheet

TravelPayouts: Turn your trips into income and earn!

Gondola AI: Find better hotels, earn more points, travel for free!

Kit: Grow and monetize your email list

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Make.com: Build Smarter Automated Workflows with no code

Rakuten : Earn cash back on every purchase!

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

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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.