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(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 64, family travel expert Dia Adams shares how her love for global adventures—from Mexico to Cuba—evolved into mastering points and miles to travel smarter with kids. A key moment? Scoring a 100% AMEX transfer bonus that helped fund a family trip to Guatemala. From riding trains across Europe to planning a $5,400 dream vacation packed with fireworks at the Eiffel Tower and kissing the Blarney Stone, Dia proves travel memories don’t need to break the bank.
She also dishes out smart tips for visiting Disney parks abroad—like Paris and Tokyo—as affordable alternatives to Orlando. From scoring discounted train tickets to bidding on upgrades and booking off-site stays, Dia’s advice blends cost-efficiency with comfort. Whether you’re planning around school calendars or choosing travel insurance, her approach focuses on flexibility, intentional planning, and keeping travel fun for the whole family.
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!
Rakuten: Earn cash back/rewards on every purchase!
Kit: Grow and monetize your email list
ClickUp: Stay organized and master projects
Make.com: Build Smarter Automated Workflows with no code
Function Health: Optimize your health, explore the world!
Carry: The modern Solo 401(k) for business owners
Dia's Social Media Links:
https://thediaadams.com/
Disney World Hacks Book
YouTube:
https://www.instagram.com/thediaadams?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==
https://thediaadams.com/
Disney World Hacks Book: https://www.amazon.com/Disney-World-Hacks-Proven-Vacation-ebook/dp/B077H6F7P3
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.
By Ross Alcorn5
1717 ratings
(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 64, family travel expert Dia Adams shares how her love for global adventures—from Mexico to Cuba—evolved into mastering points and miles to travel smarter with kids. A key moment? Scoring a 100% AMEX transfer bonus that helped fund a family trip to Guatemala. From riding trains across Europe to planning a $5,400 dream vacation packed with fireworks at the Eiffel Tower and kissing the Blarney Stone, Dia proves travel memories don’t need to break the bank.
She also dishes out smart tips for visiting Disney parks abroad—like Paris and Tokyo—as affordable alternatives to Orlando. From scoring discounted train tickets to bidding on upgrades and booking off-site stays, Dia’s advice blends cost-efficiency with comfort. Whether you’re planning around school calendars or choosing travel insurance, her approach focuses on flexibility, intentional planning, and keeping travel fun for the whole family.
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!
Rakuten: Earn cash back/rewards on every purchase!
Kit: Grow and monetize your email list
ClickUp: Stay organized and master projects
Make.com: Build Smarter Automated Workflows with no code
Function Health: Optimize your health, explore the world!
Carry: The modern Solo 401(k) for business owners
Dia's Social Media Links:
https://thediaadams.com/
Disney World Hacks Book
YouTube:
https://www.instagram.com/thediaadams?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==
https://thediaadams.com/
Disney World Hacks Book: https://www.amazon.com/Disney-World-Hacks-Proven-Vacation-ebook/dp/B077H6F7P3
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.

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