(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 52, Ross and Caroline talk about the practical strategies for affordable travel, swapping stories from their journeys across 121 countries. Caroline, an engineer-turned-travel-blogger and Forbes Advisor writer, shares her expert tips on using points and miles, picking the best travel credit cards, and managing loyalty programs like a pro. Together, they reveal how to stay organized with multiple rewards accounts, avoid point expiration, and make the most of tools like AwardWallet, Travel Freely, and Points.com.

Discover how to balance personal preferences with popular destinations, whether it’s finding hidden gems for better value or deciding which hotel and airline programs fit your lifestyle. Caroline’s favorite spots—from Kalala Island in Nicaragua to Canave Suites in Santorini—show how a mix of points, bookings and open-mindedness can unlock memorable adventures. You’ll also hear about her upcoming travels to Italy, where she’ll be claiming her Italian citizenship, and her top food destinations like Japan, Italy, and Trinidad. Tune in for a blend of travel inspiration, money-saving tips, and the motivation to plan your next great getaway!

Affiliate Links:

The Platinum Card® from American Express

American Express® Gold Card

Capital One Venture X Rewards Credit Card

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com⁠

⁠Best Credit Cards for Travel⁠

⁠⁠Free Stress- Free Travel Starter Kit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

⁠Travel Freely⁠: Maximize Rewards, travel smarter!

⁠Rakuten⁠: Earn Cash Back on All Purchases

⁠Function Health⁠: Optimize your health, explore the world!

Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠Instagram⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠Threads⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Caroline's Socials

• Instagram

• carolinelupini.com

  
  

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

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.