(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 88 of World Travel Made Easy with Itinerary Boss, Ross sits down with Kat Medina—author, speaker, and world traveler who's journeyed through over 40 countries—to unpack the mindset shifts that make everyday life feel more adventurous. They explore how to overcome self-imposed limits, embrace remote work opportunities, and infuse the “vacation mindset” into your daily routine. If you’ve ever felt stuck or uninspired, this episode will help you find freedom and joy wherever you are.

Kat shares stories from the road, like battling heat exhaustion in Thailand and thriving while living abroad, all while offering powerful reframes and practical strategies you can use immediately. Learn about her inspiring children’s book Grumple the Great and mindset guide The Joys of Jet Lag, and discover how travel can become a lifestyle—even without a passport in hand. Whether you're planning a trip or just seeking more awe in your week, this episode delivers the goods.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

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Make.com: Build Smarter Automated Workflows with no code

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Function Health: Optimize your health, explore the world!

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

Kat Medina’s Social Media:

⁠Instagram⁠

⁠Website⁠

⁠Amazon⁠

⁠Bookshop

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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 87, we dive into the top personal credit cards for travel, focusing on flexible options like the American Express Platinum Card and Capital One Venture X, as well as hotel-branded choices such as the Marriott Bonvoy Boundless and World of Hyatt cards. You'll learn how to effectively use transferable currencies, bonus points, and strategic card combinations to unlock free flights, luxury hotel stays, and exclusive perks. Whether you're a frequent flyer or planning your dream vacation, the episode provides actionable tips to help you maximize every dollar spent. 

Additionally, discover how to optimize rewards through expense tracking and pairing the right credit cards with your unique travel habits. Ross shares insider tips for business travelers, including using personal cards for work expenses to accumulate points more quickly. You'll also hear success stories, such as how he and his partner earned free nights for their wedding and travel using the IHG One Rewards Premier card. By the end, you'll have a clear roadmap to transform your travel experience and save significantly on your next adventure.

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

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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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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 86 of World Travel Made Easy, Ross breaks down how to explore Croatia—specifically Dubrovnik and Split—without paying full price. Learn how to use points from your credit card rewards and loyalty programs to fly to Croatia and stay at top-tier hotels like Hilton, Hyatt, and Marriott. Ross walks you through using tools like SeatArrows and Aeroplan to find award flights with low fees and shows you how to optimize search filters for the best redemptions.

He also shares personal travel tips for making the most of your time in Croatia, including must-see spots in Dubrovnik, hidden bars, and a restaurant you can only reach by boat. Plus, get recommendations for hotels in Split, how to get value out of your points, and ideas for regional day trips to Montenegro, Albania, and Hvar. Whether you’re a seasoned points user or just starting out, this episode is packed with actionable tips to travel smarter and stretch your budget further.

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:

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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 85, Ross sits down with Dave from Miles Talk to explore how a personal passion for points evolved into a high-impact rewards ecosystem. Dave shares how he scaled Your Best Credit Cards from a humble tool into a robust platform that helps users align their spending habits with the most effective credit card choices.

They cover decades of credit strategy insights, the changing landscape of airline and hotel loyalty programs, and how to navigate it all without falling into debt. Whether you're looking to elevate your family travel game or streamline business expenses, this episode gives you the tools to turn everyday spending into extraordinary experiences.

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:

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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 84, you'll learn how to maximize your credit card rewards and take your everyday spending. We dive deep into the best credit card options for beginners, savvy travelers, and families looking to earn more on dining and groceries. Whether you're just starting out or ready to upgrade to mid-tier or premium cards, you'll discover actionable tips to boost your points and miles. Learn how to choose the right card for your lifestyle and unlock exclusive perks like cashback, travel upgrades, and dining rewards.

By the end of this episode, you'll have a clear strategy to optimize your spending and maximize your rewards. We’ll show you how to leverage tools like the Rakuten portal for extra points and highlight the best cards for travel, dining, and everyday purchases. Plus, get access to our free points and miles cheat sheet to simplify your journey into the world of rewards. Tune in now to transform your spending habits and start earning more from every dollar!

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:

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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 83,  Jason Steele’s journey from tech expert to travel rewards authority is a masterclass in transforming personal passions into professional influence. As a writer and consultant, Jason has not only unlocked the power of points and miles for his own family’s travel but also guided countless others toward financially accessible adventures. His role in founding CardCon and shaping industry conversations illustrates how his expertise extends beyond content to meaningful community-building. Through personal stories—like helping families attend overseas competitions without financial strain—Jason highlights how travel can strengthen relationships and create lasting memories.

In conversation with Ross, Jason dives deep into the shifting terrain of content creation, the nuanced evolution of airline rewards, and the growing desire for human connection in an AI-driven world. From breaking down the complexities of dynamic point valuations to offering savvy family travel tips—like leveraging lap-child policies or planning 11 months ahead—Jason combines tactical knowledge with lived experience. He also shares a refreshing take on car rentals, lounge access, and the underappreciated perks of Frontier Airlines’ elite status. Whether you’re a travel rookie or seasoned rewards enthusiast, Jason’s insights deliver both strategy and soul.

Jason’s Social Media:

Jason’s Website

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:

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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 82, Ross talks about credit cards and travel perks can easily save you over $3,000 a year—if you know how to unlock their full value. In episode 82, I break down how a single $95–$695 annual fee can deliver free hotel nights, airport lounge access and meals, monthly Uber credits, and even premium travel protections. Whether you’re overwhelmed by choices or skeptical of the fees, I’ll show you why this upfront “cost” is actually one of the smartest investments travelers can make.

We’ll cover five key value buckets from 5 free nights in Grand Cayman to earning 5–10x points on everyday spending like Lyft rides and travel. You’ll learn how to track monthly credits, avoid rookie mistakes, and use simple strategies to earn back your fee once you receive your card in the mail. Plus, I’ll give you a checklist to stay organized, evaluate which cards to upgrade or downgrade, and show you how to make smart decisions that turn confusion into clarity.

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:

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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 82, Ross talks about touching down in Spain’s two superstar cities with this ultimate 7-day Barcelona + Madrid itinerary. I start by flying you into Madrid, usually the cheaper trans-Atlantic gateway, before zipping east on the high-speed AVE train to Barcelona. You’ll hear exactly where to base yourself on any budget, from points-friendly gems like the Hyatt Regency Madrid and Hotel Sofía to sociable hostels steps from Puerta del Sol or Las Ramblas.

Then we dive into must-do experiences: touring the Santiago Bernabéu or catching a Real Madrid match, wandering Retiro Park, tasting your way through Mercado de San Miguel, and feasting on tapas in Malasaña.

Next, I map out four sun-soaked days in Barcelona: sunrise at Park Güell, photos at La Sagrada Familia, cable-car views from Montjuïc, Gothic-Quarter nights, and a day trip to Montserrat or Tibidabo. I’ll show you how to score tickets for an FC Barcelona game (or the stadium tour if it's offseason), plan a relaxed Barcelona beach day, and tack on a quick, low-cost hop to Mallorca or Ibiza if you’ve got an extra weekend. Consider this episode your grab-and-go blueprint for flights, trains, beds, bites, and bucket-list moments plus the points-and-miles plays that make it all cheap or even free.

Real Madrid Stadium Tour

Royal Palace of Madrid

Sagrada Familia

Park Güell

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:

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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 80, coach Chris unwraps his step-by-step blueprint for turning everyday spending into 75 complimentary hotel nights across 11 countries—all while holding down a career and raising a family. By pairing long-range trip planning with targeted credit-card sign-up bonuses, transferable points, and the hidden value of timeshare rentals on platforms like RedWeek and TUG, he shows how anyone can swap sticker shock for suite upgrades without sacrificing PTO or the kids’ soccer schedule.

The episode closes with an action list you can use tonight: map trips a year out, stay flexible on dates and departure airports, negotiate directly with timeshare owners, and grab Coach Chris’s free points-and-miles cheat sheet for a personalized card strategy. If these tips help you re-price luxury down to everyday numbers, drop a 5-star review and visit coachchrisspeaks.com or his YouTube channel for deeper dives.

Coach Chris’ Social Media:

https://coachchrisspeaks.com/

https://www.linkedin.com/in/coachchrisklesh/

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:

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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.

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In episode 79, Ross talks about credit cards and travel that can unlock luxury flights and dream stays for pennies if you know how to play the points game. In episode 79, I break down why the first 60–100k points you earn from welcome offers are the most valuable you’ll ever collect. From lie-flat seats in London for the cost of groceries, to ocean-view villas in Bali booked with one welcome offer, you’ll learn real stories, real numbers, and the exact strategy I use to travel in style without breaking the bank.

I walk you through the beginner-friendly guide: how to pick your first flexible points card, what co-branded card to stack, and how to map your expenses to effortlessly hit the bonus. Plus, we’ll cover supercharger tips like transfer bonuses, the pitfalls to avoid, and how one signup can equal one bucket-list trip. 

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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.