In episode 42 of World Travel Made Easy, host Ross and guest Paul Thorton, the creator of The Joy of Cruising podcast, delve into their shared passion for travel and cruising. Paul shares his journey from a medical career to becoming a seasoned cruise enthusiast, travel advisor, and author of three books about cruising. Their discussion covers a wide range of topics, including the evolution of Paul's love for cruising, tips for first-time cruisers, and the value of proper planning and preparation.

Paul emphasizes the high satisfaction rate of cruise vacations and offers practical advice on budgeting, dining options, and choosing the right cruise line to ensure a memorable experience. The conversation also highlights unique options like child-free cruises with Virgin Voyages and affordable repositioning cruises for those looking to explore the Mediterranean or transatlantic routes.

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In episode 41 of World Travel Made Easy, Aisha shares her journey of embracing a nomadic lifestyle with host Ross while juggling the challenges of remote work, financial stability, and the pursuit of adventure. Drawing on her personal experiences and expertise, she offers practical tips for thriving as a digital nomad, from finding steady work opportunities to budgeting effectively and staying productive on the go. Aisha emphasizes the importance of balance, showing how to maintain a fulfilling career without sacrificing the joy of exploration and cultural immersion.

Aisha discusses overcoming common obstacles, such as managing time zones, staying connected with loved ones, and adapting to new environments. Whether you're a seasoned traveler or considering your first leap into remote work abroad, Aisha’s insights provide a roadmap to living a life full of freedom, adventure, and purpose while maintaining stability and connection.

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In episode 40, Ross chats with Ralph Velasco, a professional travel photographer, tour organizer, and author of The Mindful and Intentional Traveler. Ralph shares stories from his 120+ international trips, including fascinating insights from his 19 visits to Cuba and his recent adventure to Antarctica. Listeners will learn about the benefits of small ship travel, the magic of slow and mindful travel, and why Ralph’s approach to “going deep, not wide” creates richer experiences. The conversation also dives into Ralph’s passion for local cultures, food, and markets, offering tips on how to engage with locals and make travel more meaningful.

Ralph and Ross discuss practical travel tips, such as extending layovers to explore new destinations, traveling affordably without sacrificing quality, and the importance of balancing social media with being present during trips. They also highlight Ralph’s new book and YouTube channel, Continental Drifter, where he shares snippets of his journeys and travel advice. Whether you’re curious about hidden gems like Cartagena, slow travel in France, or exploring bucket-list destinations like Antarctica, this episode is packed with inspiring stories and actionable insights to enhance your next adventure. Tune in to discover how Ralph creates unforgettable, 5-star travel experiences for his clients and why mindful travel should be part of everyone’s journey.

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In episode 39, host Ross connects with Paul, a seasoned public transit industry expert and YouTube host. Ross shares how his passion for travel inspired his podcast, which highlights unique destinations and travel planning tips. Paul reflects on his diverse career journey, from serving as the CEO of one of America’s largest transit systems to his current role as a senior executive at Medaxo, the world's leading transit software company. The two discuss their shared enthusiasm for exploring cities through food, culture, and transit.

The conversation dives into their favorite travel recommendations, with Paul suggesting must-visit spots like Nashville, Halifax, and Greece, while Ross shares his excitement for his upcoming trips to Thailand and Bali. They also touch on navigating public transit systems around the globe, highlighting Paul's expertise and Ross's curiosity.

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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.

In episode 38 of World Travel Made Easy with Itinerary Boss, Ross explores the pros and cons of Airbnb and VRBO, two popular platforms for booking unique accommodations and experiences. Drawing from his experience using these services since 2016, Ross shares best practices for maximizing their potential, including creating wish lists, using filters to find the perfect stay, and messaging hosts for personalized recommendations. He highlights Airbnb’s strengths for group trips, unique stays, and tailored experiences, such as planning itineraries and leveraging amenities like washers, cribs, and workspaces. Additionally, Ross discusses how to use reviews and communication with hosts to ensure a smooth stay, from early check-ins to local tips on activities and logistics.

Ross also compares Airbnb with VRBO, positioning the latter as a solid backup option for larger group trips and reward points accumulation through its integration with One Key Cash and Expedia. While VRBO offers fewer experiential options, its interface and rewards system make it a viable alternative for travelers. Ross concludes by sharing insights on credit card travel hacking, including leveraging points for major trips like his honeymoon and a luxury flight to Bali. He invites listeners to tune in for future episodes, where he will dive deeper into travel hacks and credit card strategies for smarter travel planning.

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Links Mentioned In Episode (Favorite Stays)

1. Dubrovnik, Croatia:

2. Dana Point, California:

3. Scottsdale, Arizona

4. Sedona, Arizona

5. Monteverde, Costa Rica

6. Lake Tahoe, California

7. Mykonos, Greece

8. Hotel Verde Mar Whistler, Canada

9. The Royal Suite Whistler, Canada

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In episode 37 of World Travel Made Easy with Itinerary Boss, host Ross explores the world of rental cars and the Turo platform, offering insights on how to maximize rewards and enjoy more personalized travel experiences. He begins by discussing the benefits of traditional rental car companies like Hertz, Enterprise, and Avis, emphasizing the importance of signing up for rewards programs to access perks like free upgrades and streamlined check-ins. Ross highlights how rental cars are ideal for multi-city trips, where travelers can pick up a vehicle in one location and drop it off in another, making them a versatile choice for both business and leisure travel.

Ross then introduces Turo, an innovative platform often described as the Airbnb of car rentals. He shares personal experiences using Turo for luxury and specialty vehicles at lower costs, citing examples like renting a Range Rover for a vacation or a pickup truck for a snowboarding trip. Turo's flexibility, convenience, and personalized service—such as direct communication with hosts for custom delivery options—make it a favorite for unique travel needs. Ross wraps up by encouraging listeners to explore both options, subscribe to the podcast, and stay tuned for more travel tips in upcoming episodes.

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In episode 36 of World Travel Made Easy with Itinerary Boss, host Ross dives into the world of travel portals, sharing tips and strategies to help travelers maximize their budget. Ross explores the benefits of using platforms like Expedia, Priceline, Booking.com, Hostelworld, and others to find deals on flights, hotels, and vacation packages. Drawing from his own experiences, such as a budget-friendly trip to Barcelona and Rome, he highlights the advantages of bundling travel services, earning rewards points, and leveraging tools like credit card perks for additional savings. He also provides insights into unique features of these platforms, like Priceline’s Express Deals and Booking.com’s flexible cancellation policies, offering practical advice for travelers at different life stages and budgets.

Ross also covers specialized platforms like Hostelworld for budget and solo travelers, Scott’s Cheap Flights for discovering low-cost airfare deals, and Skip Lagged for taking advantage of hidden city ticketing. He discusses key considerations like customer service challenges, cancellation policies, and tips for avoiding common pitfalls. Whether listeners are planning a luxury vacation, backpacking adventure, or family trip, this episode equips them with tools and strategies to simplify the process and stretch their travel dollars further.

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Linked Mentioned In Episode:

2. Porto, Portugal

3. Playa Hermosa, Costa Rica

4. Santorini, Greece

5. Milos, Greece

6. Grace Bay, Turks and Caicos

7. Grace Bay, Turks and Caicos

8. Sao Miguel, Azores Islands- Portugal

9. Wombats City Hostel, London

10. Hostel One Rambas, Barcelona

11. Kinlay Hostel, Galway Ireland

12. Flying Pig, Amsterdam

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In episode 35 of World Travel Made Easy with Itinerary Boss, host Ross explores the world of airline rewards programs, emphasizing their importance for both novice and experienced travelers. Ross highlights the common mistake of signing up for just one program based on a local hub, instead encouraging listeners to join multiple programs like American Airlines AAdvantage, Delta SkyMiles, United MileagePlus, and Southwest Rapid Rewards. Drawing from personal experience, Ross shares how early enrollment in various programs allowed him to accumulate miles, understand airline benefits, and leverage credit cards for travel rewards. He provides practical examples, such as booking affordable flights to destinations like Turks and Caicos, and explains how rewards programs can unlock perks like free checked bags, priority boarding, and upgrades.

Ross also touches on advanced strategies for maximizing points and miles, including utilizing alliances like OneWorld and Star Alliance, and transferring credit card points for international travel. He underscores the simplicity of getting started, emphasizing that the key step is creating accounts and gradually learning the programs. Future episodes promise a deeper dive into advanced topics, such as how Ross saved over $15,000 on honeymoon flights by strategically combining rewards programs. Whether you're a casual traveler or looking to master travel hacking, this episode offers a practical guide to building a solid foundation with airline rewards.

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In episode 34 of World Travel Made Easy, host Ross dives into the importance of hotel rewards programs and how travelers can maximize their benefits for both personal and business stays. Drawing from personal experiences, the episode highlights key rewards programs like Hyatt, Hilton Honors, Marriott Bonvoy, and IHG, emphasizing the value of signing up early and strategically using credit cards to accumulate points. The host shares tips on leveraging transferrable points for Hyatt stays, the advantages of Hilton’s high-value credit card bonuses, and Marriott’s extensive network of properties. Practical advice includes optimizing work-related travel spending, taking advantage of sign-up bonuses, and utilizing hotel points for free nights at desirable locations.

The episode is packed with actionable insights, such as using personal credit cards for business expenses to earn rewards, negotiating hotel block points for events like weddings, and choosing the right loyalty programs based on travel patterns. Listeners are guided through step-by-step instructions to join these programs and maximize their benefits. Personal anecdotes, such as earning free stays for trips to Europe and Oktoberfest, underscore the long-term value of these strategies. Whether you're a seasoned traveler or just starting out, this episode offers a comprehensive introduction to hotel rewards programs, equipping listeners with tools to save money and enhance their travel experiences.

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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.

In episode 33 of "World Travel Made Easy with the Itinerary Boss," host Ross welcomes experienced travel agent Samantha Green to discuss responsible tourism. Samantha shares how her passion for exploring different cultures began at a young age and has since evolved into a dedication to meaningful travel. Throughout their conversation, she emphasizes the importance of experiential and responsible travel, recounting powerful moments such as visiting Cambodia to learn firsthand about its historical tragedies. Samantha argues that travel should go beyond tourist attractions and beach lounging, focusing instead on connecting with local cultures, history, and sustainable travel practices.

Ross and Samantha explore the concept of making travel experiences memorable and meaningful, sharing anecdotes about their own adventures, from navigating crowded tourist attractions to riding trains in India and Thailand. Samantha highlights her work promoting ethical tourism practices, particularly with animals, advocating for experiences that do not exploit wildlife but instead educate travelers about their natural behavior. The episode encourages listeners to plan their trips with awareness and empathy, focusing on experiences that create lasting memories and foster cultural understanding.

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Some of the links on this site 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.