World Travel Made Easy With Itinerary Boss

Ross Alcorn
  • 5.0 (11)
  • PLACES & TRAVEL
  • UPDATED WEEKLY
World Travel Made Easy With Itinerary Boss

Are you tired of limited vacations, overwhelmed by travel planning, and stuck in a cycle of last minute stress? Join Ross, your trusted travel guide, where we transform your travel dreams into reality. With expert tips, strategic insights, and actionable tools, we help you master seamless trip planning, maximize rewards, and escape the stress of chaotic itineraries. Tune in for interviews with seasoned travelers and industry experts, step by step walk through's and start your journey towards becoming a confident traveler.

  1. 4 DAYS AGO

    Exploring Cities Through Food, Culture, and Public Transit with Paul Comfort

    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. (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 MileValue.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. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com Connect with Paul: ⁠LinkedIn⁠ ⁠YouTube⁠ ⁠Instagram ⁠How to Plan the Perfect Surprise: Free Webinar 2024 Holiday Travel Gift Guide: 31 Gift Ideas⁠ Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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. Itinerary Boss Socials: ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube ⁠⁠⁠⁠⁠⁠⁠⁠Threads ⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠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.

    55 min

  2. 4 DAYS AGO

    Mastering Airbnb and VRBO: How to Find the Perfect Stay and Get the Most Out of It

    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. (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 MileValue.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. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com 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 How to Plan the Perfect Surprise: Free Webinar 2024 Holiday Travel Gift Guide: 31 Gift Ideas ⁠Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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. Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠ Instagram ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠ Threads ⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    20 min

  3. DEC 11

    Unlocking Rental Car Rewards & Discovering Turo: The Smarter Way To Drive

    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. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com ⁠ How to Plan the Perfect Surprise: Free Webinar 2024 Holiday Travel Gift Guide: 31 Gift Ideas⁠ Amazon Travel Store ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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. Itinerary Boss Socials: ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube ⁠⁠⁠⁠⁠⁠⁠⁠Threads⁠⁠⁠⁠⁠⁠⁠ TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    13 min

  4. DEC 4

    Travel Portals 101: How to Maximize Your Travel Budget

    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. (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 MileValue.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. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com Linked Mentioned In Episode: 1. Madrid Spain 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 ⁠How to Plan the Perfect Surprise: Free Webinar 2024 Holiday Travel Gift Guide: 31 Gift Ideas ⁠Amazon Travel Store ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ConvertKit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ManyChat⁠ Fiverr 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. Itinerary Boss Socials: ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Pinterest ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ Threads⁠⁠⁠⁠⁠⁠⁠ TikTok ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    25 min

  5. NOV 27

    (Bonus) Maximizing Airline Rewards: Your Guide To The Best Programs

    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. (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 MileValue.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. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com How to Plan the Perfect Surprise: Free Webinar 2024 Holiday Travel Gift Guide: 31 Gift Ideas Amazon Travel Store ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ConvertKit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ManyChat⁠ Fiverr 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. Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠ Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube ⁠⁠⁠⁠⁠⁠⁠⁠Threads⁠⁠⁠⁠⁠⁠⁠ TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    31 min

  6. NOV 26

    (Bonus) Introduction To Hotel Rewards: Get Started With Points & Perks

    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. (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 MileValue.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. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com ⁠How to Plan the Perfect Surprise: Free Webinar 2024 Holiday Travel Gift Guide: 31 Gift Ideas⁠ Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ConvertKit⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ManyChat⁠ Fiverr 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. Itinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠ Instagram ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ YouTube⁠⁠⁠⁠⁠⁠⁠⁠ Threads⁠⁠⁠⁠⁠⁠⁠ TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    28 min

  7. NOV 20

    Responsible Travel & Hidden Destinations: Insights From An Experienced World Explorer

    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. Samantha's website: https://samanthagreen.notjusttravel.com/ Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com⁠ How to Plan the Perfect Surprise: Free Webinar ⁠Amazon Travel Store⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠ConvertKit⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠ManyChat⁠ Fiverr Our Favorite Credit Cards: Chase Sapphire Preferred Chase Sapphire Reserve Capital One Venture Chase Freedom Unlimited Chase Business Unlimited Chase IHG One Rewards  Itinerary Boss Socials: ⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠ Threads ⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠X⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ 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.

    1h 2m

  8. NOV 18

    Bonus: (Free Webinar) How to Plan the Perfect Surprise Trip

    Ready to plan the perfect surprise trip for someone special? Watch the free webinar to learn the secrets of creating unforgettable experiences! Ross Alcorn, an experienced trip planner, shared his expertise on organizing surprise trips. He emphasized the importance of planning logistics, budgeting, and creating memorable itineraries. Ross has been planning trips for 10 years including trips to over 25 cities in Europe, nine annual snowboarding trips all over North America, five surprise trips for his partner, and many more all around the USA for himself and others. He shares advice on how to start mapping out your surprise, his favorite tools to use, suggested setting a realistic budget for flights, accommodations, and activities. He also highlighted the value of planning special moments and integrating unique experiences. This is jam packed with actionable takeaways to get you started ASAP. Ross introduced his "Travel Takeoff: Blueprint to Easy World Travel" digital course to help others plan stress-free trips, offering exclusive community access and personalized support. 🌍✨ Sign up for the digital course here: https://buy.stripe.com/00g5ktcpK1fVcvu4gn

    28 min
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5
out of 5
11 Ratings

About

Are you tired of limited vacations, overwhelmed by travel planning, and stuck in a cycle of last minute stress? Join Ross, your trusted travel guide, where we transform your travel dreams into reality. With expert tips, strategic insights, and actionable tools, we help you master seamless trip planning, maximize rewards, and escape the stress of chaotic itineraries. Tune in for interviews with seasoned travelers and industry experts, step by step walk through's and start your journey towards becoming a confident traveler.

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