By Ross Alcorn
5
1111 ratings
The podcast currently has 38 episodes available.
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.
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
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2024 Holiday Travel Gift Guide: 31 Gift Ideas
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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.
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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.
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.
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:
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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.
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.
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:
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Facebook
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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.
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.
Website: itineraryboss.com
How to Plan the Perfect Surprise: Free Webinar
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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.
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
Episode 32 of World Travel Made Easy with the Itinerary Boss features travel blogger Lana Sitler, who shares insights on balancing full-time work with exploring new countries and building a successful travel blog. Ross and Lana connect over their mutual love of travel, discussing the influence of formative experiences, like Lana's first trip to London, on shaping their passion for international exploration. The conversation covers practical strategies for maximizing travel experiences, from travel hacking with points and rewards to finding balance through time-blocking and prioritizing blogging goals. Lana emphasizes the importance of detailed travel itineraries on her blog, offering users actionable guides that remove planning stress and enable seamless adventures.
The episode dives into memorable travel highlights, including Lana's visits to Iceland for the Northern Lights and a bucket-list honeymoon in Bora Bora. She reflects on the joys of travel planning, often assuming the role of the organizer among friends and family, and acknowledges the challenges of managing a blog while working. The discussion extends into travel hacks for maximizing corporate travel benefits, achieving status perks, and tips on leveraging business trips for personal exploration. Together, the host and Lana underscore how intentional travel planning enriches both professional and personal lives, with thoughtful insights and practical advice for aspiring travel bloggers and travelers alike.
Website: itineraryboss.com
Links Mentioned In Episode:
Conrad Hotel Bora Bora Nui
Connect with Lana:
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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.
In episode 31 of World Travel Made Easy with the Itinerary Boss, the host interviews Margie Piliere, an experienced travel agent who brings valuable insight into planning memorable and efficient travel experiences. Connected through Lorene Burton, a former guest and friend, Margie joins the podcast to share her extensive knowledge in travel insurance, budgeting, and travel logistics. She explains her journey into the travel industry, driven by her love for travel and the desire to make it financially viable. For over a decade, she has helped clients plan customized trips, specializing in destinations like Italy and Greece, while also staying updated on the evolving landscape of travel. Margie discusses how the role of travel agents has become even more significant as people seek ways to avoid common travel pitfalls and explore new, off-the-beaten-path destinations.
Throughout the conversation, Margie shares her expertise on navigating popular travel spots and the increasing trend toward unique experiences. She notes that high-traffic destinations such as Santorini and Venice are now heavily impacted by tourism, urging travelers to consider quieter, equally beautiful alternatives. Margie emphasizes the importance of planning based on personal interests, recommending iconic spots like Rome, Florence, and Venice for first-timers, while suggesting lesser-known places for repeat visitors. She also provides practical tips on budgeting, advising on accommodation options, transportation choices like rail and ferry, and avoiding unnecessary expenses. Margie encourages travelers to invest in experiences that align with their passions and offers a reminder that a well-planned trip often leads to more memorable, meaningful experiences.
Website: itineraryboss.com
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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.
In episode 30 of World Travel Made Easy with Itinerary Boss, Ross shares a detailed travel guide for planning a memorable trip through Northern Arizona, highlighting must-see landmarks, travel tips, and accommodations. After a New Year's Eve wedding in Scottsdale, Arizona, the host extended their stay to explore the state’s northern region, opting to rent a Jeep via Turo for convenience and winter preparedness. They began their journey with a visit to the Grand Canyon, staying at the Maswik Lodge for easy access to the canyon and views of a breathtaking sunset and sunrise. The itinerary also included Antelope Canyon and Horseshoe Bend near Page, Arizona, where they took a guided tour of the iconic slot canyons, explored scenic viewpoints, and snapped photos of the stunning landscapes. The host emphasizes practical tips, like dressing warmly for winter conditions and arriving early for the best photo spots.
The journey continued with a scenic drive to Sedona, known for its red rock formations and tranquil atmosphere. They secured a conveniently located Airbnb in West Sedona, which provided ample workspace and was close to local attractions. Highlights in Sedona included dining at Elote, Mariposa and Cress on the Creek, recommended to book six to eight weeks in advance—and a drive through the Red Rock Scenic Highway. The episode offers useful advice for navigating Arizona’s top sites, tips for leveraging travel platforms like Turo, and the benefits of strategic trip planning, making this a handy guide for listeners considering a similar adventure.
Website: itineraryboss.com
Links Mentioned In Episode:
Amazon Travel Store
ClickUp
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Our Favorite Credit Cards:
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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.
In episode 29 of World Travel Made Easy with the Itinerary Boss, Ross delves into planning surprise trips, using a recent experience helping his best friend’s wife organize a surprise trip to Greece as an example. He discusses his passion for gifting experiences over material items, emphasizing the joy and lasting memories that surprise trips bring. The episode serves as a teaser for an upcoming webinar on planning surprise trips, promising to walk listeners through every step, from initial planning to creating a meaningful travel experience. This trip to Greece, which includes stops in Athens, Mykonos, Santorini, and Milos, also serves as an opportunity to showcase practical travel advice based on past European adventures.
Ross reflects on past travels across Europe with friends, explaining how these experiences honed his trip-planning skills. He shares insights on how to organize a group trip, including scheduling around peak tourist seasons, budgeting, and accommodating individual needs—like childcare. With tips on how to creatively reveal the surprise trip, he encourages listeners to seize the opportunity to create unforgettable memories. Listeners are invited to follow the podcast for future episodes, which will include deep dives into specific locations in Greece, detailed itinerary breakdowns, and valuable travel lessons.
Website: itineraryboss.com
Links Mentioned In Episode:
1. 2 bedroom villa Mykonos
2. Santorini (Etherum Luxury Cave)
3. 2 bedroom seaside apartment Milos
4. Santorini: Catamaran Sunset Tour
5. Milos: Full Day Catamaran Tour
Amazon Travel Store
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Our Favorite Credit Cards:
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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.
Episode 28 focuses on planning the perfect destination wedding in Italy with guests Dave and Ashley. The couple, who were introduced through a mutual connection, shared their recent experience of planning and hosting their wedding at Lake Garda, Italy. They discussed how travel has been a significant part of their lives, influencing their decision to choose a destination wedding. With Dave's background as a professional yacht captain, he highlighted the unique opportunity a destination wedding offers to immerse loved ones in their lifestyle, allowing for more extended interactions compared to traditional local weddings. The couple also touched on the importance of finding the right location and how they quickly fell in love with their chosen venue after visiting it in person.
Dave and Ashley delved into the practical aspects of planning an international wedding, emphasizing the need for careful research and trusting reliable local vendors. They recommended visiting venues in person, using planners suggested by the venue, and reaching out to others who had similar wedding experiences to avoid potential pitfalls. They shared how they navigated the logistical challenges of their island venue, balanced their budget by negotiating with vendors, and ensured their guests enjoyed a unique and memorable experience. Ultimately, the couple's approach to quality over quantity allowed them to provide their friends and family with an intimate, unforgettable celebration that reflected their passion for travel and adventure.
Website: itineraryboss.com
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
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Threads
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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.
The podcast currently has 38 episodes available.
16 Listeners