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. 1 DAY AGO

    How to Explore New Countries & Build A Travel Blog While Working Full Time

    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:⁠ 3 bedroom apartment Dubrovnik, Croatia Conrad Hotel Bora Bora Nui Connect with Lana: Instagram Website ⁠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.

    43 min

  2. NOV 6

    Lessons from the Road: Travel Insurance, Budgeting, and Problem-Solving Abroad

    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 Albergo del Senato Hotel ⁠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.

    52 min

  3. NOV 5

    How To Plan A Northern Arizona Trip & How To End It With A Proposal in Sedona

    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: ​ 4 bedroom home Scottsdale​ 7 bedroom villa Scottsdale ​ Grand Canyon (Maswik Lodge) ​ Sedona Loft​ Lower Antelope Canyon Tour​ Upper Antelope Canyon Tour ⁠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.

    29 min

  4. OCT 29

    How To Plan A Surprise Trip For Your Friend To Greece

    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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠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.

    17 min

  5. OCT 23

    How to Plan the Perfect Destination Wedding in Italy

    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 ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠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.

    39 min

  6. OCT 16

    Travel Smarter: Budget-Friendly Tips from Alaska, USA Hiking Adventures, and Central America Tour Guide

    Val Clemens, a seasoned tour guide and current travel industry professional, shares her diverse experiences on episode 27 of the podcast. She has worked in places such as Alaska, Guatemala, and various regions across the US. Val's journey began with a love for travel that led her to backpack across Southeast Asia, work at a nonprofit in Guatemala, and eventually guide tours in the US and Central America. Her current role allows her to combine her background in education with her passion for travel, helping organize student trips that inspire young people to explore the world. During the discussion, Val highlights her favorite travel destinations, particularly Guatemala. She describes the beauty and cultural richness of places like Antigua, a UNESCO World Heritage site known for its colonial architecture, and Lake Atitlán, surrounded by volcanoes and indigenous Mayan villages. Val emphasizes the significance of travel in shaping one's perspective, noting how it enhances cultural understanding, adaptability, and awareness. Through her career, she has found fulfillment in helping others discover the joys of travel and navigate new experiences. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com⁠ Links Mentioned In Episode: La Fortuna Atitlan Case Particulares, Cuba ⁠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.

    57 min

  7. OCT 9

    Solo Travel Secrets: Experiences in Bali, Mexico City, Guatemala and Beyond

    In this podcast episode, Ross invites his friend Joe Salma to share his experiences and insights on solo travel. Joe has traveled extensively to places like Bali, Mexico City, and Guatemala, and began his journey post-college, initially traveling with friends before transitioning to solo trips. He emphasizes the freedom and flexibility of solo travel, which allows him to explore new destinations without the logistical challenges of coordinating with others. Joe's solo travel journey was largely inspired by a period of unemployment in 2019, during which he had both the time and severance pay to travel extensively. His first major solo trip was to Bali, where he experienced the eye-opening adventure of visiting a third-world country, meeting diverse people from around the world, and pushing himself outside his comfort zone. Joe also highlights the social aspects of solo travel, especially when staying in hostels, which attract open-minded travelers. He shares stories of meeting fellow adventurers from places like Germany and the U.S., bonding over shared experiences, and forming impromptu friendships that enhance the travel experience. The ease of meeting new people and forming connections while traveling solo is one of the things Joe enjoys most. He also reflects on how solo travel has expanded his worldview, making him value experiences and relationships over material possessions, while giving him a fresh perspective on life, work, and what truly matters. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com⁠ Links Mentioned In Episode: Viajero CDMX Centro Hostel (Mexico City) Guatamela (Antigua)- Selina Hostel Selina Tulum Bali (Ubud) Bali (Seminyak) Gili T Island (Indonesia) Galway, Ireland (Abbey Court Hostel) Amsterdam (Flying Pig Hostel) Amsterdam (The Bulldog Hostel) ⁠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.

    45 min

  8. OCT 8

    How To Plan A Birthday Surprise Trip To Turks and Caicos

    In this episode of "World Travel Made Easy with Itinerary Boss," host Ross shares insights from a surprise trip he planned for his fiancée, Audrey, to Turks and Caicos for her 30th birthday. He talks about the importance of planning experiences over material gifts and how the direct, three-hour flight from Charlotte on American Airlines helped him choose Turks and Caicos as a destination. He also highlights budget-friendly options like the Royal West Indies hotel, which offers access to the beautiful Grace Bay, nearby restaurants, and bike rentals for convenient exploration. The episode offers tips on saving money with airline points, insights into restaurant reservations, and the value of booking experiences like horseback riding with Provo Ponies. The host further discusses the itinerary, sharing key details about excursions and dining experiences. From a sunset catamaran cruise and visiting Coco Bistro to exploring Chalk Sound by kayak, the trip was filled with memorable moments. He also offers practical advice on making reservations early and choosing the best times to visit Turks and Caicos for great deals, especially during the December window before Christmas. Listeners are encouraged to join an upcoming webinar for more tips on planning surprise trips. Website:⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ itineraryboss.com⁠ Links Mentioned In Episode: 1. Royal West Indies Resort 2. Seven Stars Resort & Spa 3. 2 Hour Champagne Sunset Cruise 4. 4-Hour Catamaran Sail and Snorkel Tour ⁠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.

    26 min
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5
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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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