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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.

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

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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.