(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  YourBestCreditCards.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. 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.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 Mykonos2. Santorini (Etherum Luxury Cave) 3. 2 bedroom seaside apartment Milos4. Santorini: Catamaran Sunset Tour 5. Milos: Full Day Catamaran TourWebsite: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.comBest Credit Cards for TravelBonus Offer NotificationsTransfer Bonus NotificationsPoints and Miles Cheat SheetTravelPayouts: Turn your trips into income and earn!Gondola AI:⁠ Find better hotels, earn more points, travel for free!⁠Rakuten⁠: Earn cash back/rewards on every purchase!Kit: Grow and monetize your email list⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projectsMake.com: Build Smarter Automated Workflows with no codeFunction Health: Optimize your health, explore the world!Carry: The modern Solo 401(k) for business ownersItinerary Boss Socials:⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠Itinerary Boss LLC has affiliate partners and some of these 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.

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