(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 59, Ross’s Greek Islands Travel Guide provides an in-depth look at an 11-day itinerary through Athens, Mykonos, Santorini, and Milos. He begins by noting the convenience of direct flights from Charlotte to Athens—especially beneficial for those able to use rewards points and miles—and underscores the importance of leaving ample time for layovers and customs. While in Athens, Ross suggests staying in the Plaka area to enjoy its central location, historic charm, and quick access to highlights such as the Parthenon and the Acropolis. He emphasizes the value of planning ahead by booking ferries in advance for island hopping, as well as scheduling ground transportation, particularly in Santorini and Mykonos where rides can be in high demand.

Beyond Athens, Ross’s tips concentrate on beach clubs and restaurants in Mykonos, recommending reservations at popular spots like Santa Ana Pool, Bar Negrita, and Cavo Paradiso. In Santorini, he suggests staying in Imerovigli for scenic caldera views without the premium prices of Oia, plus activities like a sunset catamaran cruise and dinner at Argo. Milos is a highlight for explorers who enjoy renting four-wheelers to discover secluded beaches, and Ross cites O! Hamos as a can’t-miss dining experience. For overall stress reduction, Ross recommends not checking luggage and using the Priority Pass app to locate lounge access—particularly at Athens International Airport—ensuring a smoother journey between destinations.

Athens Accommodation: https://booking.tp.st/fWHinVgc

Santorini Accommodation: https://booking.tp.st/CGRTOJIp

Santorini Catamaran Cruise: https://booking.tp.st/dybB9qvy

Mykonos Accommodation: https://booking.tp.st/bh1kpo1Y

Milos Accommodation: https://booking.tp.st/hIrFjxLJ

Milos Catamaran Cruise: https://booking.tp.st/46BOfK7l

Website: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠itineraryboss.com

Best Credit Cards for Travel

Bonus Offer Notifications

Transfer Bonus Notifications

Points and Miles Cheat Sheet

TravelPayouts: 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 list

⁠⁠⁠⁠⁠⁠⁠⁠⁠ClickUp⁠⁠⁠⁠⁠⁠⁠⁠⁠: Stay organized and master projects

Make.com: Build Smarter Automated Workflows with no code

Function Health: Optimize your health, explore the world!

Carry: The modern Solo 401(k) for business owners

Itinerary Boss Socials:

⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠Pinterest⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Facebook ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠

Itinerary 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.