Top Tips for a Great Greek Trip

When I met my Greek husband a dozen years ago, he promised to take me to Greece. We were living on different continents at the time, and I wasn't thrilled at the prospect of embarking on an international long distance relationship, but I also really wanted to go to Greece. 

Here is the first place he took me to in 2012. Imerovigli, Santorini. I was sold. 

 

Rachel Upshaw in 2012, a white woman in her mid-20s stands in front of the Santorini Caldera

I've now visited Greece a dozen times, including hosting our own Big Fat Greek Wedding in the Athenian Riviera. 

Here are secrets to having an amazing trip to Greece: 

1) Marry a Greek ... or Hire a Tour Concierge 

No, but seriously, when my friends say it must be amazing to have a Greek husband worry about all the logistics as he shuttles me, our three kids, and my parents around Greece. Yes it is. 

If marrying a Greek isn't available to you, I would suggest working with a really great travel concierge like Kat Paraskevopoulos with Eyia Retreats. As a Greek American who now lives in Athens, Kat can come up with the perfect itinerary for your group, or if you're a solo traveler looking for community, her retreats would be an unbelievable way to experience Greece. 

2) You Cannot Do It All

Do not try to see everything. It is actually antithetical to Greek society to rush around and zip by all the beauty. The absolute most Greek thing you can do is go to a Greek coffee shop, order a freddo cappuccino metrio (a slightly sweet cold whipped coffee-chefs kiss), and sit there for at least an hour. There is an entire scene in my book Greek Lovers where one of the characters has to learn this delicious, relaxing lesson in order to truly appreciate Greece.  

This is all to say, plan to only visit a few places. Getting around Greece is not as simple as pointing a line on a map. Instead of checking islands off a list, spend your time soaking up the natural beauty of one or two places, falling into the local rhythm. Less is more in Greece. (Unless you're talking about what to order at a taverna, in which case try it all!)

3) Always Go On a Boat 

No matter what island you're on, book a boat cruise. You will see a completely different perspective. The swimming and the homemade lunch will feed your soul for months to come.  

Rachel Upshaw stands on a sailboat off the coast of Skopelos, an island in Greece.

4) Making a Pilgrimage to Skopelos, the home of Mamma Mia, is Actually the Best You Can Do For Your Mental Health

In 2024, my Greek husband suggested we visit the group of islands north of Athens called the Sporádes. "They're very green," he said. "The pine trees grow all the way to the edge of the sea." "It's the real life location of Mamma Mia!!" I shrieked.

Having written a book about a filming a fun rom-com in Greece, going to Skópelos was like a religious pilgrimage for me. Mamma Mia is cannon! 

The island did not disappoint. I saw no fewer than a dozen Mamma Mia photographs in Tavernas from when they filmed there. It was amazing. 

 

The cast of the movie Mamma Mia including Meryl Streep, Pierce Brosnan, and Colin Firth stand with taverna owners on the island of Skopelos.

 

But the best thing about Skópelos? The fried cheese pie. 

Better than anything I've ever had at the Texas State Fair. Worth the price of the airfare alone.

 

Rachel Upshaw eats a Greek fried cheese pie aka tiropita

 

Okay, drop me a message or find me on Instagram (@rachelupshaw) or on TikTok (@rachelwrotethat) if you have any other Greek travel questions! xx Rach