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The Celebrity Silhouette: How to (and not to) Travel in Santorini, Greece

Since I’ve sent clients in the past and received a good amount of feedback about seeing Santorini without a guided tour (I love when my clients become my travel agents…), this was the only stop where we didn’t have a private excursion planned. Instead, we had planned on renting four wheelers until we really started to think about our lack of grace and sense of direction. The night before we arrived in Santorini, we attended a seminar on the destination, where they advised against the four wheelers if you aren’t familiar with handling them, especially on steep and winding roads.

Instead of booking a shore excursion, we decided just to wing it, which is the perfect way to see Santorini. Let it be known, however, that there are many terrible ways to see the island if you are winging it. For what I’ve seen firsthand today, take my advice on what not to do while here.

First thing you need to know: the boat arrives about 1,000 feet below the main town of Fira, meaning that travelers have to find a way up to the town in order to go anywhere else on the island, especially the most notable city of Oia (also spelled Ia, depending on what map you consult).

The options for traveling to the top of Fira are as follows:

  1. Guests can climb up the 600+ steps to reach the tip-top. This is great if you are in pristine shape and want to waste all of your energy before even getting to the destination. Our group does not qualify for either.
  2. Taking a cable car is the most efficient way to the top. However, assuming you are getting off of a cruise ship with 3000 of your closest friends and neighboring cruise vessels, the line for a cable car will be at least a 30 minute wait, probably longer. You will stand in the sun, you will get burned, and you will be in a bad mood once you finally reach the top.
  3. There’s always the good, old fashioned option of riding a donkey. I always thought travelers were joking when they said this was even an option. It’s so cruel! It’s so inhumane! It’s so ancient Greece! To give some credit: I would assume that this option makes for a very interesting story. In fact, I overheard a man at the dinner table beside me talking about his choice to ride a poor donkey to the top of Fira. This man is at least 350 pounds. Poor, poor donkey. To avoid risking your own safety, as I have heard horror stories about the little donkeys slipping, etc., and to spare the back of a sad little donkey, try to avoid this option. We need more cute donkeys in the world. (Side note: even as an English major, the plural form of the word “donkey” still throws me off.)


Save a donkey, ride a speedboat.

If you are wise, like one Epperly/Hawkins clan happens to be, as soon as you step off of the cruise ship, you will see a sign that says “Speedboat Transfers to Oia.” Quick thinking will lead you to realize that you can actually access Oia via the ocean, bypassing the need to take any of the options to the top of Fira. No lines, steps, or donkey cruelty. Just hop in the boat and fifteen minutes later you’ll be walking the cobblestone streets of the hilltop city of Oia.

Oia reminded me of a Grecian version of Eze in the South of France. Anyone who loves storybook European towns will find Oia equally as charming with breathtaking views of the ocean below.

The narrow streets were filled with souvenir shops, fine jewelry stores, cliffside restaurants, and….fish pedicures? I’ve heard about these “fish spas” on TV shows before: people rest their feet in aquariums where tiny gray fish eat off the dead skin. I am grossed out just typing this, I can’t believe I’m even recollecting the story. Just imagine watching it! There are some things in life I might never understand.

Weirdest thing about this photo: those are a man’s legs in the tank…

And if there is any doubt in your mind, reader, let me clarify: Lord, no, I did not personally try out the fish spa. My mother actually said, “I bet it would feel good.” I must’ve looked at her like she just sprouted a second head. If you know anything about my mom, you know that she is bizarre about feet, especially the sanitization of feet. She refuses to get pedicures and carries spare flip flops for the showers of every trip we’ve ever been on. I can’t believe she would have anything positive to say about these pesce-pedis.

For the split second that I entertained the thought, I decided that no, it would not feel good. It would probably just tickle. I think I’ll wait for the bamboo massage I have scheduled for tomorrow morning.

We spent about an hour touring the town before taking the bus transfer back to the top of Fira, where we rode the cable car down to the bottom and snickered at the people still waiting in line. Winging it in Santorini was definitely a success.


Lindsey Epperly

My name is Lindsey Epperly and I’m a travel consultant and owner of Epperly Travel, a national affiliate of Century Travel. I’m most passionate about building lifelong relationships with my clients and suppliers, discovering the globe in a way that makes me a better agent, and celebrating with my team when we reach a new milestone. One of our core values at Epperly Travel is to create fun and celebrate constantly – and I’m fortunate to be in a career that allows me to do just that. I’m proud to announce my recent achievements: landing a spot on Wendy Perrin’s WOW List as their Caribbean expert, being nominated for Virtuoso’s Rising Star Award and receiving a place on Jezebel Magazine’s Trailblazing Ten list.

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