I went to Skiathos, a small island of Greece in August of 2000 with my friend Jennifer.

It was pretty much entirely by the seat of our pants.

Here’s how it went down.

I met Jennifer in Heidelberg, Germany for vacation (she flew in from Japan, I came from Ohio.) She studied there and had a strong group of friends to welcome us. We spent some time enjoying their camaraderie (beer!) and had plans to travel to either Barcelona or Greece for something new. When the time came to leave, we boarded a train to the airport with no agenda. We flipped a coin on the way—Barcelona heads, Greece tails.

Barcelona won the toss.

We looked at each other and said —almost in unison— “Let’s go to Greece.” (This was back in the day when you could show up at an airport and buy a ticket to go somewhere on the spot.)

We get to Athens and it’s the Day of Mary. Essentially EVERYTHING was shut down and there were celebrations in the streets. We luckily found a hotel that was open and enjoyed a brief stint in the capital.

When it was time to move on, we got in a cab with our bags and asked the driver where should we go. He suggested going to an island like Skiathos, which required a ferry ride.

To get to the ferry would take a very long bus ride. Or… he could drive us 3.5 hours to Volos.

We said, let’s do it.

We get on the ferry and arrive with no hotel or plan. Once docked in Skiathos we are greeted by an older couple that barely speak English. They ask if we need a room. We do! So we follow them home and they set us up in a modest room with our own bathroom down the hall.

Our days are spent on beaches around the island. Harry Potter and the Goblet of Fire just came out so I’m all set between sunning and swimming.

Our evenings are filled with AMAZING food and much revelry. Jenn’s friends meet us a few days in and we spend every night afterward at a discotheque until the wee hours.

It was hands down, my favorite vacation ever.

Whatever the coin flip, do what your gut says.

📷 Photos from when my website was less than 640 pixels wide.