{"id":35515,"date":"2025-06-20T01:00:00","date_gmt":"2025-06-19T15:00:00","guid":{"rendered":"https:\/\/www.intrepidtravel.com\/adventures\/?p=35515"},"modified":"2025-06-26T20:16:50","modified_gmt":"2025-06-26T10:16:50","slug":"sailing-in-greece-trip-story","status":"publish","type":"post","link":"https:\/\/www.intrepidtravel.com\/adventures\/sailing-in-greece-trip-story\/","title":{"rendered":"11 strangers, 10 days, 1 boat: my life-changing sailing trip in Greece"},"content":{"rendered":"\n

This article was originally published in June 2019.<\/em><\/p>\n\n\n\n

I stared at myself in the bathroom mirror, pressing the palm of my hand against my right eye. Distracted by what the day would bring, I\u2019d jabbed myself in the eye trying to put in my contact lenses. The result? My right eye was blood red, swollen, and streaming with tears.<\/strong><\/p>\n\n\n\n

\u2018Great,\u2019 I thought to myself. \u2018Now I look like an ogre.\u2019 A quick glance at the time told me I had about 30 minutes to get myself together before I threw myself into what could potentially be an incredibly uncomfortable situation: a group trip.<\/p>\n\n\n\n

After travelling to 57 countries, I was joining my first proper group tour \u2013 a sailing trip through the Greek islands<\/a> with Intrepid. I\u2019d done an overnight Sahara tour in Morocco and a three-day adventure through Jordan, but this was different. This was 10 days with 11 strangers on a sailboat. A small sailboat with limited space, where I\u2019d be sharing a tiny room with a random person I knew nothing about.<\/p>\n\n\n\n

I\u2019d be lying if I said I wasn\u2019t nervous.<\/p>\n\n\n\n

<\/div>\n\n\n\n
Greece Sailing Adventure: Cyclades Islands<\/a><\/div>
10 days<\/span><\/div>
View trip<\/a><\/div><\/div><\/div><\/div>
Sail Greece: Santorini to Mykonos<\/a><\/div>
8 days<\/span><\/div>
View trip<\/a><\/div><\/div><\/div><\/div>
Greece Sailing Adventure: Corfu to Kefalonia<\/a><\/div>
8 days<\/span><\/div>
View trip<\/a><\/div><\/div><\/div><\/div><\/div>\n\n\n\n
<\/div>\n\n\n\n

I had a million thoughts racing through my head as I finished packing. What if the group is all couples? What if it’s a bunch of cliquey girls who don\u2019t want to make new friends? Or a bunch of frat boys? Or 19-year-olds fresh from their first year at uni who just want to get drunk and party all the time? Oh, god<\/em>.<\/p>\n\n\n\n

I processed every possibility until I transformed from a strong, independent traveller to a nervous wreck who felt like the new kid at school.<\/p>\n\n\n\n

It sounds silly, but I\u2019d become so used to travelling solo and doing what I wanted, when I wanted, with who I wanted, that the prospect of literally being trapped on the ocean for hours each day with a group of strangers made me feel, well, kind of seasick \u2013 to the point where I made an escape plan (yes, really). <\/p>\n\n\n\n

I only had two small bags and I knew how the ferries worked. So, if worse came to the worst and I was miserable, I told myself I could just bail on one of the islands and do my own thing.<\/p>\n\n\n\n

Read more: <\/strong>Greece vs Croatia: Where to travel next?<\/strong><\/a><\/p>\n\n\n\n

<\/div>\n\n\n\n
\"sailing
Paros<\/figcaption><\/figure>\n\n\n\n
<\/div>\n\n\n\n

With my contact lens reinserted (but still red-eyed), I flipped my sunglasses over my face and headed downstairs to meet the group. The itinerary said to meet at 11 am, but I planned to arrive 20 minutes early, hoping to be the first one so I could scope out the others. Yet as I approached the table with the red Intrepid sign, I was greeted by name.<\/p>\n\n\n\n

‘You must be Hannah?’<\/p>\n\n\n\n

‘Yes.’ I answered. ‘How did you know?’<\/p>\n\n\n\n

‘You\u2019re the last one.’<\/p>\n\n\n\n

And that was when all my expectations went out the window.<\/p>\n\n\n\n

<\/div>\n\n\n\n

\"sailing<\/p>\n\n\n\n

<\/div>\n\n\n\n

Our group of 11 consisted of three couples, four single women and our skipper \u2013 a local Greek man named George. Our ages ranged from 25 to 60, and as we made our introductions and talked a little about ourselves, I quickly learned I was the only one who’d never been on an Intrepid trip. <\/p>\n\n\n\n

I listened as the others shared stories about boat rides in Italy<\/a>, plane wrecks in Iceland, hiking the Inca Trail<\/a> and travelling overland through Africa<\/a>. My perspective began to change.<\/p>\n\n\n\n

These weren\u2019t newbies who needed their hands held every step of the way. They were experienced travellers hungry for adventure, just like me. And although we were still strangers (and I had already forgotten half of their names), I felt some of my initial apprehension dissolve.<\/p>\n\n\n\n

<\/div>\n\n\n\n

\"sailing<\/p>\n\n\n\n

<\/div>\n\n\n\n

As you can imagine, life on a small sailboat is pretty, well, personal. It didn\u2019t take long to figure out people\u2019s routines \u2013 who\u2019d get up early in the morning, who slept in, who liked to chat, and who was happier listening in or reading as we sailed the Aegean Sea.<\/p>\n\n\n\n

Of course, they figured me out pretty quickly too: the sarcastic, clumsy girl who knocked over wine glasses and broke door handles just by touching them. As the first one to jump in at most swim stops, I was the unofficial water temperature tester \u2013 and maybe a bit of a rule breaker when it came to staying close to the boat (sorry, George!).<\/p>\n\n\n\n

I think the group did a good job at understanding and accepting my kind of crazy. Well, most of the time! Or at least enough that I felt like I’d bonded a little bit with everyone.<\/p>\n\n\n\n

It could’ve been awkward with 11 people staying in such a confined space, but it wasn\u2019t. This was a group of seasoned travellers and we all made it work to the point where it was actually comfortable. Having just spent two weeks alone, I actually liked the sense of community that formed between us and began to think of the group as my boat family. Any thoughts about an escape plan vanished. I realised how much I actually liked these people, and how much I truly loved sailing.<\/p>\n\n\n\n

Read more: <\/strong>Connecting with Crete’s traditions in the White Mountains<\/strong><\/a><\/p>\n\n\n\n

<\/div>\n\n\n\n
\"sailing
Naxos<\/figcaption><\/figure>\n\n\n\n
<\/div>\n\n\n\n

I\u2019ve always loved boats. I grew up by the water and spent the past few years scuba diving around the world. That said, I did worry about spending more than half a day on a small sailboat, as I’m someone who likes to be on the move and explore lots of places when I travel.<\/p>\n\n\n\n

But it turns out I can happily spend hours scanning the waves and horizon for sea life, spotting \u2018medium-sized\u2019 sea turtles (only according to George, the rest of us thought it was pretty big), and watching pods of dolphins dance and spin in the waves and under our boat. Whenever the winds picked up and we gained momentum, I laughed nonstop as waves crashed over the front, leaving me covered in a glittering white salt crust.<\/p>\n\n\n\n

The mornings soon became a welcome routine of pulling shorts and a t-shirt over my swimsuit and waiting on deck to see if George needed a hand. I had my favourite places to sit \u2013 on the front watching the waves in front of me, or on the side with my legs dangling over the edge. Sailing allowed me to relax in a way I didn\u2019t expect.<\/p>\n\n\n\n

<\/div>\n\n\n\n

\"sailing<\/p>\n\n\n\n

<\/div>\n\n\n\n

Every time our boat, the Big Blue, pulled into port, I felt mixed emotions \u2013 excitement to explore a new island and sadness to leave the sea behind. I fell in love with the boat life, and honestly, I think I could’ve stayed on board for the rest of the season. Awkward boat shower and all.<\/p>\n\n\n\n

The trip went far too quickly. It was a blur of traditional Cycladic villages, swimming in turquoise sea caves and hiking up to cliff-side monasteries. I became a zucchini-ball enthusiast and mastic connoisseur. I stayed up late and woke up early. My skin was constantly covered in sea spray, my long hair got more tangled and my smile grew bigger each day we sailed. I\u2019ve met hundreds of people, experienced dozens of sunsets and have thousands of incredible memories, but this sailing trip was something else.<\/p>\n\n\n\n

<\/div>\n\n\n\n

\"sailing<\/p>\n\n\n\n

<\/div>\n\n\n\n

We spent our second last night in Greece on the Big Blue, forgoing a taverna dinner for a simple meal of takeout souvlaki, a few bottles of mystery-label Greek wine and a jug of homemade tsipouro. Sitting under the stars, we shared jokes, stories and memories both old and new. It was our simplest night, but also my favourite.<\/p>\n\n\n\n

As I watched my shipmates laugh, half-empty glasses of wine in hand, I finally got it. As a solo traveller who often craves company, these trips offer the perfect compromise \u2013 the ability to share an adventure with like-minded people while also having time to explore on your own. I caught the group travel bug.<\/p>\n\n\n\n

Ready to set sail? Check out Intrepid’s sailing trips<\/a>.<\/a><\/strong><\/p>\n\n\n\n

—<\/p>\n\n\n\n

(All images courtesy of author Hannah Logan)<\/em><\/p>\n\n\n\n

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