In September 2024 I undertook a 10-day sailboat adventure with Intrepid Travel in the Greek Cyclades Islands. I’ve been a sailor since I was six-years old. I’ve cruised and raced on everything from dinghys to 12-Meters. But I always dreamed of cruising overseas, and one of my top bucket list destinations is Greece. Experiencing the islands by sailboat allows explorations of intimate places and cultural experiences the big cruise ships due to size and sheer numbers of guests cannot offer.
This experience is not for everyone, but 100% perfect for me. There are no casinos, water parks or black tie dinners. On this trip we had a 55-ft sloop with George, our captain. We were 8 women and two men. Some were single, others were married without spouse, and there was a mother and daughter. We were a mix of American, Australian, Australian England resident, and Iranian now Australian. We were complete strangers all excited to become a team. We had shared cabins each with its own bath. We shopped for breakfast and lunch food and made it on board. We all took a hand at sailing. Our days typically began with breakfast, shoving off about 8 or 9, stopping in a cove for snorkeling and lunch, and then arriving at our island destination about 3 p.m. Then explore, with a dinner out at a local restaurant. Each island offered its own highlights. All had beaches with lovely “Horas,” or main villages. Others had ancient Greek ruins, cliffside monasteries, lively downtowns, and marina districts which varied from cozy Hemingway novel waterfronts to bustling with cruise ships like Mykonos.
We first met on the waterfront on Santorini, then took a fast ferry to Ios, where Big Blue, our sailboat, awaited. The waterfront had maybe two dozen boats like ours, hailing from many countries. Sweden, Poland, Belgium, New Zealand, Singapore, Germany and many more. One was from Marblehead, Massachusetts! I lived there and raced there! Big Blue had two wheels and a generous cockpit.
Big Blue had many modern features which made it easy to sail. It had a remote controlled anchor system. It had a self-steering GPS guided navigation system. The toilets flushed with a push button. And the mainsail furled into the mast. The galley was well equipped and generously sized.
Once settled into our cabins, George held an orientation session. Here, he explained life aboard. As with all sailboats, they heel, so cabinet doors and drawers had special closures. Windows/hatches must be closed when sailing. Loose items must be off tables. There were 3 coolers/refrigerators, a radio, stove, oven, kitchen sink. When conditions get rough, always hold on to something when moving about.
One of the most important items to get settled right away is the group Kitty. On most Intrepid Travel trips, guests contribute to a group kitty, and the guide uses this to pay admission fees, certain transportation, tips for local guides and bus drivers, and such. On this trip, the kitty is used to pay for groceries and rental cars and such.
Once orientation was complete, George told us about activities on Ios. Strolling the waterfront. Grocery shopping and provisioning. Later, enjoy a sunset cocktail at the spectacular hillside Volcano Bar, and then dinner in the Hora at a restaurant called Lord Byron. It was a bit more than my budget to do all, but I went ahead and WOW it was worth all of it.
The sunset view at the Volcano Bar. You can take in the whole Aegean Sea with an infinity pool right in front. And 100% perfect weather!
Next, we took a bus down to the Hora, strolled the streets. Like all the Cyclades, the Chora is a village with white buildings up on a hill, with small, steep streets and walkways. And very neat and clean.
As dusk drew close, we headed to Lord Byron. Decorated in an eclectic cluttered style, each turn revealed something to feast my eyes. We ate with windows open and a moonlit view.
Completely over stuffed with full bellies, we waddled to the bus stop. The local bus takes about 10 minutes down the hill right to the marina where Big Blue was tied up. It wasn’t long before we were in our cabins fast asleep.
I awoke early and stepped out. Ios port had several cafes open early, and I checked out out.
It was chock full of fresh baked goods, and an espresso bar. I picked out a bakery item and was good to go!
We pulled out of the dock and were on our way to Amorgos, the next island. It was a beautiful morning with a light wind. We used the motor to make time.
Here’s a sailing video!
We stopped for lunch and a snorkel in a warm, windswept cove before arriving in Amorgos!
Cabin Fever Chronicles - Getting Outdoors with Rod 