From Sailboat to SUP Through the Greek Isles


The sailboat motored away, leaving me alone on the glassy water. I gripped the paddle and started chasing after the boat’s widening wake. Aquamarine water stretched smooth and mirrored for what seemed like miles in each direction. Bright white windmills topped dusky ridgelines on both sides of the huge bay, motionless in the mid-morning haze. I fell into an easy rhythm. 

The board glided easily through the calm water. Schools of fish splashed wildly on the surface, chased (at least in my mind) by a much larger predator. Gulls followed the fish, landing here for a few moments and then flying a hundred yards away to the next commotion. Far off, sailboats puttered toward their destinations and colorful fishing boats plied the deeps. I’d been paddling nearly an hour and had lost sight of our boat, which had disappeared into a large bay that arched into the rocky shore. I paused to catch my breath and stretch my back before resuming my cadence.

Chris paddles in a bay near the town of Ermioni.

Four months prior, my brother had invited my wife and me to join his family of four on a sailing trip in Greece. We pretended to think about it for a couple of days before we enthusiastically accepted. Always scheming for my next paddle, I drifted off to sleep fantasizing about exploring the Mediterranean Sea on a SUP.

But it wasn’t a paddling trip. It was a family vacation. And it we’d be sailing, a longtime passion of mine. I told myself to focus on how lucky I was to even be going, not on how I could finagle a paddleboard onto a 45-foot sailboat half a world away. I reasoned I could just chill out and relax for once. I’d read a book or two, do some snorkeling and hang out with my niece and nephew. I had all summer to paddle back home in Montana.

As it turned out, my brother also thought having a board on board would be fun. So, I offered to explore how to get one. The charter company didn’t rent them, and my Google searches for a rental shop near our embarkation point proved more confusing than helpful. I asked the local UPS store for an estimate on how much it might cost to ship my inflatable: At least $1,000, with no guarantee it would even arrive. Clearly, that wasn’t an option.

Losing hope, I joined a Greek SUP Facebook page a month before we left, and asked if anyone knew where I could rent a board for a week of sailing through the Argolic Gulf. To my surprise and delight, Gerry replied a couple of days later. He’d rent me his extra inflatable board for 20 Euros a day. He was even willing to meet me at the port where we caught the ferry to our sailboat. I jumped at the chance, marveling at how great the SUP community is, even internationally.

“Oh man, Gerry forgot the fin,” I exclaimed. It was the first day of our trip and we were getting settled onto the boat, still in the main harbor on the Island of Poros, where we met the boat and our captain.

“Are you sure?” my brother called out from the cockpit. I rifled through the board bag, the paddle case, and looked through the pile of gear on the boat’s deck a second time…no fin.

“Well, that’s a bummer,” I said. “At least he didn’t forget the pump and a paddle.” I looked up toward the cockpit, but found my attention diverted by the stunning blue water and craggy, chaparral-covered island that sprawled out behind us. I wasn’t going to let a missing fin dampen my mood.

Even without the fin, the board worked fine, and I soon found my paddling groove. My pre-trip fantasies had me getting up early and paddling miles each day. Or setting a rendezvous spot and meeting the boat in some secluded harbor hours after I pushed off. But those opportunities didn’t materialize.

Instead, I grabbed 30 or 40 minute-long paddles as opportunity allowed. On the Island of Spetses, I poked around the colorful harbor, paddling past hand-built fishing boats while horse-drawn carriages clattered along a cobblestone street that ran along the shore. In the town of Ermioni, my brother and I took turns chasing the rising sun as we walked and paddled from one quaint harbor to another, along a peninsula covered in bright green pinyon pines, otherworldly yucca plants and topped with an ancient ruin.

We all took turns adventuring deep into a sea cave near the postcard-perfect town of Tiros. I found quiet beaches where I pulled ashore and explored abandoned olive groves and crumbling outbuildings. At one lunch-time anchorage, I raced around an island that looked like a crouching frog, getting a quick workout while the rest of the crew snorkeled and munched sandwiches. The kids even paddled a time or two, trading their masks and snorkels for sunshirts and lifejackets. At one point or another, everyone hopped on the board, including our captain, Alex, who declared he would have to get one for his sailboat after his first foray.

Chris and Isabel exploring a secret sea cave just outside of the town of Tiros.

The sailboat remained out of sight, tucked inside the rocky bay ahead. Paddling closer to the rugged shore, I noticed a tiny church nestled in the rocks fifty feet above the sea. Bright white walls rose above a hand-built rock foundation, punctuated by classic cerulean-blue doors. The ubiquitous white cross rose above the rust-colored terra cotta roof. A trail of whitewashed rocks led to the sea. Festive prayer flags stretched across the small courtyard.

Rounding the rocky corner of the bay, I finally glimpsed the boat anchored a couple hundred yards away. The kids were swimming, again, while my wife and sister-in-law relaxed on deck. A breeze had come up, blowing from the shore out across the bay, and I labored with each stroke. “How was it?” Chrissy called out, catching sight of me when I eventually pulled alongside and grabbed the boat’s rail. “Perfect,” I answered, before pushing off again to paddle just a little bit longer.

Did the board make the trip? No, not really. The Greek culture, the picture-perfect towns, the beautiful water and the time we spent as a family made the trip. But having the board definitely enhanced the trip. Sailboats are close quarters and getting to sneak off for some alone time, even if only a short paddle around a harbor, provided a welcome bit of solitude. The chance to get a little exercise made indulgent breakfasts and Greek pastries a little easier to enjoy. And after some experimenting, we found the board stowed well on the foredeck under the dinghy, safely out of the way and out of the intense Mediterranean sun.

On the final day of our trip, I got up early, anxious to sneak in one final paddle. The town of Poros provided the perfect backdrop. As I dipped the blade into the still water, watching a few fishermen prepping their gear and waiting for the sun to rise above the town, I nearly had to slap myself to make sure I wasn’t dreaming. Sailboats lined the quay, graceful and soft in the early morning light; bright white houses stretched up the hillside, stacked like children’s blocks; a church tower poked into the golden blaze of the sunrise. For a “non-paddling” vacation, I had sure managed to do a lot of paddling.

Sunset on the island and town of Poros.

Pro Tip: Getting a board was hard enough. I didn’t want to mess around with having to get other key gear like a life jacket or a dry bag when I got to Greece. Fortunately, you can fly with the Zephyr Inflatable Life Jacket (just tell TSA about it during security to avoid a hand search) and it’s so small and compact, it fits easily in a carry on or checked bag.

I also brought a two-liter Ether Dry Sack, which kept my essentials secure on the board and disappeared into my luggage when I didn’t need it. With space at a premium, the NRS Guide Shirt served me well with its stretch fabric, 35 SPF and taverna-appropriate style. My fair-skinned wife practically lived in her H2Core Silkweight Shirt, wearing it while swimming, paddling, and lounging on the boat.