Sailing the Aegean Dream: A 3-Island Cruise You’ll Never Forget

Kalimera, my sun-loving explorers! It’s Laila—and today, I’m taking you on one of my favorite all-day adventures from Kos: a breezy, sun-drenched, music-filled cruise to the islands of Kalymnos, Pserimos, and Plati. This isn’t just a boat trip—it’s the Aegean on a silver platter, with everything that makes Greek island life so irresistible.

We start early in the morning from Kos Town harbor, where traditional wooden boats—known as “kaiki”—line up like a postcard come to life. You’ll hear Greek music playing, smell grilled souvlaki wafting from the galley, and see wide smiles from the crew who greet you like old friends. I’ll be right there, sunscreen in hand and camera at the ready. Ready to sail?

As we glide away from Kos, the coastline fades into the soft blues of the sea, and the energy on board shifts—relaxation mode: activated. Our first stop is Kalymnos, a beautiful mountainous island known worldwide for its sponge-diving tradition. Yes—real sea sponges, harvested by hand!

Once we dock in Pothia, the island’s vibrant harbor town, we have some free time to explore. I’ll show you my favorite sponge shop, where you can meet the divers and learn the difference between a “silk” and a “honeycomb” sponge. (Pro tip: sponges make amazing eco-friendly gifts!) The colorful neoclassical buildings, cute cafés, and friendly locals make this stop so warm and authentic.

Then it’s time to head back to the boat for lunch. Most cruises include a BBQ on board—grilled souvlaki, tzatziki, fresh bread, and a chilled drink, served as we sail toward the uninhabited island of Plati. The water here? Unreal. Think turquoise so clear you can count the fish from above. I always bring my snorkel here, and I’ll show you a spot near the rocks where tiny silver fish swirl like glitter. It’s my secret swim zone.

After a refreshing dip, we cruise gently to Pserimos, our final island. This tiny, peaceful village has only about 30 residents and one of the softest sandy beaches in the Dodecanese. You can walk barefoot, grab a local ice cream or a cold beer, or just lay under the tamarisk trees and feel time disappear.

My tip: ask one of the little tavernas for a fresh oregano salad and a shot of mastiha liqueur. The locals will chat with you like you’ve lived here for years.

As we cruise back to Kos in the late afternoon, the Aegean sun begins to dip, casting golden sparkles across the sea. The boat crew often puts on some music—Greek folk or soft pop—and people start dancing, clapping, smiling like children on summer break. It’s my favorite part. The joy is real. You can feel it in the air.

The 3-island cruise isn’t just about beaches and sun. It’s about connection—to the sea, to new friends, to local life, and to yourself. You’ll leave the boat salty, happy, and dreaming of when you can do it all again.