There’s something truly special about exploring the Greek islands by boat. Picture endless blue waters, secret coves, cliffside dinners with stunning views, and charming towns that seem to have been frozen in time. This summer, a group of us took off from Alimos Marina in Athens for a 7-day sailing adventure of the Greek Islands that turned out to be one of the most unforgettable experiences of our lives.
From the dockside cocktails in Porto Cheli to donkey rides in Hydra, here’s a breakdown of our epic Greek islands by boat itinerary, and why you may want to consider a catamaran trip for your next adventure.
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Why Explore Greek Islands on a Catamaran?
We had 8 people on board, and it never felt cramped. The spacious decks, cozy cabins, and ability to anchor right next to secluded beaches made it feel like a floating hotel, only with better views, and the freedom to change scenery every day. Plus, it’s affordable when split among friends, especially compared to staying in hotels on every island. It’s the best of both worlds: comfort and adventure.
7 Day Greek Islands by Boat Itinerary
Day 1: Alimos Marina to Lavrio
We set sail from Alimos Marina around 5 PM, with the sun slowly dipping into the horizon, painting the sky a fiery orange. The first leg was a short cruise, but just long enough for us to uncork a bottle of wine and start settling into boat life.
We docked for the night in Lavrio, a quiet port town that doesn’t get as much love as some of the more well known coastal towns. Lavrio surprised us though, its charm was undeniable.
After grabbing a table at a seaside restaurant, we dug into grilled octopus, fresh tzatziki, and of course, the first Gyros of the trip. The night wrapped up at Heffernan’s Irish Bar, a hidden gem of a dive bar with the best vibe. The crowd was fun, the music was spot-on, and it was the perfect way to kick off our week of island hopping.
Day 2: Kythnos – Cliffside Dining and Sunset Swims
Kythnos was our second stop. We spent the day swimming right off the boat in crystal-clear coves, and honestly, I could’ve stayed there forever. But the best part?
Dinner at Kolona, a cliffside restaurant perched atop the rocks with a view of the turquoise sea below. They stayed open an extra hour just to accommodate our group, and we were treated to the freshest fish, seafood, grilled octopus, and local wine, all while the stars began to twinkle above. Kythnos ended up being one of our favorite unexpected gems of the trip.
Day 3: Poros-Coffee, Charm, and Dancing
By midday, we pulled into Poros, an island that feels like it belongs in a postcard. One side of the island is lively, with cafes and boats filling the harbor, while the other is covered in pine forests and dotted with old villas.
After a leisurely day strolling through town, we sat down at Poseidon for dinner. The sea bass filet was incredible, hands down, the best I’ve ever had. I also had to try the Moussaka. It was nothing like I expected, layers of eggplant with a shepherd’s pie-style filling. It was the kind of dish you can’t stop eating.
The night in Poros was equally perfect. We ended up at Yacht+ The Bar for cocktails and dancing. Located along the harbor, this sleek lounge-bar is a great spot for a night on the town.
Day 4: Dokos & Porto Cheli-Swimming, Snorkeling, and Rooftop Cocktails
After a lazy morning sail, we dropped anchor at Dokos, an uninhabited island that felt like our own private paradise. If you’re into snorkeling, you’ll want to bring your gear here, there are underwater caves and so much sea life to explore.
Later that day, we made our way to Porto Cheli, a posh coastal town where we dressed up a bit for drinks at La Terrazza. The rooftop had panoramic views of the marina below, and balanced authentic Greek charm with just the right touch of laid-back luxury.
Day 5: Hydra-Donkeys, Brunch, and Picturesque Perfection
Hydra was a highlight of the trip. This car-free island is like stepping back in time. The only transportation here? Donkeys. After grabbing a coffee at a charming café, we spent the morning wandering cobblestone alleys, taking photos with every cat and donkey we came across. (Seriously, there were somany cats.)
The harbor is the heart of Hydra, lined with shops, restaurants, and cafes perfect for a relaxed afternoon. But don’t miss the chance to climb one of the island’s many hills, where you’ll find breathtaking views over the crystal-clear waters below.
Day 6: Aegina-Pistachios, Pastries, and Local Flavors
Aegina, known for its Pistachios, was our next stop. This place had a much more local feel to it, and fewer tourists. We explored the quaint streets, stopped by a bakery for some of the best sandwiches we’d ever eaten, and had a pistachio espresso, which was shockingly good even for someone who doesn’t usually love espresso.
Day 7: One Last Swim & Back to Athens
Our last day was bittersweet. We made one last stop for a swim, a secluded cove between Aegina and the mainland. It was the perfect way to soak in the beauty of the islands before heading back to Athens.
Final Thoughts: Greek Islands by Boat
Would We Do It Again? Absolutely. In a heartbeat. No ferry schedules, no hotel check-ins, just us, the open sea, and a new destination every day.
If you’re thinking about doing a Greek Islands trip by a catamaran, here are a few tips:
- Group Budgeting: Splitwise is a lifesaver for keeping track of expenses when traveling with a group.
- Pack Light: You don’t need much, but definitely bring swimsuits, cover-ups, and a few nice outfits for dinners.
- Don’t Over-Plan: Some of the best moments came from spontaneous swims or random explorations of little villages.
- Bring a Floatie: Having your own floatie means you can maximize your time in the water without tiring out too quickly.
If you’re looking for an adventure that blends relaxation with exploration, a Greek catamaran trip is the way to go. Trust me, you won’t regret it
