Past travel · August 2025 · Greece

Greek Cyclades

A 7 day Odyssey aboard a 42' catamaran. Starting and ending at Lavrion, we visited the islands of Kithnos, Siros, Mikonos, Tinos, and Kea. Great food, great shopping, unforgettable views, private beaches, and of course some wonderful scuba diving.

Mykonos, Greece

Overview

Dates
8/23/2025 – 8/30/2025
Departure/Return port
Lavrion Main Port
Dream Yacht Charter Office
Google Maps ↗
Meet up time 8/23
11 a.m.
Estimated disembarkation 8/30
9 a.m.

Trip notes

Intro

The Cyclades are a stunning archipelago in the heart of the Aegean Sea, celebrated for their iconic whitewashed architecture, crystal-clear waters, and rich cultural heritage. These islands were once the cradle of the Cycladic civilization, known for its elegant marble figurines and seafaring prowess. On our sailing journey, we'll visit the dramatic Temple of Poseidon at Cape Sounion, explore the neoclassical charm of Syros, the wild beaches and traditional villages of Kythnos, the cosmopolitan buzz of Mykonos, the artistic soul of Tinos, and the rugged beauty of Kea. Each island offers its own rhythm, inviting you to slow down, soak in the scenery, and savor the essence of Greek island life.

Itinerary

8/23 Saturday Day 1 - board the ship at 12pm and sail south to Sounion. Distance: 4 NM. Sailing Time: 1 Hr.

8/24 Sunday Day 2 - Sounion to Kithnos. Distance: 25.3 NM. Sailing Time: 3:10 Hrs.

8/25 Monday Day 3 - Kithnos to Empoupoli (Syros Island). Distance: 36.9NM. Sailing Time: 4:37 Hrs.

8/26 Tuesday Day 4 - Empoupoli to Mykonos. Distance: 18.4 NM. Sailing Time: 2:18 Hrs.

8/27 Wednesday Day 5 - Mykonos to Tinos. Distance: 10NM. Sailing Time: 1:15Hrs.

8/28 Thursday Day 6 - Tinos to Kea beach Otzias. Distance: 39.9NM. Sailing Time: 5:00Hrs.

8/29 Friday Day 7 - Kea beach to Kea downtown. Distance: 3.6NM. Sailing Time: 28 min. Kea Downtown to Lavrion Base: Distance: 15.1NM. Sailing Time: 1:53Hrs.

Map of the sailing route through the Cyclades
Our sailing route through the Cyclades
Our Yacht

We chartered a Bali 4.2 Catamaran. It's 42 feet long. It comes with 4 cabins all with their own bathrooms. It has an additional porthole cabin that we can use for storage and an extra bathroom on the front. Dream Yacht doesn't have great photos/details of this ship on their website but you can see what they have below:

Bali 4.2 catamaran under sailBali 4.2 catamaran layout diagram
What to Pack

We'll be out at sea, so it's a good time to practice minimalism. Not too much storage in the cabins. The Charter company provides life jackets, bed sheets, blankets, and pillows. Everything else, we'll need to bring. Here is a list of the essentials to get you started:

  • Soft-luggage only (the hard suitcases are hard to squeeze on a boat). If you have a carry on hard case bag you use for airplanes, you can use that too if you're ok with it standing up in your cabin and having to climb over it.
  • Medications (bonine for seasickness, works much better than dramamine and doesn't leave you drowsy); can buy on Amazon
  • Swimming gear - towels, suits, reef safe sunscreen, sunglasses, snorkel, fins, mask, booties. Greek beaches are more rocky than the sand beaches you are used to. You can get some cheap booties on Amazon.
  • Bio soap, bio hair shampoo. We will be in some marine protected areas.
  • A jacket for night time. We'll be on the water and the sea breeze does tend to make things chillier than usual.
  • Clothes to wear for whatever excursions you're planning on doing. There are a lot of options for things to do at each port. You can look around the city/town, go explore ruins, hang out on a beach, or go on a scuba diving expedition. Pack as you see fit for your activity level. We'll also be eating at a lot of restaurants, so bring some cute Greek clothes for that.
  • Portable Chargers. We will have electricity on the boat. But it's good to have a backup battery pack in case of emergency loss of power.
  • Sailing Shoes or sneakers with light soles to avoid dark streaks on deck
  • Optional dry bag to keep your electronics dry and secure
Food and Drinks

Most (if not all) of our meals are going to be on land. Our grocery shopping will be at a minimum. Mostly we will want to load up on any snacks, light breakfast items, and drinks. All costs are split by the group so whoever buys groceries, please put the total into Splitwise. We will have some time to do grocery shopping in Lavrion while the captain/co-captain are doing the boat check out. We can also grab more food/drinks at each destination.

Sailing Safety

The trip will be a blast and we aren't expecting to have any major issues arise. Those of you who have already joined us on one of our sailing adventures know what to expect. Those of you who are new, please take the time to go over the links below:

  • FAQ Page
  • How to Use a Sea Toilet - you'll be shocked how many people are intimidated by the toilet!
  • Sailing Knots - Don't stress memorizing these. Main ones to look at are Cleat Hitch and Round turn and 2 half hitches if you're interested

The Islands, Day by Day

SounionDay 1

The start of our journey. We will make our way from Athens to Lavrion in the morning. We need to be in Lavrion for boat check out at 11 a.m. Once we have the boat ready, we will make our short voyage down to Sounion to see the Temple of Poseidon. We will anchor near the site by a beach. For those interested in exploring the ruins, we will take the dinghy and make the hike up to the Temple. Whoever doesn't want to go, can stay on the boat and enjoy a beach day. After we're done in the area, we will make our way to the nearby pier, where we will dock for the night.

Anchoring area near the Temple of Poseidon
Anchoring area for the Temple of Poseidon
Overnight docking area at Sounion
Overnight area for Sounion
KithnosDay 2

We have a 3 hour 10 minute sail to our next island today. Ideally, would like to start moving around 7 a.m. to get to our destination in the morning. We have some options to choose from. We can decide to go to Kolona Beach and anchor there for morning swim/food. When we're done swimming, we can raise anchor and sail into the main port of Merihas. Here are some ideas for things to do in Kithnos:

  • Kolona Beach - This double-sided sandbar beach is one of the most iconic in the Cyclades. You can swim on either side of the strip, with turquoise waters and a wild, untouched vibe.
  • Σπήλαιο Καταφύκι – Katafiki Cave - Located in Dryopida, this cave blends natural wonder with history. It's been used as a shelter, mine, and even a place of worship. The stalactites and underground chambers are mesmerizing - this cave looks pretty cool. Kind of a drive away from Merihas port.
  • Oria Castle - Perched on a hilltop, this medieval ruin offers panoramic views and a peek into Kythnos' defensive past. It's a great spot for a sunset hike and some quiet reflection.
  • Archaeological Site at Vryokastro - Explore the remains of ancient Kythnos, including temples, homes, and public buildings. It's a fascinating walk through time, especially if you're into ancient Greek urban planning
Sailing route from Sounion to Kithnos
Day 2 route — Sounion to Kithnos
SyrosDay 3

We have our second longest sailing day today. 4 hours and 37 minutes. Ideally we get up and start sailing around 6. Everyone can continue to sleep while the boat is underway. Ermoupoli is a pretty large, industrial city. We should have some good restaurant options here. Along with some cool museums to check out. Since it's an industrial city, there are no good beaches here, but on the way, we could stop by Didimi Island for a morning swim. It is an uninhabited island, so we would need to have morning snacks ready. It does have a sandy beach though. Here are some top things to do at Ermoupoli:

  • Industrial Museum of Ermoupolis - Dive into Syros' industrial past with exhibits on shipbuilding, printing, and textile production. It's housed in restored factories and offers a fascinating look at the island's economic history.
  • Archaeological Museum of Syros - Located in the heart of Ermoupoli, this museum showcases artifacts from the Cycladic civilization, including pottery, tools, and burial items. A compact but rich stop for history lovers
  • National Resistance Monument - A quiet but powerful tribute to those who fought during WWII. It's open 24/7 and makes for a reflective pause amid your explorations.
  • Gria Cave - This natural wonder near Ermoupoli is steeped in legend and offers a cool escape with dramatic rock formations. Great for a short hike and some mythic storytelling. This could be a cool alternative to stopping by Didimi Island. There's a beach and an anchorage here as well so we could do some swimming along with checking out the cave. Would also save us a little sailing time than going to Didimi.
Sailing route from Kithnos to Syros
Day 3 route — Kithnos to Ermoupoli, Syros
MykonosDay 4

A shorter sailing day today, only 2 and a half hours. Mykonos gets very busy, so we will still probably want to get an earlyish start to the day. Mykonos is the biggest stop for tourists that we'll be visiting. I'm hoping to get an anchorage at Mykonos Old Port, but if it's too packed, we might have to pivot. The island itself is a destination—famous for its nightlife, whitewashed architecture, and beach clubs. Whether you're strolling through Chora or lounging at Psarou Beach, the vibe is electric.

  • Windmills of Mykonos - These iconic 16th-century windmills perched above the sea are a photographer's dream. They're open 24/7 and offer stunning views, especially at sunset
  • Archaeological Museum of Mykonos - A compact but rich museum showcasing ancient urns, funerary art, and figurines from prehistory to the Hellenistic period. It opens at 9 AM and is perfect for a cultural detour
  • Armenistis Lighthouse - Set atop a steep hill, this historic lighthouse offers panoramic views of the Aegean and neighboring islands. It's a peaceful spot for reflection or a breezy hike
  • Mykonos Old Port - A charming harbor area with tavernas, shops, and a laid-back vibe. It opens at 8 AM on Mondays and is a great place to start your day or unwind in the evening
TinosDay 5

Today we have a big choice to make. We could hang out at Mykonos longer and enjoy the city. Maybe do a scuba diving tour with the local shop. Or we could sail over to Delos island, a UNESCO World Heritage Site, filled with ruins to explore. Our sail time to Tinos is only an hour and a half, so we could get there before sunset to check out some restaurants and get us a little closer for our big day 6 sailing day. There isn't as much to do on Tinos as Mykonos or Delos, but if people want to go spend more time there, that could be an option also.

Sailing route from Mykonos to Tinos
Day 5 route — Mykonos to Tinos
Kea, Otzias BeachDay 6

Our biggest sailing day of the trip. We have just over 5 hours to get to our next island of Kea. After the hustle and bustle of the previous 2 days around Mykonos, this will be a day of relaxation. We can rest up on the long passage and, when we get to our destination, there will be more relaxing on the books. Otzias beach looks like a great spot to anchor and enjoy a relaxing beach day. There are plenty of restaurants and a dock we can dinghy to. Great day to unwind.

Sailing route from Tinos to Kea
Day 6 route — Tinos to Otzias Beach, Kea
Kea & Lavrion BaseDay 7

Our final day at sea! We have some options today as well. We'll need to be back at Lavrion Base before they close at 6pm, but we have the rest of the day to enjoy. Kea has some good scuba diving options, so this will be the best day to hop on a morning scuba diving tour. We can enjoy a morning swim at Otzias beach, then do the 30 min sail over to the main port. Check out the town there. Find another beach. Lots of options. Will need to start heading back to Lavrion around 3:30 pm. When we get back to Lavrion, they'll help us dock the boat. We can have dinner there and enjoy the last night of sleeping on the boat. Come next morning, we'll be leaving the ship.

Sailing route from Kea back to Lavrion
Day 7 route — Kea to Lavrion Base