A sail of a lifetime
Join us on a 8-day sail through the Greek Islands on an unforgettable journey from Santorini to Mykonos.
MAY 17 – 24, 2025 (sold out)
MAY 27 – JUNE 3, 2025 (sold out)
The Greek Experience
Spending your first summer days island-hopping in the Cyclades, swimming in the clear waters of the Aegean and sleeping aboard a yacht sounds like a dream, doesn’t it? This trip takes you from Santorini to Mykonos stopping at the quieter, fishing village islands along the way.
Your vessel
Climb aboard the Ocean Star 56, a monorail sailing boat to cruise through the Aegean Sea.
This unique sailing experience is aboard a real yacht. This means close quarters and shared bathrooms and showers. While sleeping quarters are compact the majority of your time will be spent in the shared areas, the open ocean, or on land excursions.
What we’ll do
Day 1: Santorini to Los
Meet your skipper and shipmates at 1pm Café Spartakos at Athinios Port and take a private boat transfer over to the island of Thirasia where you will board the yacht that will be your home for the next 7 nights. After the welcome meeting you’ll set sail (approximately 4 hours) cruising across the Aegean Sea to drop anchor at the island of Ios (the boat will stop at Manganari Beach along the way).
Day 2-6: Sail the Greek Islands
Small Cyclades
Today we cast off for a short amble (approximately 3 hours) to the Small Cyclades. While all the islands harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Schinousa and Donousa have permanent residents, with the largest population said to be somewhere around 300. Here you’ll discover clear waters, great beaches, friendly locals and sleepy tavernas all built around quaint fishing villages.
Amorgos
Continue to the rugged mountainous island of Amorgos. At Katapola, the island’s main port, you’ll see classic Cycladic architecture with windmills and an old Venetian castle. On our way north to Naxos we will cross the Small Cyclades area once more. These magical little islands demand more of our time, so we will spend one more night here.
Naxos
Continue to Naxos to discover the beautiful beaches, charming villages and fragrant olive groves of Hora (the capital of Naxos). This place has a colourful mythological history. The old town areas of Hora are perfect for a stroll, and the nightlife is vibrant.
Syros
Sail to the island of Syros (approximately 4 hours), dropping by the Bay of Gaidharos along the way for a swim. Sample authentic Greek food and culture in the capital of Syros and the Cyclades, Ermoupoli, and check out the magnificent town hall in the main square.
Day 7-8: Mykonos
Lifting anchor, set off on a short sail to Mykonos (approximately 3 hours) arriving late afternoon and where you’ll spend your final evening. This classic Mediterranean island is packed with excitement, beauty and glamour. White-washed architecture clings to the labyrinth of narrow streets and laneways in the town’s old area. The hum of the nightlife, chic cafes, restaurants, galleries and boutiques give way to the island’s wonderful sandy beaches.
Meet Intrepid
I have loved working with Intrepid Travel for my group tour experiences. They go above and beyond to make sure I’m creating a local experience as close to how I travel as possible.
Intrepid works within my budget while still offering an unbelievable experience. And as a certified b-corp, you know you’re getting an ethical trip.
This experience cannot be changed from the itinerary and you can find more details on this specific trip here.
Is Greece right for you? probably.
What I love about hosting group trips is creating really unique experiences for you. Sailing the Greek Islands aboard an actual yacht? Yup, that’s certainly one of them.
When else will you get a chance like this? Not often.
But coming aboard a sailing vessel comes with a few suggestions to ensure this trip is the right fit:
– We will be on a boat, which means close, shared quarters. Rooms are small to maximize the shared space aboard the ship. that meals small bedrooms and bathrooms. It also means you might be sharing a room with a stranger.
– The majority of this trip takes place on a boat, which means you’ll need to get your sea legs. Some people this comes naturally while others might need some medications to help.
– We will be using a zodiac to get to the mainland from the yacht. You’ll need to be comfortable getting in and out of the zodiac to climb on the docks and/or the boat.
– This trip is entirely up to the weather, so changes in the itinerary can happen. We might need to take an alternate route or activity, so a go-with-the-flow attitude is important.
pricing breakdown
$1,499
What’s included
- Private 1-on-1 with me to talk through your personal travel logistics, like airfare and additional travel
- Two 1-hour group chats to talk through logistics and planning
- All breakfasts and lunches aboard the yacht
- Snorkeling gear
What’s not included
- Transfers to and from the marina on Day 1 and Day 8 (don’t worry, we can coordinate and share rides as needed)
- Dinners on the islands
- Any visas required (US citizens currently do not need an entry visa)
- Flights to and from Greece (Don’t worry, we’ll work together to create your plan to get here affordably)
- Required travel insurance (I recommend VisitorsCoverage to find your policy)
- Personal expenses such as souvenirs
- Individual tip for our skipper
payment plan options available