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Sail & Hike Greece: Mykonos to Athens





Say ahoy! to ancient ruins, fishing villages and bright blue swimming coves
Spend eight salty-skinned days sailing, hiking and swimming your way through some of the lesser-known Cyclades. Starting in lively Mykonos, you’ll cruise the sparkling Aegean Sea aboard a private yacht and drop anchor at islands that seem unchanged by time. Hike to a clifftop castle in Kythnos, share a homemade dinner with a local family in Syros and unearth the stories of legendary gods and ancient civilisations on the UNESCO-listed Delos. With a passionate skipper at the helm, daily swims and plenty of free time to enjoy the Cyclades’ laidback pace, this is Greek island hopping done right.
5.0
6 reviewsStart: Mykonos, Greece
End: Lavrio, Greece
- Duration
- 8 days
- Group size
- 1 to 11
- Minimum age
- 15 years old
- Style
- Original
- Theme
Our themes categorise trips based on a common interest or activity, while showcasing the highlights of a destination.
- Sailing, Walking & trekking
- Physical rating
Indicates how physically exerting a trip is, and how fit you will need to be to enjoy it. More info on physical ratings
Where you’ll stay
The Ocean Star 56 is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, the Ocean Star 56 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins, 2 twin cabins and 1 triple cabin, the Ocean Star 56 is the perfect yacht for novices to learn the ‘ropes’.
The Ocean Star 56 is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, the Ocean Star 56 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins, 2 twin cabins and 1 triple cabin, the Ocean Star 56 is the perfect yacht for novices to learn the ‘ropes’.
Why you'll love this trip
- Experience life at sea with a local skipper and a crew of adventure-keen travellers aboard a private yacht. Wake up to ocean views, soak up the sun on deck and snorkel in peaceful bays far from the crowds.
- Join a local family for a home-cooked dinner at their home in Syros to get an authentic taste of Greek hospitality.
- Step back in time on Delos – one of Greece’s most significant archaeological sites. Wander the Avenue of Lions, visit the House of Cleopatra and imagine ancient crowds at a 5000-seat theatre.
- Hike trails that take you into the heart of the Cyclades. Walk past grazing goats and whitewashed chapels, say kalimera (hello) to farmers and climb to the medieval Castle of Oria for amazing Aegean views.
- Watch the Cyclades’ famous tangerine sunsets from the deck of your yacht, cold drink in hand, while the waves lap against the hull.
Itinerary
Kalimera! Welcome to Greece. Your adventure begins in cosmopolitan Mykonos – known for its beach bars, boutiques and nightlife. If you arrive early, maybe wander the laneways of Little Venice – a picturesque neighbourhood lined with old houses, shops and cafes. At 4 pm, you have a welcome meeting at a restaurant called De-Tox Café in Marina Tourlo, where you’ll meet your skipper and fellow travellers and find out what to expect over the next eight days on the water. Then, head to a supermarket to stock up on breakfast, lunch and snack supplies. Tonight, perhaps get to know everyone over dinner at a local taverna, then settle in for your first night aboard the yacht – your floating home for the week ahead!
- Overnight boat (1 night)
There are no meals included on this day.
It’s very important that you attend the welcome meeting as we’ll be collecting insurance details and next of kin information at this time. If you’re going to be late, please let us know.
As most meals are not included on this trip, you may want to opt into a group kitty to buy supplies and prepare meals as a group on the yacht. If you’re staying overnight in a port/marina, you can also eat at local tavernas at your own expense. Please make sure you notify us about any dietary requirements when booking so we can accommodate you.
Rise and shine for your first day on the water! First, stop at the uninhabited island of Rinia. There’s no noise here aside from a few grazing goats, so take the chance to relax on the crowd-free shores. Rinia was the necropolis during the Peloponnesian War in the fifth century BC, and you may stumble on remnants of temples and burial stones as you explore. Then, nip over to Delos – the legendary birthplace of Apollo (god of the sun) and Artemis (goddess of the moon). The entire island is a UNESCO World Heritage site with heaps of archaeological sites – including the Terrace of the Lions, Temple of Isis and Sanctuary of Apollo. Your final stop is Syros. Do a self-guided walk around the port town of Ermoupoli and the fortified village of Ano Syros – your skipper will suggest things to see and do. Then, regroup for a special dinner with a local family at their home in Finikas Bay.
- Overnight boat (1 night)
There are no meals included on this day.
- Delos - Archaeological Site
- Syros – Traditional Greek dinner in family home
Your sailing time today will be approximately 3 hours.
Set sail to Kythnos – a sleepy island dotted with bald hills, dry-stone walls and hundreds of white chapels. Dock in Loutra – a traditional fishing settlement named after the thermal springs (loutra means ‘bath’ in Greek) that flow into the bay – and enjoy a soak. These mineral-rich waters have been used for their healing properties since ancient times. This afternoon, get your blood pumping on a hike to the Castle of Oria – the former medieval capital of Kythnos. You'll wind past traditional stone farmhouses and rocky outcrops before arriving at the castle which sits on a 250 m-tall cliff. Soak in the views of the eastern Cyclades and learn about the castle’s history – it was part of a fortified town that housed hundreds of people, including the powerful Gozzadini family from the 14th to the 17th century. Return to Loutra, then perhaps refuel with some local specialities – like tangy kopanisti cheese or strapatsada (a local take on scrambled eggs).
- Overnight boat (1 night)
There are no meals included on this day.
- Kythnos – Castle of Oria guided walk
Your sailing time today will be approximately 3 hours.
Your hike today will be approximately 6.5 km or 3 hours. It’s a moderate hike, with many stairs during the first half. The terrain is rocky and uneven in parts, so a sturdy pair of walking shoes is essential.
Cruise to Serifos this morning, stopping off to swim or snorkel in the clear waters of Agios Stefanos Bay. In the afternoon, you’ll do a moderate hike from Livadi to the town of Chora which sits on a 230-m-tall hill. Follow a stony path past terraced fields, whitewashed houses and olive groves before arriving at Chora where you'll be rewarded with sweeping views across the Aegean Sea. Before returning to Livadi, take some time to wander the medieval alleyways – and maybe treat yourself to a local pastry. The rest of the evening is free to enjoy at your own pace. How about kicking back with a cocktail or feasting on meze along the seafront?
- Overnight boat (1 night)
There are no meals included on this day.
- Serifos – Chora Village hilltop guided walk
Your sailing time today will be approximately 3 hours.
Your hike today is moderate and will be approximately 6 km or 3 hours.
Cruise back to Kythnos this morning – but this time, drop anchor in Apokrousi Bay, a peaceful cove hugged by low hills. The water here is ideal for a refreshing dip, or you could simply take in the scenery from the deck with a good book or drink in hand. If you're feeling active in the afternoon, join an optional hike from Apokrousi Bay to Vryokastro – the ruins of the island’s ancient capital. Explore remnants of cisterns, homes and temples dedicated to Apollo, Artemis, Aphrodite and Demeter. Then, return to Apokrousi in time to eat dinner on deck while the sun dips below the horizon.
- Overnight boat (1 night)
There are no meals included on this day.
- Kythnos - Vryokastro self- guided walk - Free
Your sailing time today will be approximately 4 hours.
Your hike today will be approximately 6 km or 3 hours.
Next stop: Kea. This charming island is known for its vineyards, olive groves and laidback villages. On the way, make a stop at Karthaia Bay on the southeastern side of the island to swim or snorkel in the turquoise waters, then go ashore to discover the impressive ruins of the ancient city of Karthaia. Walk through weathered temple columns and the bones of a 6th-century BC theatre set against the sea. Eat lunch on deck, then dock in Kea village where you’ll spend the night. You could dig into local produce at a seaside taverna for dinner this evening.
- Overnight boat (1 night)
There are no meals included on this day.
Your sailing time today will be approximately 3 hours.
Take a private transfer to the village of Ioulida this morning for a scenic hike to Otzias Beach – a shaded downhill trail perfect for your final hike! Cool down with a dip at Otzias Bay, then refuel with an optional lunch at a nearby fishing village – it's a great chance to dig into some fresh seafood. Then, it’s time to jump back on the yacht to sail to Lavrio near Athens. As this is your last night as a group, you might like to go for a farewell dinner together and raise a toast to an unforgettable week in the Cyclades. Yiamas!
- Overnight boat (1 night)
There are no meals included on this day.
- Kea - Ioulida Village to Otzias Beach guided walk
Your sailing time today will be approximately 2 hours.
Your hike today will be approximately 6 km or 2.5 hours.
Your sailing adventure comes to an end this morning. If you’d like to spend more time in Athens, just speak to your booking agent ahead of time.
There are no meals included on this day.
Lavrio is 34 km (30 mins by taxi) from Athens airport and 60 km (1 hour by taxi) from downtown Athens. Public transport is also available – your skipper can provide more information on the ground.
Inclusions and activities
Included activities
- Delos - Archaeological Site
- Syros – Traditional Greek dinner in family home
- Kythnos – Castle of Oria guided walk
- Serifos – Chora Village hilltop guided walk
- Kea - Ioulida Village to Otzias Beach guided walk
Optional activities
- Kythnos - Vryokastro self- guided walk - Free
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Before you book you should know
- As the majority of this trip takes place on a sailing boat, you’ll need to feel comfortable with moving about the vessel, including the use of stairs. With that said, sea legs come naturally to some but not so much for others. Your friendly skipper will be able to help with the effects of sea sickness if needed.
- Our yachts have a small Zodiac on board, which is used to transport travellers to shore if we need to anchor in the bay. Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and a can-do attitude are all you need.
- This trip includes walks on most days between 2-3 hours duration. You need to be in good health to complete the walks. Please ensure you bring sturdy walking shoes and comfortable clothes. To make the most of the trip, it's best if you have at least a moderate level of fitness.
- This is an adventure on board a real yacht, which means living spaces, cabins, bathrooms and showers need to be shared with other passengers. Sleeping quarters can be quite compact, but you will be spending the majority of your time above board in the open air.
- On your trip, the skipper will move the boat using the sails and motor; occasionally, they will need to use the motor for the whole trip. This choice is weather-dependent, so is unpredictable, but our expert skippers will keep you updated on any necessary itinerary changes. They love to sail and will raise the sails at every opportunity.
This trip starts in Mykonos on day 1 at 4pm and finishes on day 8 in Lavrio port, Athens after breakfast.
ACCOMMODATION ON BOARD THE YACHT
This trip is accommodated entirely on board a yacht of between 54ft to 56ft. The yacht can accommodate up to 11 traveller’s in the following cabin types:
double bed cabins (x2)
twin bunk bed cabins (x2)
triple bunk bed cabin (x1)
There are 5 shared bathrooms. Our boats are real yachts, and this is a real sailing trip. Yachts are designed to keep sleeping areas to the absolute minimum of space, while maximising common areas as much as possible. Everyone including the skipper shares the bathrooms on board.
Solo customers can choose to book either a twin bunk bed cabin or a triple bunk bed cabin and will be matched up with other solo customers of the same gender. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge when booking either a twin or double cabin.
Rooms are allocated on arrival by our skipper according to group composition, which means it is not possible to reserve or guarantee any specific berth. If you are booking a bunk bed cabin you must be willing to sleep on the top bunk.
Double bed cabins can only be booked by 2 people travelling together or a solo customer who pays for a single supplement.
While not everyone may feel entirely comfortable living in such close quarters, those who are looking to revel in the adventure and exhilaration of an authentic sailing trip usually find any discomfort from cramped living conditions is more than made up for by the whole experience.
HOT WEATHER:
Summer temperatures can reach up to 40 degrees Celsius, which can be uncomfortable for those not used to the heat. Please consider the time of the year you wish to travel and your suitability to that season.
PASSPORT DETAILS:
Please provide full passport details at time of booking including exact name as per passport, date of birth, nationality, issue and expiry dates as these are essential for booking services on this trip.
ADDITIONAL ACCOMMODATION:
Please note that the majority of our sailing trips start and/or finish at a marina or port. If you have pre-booked any additional accommodation through us, you will need to make your own way to the joining point on day 1 and from the finish point on the final day. We do not provide transfers between hotels and the port/marina. Please check the Essential Trip Information for joining and finishing points.
TRIP KITTY:
This trip has a compulsory group kitty of EUR100 per person. The kitty is an on-ground payment put into a central fund managed by travellers. It helps fund for breakfast and lunch on the boat and other small items such as ice, water, snacks and drinks. Travellers are responsible for the preparation of these meals onboard and to shop at port where supermarkets are often very close to the mooring. Kitty amounts are subject to change to reflect local price increases. On day 1, the skipper will talk through the kitty and how it will be managed by the group. The kitty will be collected when you arrive at the welcome meeting or in stages throughout your trip. The kitty amount should be used as a guide. More than likely, you will not spend the full amount recommended however it's advisable to budget for this amount.
Visa information is provided by Sherpa, a third-party. The "Add connection" feature shows transit visa requirements only and does not include full entry visa needs. Please note, additional service fees apply if you choose to purchase a visa through Sherpa.
Travel and visa requirements
ACCOMMODATION ON BOARD THE YACHT
This trip is accommodated entirely on board a yacht of between 54ft to 56ft. The yacht can accommodate up to 11 traveller’s in the following cabin types:
double bed cabins (x2)
twin bunk bed cabins (x2)
triple bunk bed cabin (x1)
There are 5 shared bathrooms. Our boats are real yachts, and this is a real sailing trip. Yachts are designed to keep sleeping areas to the absolute minimum of space, while maximising common areas as much as possible. Everyone including the skipper shares the bathrooms on board.
Solo customers can choose to book either a twin bunk bed cabin or a triple bunk bed cabin and will be matched up with other solo customers of the same gender. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge when booking either a twin or double cabin.
Rooms are allocated on arrival by our skipper according to group composition, which means it is not possible to reserve or guarantee any specific berth. If you are booking a bunk bed cabin you must be willing to sleep on the top bunk.
Double bed cabins can only be booked by 2 people travelling together or a solo customer who pays for a single supplement.
While not everyone may feel entirely comfortable living in such close quarters, those who are looking to revel in the adventure and exhilaration of an authentic sailing trip usually find any discomfort from cramped living conditions is more than made up for by the whole experience.
ADDITIONAL ACCOMMODATION:
Please note that the majority of our sailing trips start and/or finish at a marina or port. For most of our destinations, we can provide transfers between the airport/hotel and the port/marina. Please check the joining and finish point information in the trip notes for details.
ELECTRICITY:
While there should be electricity on board throughout your trip the voltage is likely to vary widely, from 12V to 220V, and when in port or moored we are dependent on the supply available. Please be aware that the supply may not be sufficient to power some electronic devices all the time and that you may need a voltage adapter or similar (such as portable inverter used in cars). On some trips it may be possible to charge devices ashore at restaurants or resorts, however this is not guaranteed.
WI-FI:
Please note that our sailing boats do not have Wi-Fi. You will be getting off the boat and visiting towns regularly so you will be able to connect with the outside world then.
De-Tox Cafe
Marina Tourlos
Mykonos
846 00
GREECE
Phone: +30 2289028760
Description
Your adventure begins with a welcome meeting at a restaurant called De-Tox Cafe located at Marina Tourlos on Mykonos island. Please check day one of your itinerary for the exact meeting time.
De-Tox Cafe is located 550 meters from the main – new port of Mykonos , approximate 8 mins walk. If you arrive to the port of Mykonos by ferry, you can walk the short distance or you can take a Taxi from the port to the restaurant. In the same building there is a mini market called Flaskaki.
Kindly note that our meeting-point cafés and restaurants do not provide luggage storage facilities. Guests arriving early are welcome to enjoy a beverage or meal before the meeting time.
Instructions
If you have prebooked an airport arrival transfer from Mykonos Airport to Marina Tourlos with Intrepid your transfer driver will be waiting at the airport for you with your name on an Intrepid sign.
Alternatively, taxis are available from Mykonos Airport to the Marina Tourlos. (cost is appx 40 euro) or you can take the public bus from airport to new port and then you can walk 8 mins. Please check this website https://mykonosbus.com/bus-timetables/ for public bus timetable.
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July 2026
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