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Sailing Greece with Luke Berg

Jul 13, 2024 - Jul 20, 2024

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Sailing Greece with Luke Berg

Jul 13, 2024 - Jul 20, 2024


Make an Enquiry


Envisioning pristine sapphire waters, whitewashed villages, historical ruins, vibrant Greek culture, and exquisite cuisine sourced from both land and sea? Embarking on a sailing journey from Santorini to Mykonos in Greece might be the perfect prescription. Immerse yourself in eight days of tranquility under sun-soaked skies, reveling in the finest experiences that the Greek Islands of Santorini, Ios, Amorgos, Small Cyclades, Naxos, and Mykonos have to offer.

8 days, 7 nights

11 people

July 13th, 2024

July 20th, 2024



Yacht skipper


Ios island

Small Cyclades







Travel insurance (required)


Group kitty €100 per person

Your host

Luke Berg

I’m a professional videographer and photographer with a great passion for capturing breathtaking moments around the globe. Armed with top-notch equipment and an artistic eye, crafting visually stunning content that leaves my followers in awe. Dedicated to delivering high-quality productions, I aspire to inspire others through captivating storytelling and bringing the world’s beauty to screens across the globe.


Day 1. Santorini to Ios

Welcome to Greece! Your rendezvous with the skipper and fellow shipmates is scheduled for 1 pm at Café Spartakos in Athinios Port. From there, a private boat transfer will whisk you away to the enchanting island of Thirasia, where you will board the yacht that shall be your haven for the next 7 nights. During this meeting, the skipper will gather the trip kitty and discuss group shopping to procure supplies for the journey. If you have any specific dietary requirements, kindly inform us at the time of booking to ensure we can accommodate your needs.

Consider arriving a couple of days early to relish the charms of Santorini and its breathtaking caldera. Explore the variety of restaurants, shops, and bars in Fira, the island’s capital. A definite highlight is strolling along the caldera’s rim to Firostefani, Imerovigli, and Oia. This experience is particularly memorable at sunset, but plan accordingly to avoid walking in darkness. Don’t miss Santorini’s volcanic beaches, including Red Beach or the black beaches of Perissa, Vlhada, Perivolos, and Agios Georgios. The Orthodox Metropolitan Cathedral, Catholic Cathedral, and Dominican Convent are worth a visit, as is the Megaron Gyzi Museum.

Following the welcome meeting, you’ll embark on a captivating sail, approximately 4 hours, across the Aegean Sea to reach the island of Ios (with a stop at Manganari Beach en route). Explore Hora’s vibrant shops, restaurants, and bars, conveniently located a short walk from the harbor. Panagia Gremiotissa (Church of the Virgin) promises stunning sunset views from its hilltop perch.

Key Information:
– Your skipper will collect the trip kitty of EUR 100 during today’s pre-departure meeting.
– If you are arriving today, allocate at least 1 hour for travel from Santorini Airport to Athinios Port.

Sailing offers the beauty of unique, flexible daily experiences. While we have a destination in mind, we remain adaptable to weather changes or group preferences. The itinerary is subject to weather conditions, and your skipper will make the final call to prioritize your safety. Depending on weather and yacht berthing availability, we may cross from Santorini to Ios by ferry, allowing you to board the yacht in Ios, affording you more free time to explore this captivating island in the afternoon.

Day 2-6 Saling the Greek Islands

**Small Cyclades**

Embark on a brief journey (approximately 3 hours) to the Small Cyclades. Although these islands once hosted thriving communities in ancient times, the Middle Ages witnessed a reduction to mere inhabitants of pirates and goats. Presently, only Koufonisia, Iraklia, Schinousa, and Donousa boast permanent residents, with the most populous being around 300. Immerse yourself in the charm of clear waters, pristine beaches, warm locals, and quaint fishing villages enveloped by serene tavernas. Explore the town, savoring fresh seafood at a waterfront taverna – a delightful way to embrace the enchantment of the Mediterranean.


Proceed to the rugged, mountainous terrain of Amorgos, renowned as the captivating backdrop for Luc Bresson’s film, ‘The Big Blue.’ Amorgos boasts a history dating back to 4,000 BC, marked by colonization and occupation. Katapola, the island’s primary port, showcases classic Cycladic architecture with windmills and an ancient Venetian castle. Wander along the waterfront and consider delving into the nearby ancient Minoan Settlement. The village of Hora (Amorgos town), perched on the rocky mountainside, beckons exploration through narrow stone laneways and Byzantine churches. Discover the Amorgos Archaeological Collection in Gavros Tower, one of the island’s remaining towers. Optionally, venture to the 11th-century Moni Hozoviotissis, clinging to the cliff-face, for breathtaking panoramic views. As we journey north to Naxos, we will revisit the Small Cyclades, dedicating another night to these captivating islands.


Continue the voyage to Naxos, unveiling its beautiful beaches, charming villages, and fragrant olive groves in Hora, the island’s capital. This locale boasts a rich mythological history, and the old town areas of Hora invite leisurely strolls amid vibrant nightlife. Optimal beach choices lie to the south, offering water sports enthusiasts an array of activities. Ascend to the impressive Venetian Kastro, where medieval spirits linger in a maze of winding laneways adorned with mansions, monuments, and churches. Explore the old Roman Catholic Cathedral and the nearby Archaeological Museum housed in the former Jesuit School of Commerce. The colossal Portara marks the entrance to the unfinished Temple of Apollo on the islet of Palatia, just north of the marina. Additionally, an optional excursion into the countryside offers glimpses of rural life, a visit to one of Greece’s oldest temples, and a serene lunch at a family tavern. Sample the local Kitron, akin to lemon liquor, and conclude with a seaside stroll.


Sail approximately 4 hours to Syros, making a stop at the Bay of Gaidharos for a refreshing swim. Recognized for its relaxed ambiance and neo-classical architecture, Syros played a neutral role during the Greek revolution, becoming a sanctuary for the persecuted. Consider taking a bus to the fortress-like village of Ano Syros, exploring stone archways and narrow alleyways with stunning Aegean views. Immerse yourself in authentic Greek cuisine and culture in Ermoupoli, the capital of Syros and the Cyclades, and admire the magnificent town hall in the main square.

Day 7-8 Mykonos

Weighing anchor, embark on a brief sail to Mykonos (approximately 3 hours), reaching the destination in the late afternoon for your final evening. This quintessential Mediterranean island radiates excitement, beauty, and glamour. The old town area is adorned with white-washed architecture clinging to a labyrinth of narrow streets and laneways. The vibrant nightlife, chic cafes, restaurants, galleries, and boutiques seamlessly transition to the island’s picturesque sandy beaches.

Immerse yourself in the atmosphere by joining fellow sun-seekers and revelers on the beach, or opt for a day trip to the sacred island of Delos, the birthplace of Apollo and Artemis. Little Venice, characterized by colorful wooden balconies hanging over the sea, provides the ideal setting to unwind with a cocktail and witness a magical Aegean sunset. The Church of Panagia Paraportiani, with its unique arrangement of lines and angles, is a captivating visit.

On the final day, disembark from the boat at 10 am, with no planned activities for the day. It is advisable to secure an additional night’s accommodation post-trip, allowing ample time to explore the charms of Mykonos at your leisure.

Trip Photos

Important Notes

If you cancel a Pending trip, your deposit will be fully refundable.

If you cancel your booking for a confirmed trip, some fees may apply.

Cancellation of a confirmed trip 61+ days before the commencement of your trip, your deposit will be transferrable to another trip. If you cancel a confirmed trip 60 days or less before its commencement then payments will not be refundable.

View our Terms & Conditions for more about our Cancellation policy.


This trip starts on Day 1 in Santorini at 1pm.

This trip is accommodated entirely on board a yacht of between 54ft to 56ft. A typical yacht for 11 travellers is equipped with a mixture of 2 x double cabins, 2 x twin cabins and 1 x triple cabin. 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.

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 or cabin. Single passengers will be paired up with another passenger of the same gender, this may mean sharing a double cabin with a double mattress. If you’d prefer not to share a cabin, a single cabin supplement is available at an additional charge. Everyone including the skipper shares the bathrooms on board.

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.

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.

The minimum age on this trip is 18.

There are many opportunities for snorkelling during this trip. Diving masks, snorkels and fins are provided onboard the yacht and are for use by all passengers. They are disinfected prior to use. Some customers may prefer to bring their own diving mask and snorkel from home and just use the fins available on board.

On this trip we highly recommend that you contribute to a 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 yourself or fellow travellers) The kitty will be collected when you arrive at the welcome meeting or in stages throughout your trip.

** Please note, 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 **

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