Santorini to Mykonos Sailing Dream - cover photo

Santorini to Mykonos Sailing Dream

23 August 2025 - 30 August 2025

  • Santorini, GR
  • 7 days trip
  • 11 places avaliable
  • Sailboat
  • Shared cruises may require a minimum number of guests.
  • Price may vary depending on the cabin type, occupancy and cruise date.
  • Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
 Price per Person
€ 1650
Gallery
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
From
€ 1650 per Person

Your sailing trip

One-Way Itinerary from Santorini to Mykonos – Discover the Magic of Greece’s Aegean Gems

Spending your days island-hopping in the Cyclades offers an idyllic escape into the heart of the Aegean Sea. Imagine swimming in its crystal-clear waters and sleeping aboard a yacht, rocked gently by the waves. The blue and white villages of Santorini, perched on the rim of an ancient volcano, provide a picturesque backdrop. Here, the only fire you'll witness is the breathtaking sunset, painting the sky in vibrant hues.

In the sleepy fishing villages of the Small Cyclades, the charm lies in their simplicity and authenticity. It’s a place where you're more likely to share a meal with a local than encounter another tourist, offering a genuine taste of Greek island life.

For a blend of rural tranquility and historic charm, the large island of Naxos beckons. Strolling through its historic neighborhoods while sipping Kitron liqueur provides a perfect mix of culture and relaxation.

Meanwhile, stylish Mykonos stands out as a playground for Europe's chic and beautiful. Its exclusive, boutique feel attracts those seeking a glamorous escape, where luxury and sophistication abound.

The beauty of sailing lies in its spontaneity. While we have a set destination each day, the itinerary is flexible, allowing us to adapt to changes in weather or the group's interests. The skipper will make the final decisions to ensure everyone's safety at all times.

Please be aware that, depending on weather conditions and the availability of berths for our yachts, we might take a ferry from Santorini to Ios and board the yacht there. This means you'll arrive in Ios in the afternoon, giving you extra time to explore this beautiful island.

The skipper will collect the cash box and discuss plans for purchasing supplies for the trip. If you have any specific dietary needs, please let us know when you book so we can accommodate you.

Itinerary

Day 1
Santorini
Meet your skipper and fellow travelers at 1pm in Athinios Port. From there, enjoy a private boat transfer to the island of Thirasia, where you'll board the yacht that will be your home for the next seven nights. Consider arriving a couple of days early to fully enjoy the beauty of Santorini and its stunning caldera. Explore the variety of restaurants, shops, and bars in Fira, the island's capital. Don't miss a walk along the caldera’s rim to Firostefani, Imerovigli, and Oia—especially breathtaking at sunset. Make sure to allow enough time to complete the walk before dark. Santorini’s volcanic beaches are also a must-see, including Red Beach and the black sand beaches of Perissa, Vlychada, Perivolos, and Agios Georgios. Be sure to visit the Orthodox Metropolitan Cathedral, the Catholic Cathedral, the Dominican Convent, and the Megaron Gyzi Museum. After the welcome meeting, you’ll set sail on a four-hour journey across the Aegean Sea, anchoring at the island of Ios with a stop at Manganari Beach along the way. In Ios, explore Hora's shops, restaurants, and bars, which come alive in the evenings. A visit to Panagia Gremiotissa (Church of the Virgin) provides stunning sunset views from its hilltop location.
Day 2
Small Cyclades
Today, we set sail for a short journey of about three hours to the Small Cyclades. In ancient times, all these islands had communities, but by the Middle Ages, they were home only to pirates and goats. Nowadays, only Koufonisia, Iraklia, Schinousa, and Donousa have permanent residents, with the largest population around 300. Here, you'll find clear waters, beautiful beaches, friendly locals, and charming fishing villages with sleepy tavernas. Explore the town and perhaps enjoy some fresh seafood at a waterfront taverna—a perfect way to soak in the magic of the Cyclades.
Day 3
Amorgos
Next, we journey to the rugged, mountainous island of Amorgos. In Katapola, the island’s main port, you'll encounter classic Cycladic architecture, complete with windmills and an old Venetian castle. Take a leisurely stroll along the waterfront and consider exploring the nearby ancient Minoan Settlement. The village of Hora (Amorgos town) is another must-see, perched high on the rocky mountainside. Wander through the labyrinth of narrow stone lanes and Byzantine churches that surround the town square. Nearby, the Amorgos Archaeological Collection is housed in Gavros Tower, one of the island's few remaining towers. You might also opt for a drive to the spectacular 11th-century monastery, Moni Hozoviotissis, either in the late morning or early evening. Built into the cliff face, the monastery offers breathtaking panoramic views of the Aegean Sea.
Day 4
Small Cyclades
As we head north to Naxos, we'll once again cross the Small Cyclades. These enchanting little islands deserve more of our time, so we'll spend another night here. Here, you'll find clear waters, beautiful beaches, friendly locals, and charming fishing villages with sleepy tavernas. We will spend time in bay and coves different from the previous visit.
Day 5
Naxos
We head to Naxos to explore its stunning beaches, charming villages, and fragrant olive groves. The capital, boasts a rich mythological history. The old town areas are ideal for a leisurely stroll, and the nightlife is lively. The best beaches are located to the south, where you can also enjoy various water sports. Take a pathway up to the impressive Venetian Kastro, where mansions, monuments, and churches preserve their medieval charm amid winding laneways. Be sure to visit the old Roman Catholic Cathedral in the square and the nearby Archaeological Museum, housed in the former Jesuit School of Commerce. The massive Portara, a gateway to the unfinished Temple of Apollo, stands on the islet of Palatia, just north of the marina. Consider an optional trip into the countryside to experience local rural life, visit one of Greece's oldest temples, and relax in the hills with lunch at a family tavern. Don’t miss tasting Kitron, a local lemon liqueur, and finish your visit with a walk along the beach.
Day 6
Syros
We set sail for the island of Syros, a journey of approximately four hours, with a swim stop at the Bay of Gaidharos along the way. Renowned for its relaxed atmosphere and neo-classical architecture, Syros became a safe haven during the Greek revolution due to its neutral stance. Consider taking a bus up the hill to the fortress-like village of Ano Syros, where you can explore the town’s stone archways and narrow alleyways, offering stunning views of the Aegean. In Ermoupoli, the capital of Syros and the Cyclades, immerse yourself in authentic Greek food and culture, and don't miss the magnificent town hall in the main square.
Day 7
Mykonos
Set sail for Mykonos with a short three-hour journey, arriving in the late afternoon to spend your final evening on this classic Mediterranean island. Mykonos is brimming with excitement, beauty, and glamour. Its white-washed architecture winds through the labyrinth of narrow streets and laneways in the old town. The vibrant nightlife, chic cafes, restaurants, galleries, and boutiques lead to the island's beautiful sandy beaches. Enjoy the lively atmosphere by joining fellow sun-seekers and party-goers on the beach, or take a day trip to the sacred island of Delos, the birthplace of Apollo and Artemis. In Little Venice, colorful wooden balconies hang over the sea, creating the perfect spot to relax with a cocktail and enjoy a magical Aegean sunset. The Church of Panagia Paraportiani is also worth visiting for its unique and fascinating architecture. We will disembark the boat on the final day at 10 am, with no activities planned for that day.

Cruise price details

Price per person

€ 1650

Accomodation on selected shared cabin, check out single use and details

Minimum guests for departure

1 person

Departure is guaranteed.

Yacht - Ocean Star 56

Explore the Ocean Star 56.

The Ocean Star 56 is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, it has an impressive saloon and offers spacious cabins and deck space for sun bathing! 

Yacht
Model
2016 Ocean Star 56
Length
16 m
Yacht services
Snorkeling equipment
Yes
Accommodations
Max guests
11
Double cabins
4
Triple cabin
1
Bathrooms
6
Private Bathrooms
Yes
Crew
1
Chef on board
No
2016 Ocean Star 56
Cabins
Stern Cabin
  • cabin capacity
  • double bed
  • private bathroom
Bunk Bed Cabin
  • cabin capacity
  • bunk bed
  • private bathroom
Triple Cabin
  • cabin capacity
  • private bathroom

Whos’ on board

Crew

Travelers

+ 11 FREE Places
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Cruise activities and tips

Travel activities

Cruise activity SNORKELLING

SNORKELLING

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.

Travel organizer tips

Stay Longer!
It is recommended to arrive a day before and depart at least a day after the sailing trip to give yourself ample time to explore and enjoy Mykonos and Santorini.
Return
On arrival at the port, your skipper can assist with taxis to a hotel, or to the airport for your onward flight. Please remember our trips are very dependent on the weather so please allow plenty of time to travel to the airport and allow enough time for any delays.
Trip Cash Box
On this trip we highly recommend that you contribute to a cash box of EUR100 per person. It 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. The 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) it 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 **
Passport
For international travel, a valid passport is essential. Many countries stipulate a minimum validity of six months, so be sure to verify your passport's expiration date.

To ensure smooth preparations for your trip, we require your passport information. It's crucial that the details on your booking match those on your passport precisely. Please take care to provide accurate information.

While traveling, we recommend carrying a copy of your passport's photo page and leaving another copy with family or friends at home. This precaution can be invaluable in case of loss or emergency.
Food and Dietary Preferences
The delectable cuisine available is undoubtedly one of the highlights of any European journey. To fully savor this experience, we've organized our meal arrangements to offer both flexibility and diversity.

For most dinners and some lunches, we'll be moored near a port or marina, providing the group with a variety of onshore dining options. While it's common for our group to dine together, you're free to explore other dining choices independently. Our skippers are happy to suggest restaurant options and often join the group for meals.

While your skipper oversees the shopping and meal preparation, we've found that the most enjoyable trips are those where everyone contributes to the cooking process. Your participation in meal preparation enhances the sense of camaraderie and adventure during the journey.
Travel insurance
Travel insurance is compulsory on all our trips for those travelling internationally. We require that at a minimum you are covered for medical expenses including emergency repatriation. If you are travelling within your home country or region please confirm before travel that you are entitled to access the public medical system easily should an accident occur. We strongly recommend all travellers have a policy that also covers personal liability, cancellation, curtailment and loss of luggage or personal effects.

MINIMUM AGE:
The minimum age on this trip is 15.
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Santorini to Mykonos Sailing Dream
Featured cruises
€ 1650
  • Shared cruises may require a minimum number of guests.
  • Price may vary depending on the cabin type, occupancy and cruise date.
  • Reservations are subjected to acceptance after availability checks. In case, the selected cruise is not available we will contact you with similar offers.
 per Person