Sail Greece - Santorini to Mykonos Trip Notes

  • Trip code : IZSRR
  • Trip length : 8 Days
  • Trip starts in : Santorini, Greece
  • Trip ends in : Mykonos, Greece
  • Maximum group size : 9
  • Ages : Min 15
  • Meals : 4 breakfasts, 3 lunches
  • Accommodation : Overnight boat (7 nights)
  • Transport : Boat




Kalimera. Welcome to Santorini, Greece.

Your adventure begins with a welcome meeting at 1.30 pm. Meet your skipper at the self-service beachfront restaurant, which is right in front of Akrotiri Hotel that's located at Akrotiri Beach. Insurance details and next of kin information will be collected at this meeting, so ensure you bring these details to provide to your leader. The skipper will then give you a detailed trip briefing aboard the yacht. Get acquainted with your new shipmates, as you sail for four hours to the island of Ios. In the evening, enjoy your first dinner with the group and spend your first night on the boat, strengthening your sea legs for the week ahead.

It’s worth arriving into Santorini a few days before the trip begins to enjoy some time on the island. In 1,500 BC, a volcanic eruption changed the landscape of the Mediterranean and caused the island of Santorini to sink in the middle - creating the caldera. If you do arrive early, visit the volcanic red and black beaches, explore the cobbled alleys, restaurants and shops of exuberant Fira or walk along the island’s volcanic rim to Oia at sunset.

Notes: The marina in Santorini is currently closed for dredging. Until further notice you will be met at the existing meeting point and transferred to the yacht by vehicle or water taxi. If you can't arrange a flight that will arrive in time, you may wish to arrive a day early so you're able to attend. We'll be happy to book additional accommodation for you (subject to availability).

***The beauty of sailing is that each day is unique and, while we have a destination to reach, if the weather changes or something takes the group’s fancy, we are flexible on the day's itinerary***


Sailing the Greek Islands


Inhabited since early Cycladic times the Ionians settled Ios around 1050 BC, suffering similar periods of occupation and foreign rule as many of its neighbours. The isle of Ios is also thought to be the burial place of epic Greek poet, Homer. Wander the old town or relax on the popular beaches of Gialos and Mylopotas. These sands offer water sports during the day and a hub for nightlife in the evening. If you’re after something quieter, head to the beaches of Valmas, Kolitsani or Tsamaria. Enjoy sunset views from the hilltop Panagia Gremiotissa (Church of the Virgin). The distinctive single palm tree next to the church makes it an instantly recognisable icon throughout town.


Sailing for around four hours, reach the rugged, mountainous island of Amorgos - known as the stunning location of Luc Bresson's film, 'The Big Blue'. This island is packed with a history of colonisation, with influences of the Venetians, Byzantines and Ottomans. Katapola, the island's main port, boasts classic Cycladic architecture with windmills and an old Venetian castle. The waterfront is an excellent place to relax with its restaurants, cafes and bars. Perhaps drive up to the 11th-century monastery, Moni Hozoviotissis, where you can examine historical relics and indulge in breathtaking views of the Aegean Sea. You’ll also have the chance to visit the nearby Minoan settlement or visit the mountain village of Hora. The Amorgos Archaeological Collection is housed nearby in Gavros Tower, which is one of the few remaining towers on the island.

Small Cyclades

It's time to feel the wind in your hair once again, as you sail along for around three hours to the Small Cyclades. This group of islands feature great beaches and small fishing villages filled with friendly locals. While all of the islands harboured communities in ancient times, the middle ages saw this reduced to just pirates and goats. Today, only Koufonisia, Iraklia, Shinousa and Donousa have permanent residents with the largest population said to be somewhere around 300. Featuring clear waters, great beaches, friendly locals and sleepy tavernas that are all built around quaint fishing villages, the islands are an ideal overnight anchorage and exploration. Indulge in fresh seafood in a quiet taverna and sit back to enjoy a taste of traditional Mediterranean life.


Continue across the Aegean to Naxos where the boat will anchor for the next two nights. Possibly go on an optional day trip around the island or hike up to the Roman Catholic neighbourhood of Kastro, where winding laneways, mansions and churches retain a medieval feel. Stop by the cathedral in the square and visit the nearby Archaeological Museum. Soak up the sun and take part in optional water sports on the southern beaches of Naxos. Dependent on time, perhaps visit the unfinished temple of Portara and look out over the islands from its vantage point. Maybe even join an optional jaunt out into the countryside - glimpse local rural life, visit one of the oldest temples in Greece and then chill out up in the hills with lunch at a family tavern. Get a taste of the local brew with a shot of Kitron, which is best described as lemon liquor. There are plenty of things to see and do over the next couple of days, but your crew will steer you in the right direction if you need any recommendations.

Accommodation: Overnight boat (5 nts)



Lifting anchor, set off on a short three hour sail to Mykonos 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.

Check out the Church of Panagia Paraportiani - its unique array of lines and angles are simply fascinating. Soak in the atmosphere by joining fellow sun-seekers and party-goers on the beach or take a day trip to the sacred island of Delos, birthplace of Apollo and Artemis. Little Venice has colourful wooden balconies that hang precariously over the sea - the perfect spot to sit back with a cocktail and enjoy a magical Aegean sunset.

Depart the boat on the final day at 10 am, as there are no more activities planned. We recommend booking an extra night's accommodation after this trip, so you have plenty of time to explore Mykonos.

Notes: This itinerary is subject to change depending on weather and berth availability. Your skipper will make the final call to ensure your safety at all times.

Accommodation: Overnight boat (1 nt)

not-included1International flights, departure transfers, departure and airport taxes, visas, all other meals, all optional tours or activities during free time, transfers outside of the tour program, travel insurance, tips and items of a personal nature.




Our Basic tours offer superb value and are ideal for those who are happy to forgo some creature comforts in favour of an authentic and fun experience. Under the leadership of a fully trained tour leader, you will enjoy all the highlights and freedom of independent travel with the convenience, security and companionship of a small group.

Style Facts

  • Plenty of free time to explore independently
  • Optional activities to suit your budget
  • Freedom to choose your own meals
  • Simple family run hotels
  • Mostly public transportation
  • Fully trained and experienced leader


On our sailing adventures there is no need for any experience - learn the ropes from our qualified crew or simply sit back & relax. The skipper will take charge of the vessel - but it's more fun if you have a 'hands on deck' approach! Spend days cruising around impressive coastlines, exploring lush national parks, wandering through medieval towns or rolling off the boat into warm, turquoise waters to swim.

This tour is operated by our partners Intrepid.


visa1A necessary bugbear of adventure travel, visas can appear complicated, costly and confusing to apply for. Imaginative Traveller recommend applying for visas with a professional visa service who can guide you though the process and take care of lodging and collecting your passport with multiple embassies, so we have teamed up with The Visa Machine.The Visa Machine ‘live and breathe’ visas and have the expertise to provide current and accurate information and arrange the correct visas for your trip, quickly and at a good price.Please click here for more information.


medical-preparation1We strongly recommend you visit your doctor to discuss health requirements for your trip. They will advise you regarding the appropriate inoculations. In some places anti-malaria medication may also be required. Some vaccines need to be administered a few weeks before departure so allow yourself plenty of time. Obtain a certificate of vaccination and carry this with you on this trip. A dental check up is also highly recommended.


Money1Every traveller is different and therefore spending money requirements will vary. Some travellers may drink more than others while other travellers like to purchase more souvenirs than most. Please consider your own spending habits when it comes to allowing for drinks, shopping, participating in optional activities, and tipping. Please also remember the following specific recommendations when planning your trip.

You will need to take cash to cover all additional expenses not included in your tour cost. These include food, drinks, optional sightseeing, tips, laundry, souvenirs and possible delays. If in doubt, bring more than you think you will need. It is always useful to carry an additional amount for emergencies. If there is a medical emergency you are sometimes required to pay at the time; providing your claim falls within the scope of your policy, your insurance company will make reimbursement later


travel-insuranceYou must have extensive travel insurance as a condition of booking with us, and without evidence of a valid policy you won’t be allowed to start your trip. Please click here for more information.


responsible-travel1Responsible tourism is at the heart of Imaginative Traveller. For 20 years we have taken customers to places around the world in social and environmentally responsible manner, ensuring everyone involved respects and maintains the natural and often delicate balance of the destination.As travellers ourselves we are well aware of the impact that tourism can have and whilst economic gain from tourism is often fundamental to a country, it should never be at the expense of its culture or the environment. It is our aim to provide journeys that have minimal negative and maximum positive impact on the places we visit. We do not believe that, as visitors, we should impose our own cultures on others; rather that we should experience foreign cultures and appreciate them for what they are.We believe giving something back is essential. We therefore work with our customers and the people we visit to ensure the benefits go directly to contribute to local cultures and environmental conservation. This is not only good the communities we visit but it also gives our travellers more enriched adventures.For further information about responsible travel please click here.

At Imaginative Traveller we always aim to provide accurate information for our travellers. Unfortunately information such as the price of optional activities is occasionally subject to change, and this means that we are constantly revising our trip notes. In order to ensure that you have the most up to date information for your trip we suggest that you check the trip notes for your tour around one month before departure.


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