Ready, set, sail from Mykonos to Santorini on this Greek Island adventure

Embark on a true sailing adventure through the Greek Islands, a forever favourite with young travellers for various sun-drenched delights. On this 8-day journey you get the perfect mix of sleepy islands, secret spots and iconic nightlife. Knock back cold drinks while the sun sets over the volcanic cliffs of Ios and let the water of the Aegan Sea rock you to sleep each night. Sail between perfectly white towns built into awesome cliffs and anchor off deserted beaches for a secluded swim. Slurp oysters and sip ouzo, and hey, if you happen to over-indulge, there’s nothing like clearing your head with a dip in warm aquamarine waters the next morning.

This trip is for 18 to 29-year-olds

Some of our under-30 travellers prefer to get around with people their own age. If that’s you, you’re in the right place!

Over 29? We’ve got over 900 other great adventures to choose from for solo travellers, friends, families, food lovers, hiking enthusiasts, and more.

10% OFF 18-29s Early-bird

Book an 18-29s trip 12 months in advance or more and get 10% off. Learn more>

Terms & Conditions

Mykonos, Greece
Santorini, Greece
18 to 29s, Sailing
Physical rating
Min 18, Max 29
Group size
Min 1, Max 11

Travel solo, together

You're never alone when travelling solo with Intrepid

Why you'll love this trip

  • Sailing is THE way to see these stunning islands. Jump off the side of the boat into the glittering Aegean Sea and let the waves rock you to sleep each night.

  • Santorini has some of the most crazy beautiful landscapes in the world. Pass bleached-white villages that are stuck to plunging cliffs and along the rim of a volcano.

  • The remote Small Cyclades islands are chock-full of tavernas serving fresh seafood, far away from sweaty tourists and the rest of the world.

  • Take a swim off the coast of near-deserted (and allegedly haunted) Rhinia Island.

  • Grab a snorkel and explore the massive caves and coves of Koufonisis, keeping your eyes peeled for pirate treasure.

Is this trip right for you?

  • 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 crew will be able to help with the effects of sea sickness if needed.

  • A Zodiac is used to transport passengers from the boat to the mainland, with landings taking place at piers (dry landings) as well as on beaches (wet landings). Zodiacs can sometimes be awkward to climb in and out of, but a sense of humour and good attitude is all you need.

  • 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 (and sea).

  • Time on the water also means time in the sun. Remember to pack sun protection, such as sun screen and a hat, and drink plenty of water to keep hydrated. See ‘Essential Trip Information’ below for a full packing list.

  • Please note that smooth sailing is dependent on the weather, so itinerary changes may occur at the last minute if the weather becomes unfavourable. If any changes are made, you can trust in your knowledgeable skipper to choose an alternative route or activity.

  • Due to the size of the yachts, sound carries easily from one side to the other and can wake your fellow travellers. If you’re planning to have a late night, it’s a good idea to head into town and experience the local night life.


Welcome to paradise! Your sailing adventure kicks off with a welcome briefing at 4 pm. Meet the rest of your crew and group leader and make sure you’ve got insurance and next of kin info to pass on. You group leader will run you through the kitty process. It’s basically a group pool of money that can be used to buy food and give tips where needed. Most breakfasts, and some lunches and dinners, will be made by you and the rest of your group. It’s totally voluntary, but sometimes a lot easier than trying to figure it out on your own. If you’re part of the kitty you won’t be scrambling for your wallet every time you want to grab something to eat on shore, or having to go in search of a snack when your crew heads off to the beach with a picnic. For meals off the boat, our skippers will suggest locally-run restaurants that specialise in local produce and delicacies. For now, we’ll make a trip to the supermarket to buy some stuff – the produce, particularly fruit, is super fresh and colourful. Then, grab an early dinner and get to know your group over a couple of beers at a few local haunts. We recommend you keep it fairly contained however, as you’ll be setting sail early tomorrow morning. The only thing worse than a hangover is a hangover PLUS seasickness.
Meals Included
There are no meals included on this day.
Rise, shine and grab some breakfast on board before stopping for a dip at Rhinia, a small island with beautiful sandy beaches. Unoccupied and too small for a lot of tour boats, it’s likely you’ll be the only ones splashing around along the shore and the warm water is ideal for washing away any residual queasiness. It’s also allegedly haunted, but it’s hard to feel spooked in a place that is this pretty. Sail on to Paros and drop anchor near Naousa, a cute fishing village with whitewashed buildings, cobblestone streets and dynamite seafood. Go ashore and wave to the last of the smoking fishermen as they bring in their catch. Be friendly – you'll probably be eating on something they caught for dinner. Grab a seat at a local taverna and soon you’ll be slurping down oysters and munching mussels like a local.
Meals Included
There are no meals included on this day.
Catch the breeze to Iraklia, where you can jump right off the side of the boat into aquamarine water. Let the salt water dry on your skin as you cruise on to Koufonisis, three tiny islands where it’s all rocky cliffs and massive, hollow coves. They’re so cavernous that pirates used to be convinced the whole island was a big, empty shell. Unlike many of the islands nearby, Koufonisis is still relatively secluded. There’s nothing to do except munch on fresh seafood, swim, relax, sunbathe and snap envy-inducing pictures. Basically, the perfect holiday. There’s a couple of awesome local taverna’s, so maybe wander through the white, winding alleyways in search of a mediterranean feast. 
Meals Included
There are no meals included on this day.
Start the day by exploring the deserted caves around Koufonisi. Strap on a snorkel and search for hidden hollows and, perhaps, treasure. It was mainly pirates who docked here over the years, after all. Then, set off for Naxos, where crumbling ruins sit next to sand that’s as soft and white as powdered sugar. After the isolation of Koufonisis, Naxos will feel positively electric, full of bars to chill out in and a hillside olive groves and villages to explore if you’re feeling active. Get a taste of local life with a shot of Kitron (similar to lemon liquor) and a wander along the beach.
Meals Included
There are no meals included on this day.
Today is as clear as the water around you. Maybe start with a swim to get your head in the same state. You might want to get up close and personal with history at Portara, the doorway to a temple built over 2000 years ago and never finished. In a place where most of the hills are bare or covered with low shrubs and trees, this eight-metre-high marble door stands out. It's the perfect place to grab a few photos with the water glittering behind you. There are a few local snacks you should try while you’re here. As it's pretty much always picnic weather, it's a great idea to make a spread and take your pick of scenic locations. Maybe grab some arseniki (aged hard cheese), Zamboni (cured pork leg), bread, olive oil and wine and head for one of the many beaches. If you’d like a taste of village life, jump on a bus and head into the mountains, where tiny white houses with bright shutters and doorways sit perched in valleys filled with olive trees.
Meals Included
There are no meals included on this day.
Set sail for Ios, where the nightlife is almost as iconic as the cubed houses stacked on the shore. Crammed with dome-topped churches, sun-drenched beaches and heaving bars, this town wakes up when the sun goes down. If you feel like exploring the streets, the day is the time to do it. While everyone else is on the beach, you might want to walk the narrow streets of Chora – the main village – in search of a nice coffee. If the seclusion of the last few days has given you a slight case of Island Fever (Google it), the popular beaches of Gialos and Milopotas offer crowds and a range of water activities. Ios is overflowing with hole-in-the-wall bars to busy backpacker-packed clubs. Don't worry if throbbing beats and sweaty bodies aren't your thing, your leader can point you in the direction of rock bars and cave-formed cocktail haunts.  
Meals Included
There are no meals included on this day.
Sail in past the caldera, the rim of a former volcano that formed when the center collapsed into a magma chamber. That’s right, you’re literally sailing over a (mostly dormant) volcano. There’s evidence of the islands explosive history everywhere you look, even when you’re chilling on the beach – from the red shore and lava cliffs of Red Beach to the black sand of Perissa, Vlhada, Perivolos and Agios Georgios. Fira, the capital of Santorini, sits high on the edge of the caldera and is one of the best places to get views out over the islands. It’s also full of restaurants and bars built into the cliff, so get climbing and you’ll find plenty of places to sip and munch on tiny balconies. If you’re keen to learn more about the weird history of this beautiful place, the Museum of Prehistoric Thera and Archaeological Museum are the places to hit. In the evening, toast your travel buddies during one of the most beautiful sunsets ever, watching the buildings turn yellow before heading out for a final taste of island life. Have fun, but remember we have another VERY early start tomorrow. 
Meals Included
There are no meals included on this day.
Your Greek island adventure comes to an end today at 8 am. Dry your tears (and swimsuit) in the Santorini sun before heading home or continuing your adventure elsewhere.
Meals Included
There are no meals included on this day.


No meals are included on this tour




Overnight boat (7 nights)

Dates & availability

Trip search is unavailable.

There are currently no scheduled departures on our One Week Sailing Mykonos to Santorini trip. If you are interested in other trips in the region visit one of the links below.

Prices may change, so secure your trip today!
Jump to a departure month

Important notes

The trip commences on day 1 in Mykonos at 4 pm.

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.

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.

Dietary requirements are required at the time of booking so that any included meals can be properly catered for.

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 joining and finish point information in the trip notes for details.

Essential trip information

Want an in-depth insight into this trip? Essential Trip Information provides a detailed itinerary, visa info, how to get to your hotel, what's included - pretty much everything you need to know about this adventure and more.

View Essential Trip Information