Day 1 : Embarkation in Athens

Number of steps: 1,000
Hours sailing: 4

Our trip starts in Athens, the capital of Greece and the site of ancient ruins and the roots of the great Greek Empire.

We recommend you arrive a day early to explore Athen’s Acropolis on your own and get over the jetlag, we have a busy week ahead of us and you won’t want to be tired and miss the fabulous stops!

In the late morning, make your way to the meet up brunch spot to meet your fellow travelers and toast to the amazing trip that is about to begin.

Get into vacation mode as we walk you through an orientation of the week and you get to introduce yourself to the rest of the sailing crew.

After brunch, we will be picked up and taken to the marina where our sailing yacht awaits, ready to take us on this great island hopping adventure.

Upon embarkation, we will complete registration and unpack our luggage as we meet the rest of the crew. We will depart the marina at around 4pm and set sail towards Poros.

We will see the sun gown down and enjoy Happy Hour on deck.

Dress up for our Welcome Captain’s Dinner which will be served onboard as we sail through our first glimpses of the Cycladic islands before arriving in Poros.

Quaint Poros is a small fishing island that is practically attached to the mainland.

Unlike the other more famous islands we will visit on this trip, Poros has remained almost untouched by international tourism and is a quiet respite from the buzz of Athens and other more popular islands such as Santorini and Mykonos.

We will dock at port after dinner and have some free time to walk up to the lighthouse, enjoy an ice cream (which is a must!), have a drink by the sea or just take a stroll and stretch our sea legs on land.

We will all be back onboard by midnight, like Cinderella, so the Captain can set sail to our next stop.

Inclusions: Welcome brunch, happy hour welcome drinks and Captain’s dinner with wine. Overnight in your chosen cabin.

Day 2 : Polyegos & Folegandros

Number of steps: 3,000
Hours sailing: 11 (mostly during the night)

Today we will make our way to Folegandros, perhaps the Cyclades’ best kept secret and one which you are about to discover.

On the way, we will stop for your first swim of the trip at stunning Polyegos.

Polyegos is a large uninhabited island where only goats live, hence its name. But we didn’t come here for these four-legged animals but for the crystal clear waters around the island.

Jump off the side deck and into the warm and clear waters at this private stop only accessible by boat and enjoy all that you came here for: the beautiful Aegean Sea.

Tip: The beaches and bays we will stop at are remote and we will most likely have them all to ourselves.

Take a dip while our chefs cook a wonderful BBQ on deck with plenty of skewers, freshly cooked salads and wonderful Greek food. This is what all of Greek’s island hopping dreams are made of!

After lunch, we will depart towards Folegandros, another quiet and yet to be discovered island in Greece that is starting to make waves with the locals. You heard it here first!

We will take a shower and freshen up to venture into this peaceful slice of paradise for a walking tour and winery dinner.

Don’t expect Gucci shops or flashy bars here, Folegandros doesn’t even have public transportation or taxis, this is where slow travel takes a whole new meaning.

Our wonderful host Stella, will give us a quick introduction into the island as we walk the small and cozy streets of one of the main villages. We will then have some free time to do some shopping, or enjoy the beautiful simple life of the small islands.

For dinner, we will share a casual set-up at a local winery where we will taste seasonal dishes with great local wines grown right on the island in a stone patio surrounded by olive trees.

We will share lively conversation under the starry skies and then have some free time to wander the little village streets some more.

We will return to the yacht after dinner and perhaps enjoy another drink at the bar.

Inclusions: Breakfast onboard, BBQ lunch at Polyegos, dinner and wine, family style, transfers from the yacht to the village and back, overnight in your chosen cabin.

Day 3 : Santorini

Number of steps: 10,000-15,000, depending on what you choose to do during your free time
Hours sailing: 3

Santorini is perhaps the most famous of the Greek Islands and can be credited with practically putting the Cyclades on the map. Today is the day when you will find out why.

We will set sail early in the morning to arrive in Santorini before the large cruise ships disembark to make sure we are not caught in the snaking queues up the cable car that take hours to clear.

We will ride the cable car to the top of Santorini’s famous volcanic cliff and head over to Oia, probably the most picturesque and photographed village in the entire country.

Oia is a small blue-domed, white washed village now populated by restaurants, luxury hotels and shopping.

Its narrow pedestrian streets are packed to the brim in the summer and at sunset and afford beautiful views of the caldera below.

We will have free time in the morning to take photographs, do some shopping for classy and elegant clothing, enjoy a drink or a coffee at one of the many cliffside bars or simply wander this postcard-perfect village.

OPTIONAL: For those who want to immortalise the trip and the experience with professional photography and a dress to die for, there is the option to book a Flying dress photoshoot. Spots will be limited and booked on a first come first serve basis.

Lunch will be free at Oia where you can pick any of the restaurants and enjoy beautiful views.

After lunch, we will meet again to go to Argyros Wines, one of the oldest and most interesting wineries in Santorini, for a brief walking tour of the vineyards and a wine tasting of the famous Assyrtiko wines and the locally made sweet Vinsanto dessert wine.

Vineyards in Santorini have to struggle through more than 320 days with no rain, arid volcanic soils and continuous sun and wind.

Vines produce very few kilos of grapes and the locals have learned to grow them in a basket shape that is unique of the island.

We will taste 4 local wines along with local cheeses and breads at Argyros bright wine tasting room.

After the winery visit, you can take your pick at what to do next depending on your preference and we will provide transportation to each.

You can either return to Oia for more independent exploration or for another Flying dress photoshoot, visit the nearby local village of Pyrgos or go back to the boat to rest and freshen up before dinner.

You can of course also take a taxi and go anywhere else on the island on your own for example to visit the prehistoric city of Akrotiri, go down to Fira, to the beach, etc.

Dinner will be free for you to choose where to enjoy it and we suggest you pick an amazing spot to see the sunset.

Make sure to return to the boat before we set sail!

Inclusions: Breakfast onboard, cable car return tickets, transfers in Santorini from port to Oia, to the winery, back to Oia/Pyrgos, overnight in your chosen cabin. Dinner on your own.

Day 4 : Paros

Number of steps: 10,000-15,000
Hours sailing: 6 (during the early morning)

After popular and no doubt busy Santorini, Paros will feel like a breath of fresh air and a return to the quiet life of the Greek Islands.

We will start the day with a visit to Paros highest and oldest village of Lefkes with its labyrinthine streets, quaint white-washed houses and many chapels and churches where we will meet the team behind Paros Olive Oil Tasting for a delicious back to nature morning.

We will start our leisurely 5km circular hike in Lefkes which will follow The “Lefkes Village-Byzantine Way”.

This trail covers half of the Byzantine Way, a 1000-year-old, stone-paved footpath that used to be part of the island’s main throughway in medieval times.

Some parts are covered in marble, some are dirt tracks and some are centuries-old hillside footpaths among the terraced olive groves, vineyards and cereal fields in the valley below Lefkes village.

En route, we will enjoy the view to the countryside and the sea, as well as the smell and sight of wild aromatic herbs and flowers which our guide will point out.

This is a walking tour with a female touch that will introduce you to the history and culture of the island while emphasizing on the importance of olive oil on the environment and the Mediterranean diet of the islanders throughout the centuries.

After our walk, we will round off the morning with an olive oil food pairing and a gastronomic tasting of vegetarian dishes made with local extra virgin olive oil in a beautiful, traditional village tavern owned and managed by two generations of Lefkes women.

After a gastronomic presentation of the select local dishes & products in the menu, you will also be introduced to the transformative powers of Extra Virgin Olive Oil (EVOO), particularly in the context of Cycladic cuisine, through the process of ‘food pairing’.

We will indulge in freshly prepared Greek & Parian dishes such as Lefkes artisan bread served with oregano and local fleur de sel, Greek salad with xinomitzithra (local soft goat-milk cheese), Taramosalata (fish roe salad), fried wild fennel balls and so much more, this is your chance to enjoy fully seasonal and local dishes made with love.

After lunch, we will return to the yacht for a shower, rest and maybe a siesta before we set back out to explore the picture-perfect fishing village of Naoussa with its white cobblestoned alleyways and its seaside bars.

Naoussa is a laid-back version of Mykonos and has pretty squares with lapping fishing boats, narrow shopping streets with unique finds and bright bougainvillaea.

To some, this is the preferred island to Mykonos.

You will have free time to wander and look for hidden finds, enjoy a traditional Mediterranean dinner at one of the town squares, or see the sunset.

After dinner, enjoy a drink or a dose of nightlife in town. Make your way back to the boat before we set sail.

Inclusions: Breakfast onboard, guided hiking tour, olive oil pairing lunch, transfers to hiking, back to the yacht, and to Naoussa, overnight in your chosen cabin.

Days 5 : Mykonos 

Number of steps: 5,000-10,000 (depending on what you do in your free time)
Hours sailing: 4 (during the early morning)

Mykonos is Santorini’s grown up, fun sister and the premier beach and party destination in the Cyclades Islands.

The rich and famous fight for front row sun loungers at the most famous beach clubs while the fashionable shop in the luxury branded stores in town.

There isn’t a more chic and high-end address in the whole country.

Today, we will do like the celebrities that we are and lounge the morning away at a quiet lagoon on Super Paradise Beach, the famous and exclusively posh JackieO’ Mykonos Beach Club where we have reserved sun loungers with umbrellas, food, and drinks.

Sunbathe, dance to the sound of the DJs, get entertained by Priscilla, people watch and generally mingle with the beautiful people that frequent the club as we make the most of our time in this precious bit of paradise.

JackieO’ has a jacuzzi, pool, raised terrace, a boutique and even a hotel and is fabulously sculpted to look like a wedding cake.

If you ever wondered where the celebrities who flock to Mykonos spend their days (besides on the decks of their luxury yachts) this is it.

With a new glow, we will return to the yacht for a shower and change of clothes.

Later on, all glammed up, we will take the sea bus back to Mykonos town for a brief guided tour with Stella before enjoying free time for shopping, taking photos and exploring the main white and blue village of Chora on the island.

Tip: As you are walking the streets of Mykonos, look our for the famous pelican who casually wanders the alleys.

Find a spot for a sunset drink in Little Venice, walk up to the iconic windmills or sit by the port to watch the boats come and go until its time for dinner.

Dinner will be free for you to enjoy. Book a sot at the island’s most exclusive restaurants, white washed Koursaros, for a premium seafood dinner and wine under the stars, or pick one of the more laid-back casual eateries along the coast.

Stay out for as long as you like, Mykonos is an island where parties run the night away, sea buses run until 1am and you can always take a quick taxi ride back to the yacht, the night is always young in Mykonos!

Tip: Tonight we will sleep at port in Mykonos so you can stay up as late as you like.

Inclusions: Breakfast onboard, return transfers to Jackie O, sun lounger, towel and 100 EUR credit for food and drinks at Jackie O, walking tour of Chora, sea bus transfer back to the island, overnight in your chosen cabin.

Day 6 : Delos and Tinos

Number of steps: 10,000-15,000
Hours sailing: 2

After breakfast we will leave Galileo behind, take the sea bus followed by a boat and arrive at the UNESCO-listed site of Delos, Antiquity’s holiest place and one of the most important mythological and archeological sites in Ancient Greece.

Delos is uninhabited today but was once a major cult centre for Dionysus and Titaness Leto, mother of Apollo and Artemis.

Through purifications of the island to make it fit for the revering of Gods, Delos ended up being uninhabited as nobody was allowed to be born or die on the island.

We will take a 2-hour guided tour of Delos with an extremely knowledgeable and expert local storyteller, who will talk of myths and muses and tell us all about this fascinating mythological island.

There will be free time for photos before we take the boat and sea bus back to the yacht and depart Mykonos on our way to Tinos, Greece’s most recent island discovery.

We will enjoy lunch onboard as we sail the waters of the Cyclades and take in the views, perhaps sun bathing on deck or enjoying a drink at the bar.

Tinos has recently been awarded best island in Europe and is a rough diamond waiting to be polished.

The island boasts over 80 windmills, about 1,000 artistic dovecotes, a few dozen active villages and several Venetian fortifications.

Upon arrival, we will take a scenic ride to the main village of Pyrgos where we will have some free time to wander the streets.

We will then continue to dinner which will be enjoyed at a farm house where our local female host lives.

Our host is a prolific and widely recognised cooking book writer and will open her house and garden to us for a home made dinner prepared with seasonal ingredients that showcase the local cuisine.

As we enjoy our casual meal, she will demonstrate some of the dishes and tell us more about the local foods of Tinos.

Dinner will consist of a series of sharing platters enjoyed around a table as we mingle and exchange our favorite parts of the trip so far.

This will be a casual affair that best showcases Greece’s way of life: a meal shared among friends around a table filled with food to the brim.

Inclusions: Breakfast onboard, guided tour of Delos including return transportation by boat and entrance tickets, lunch onboard, return transfers to dinner, home made dinner with wine, overnight in your chosen cabin.

Days 7 and 8 : Kythnos

Number of steps: 1,000-5,000
Hours sailing: 11

Our last day on the islands will start with a leisurely breakfast as we sail back from Tinos towards Athens.

We will be saying goodbye to the Cyclades with a swimming spot at the isthmus of Kythnos with its clear blue waters and its double crescent beaches.

Lunch will consist of a BBQ on deck as you take dips in the sea and enjoy the last few rays of sunshine before we return to port.

Sunbathe on the sun deck, chat with your new found friends, enjoy a cocktail, read a book and make the most of the last few hours of our vacation time.

After a shower and change of clothes for our farewell dinner, we will get back on deck for a final Happy Hour as we stop in front of the mythical Temple of Poseidon where we will see the sun set one last time in the horizon.

Our farewell Captain’s dinner will be your chance to say goodbye to the crew and indulge in one last seasonal Greek dinner in the best company.

We will arrive in Athens just after dinner and dock at the marina. Our last night will be spent onboard before checking out and departing the next day.

On day 8, make your own arrangements to the airport on to your onward travels in Greece and beyond.

Inclusions: Breakfast onboard on day 7 and 8, BBQ lunch on deck, Captain’s dinner with wine on day 7, overnight in your chosen cabin.