Personality Journeys Blog

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Our Best of Greece 10-Day Tour takes you on a fabulous adventure around the highlights of Greece with handpicked local guides at each major site of interest. From ancient Athens to breathtaking Santorini, our itinerary is packed with unforgettable ancient Greek sites to visit along with world-class museums, vineyards, whitewashed villages and local cuisine. Look forward to absorbing the unique history, culture and heritage of this unique multi-destination sailing holiday which is ideal for private groups, families and corporate getaways. It’s one of the best luxury Greece tours available.


  • Visit the Acropolis with an informative local guide
  • Marvel at the archaeological sites of Ancient Olympia, Delphi and Mycenae
  • Enjoy scenic drives and breezy ferry trips on this Best of Greece adventure
  • Explore the delightful islands of Mykonos and Santorini


Day 1   Arriving in Athens City

Welcome to Athens, a vibrant city brimming over with striking ancient landmarks at every turn and lively, ultramodern museums, multi-arts spaces, shops, and cafes. Take a leisurely stroll and explore the beating heart of the city; Explore the colorful network of streets in the town center and in the island-like paths of Plaka neighborhood in Acropolis, and end your day relishing an elegant Greek dinner at a scenic restaurant overlooking the beautifully-lit Parthenon.

Overnight: Athens

Day 2 The Acropolis and Acropolis Museum

This informative Acropolis Tour explores the major sights of Athens (and a few less-known hidden gems) at a gentle pace. There’s plenty of time to ask questions and listen to your licensed English-speaking guide who is a local expert in archaeology.

Begin with a stroll through Anafiotika, a delightful Plaka neighborhood with quintessential whitewashed cottages, narrow alleyways and, vibrant bougainvillea. This pretty village nestles beneath the shadow of the Acropolis and the equally imposing Parthenon. Follow your guide further up the slopes of Mars Hill to the Rock of Ares (Aereopagus) outcrop, once the site of the judicial court and the burial place of kings and nobility.

Continue the scenic walk to Philopappou Hill, passing Socrates Prison where classical Greek scholars can pay their respects to this revered philosopher. The reward for the hilltop ascent is a breathtaking view over Athens. Return to the bustle of the city via Dionysiou Areopagitou, the longest traffic-free walkway in Athens. This open-air living museum is known for its history, culture and, nightlife.

Back in the cobbled pedestrianized alleys of Plaka, experience local Greek hospitality with a relaxed lunch in an authentic taverna. The afternoon continues with an optional archaeologist-led tour of the Acropolis Museum – the perfect end to the ultimate Acropolis Tour experience.

Overnight: Athens

Day 3 Ancient Mycenae

After a delicious Greek breakfast, you can look forward to the relaxing 90 km (56 miles) drive to Ancient Mycenae. This atmospheric archaeological site dates back to the second millennium B.C. when the city was a fortified stronghold. The palace complexes remain a testament to the advanced engineering skills of the Mycenaeans and provide a glimpse into everyday life in the Late Bronze Age. Marvel at the awe-inspiring Cyclopean architecture before driving west to Olympia for the night.

Overnight: Ancient Olympia

Day 4   Ancient Olympia

Today your Best of Greece Tour features the sites of Ancient Olympia, surely the jewel in the crown of the western Peloponnese region. The impressive archaeological site is dominated by the Temple of Zeus and the Temple of Hera. Built over 2,400 years ago, the magnificent Greek Temple of Zeus with its Doric columns once housed the statue of Zeus, one of the Seven Wonders of the Ancient World. You can reflect on the highlights, including the site of the Olympic flame and the Museum of Olympia, as you journey by road to Delphi for the night.

Overnight: Delphi

Day 5   Delphi

No holiday in mainland Greece is complete without a trip to Delphi. Follow our local expert archaeologist guide and immerse yourself in 3,000 years of history, cultural heritage and traditions.

Combine your awe-inspiring visit with a guided tour of the Archaeological Museum of Delphi, one of the most significant museums in Greece.

Delphi enjoys a stunning location on the sacred slopes of Mount Parnassus overlooking the Pleastos Valley. This ancient archaeological site is a UNESCO World Heritage Site, recognized for its unique place in Ancient Greek mythology, culture and Hellenic unity.

Home of the Muses, the Sanctuary of Apollo was where people consulted the Oracle of Delphi for wisdom before any major decisions were made. Stand in awe of the ruined Temple of Delphi with its 4th century BC Doric columns – all that remained after an earthquake in 375BC. Admire the ancient Theatre nearby, carved out of the hillside to give spectators the best views of the sanctuary and valley far below. It’s breathtaking.

This fascinating site in Delphi also includes the Treasury, Castalian Spring and the stadium where the Pythian Games were held every four years to commemorate Apollo’s victory over the serpent Pytho.

The private tour concludes in the timeless village of Arachova. Stroll through cobbled streets admiring the Byzantine architecture and pause to photograph the breathtaking mountain views. This laid-back tour of Delphi includes lunch at an authentic taverna enjoying traditional cuisine, local formaela cheese and wine, in true Greek style.

Overnight: Athens

Day 6   Ferry to Mykonos

Welcome to Mykonos, an idyllic getaway for cosmopolitan fun-lovers. A magnet to the world’s most glamorous personalities since the 70s, Mykonos today also attracts nature lovers, foodies, and athletes. Meet your skipper at the sailing yacht, where you will be shown to your cabin and given a briefing about life on board and the schedule of your week-long trip, and explore the island at your own pace for the rest of the day. During your Greek islands sailing tour you will discover remarkable beaches, adrenaline-rich water sports, the refined local cuisine, and an unprecedented bar scene, all among picturesque architecture, breathtaking views, iconic windmills, and maze-like streets.

Overnight: Mykonos

Day 7  Santorini

Take the ferry to Santorini, a highlight of our private Greece tours. With its colorful cliffs and white Cycladic houses, the island is an unforgettable destination with a flourishing wine industry. Voted one of the world’s most beautiful islands by Travelers Choice Awards, our land trip includes Oia, one of the most photographed hilltop villages in the Southern Aegean. Relax and enjoy a coffee and a sweet pastry before exploring the Panagia Church, castle ruins and charming main square. Our tour includes sampling traditional cuisine in the upscale ambiance of our handpicked restaurant. Don’t forget to watch the sunset light up the red cliffs at dusk.

Overnight: Santorini

Day 8 Visit Santorini Wineries

The second day on Santorini focuses on the island’s wine industry. These heritage vineyards are among the oldest in the world, dating back over 3,500 years. Thanks to the well-drained volcanic ash soil and sunny climate, Santorini wines are noteworthy. We visit local boutique wineries and learn about the grapes and wine-making process before sampling the distinctive local produce. Made from the Assyrtiko grape, Santorini wines include white, rosé and the sweet Vinsanto dessert wine.

Overnight: Santorini

Day 9 Athens

Take a scenic ferry trip back to Athens for a free day to explore your own particular interests around the city center. The National Archaeology Museum, the ancient marketplace of Agora, the fascinating Byzantium Museum, the frescoed Church of the Holy Apostles with its Ashlar exterior and the Panathenaic Stadium are some of the outstanding Greek sites to visit. See the Changing of the Guard at Syntagma Square and shops for souvenirs in the pretty Plaka neighborhood as a fitting end to your private Greece tour.

Overnight: Athens

Day 10 Athens – Trip end

All too soon your Best of Greece Tour comes to an end. It’s time to pack your bags and be transported to the airport or to the port for your journey back home or to your next destination.


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BY ADRIAN VRETTOS                                                                                                                                                                                                                                   


After a power breakfast on board – Greek yogurt with oats and a large sticky dollop of honey – it was time to set out on our morning hike. Luckily it was only to be a three-hour affair up to the castle of Oria on the northern tip of Kythnos island.

Rambling up an old kalderimi (pathway) whose dry stone walls rose as high as two meters at points, Stavros, our hiking guide, seemed to be obsessed with the varieties of thistle, a nibble favored by donkeys. Apparently, they are a much-overlooked plant and when they bloom have a bright purple crown protected by a multitude of thorns and spikes.

Donkeys, we did not come across today, but we did pass a small flock of sheep being milked by a lady with the help of her burly son and playful dog Daisy. After the cordial exchange of pleasantries, she asked whether anyone would like to have a try at milking. Once again audacious Fanni volunteered for the task and duly squirted a few shots of milk that clanked into the metal bucket. The milk would be taken back to the farm, boiled and curdled into feta cheese.

Our destination, the remains of Oria Castle was a sight to behold; there stood a hilltop fort with sheer cliffs dropping into the sea and a recorded history spanning back nearly 3,000 years.

The entrance, still somewhat intact, had embrasures above the gateway and a few steps up from there was the church of Agia Elousa, built atop earlier places of worship. Beyond were the rubbly ruins of all the buildings on the old castle, laid low by centuries of turmoil and war.

Sailing to Syros!

As I sit here at the skipper’s chart-desk below deck to blog about our morning adventure we are setting sail for Syros. As we pick up speed and the sailboat leans left and I wedge my right foot up against the solid banister of the steps that lead to the deck. In actuality were it not for the hull I would be chest high in seawater as I am partially under the water line, quite a bizarre thought as we slice through the fizzing blue waters, rocking and rolling a bit too much for my liking. Also, I’m getting a little dizzy down here so I’m going up to enjoy the thrill of sailing in the windy sunshine of the deck.

Having paid attention to Fanni’s sailing tutorial yesterday, I was doing a fabulous job, small adjustments to the left then to the right, even managing to confidently crack a couple of jokes with some of my shipmates. “Adrian! Where’s the point that I asked you to keep sailing toward?!” Giorgos interjected. ‘It’s…erm,’ I scanned the horizon again, what I thought was dead ahead was now way over to my right. “Oh, hum, it’s over there,” I answered sheepishly. The skipper nodded and smiled as I changed course.

A Real sailor?

As I got back on course, the wind blowing on my face intensified as the sailing yacht picked up speed. This is the apparent wind speed, which is the actual wind speed plus the speed of the boat. Clipping along at 9.5 knots with the ‘apparent’ wind speed of 24 knots, I was helming a sailboat on the gorgeous blue waters of the Aegean – always a dream of mine! I felt like a true sailor now, a hardened sea dog. I was closing in on the once white dot, that was transforming into a three sailed sloop.

“I’ll catch up with it soon and we’ll pass it,” I proudly announced to everyone.  “Yes well, they are actually coming towards us…!” Giorgos informed me, inciting everyone to have a little chuckle at my expense, my pride rightly deflated.

Our four-hour crossing had reached its end, and we pulled into the protected little harbor of Finikas on Syros, yet another island to discover.

Hungrily we hopped off board and traipsed down the harbor to the sea front taverna ‘Calmo Mare’, where for dinner I devoured the house speciality of the herby smoked Syros sausage on a bed of freshly-cut fries and topped with a fried egg, all washed down with a couple of glass of local red wine. The sailing was great, but I quite look forward to this break from the sea.

Day 4 – Hiking on Syros

We set off on a more leisurely hike, today at the more civilized hour of 9.30. The sun was already blazing, and it felt like summer had kicked in properly here on Syros. We followed the road that passes through elegant Poseidonia (filled with grand mansions once used by wealthy merchants from Ermoupolis as summer abodes) as far as Komito beach before venturing onto a barely discernible goat track.

The hilly landscape was strewn with rather unfriendly thorny green-grey domed bushes of broom, burnet and Greek spiny spurge, typical of the Cyclades. These were interspersed with explosions of colour; the white and gold of crown daisies, the dusky pink of flowering bindweeds and wild leaks, and the purple and violet of the tiny flowers of thyme, summer savory and French lavender. My Finnish friends remarked on how lucky we are in Greece to have all these marvelous herbs growing in abundance everywhere.

We worked our way to the southwesternmost point of the island, Viglostasi, to a spot that felt like the absolute heart of the Cyclades. From here islands to the south (Mykonos, Paros, Naxos), west (Sifnos, Serifos) and north (Kythnos and Kea) are all visible, with the top of Tinos peaking over the hills in the east.

At the tip of the peninsula is a functioning old white metal lighthouse, probably a remnant of WWII, and the remains of a cylindrical tower, that may have been the old pre-war lighthouse. My archaeological instincts (I was a keen archaeologist in my 20s) told me that this place must have been inhabited for millennia because a panoramic vista is something that would have been quite attractive to peoples of the past. However aside from the relatively modern (I figure 200-year-old) rubbly remains, there was little obvious evidence of this.

After a leisurely lunch on board, I decided to try my luck at stand up paddleboarding (SUP), something that has intrigued me for a while, mostly because I never quite saw the point of it! It’s a combination of kayaking and surfing – the board is large, maybe two and a half to three meters long and half a meter wide, and the single oar stands a little over two meters tall.

I hesitantly transferred myself from boat to wobbly board on all fours trying for all I was worth not to tumble into the water. It wasn’t the cold sea I feared – I have already relished a handful of long, refreshing swims on this trip – it was more about saving what was left of my tenuous macho reputation, already quite battered after my bungled attempts as a helmsman yesterday. Eventually, I did manage to get up and start paddling, but it’s actually all quite tricky as the board bobbles aggressively under your weight.

And the point of SUP? It’s actually lots of fun once you get the hang of it and can glide over the water, and it’s also quite the workout.

Capital Culture!

Off to Ermoupoli the capital of Syros and, indeed, all of the Cyclades. After narrowly missed the bus, a local gentleman in a car slowed down and nodded in the general direction of the capital, so I gave a thumbs up and jumped in when he stopped. On the drive he gave me a quick history of Ermoupoli, telling me that it was once the biggest port in the Aegean and that one of the first electric cars (the Enfield 8000) was once manufactured here. The mayor died suddenly of a heart attack moments after proudly announcing the name of the city (after Hermes the god of merchants) after Greece won its independence. And much more. Judging by the magnificent town hall and many impressive neoclassical buildings, the city was a thriving centre not too long ago.

It is still the cultural hub of the Cyclades with beautiful medieval and neoclassical architecture and its own “La Piccola Scala” opera house (the Apollon Theater) where the annual Festival of the Aegean takes place. There is also a university here meaning students live in Ermoupoli year-round, adding to the vibrancy of the place.

What I Learned Today: How to Keep Your Captain Happy during your sailing adventure

The captain is Queen/King so one must always listen to her/him. Never step on the hatches!

When going to the front of the boat always go from the windward side (the side that the wind blows against the boat). You’re less likely to fall in the drink.

When working with ropes on the winch keep your hands a safe distance from the said winch.

Onboard use boat shoes (light coloured soles, good grip, and fast drying material) or your bare feet.

Always have a plan, but also a plan B. Don’t disturb the captain when docking.

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  • Once in a lifetime sailing holiday in Greece’s most famous islands
  • Swimming and snorkeling at pristine beaches
  • Exploring the local culture and white-washed villages, meeting locals
  • Experience sailing Greek islands such as Mykonos, Paros, and Antiparos
  • Enjoying the authentic and trendy local cuisine and bar scene


Charter a catamaran or monohull yacht and go sailing from Mykonos to Naxos in the stunning Cyclades islands– from the most sought after cosmopolitan hotspots and super laid-back Greek villages to the tranquil places known only by a few. Our expert skipper will be your guide throughout this sailing trip in Greece and can also help you learn more about sailing during this unforgettable island hopping adventure. The Cyclades islands have it all – gorgeous and varied beaches with turquoise waters, whitewashed villages, delectable food, impressive archaeological sites, rocky landscapes excellent for hiking, and the perfect winds for great sailing.


Day 01 Mykonos

Welcome to Mykonos, an idyllic getaway for cosmopolitan fun-lovers. A magnet to the world’s most glamorous personalities since the 70s, Mykonos today also attracts nature lovers, foodies, and athletes. Meet your skipper at the sailing yacht, where you will be shown to your cabin and given a briefing about life on board and the schedule of your week-long trip, and explore the island at your own pace for the rest of the day. During your Greek islands sailing tour you will discover remarkable beaches, adrenaline-rich water sports, the refined local cuisine, and an unprecedented bar scene, all among picturesque architecture, breathtaking views, iconic windmills, and maze-like streets.

Day 02 Paros

Paros has a coastline filled with an ongoing chain of terrific sandy beaches. Start your day with a burst of sun and sea, doing some watersports and swimming. In the afternoon go for a walk in the island’s interior to explore picturesque villages such as Lefkes, Kostos or Marpissa, stopping for an aperitif at sunset. In the evening, stroll around the tiny streets of Naoussa or Parikia ports to look at the lovely shops and art galleries before dining on fresh seafood, then stay on for cocktails and dancing.

Day 03 Antiparos – Despotikon

We start today by sailing to Despotiko, an uninhabited island-museum in the heart of the Cyclades with archaeological sites dating back to prehistoric and classical times. This is an ideal spot for sunbathing while dipping in and out of the water or diving under to enjoy some snorkeling in the crystal clear depths. In the evening, head to the Chora (main town) of tiny Antiparos which although small and unassuming has drawn some of the world’s brightest personalities to it over the years for its quaint ambiance, beautiful natural scenery, warm local community, and singular tavernas and bars.

Day 04 to 06 Small Cyclades

Today your sailing adventure around the Greek islands takes you to the “Small Cyclades”. This group of islands, comprised of six main islands and numerous tiny ones, was until recently a long-held sacred secret amongst Greeks who relish their privacy, fresh seafood, non-commercial set-ups and oodles of stunning natural beauty. These places are still far from mainstream and remain a bona fide pleasure for those who love raw nature imbued with a soundtrack of lapping waves and choruses of cicadas. Enjoy the crystal turquoise sea, visit traditional settlements with tiny and familial people, relax on postcard-perfect beaches and take long, leisurely hikes along and old paths and goat tracks.

Day 07 Naxos

Naxos, your final Greek island hopping stop, is blessed with magnificent and highly revered beaches, and renowned for the excellent locally produced foods and wines (as well as the local Kitron liqueur), and remarkable archaeological sites. With an active main town where you can shop and admire the Venetian architecture and Kastro (castle) area, the island also offers endless opportunities for beach pleasures – from laid-back relaxation, windsurf and watersports spots to stretches where you can enjoy hip beats and cool crowds.

Day 08 Naxos / Trip end

All too soon it’s time to pack your bags, say goodbye to your skipper and be transported to the airport or to the port for your journey back home or to your next destination.




When presented with the opportunity to go sailing in Greece and take a week-long sailing and hiking adventure around some of the lesser-known islands of the Cyclades, I spent around seven nanoseconds deliberating before jumping at the chance. The ports of call will be Kea, Kythnos, Serifos, and Syros, and together with sailing Greece, the journey will involve some serious doses of hiking and SUP (stand-up paddleboarding), swimming and snorkeling.

Now bear in mind, I am a beginner at sailing. My only past seafaring experiences (apart from annual pilgrimages to Greek islands on ferry boats) consist of floating around rather haplessly on a windsurfer as a teenager, and a three-month stint on a dry cargo Panamax vessel, chugging across the Pacific Ocean from Japan to Baton Rouge in the US.

And while I have received thorough information about the sailing and hiking trip from the tour operator Personality Journeys, to be frank, I’ve only skimmed it for the bare essentials – date, time and pick up point etc. As such, I don’t really know what to expect, which is rather the way I like it.

All aboard!

Giorgos the skipper met me and my fellow sailors at Lavrio port on the eastern coast of Attica (about 1 hour’s drive from the center of Athens). He led us to a smart blue, 56-foot, Greek-built Ocean Star sailboat named ‘The Big Blue’, which will be our home for the next week.

Once onboard there was a quick meet and greet with my shipmates – a couple of academics from Finland and a manager from Athens, all first-time sailors like me, and an engineer from Australia, who’s an experienced sailor. Giorgos introduced us to Stavros, an expert guide and Dimitris from Personality Journeys.

The forecast for our first crossing to Kea (Tzia in Greek) was a 4-5 Beaufort strength north-easterly ‘Gregos’ wind, quite typical for these parts I was told. North of Lavrio and sheltering it somewhat is the uninhabited island of Makronissos (a place of exile in Greece’s not too distant past).

As we cruised smoothly past it at 5-6 knots my shipmates and I sat at the bow, roughing it on cozy beanbags, enjoying the fresh wind as we cut through the waves. Once past Makronissos the winds picked up and largish waves began rolling westwards – gulp. At this point we picked up speed, reaching 8.5 knots and left the coastline of Attica well behind us. Those of us up front scuttled carefully back to the relative dryness and comfort as the boat dipped to an 18-degree angle which, apparently, is an optimum sailing angle.

The wind direction meant that we couldn’t sail directly to our first destination of Korissa port on Kea, so we’d have to do some tacking – sailors speak for zig-zagging upwind, which we did for a while, but eventually the skipper decided that, as it was getting dark and the sea was turning a more foreboding elephant grey, we should save time by heading close to the coast of Kea and doing the final stretch by engine. Rounding a small headland we finally reached the enclosed bay of Aghios Nikolas, marked by a large white 1830’s lighthouse of the same name.

Land legs

We docked at the picturesque port of Korissa, one of two in the bay, a village protected by the blue turreted church of Agia Triada. Leaping off we headed hungrily to the traditional taverna Lagoudera where most of us had the appetizing rooster in a rich red wine sauce recommended by the owner and rightly so.

I have to admit that even after four hours ashore I feel like I’m still swaying, like being a little tipsy (and no, I didn’t have that much wine with my rooster). I’m now off to bed (all those blasts of fresh sea air have knocked the wind out of me somewhat) hopeful that the lull of the sea will send me off into sleep as rewarding as my day.

Happily, I have found my land legs again after a refreshing night’s sleep. As it turns out, my cabin was deceptively not as minute as it had first seemed and the single bed more than compensated my six-foot frame (I’m also relieved to note that every cabin has its own, albeit dinky, en-suite bathroom). Despite, or maybe because of, the boat gently creaking and a light chiming sound reminding me of Chinese meditation balls – sounds I assume came from the engine next to my berth – I slept really well.

The Hike

It’s a good job too, as we promptly set off for a five-and-a-half-hour hike taking us from north to south over the mountain and down to the enchanting coastal archaeological site, the ancient city-state of Karthea. On the way, Stavros, our hiking guide and a mine of information, educated us about the history and flora of the island. As we passed through the oak-forested hinterland, we were told how the acorn shells were once used on the island to tan and dye leather, imbuing it with a rich, natural brown colour. As such, the oaks were once an important part of the local economy.

When I said that I wouldn’t be picking any of the flowers, well I fibbed a little. As we trekked to the top of Profitis Ilias (567m) along ancient paths lined with poppies, lavender and flowering chamomile amongst many other May bloomers, I couldn’t resist plucking the juicy tips of the wild asparagus (delicious) growing under the oaks, as well as a few sprigs of thyme and its close cousin throubi.

Special Requests

On the way, we passed a weathered old farmer tending his vegetables on one of the many terraced fields that scale the hillsides. He greeted us with a bearded smile, an old knife he was using to dig up his produce, clenched in his right hand. After inquiring where we were from, and then ignoring our answers, he asked us if we could tell Tsipras, the current Greek PM, to stop lying to people. He then asked that we fish out some sea urchins when we reach Karthea and bring them back up to him (a rather unlikely 2 ½ hour hike). I attempted to take a snapshot of our new acquaintance but he asked that I didn’t, as the villagers would gossip about his good looks!

Ancient Karthea

As we approached the coast, the ruins of this magical site, on the hill between two sandy beaches, became discernible. The partly restored Doric temple of Athena stands out in front of the blue of the Aegean Sea, creating that quintessentially Greek experience: sun, sea and ancient mystery. Our sailboat was waiting to pick us up here and after a swim, the dingy buzzed us to ‘The Big Blue’.

Up went the sails and we were whisked across to the neighboring island of Kythnos. Charging up and down the large waves, we reached the heady speeds of 9 to 9.5 knots thanks to the favorable ‘Gregos’ winds and made the 17 nautical mile crossing in a mere two hours, berthing at the little fishing village of Loutra.

Random things I have learned Today

Poisonous hemlock grows in abundance on Kea, and this yellow-flowered plant was used by the ancient inhabitants to euthanize people over the age of 70 whose physical and mental faculties had abandoned them. This law thought up by Aristides, one of the seven sages of Ancient Greece, was lauded by Aristotle in his writings Keion Politeia. Who says we’ve got it bad now?

The spinnaker is the large billowy sail at the bow (front) of the boat that is used when the wind is behind you. Not to be confused with the genoa sail also at the bow that is used for all other types of winds.

When steering a sailboat there is a seven-second time lag between what you do and the reaction of the boat, and that’s not taking into account the wind and the waves. And this, Fanni, one of my shipmates, found out first hand when she took the helm. She also found out, along with the rest of us, that it takes some getting used too!

Some students in Finnish universities celebrate Mayday by dipping in icy rivers or lakes. Rather them than me! I’ll stick to the Med.