Sailing the Saronic Islands of Greece with MedSailors: An Epic Adventure on the Jackpot

In Europe, Greece, Travel by KatelynLeave a Comment

MedSailors Greece

Visiting Greece has always been a dream. It’s rich in history, art, and olive oil. I’ve dreamed of riding a donkey up the steep hills of Santorini amongst the white houses with their bright blue roofs for years. I pictured the markets filled with octopus and fish awaiting an old Greek woman to barter with the fisherman for her family meal. I envisioned myself staring in awe of the Acropolis and wondering what life was like in ancient Greece. Most of all, I’ve always wanted to sail the Greek isles.

Greece, especially the Greek isles, have a certain romanticism about it. What’s more romantic than some of the best sunsets in the world? I’m a total sucker for a good sunset and Greece certainly delivered for me (except in Hydra. Damn you Greece!). When I first booked my plane ticket for Greece last Fall, I had one intention… to sail the Greek isles. I began researching various tour companies, like Contiki, Intrepid, and G Adventures, but all tours cost well over $1,000 USD. It was way more than I was comfortable spending as I’m still saving for my Great Escape next year. Then I found MedSailors by chance in my Google search. After reading their website about 20 times for several days, I knew I found my company.

MedSailors Athens sailing

MedSailor yatchs sailing out of the hazy Athens Marina

Right before I left for the Azores over Thanksgiving I placed my deposit for a seven-day sailing tour of Greece for the last week of May, which happened to be their first sail of the year. I slowly counted the days down one by one until I was sitting on the plane from Boston to Athens too excited to sleep. I spend my first couple of days in Greece exploring the Acropolis and stuffing my face with amazing Greek food on the Athens Food Tour before finally hopping on the tram to the marina to depart for the trip of a lifetime!

Day 1: Perdika
Perdika Greece sunset

An epic sunset over the small harbor town of Perdika on the first night

We were told to be at the Athens Marina to meet our boat by 1 pm. Getting to the marina isn’t hard via the public transportation system. The hard part was finding pier 3 amongst the nine thousand other piers in the marina. Athens Marina is massive so make sure you pay attention to the directions, unlike my directionally challenged brain. I arrived shortly after 1 pm and met Nick, the lead skipper and our awesome skipper who was working quickly to organize our boat and prepare for our departure.

I was given several options of nearby shops and bars to grab some food and drinks for the trip as it’s cheaper to stock up on the mainland instead of the small islands. I picked up some snacks and a 6-pack of beer thinking I wasn’t going to drink much as I’m not much of a drinker at home. I was looking forward to a nice relaxing sail through the islands. Well, my intentions were quickly diminished when I was told on my return to the marina that I was sharing a book with seven guys and another American girl. As soon as I learned that they were Kiwis and Aussies I knew that my chances of having a nice quiet sail was totally off the deck.

Perdika Greece sunsent

A few of the boys on the first night – drunk, happy, and sunburnt

Soon after my return to our yacht, ironically named the Jackpot, I met the rest of sailing mates for the week in a whirlwind of names, handshakes, and beers and ice being thrown into the deck cooler. By 3 pm the ropes were thrown, the first beers were cracked, and we were off for what was going to be an epic adventure.

But first, I must stop you, dear reader, in case you missed my post last week introducing you to my motley crew of mates. My trip truly would not have been the same without each and every one of them so I urge you to read that post first then come back (plus it might save you some confusion). Now back to the story.

We sailed in the hazy heat of Athens out through the Athens shipping lanes to our first stop of the trip. The small harbor town of Perdika is located on the southwest side of Aegina. Its main cobblestone street is surrounded by the harbor on one side and a collection of white square houses and shops on the other.

We arrived a couple of hours prior to sunset allowing us enough time to jump into the sea and test our doggy paddles after a long winter in the States and in London. The shoreline of the harbor is littered with sea urchins as a few boys soon learned the hard way.

Dinner that night was pre-arranged for us at a small traditional Greek restaurant. The food was served to us tapas style. We had enough time before dinner to enjoy a few more beers and watch an epic sunset over the harbor before changing into dry clothes for an evening of delicious local food, continuously flowing wine, and hurt-your-belly-so-good laughs from all the boys antics.

We survived spilt red wine, eating from the wrong side of the plate, commenting a local woman on her “assets,” and the raki shot that nearly knocked me off my feet and continued the party at the local watering hole. From there the night gets hazy and I’m pretty sure none of the boys remember a minute of it, but it was one for the books. Can day two beat day one?

Day 2: Ermioni

The beauty of partaking on a sailing tour with a skipper is that you don’t have to get up at the ass-crack of dawn to sail out of the harbor. However, if you’re an early bird like me, you can lend a hand in throwing the ropes and pulling the anchor. I woke up early sans hangover by some miracle of God and cleaned the boat while helping Skipper maneuver the Jackpot out of the harbor to our breakfast spot at a nearby cove.

We never ate breakfast in the harbor. Instead, our skipper had a secret (okay, not so secret) map of quiet coves with turquoise water that made your heart skip a few beats in its sheer beauty. Breakfast was generally the same every morning… bread with jam or this amazing chocolate spread that I nicknamed “crack,” yogurt and cereal. Sometimes we would have French toast, crepes, or an omelet. It was enough to fill our bellies until lunch rolled around a few hours later. The first beers were cracked soon after breakfast and clean up as we splashed around in the warm Aegean Sea and explored seaside cliffs and caves.

Perdika Greece

Our first breakfast stop not far from Perdika

We soon pulled anchor and set sail for a few hours until our next stop. We’d keep ourselves occupied by napping (mostly just the Boxer), drinking and swapping travel stories and stories from home, singing and dancing along to 90s pop (this was the Big Fish’s favorite), and just chilling out and forgetting all our worries at home. Life was tough.

By the late afternoon, we arrived in the small town of Ermioni. Ermioni is one of Greece’s most historical and well-preserved villages located on the mainland. Little did we know but we were about to embark on an epic night of debauchery that topped the craziness of the night before.

We were told that MedSailors would provide us with rum punch for the evening just prior to the awesome and FREE dinner put on by the owner of the cheesy Greek nightclub called Millennium Club, where we would dance the night away. We decided to explore the small town for a bit to stretch our sea legs and grab ice cream and pastries before sitting down to listen to traditional Greek music and dancing.

We sipped on rum punch that did not taste one bit like alcohol (dangerous!), but was filled to the brim with a hodge-podge of various liqueurs. I sucked down a couple of cups and immediately felt the buzz as I sat down to munch on the meat and tofu skewers from the feast put on by the nightclub.

From there the night gets very hazy, but I know it was filled with dancing to old and new American pop music, watching the nightclub owner continuously throw napkins into the air like a strange snow globe, and living my dream as a Coyote Ugly bartender. One warning, the bartenders pour stiff drinks in Greece. The Big Fish got a rum and coke from the bar and I’m pretty sure it was straight rum with a splash of coke. You definitely get your money’s worth that’s for sure.

The night ended with First Mate stealing all the leftover skewers for our lunch the following day, which later led to a rather humorous argument between the Boxer and First Mate. Don’t mess with Santa’s eves!

MedSailors Greece

Nashville Girl and I (Photo Credit: MedSailors)

Day 3: Spetses

We once again set sail in the early morning to our next breakfast stop in a nearby cove. Most of us splashed around in the water while Skipper was hard at work making our breakfast of french toast. Many of us were feeling the effects of the past two nights of drinking and lack of sleep, so we mostly lounged around the yacht listening to a mix of Kiwi, British, and American rock and sipped on more Mythos beers.

First Mate decided he wanted to ride to our next stop in the dingy, so we let him. We sailed into another small cove to enjoy a relaxing lunch before arriving on the small island of Spetses in the early afternoon. The town of Spetses is quite large compared to our other stops, and I can imagine during the high tourist months that it is packed with people from all over Europe. No four-wheeled vehicles are allowed in town, and cars are few and far between throughout the island. The best way to explore the beautiful island is via quad bike or scooter.

Spetses Greece scooters quad bikes

Enjoying the amazing views of Spetses via quad bikes and scooters

As MedSailors we get to rent our choice of a quad bike (ATV for my American friends) or a scooter for €15 a day. Most of us got quad bikes while First Mate, Skipper, and the Komodo Wearing Aussie got speedy little scooters. We were soon zipping along the winding coast of the tiny island overlooking the steep seaside cliffs intermittent with long white sandy beaches surrounded by bright turquoise water.

The boys were clearly in their elements. Zooming around with smiles from ear to ear. Unfortunately, I got stuck on a quad bike with only one brake handle that happened to be on the same side as the throttle. Both of which were on the right. I struggled a bit with the set up as I have small hands and tendonitis in my right wrist from years of working with pipettes in a genetics lab.

The roads are winding with tight turns so you have to brake and throttle at the same time leading me to be the slow poke of the group, which was okay for me as I’d much rather leisurely ride around the island and take in the views. Plus, I’d much rather keep my skin on my body.

We stopped about halfway around the island at a seaside cave that you can swim in. Only our skipper knew this secret location and when we later told the other boats they were quite jealous. The cave was cool, both physically and metaphorically. You climb down a narrow path between boulders into a large cave with waist deep cold water. If you’re brave you can even swim out to the sea from the cave. And don’t worry, there are no sea urchins in the cave!

We continued our way around the island back into the town passing several beach resorts along the way. I couldn’t get over the color of the water. I was suddenly transported back to Belize and the Caribbean. A few of the boys decided to take a second lap around the island, but the rest of us decided after a hot day in the sun we needed ice cream. You’ll notice a trend here. We love our ice cream!

As we delivered our bikes back to the shop, the owner looked relieved to see us all back in one piece, especially the Boxer. The local police had just stopped by to tell him that someone had gone over the cliff on a bike, and he immediately thought it was the Boxer for whatever reason. Nope! All MedSailors made it back to the yachts in one piece. Well, First Mate did get attacked by a tree and came back with a few cuts and bruises.

Spetses Greece

The coast of Spetses near the “secret” cave

Spetses is a low-key island and we decided to take advantage of it. We ordered takeout pizza from a local shop and ate on the boat while drinking our own beers. The pizza was just as good as some of the pizza I had in Italy so I highly recommend trying the pizza in Greece. You won’t be disappointed.

Skipper told us that there is a local dive bar with beer pong games that was worth checking out. From that moment, the atmosphere changed and everything turned into a competition from drinking games to the upcoming beer pong tournament. The Big Fish proudly boasted to us that he never loses in beer pong. Well, there’s a first time for everything, mate.

I played the first round with the Boxer and we lost miserably to the Big Fish and First Mate. The only cup I hit was the water cup. I guess my beer pong skills are pretty rusty, but then again college was over 6 years ago for this old hag. The Big Fish and First Mate lost the second round to the Archeologists and the Locksmith. I might have been mistaken, but the Fish might have shed a tear or two.

The remaining few hours of the night were low-key. The boys taught me about cricket, which continues to confuse the heck out of me. Go Red Sox, right?

Day 4: Hydra
MedSailors Greece

Sailing to our next stop on a cooler day (Photo Credit: MedSailors)

All throughout the trip Skipper kept telling us that Hydra is home to the best sunset in Greece. As someone who swoons over epic sunsets, I was pumped for our visit to Hydra. I also secretly wanted to ride a donkey.

But, Hydra turned out to be one big disappointment. Don’t get me wrong. The town is beautiful and 110% worth the visit. We just happened to score the only day of rain. It normally doesn’t rain much in Greece, but since we booked the first sailing tour of the season, the weather has the potential to be a little less stable than in the middle of the summer when it is scorning hot and sunny.

However, I don’t regret my decision for sailing the first tour of the season because it was cheaper, the flotilla of MedSailor yachts was much smaller, and tourist season was not quite in full swing than later in the summer. I don’t deal well with large crowds.

We arrived in Hydra in the midafternoon. We had warmth and the sun for both our breakfast and lunch stops, but by the time we were rounding the island towards the small town of Hydra, the clouds were moving in at rapid speed leaving me to take the Skipper’s “jumper” (aka hoodie) hostage for the next few days. He’s really lucky I didn’t take it home as it was a really nice hoodie!

The Hydra marina is tiny and yachts and fishing boats are packed like sardines. Skipper steered the Jackpot into the marina for us to see the town before swiftly swinging her back out and around the corner to where we would tie up for the night.

What I found extremely interesting about sailing in Greece is the lack of moorings. In Maine we always moor boats in the harbor and take the dingy to shore. In Europe it’s common to back a boat into the harbor and tie her up to the docks.

Unfortunately our “home” for the night was just a quiet and empty cove where we had to tie up to some rocks and use our dingy and ropes to pull ourselves the 10 feet to shore. Miraculously, no one fell into the water doing this as they would have been met with an army of sea urchins below.

We spent most of the afternoon playing drinking games in the cabin attempting to stay dry from the showers. As an optimist, I asked Skipper if we’d see a sunset that night. Not missing a beat he replied, “do you want me to lie?” “Yes, Skipper. Yes, I do.” My hopes of seeing the best sunset in Greece was dashed just like my chances of winning the latest round of Bullshit.

Eventually, the rain stopped, but the large, gray clouds hung low in the sky. Our stomachs were grumbling for food, and we decided to grab a road soda and take our chances with the rain and walked the mile or so into town for gyros. We were on a mission to find the cheap gyro shop that Skipper told us we had to eat.

We wandered the tight, cobblestone alleyways for a few minutes when the heavens opened up again, and we ducked into a little restaurant. Lo and behold we found the gyro shop! Takeout is always cheaper in Greece, but we managed to convince the owner to give us the lower price for a sit-down meal. He made out on the deal as most of the boys ate several €2.50 gyros. They were delicious!

Hydra Greece

Sailing into the tiny marina of Hydra

The sunset bar was a huge disappoint as there was no sunset to be seen for miles. We each had an expensive drink and mingled with the other boats before heading back towards the Jackpot. Originally we planned to take a water taxi back, but the limit is eight people. We were 9. Our disappointment quickly dissipated when we spotted a nearby ice cream shop. See the pattern now? None of us knew at the moment, but our stop at the ice cream shop was going to be the most memorable moment of the trip.

I was quietly sitting on a nearby stoop with the Archeologist looking for wifi bars when the next thing we see is First Mate’s feet dangling over the front window then quickly disappearing with a loud exclamation of “we had a moment.” Laughter ensued as First Mate continued to repeat the line as the ice cream shop owner was scooping everyone’s ice cream.

She was good-hearted about the whole situation even though I don’t think she had any idea of what was happening. I think the event was the highlight of the trip, and I have no doubt the boys told all their friends back in London.

Despite the dreary weather on Hydra, our short time on the island was filled with delicious gyros, expensive drinks, and crazy antics that you could only expect from a group of guys. I don’t think I’ve ever laughed so hard in my life.

Hydra ice cream shop

“We had a moment” at the Hydra ice cream shop (Photo credit: Nashville Girl)

Day 5: Poros

I woke up early and decided to go for a short run instead of vegging out on the boat all day. Hydra was the perfect island to do so because of the road leading from our cove to town. I’ve run in a lot of places, and I’m pretty sure that Hydra is one of the most beautiful places I have run.

The morning was cool and overcast, but the sun was starting to poke her rays out promising us a nice day as we sailed to Poros. During every MedSailors tour, there is a sailing regatta between the boats. We crew the boat as the skippers sit back and watch. We thought today was the day, and we were ready to win.

We got out into the open water and immediately the wind speed dropped to about two mph. No sailing with the sails today. For most of the trip, we were motoring as the wind just really wasn’t there. I was a bit disappointed as one of the main reasons I chose MedSailors was the fact we were on sailboats. But atlas, you can’t change Mother Nature’s mind.

So instead Skipper tied a rope to the Jackpot, and we surfed on the paddleboard behind the yacht. I actually did not participate in the surfing as my hip injury doesn’t allow me to kneel. I was totally okay with this and enjoyed shooting pictures of everyone giggling like school girls before face planting into the water.

MedSailors Greece

Smiles all around

We ate lunch in the bay near the watersports company just outside of the main town. MedSailors partners with a watersports company on the island to give us reasonable prices for tubing, wakeboarding, and parasailing. They also provide us with free beer. Win, win for everyone!

Unfortunately, the wind was not right for parasailing and wakeboarding. The remaining options were tubing, something I could do at home. No one from our boat decided to partake, but some of the American doctors and Canadians hopped on the banana and the tubes for a go-around the bay.

The weather began to turn a bit and we all took cover in the cabin playing drinking games (again). After a few rounds of fingers, Bullshit, and Kings Cup, we were all in fine shape for dinner.

Dinner was at a local restaurant serving mostly traditional Greek dishes. I ordered the fish of the day and said a few explicit word about the €75 lobster dinner. Of course that led me to explain to just about the whole restaurant that where I come from lobster is about a few bucks a pound. I bet that €75 lobster came from Maine too!

Our night out in Poros was a crazy night and filled with hazy details. The same guy who runs the watersports company owns a bar. There was dancing, a captain’s hat, and several shots involved. Even Skipper was up on the bar breaking a few moves. It was about 3 am when I found myself dragging the Skipper and the rest of the boys home to the Jackpot. We had to get up early to race in the MedSailor’s regatta. And Skipper never loses.

MedSailors Greece

One of my favorite photos from the trip (Photo Credit: The Big Fish)

Day 6: Agistri

I woke up early the following morning with a massive hangover. It was bound to happen after 5 days of drinking with about 4 hours of sleep each night, but it was a tequila shot that truly did me in. I wasn’t the only one curled up in the fetal position and whining, though. The Big Fish was in the same boat (I know you love my cheesy puns!). I think age finally caught up with us. We sailed back over to the watersports company to eat breakfast and see if the conditions improved for parasailing. They didn’t, but the boys each took a few spins on the tubes.

Poros Greece Watersports

Some of the boys tubing in Poros

Once again the wind wasn’t cooperating for a sailing regatta. However, there was a championship trophy at stake, and you best bet that the Jackpot was going for gold. Nick, the lead skipper, informed us we would have a dingy race. Eight members from each boat would hop on their dingy sans motor and paddle a short course.

The game now turned from tactical to physical. There was much discussion on who should sit where and who would paddle. We started several feet behind the rest of the boats when the whistle was blown, but we quickly made up ground. One boat made the fatal mistake of taking a tight turn around the buoy and lost momentum. Our wide turn combined with the powerful kicking of First Mate and the rowing skills of the rest of the team propelled us to a clear victory. We won! And we’re damn proud!


Victory! (Photo credit: MedSailors)

Skipper put on his victory music playlist and we all serenaded the boats with “We are the Champions” while popping celebratory beers. I took two sips from mine and quickly changed to water. I was done.

We arrived on our final island of Agistri in the late afternoon. Agistri is a quaint town with a long sandy beach spotted with fishing boats and nets. The town is situated on a hill with the restaurants located near the harbor.

The final night of any Greek MedSailors trip includes the infamous toga night. Everyone yanks off their bed sheets and twists and turns them around themselves to transform into Greek gods (or more like drunk fraternity brothers). Dinner was held at the Jamaica Bar where One Team One Dream was awarded our trophy and champagne and celebrated with traditional Greek music and dancing.

I was not feeling well and decided to call it an early night. Between the hangover, the exhaustion, and the mess and smell of the Jackpot after 6 days living with 9 other people in a confined space, I was ready to get off the boat and have my own space. Don’t get me wrong, I enjoyed everyone’s company, but this old girl was ready for her own space and quietness.

Toga MedSailors Greece

Toga! Toga! (Photo Credit: Nashville Girl)

Day 7: Athens

I woke up super early and spent an hour walking from the end of the pier to the end of the beach until the bakery opened so I could buy water and pastries for the gang. We had a late breakfast feast and then it was time to sail back to reality. Finally, we had the wind! Skipper raised Jackpot’s sails, and we were hauling at 10 knots across the shipping channel.

It felt awesome to experience a good keel finally. Poor Skipper was working his little arms off for over an hour to steer her to the harbor. The last few hours of the trip were bittersweet. I was tired, hung over, and ready to get off the boat and head north to Meteora, but I was sad to leave my little family.

MedSailors Greece

One Team One Dream (Photo Credit: First Mate)

My seven days sailing the Saronic Islands with MedSailors was one of the best trips I have ever done. I got to explore some of the lesser-known islands of Greece on a yacht and met some of the coolest people who I’m lucky enough to call friends. We all live on different ends of the world, but I do plan to sleep on their couches in the near future (and the offer to visit Maine and eat lobster is always open).

If you’re looking for a fun vacation, then I highly recommend checking out MedSailors. Next week I’ll have a post about why you should book a trip with them for next year, but for now, just take my word for it.

Have you done a sailing tour? Are you ready to book your tour with MedSailors yet?

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