Day 1 (Saturday)

When my bestie, Jenny, asked me to be her maid of honor, I was incredibly touched and, of course, agreed. As wonderfully extra as it gets, she decided to have a joint bachelorette in Greece, sailing the Saronic Islands in a privately chartered yacht. The things I’m forced to do for my friends.

Due to a 3 hour flight delay, Trixie and I arrived to the Athens airport during a heatwave with no time to shower or change, lugging our overweight checked back full of bridal decorations through to the pickup point. After taxiing to Kalamaki-Alimos Marina, we met up with our captain/skipper Andreas (#scaptain), and set up our decorations under the deck of the yacht. We furiously arranged pastel flowers and mason jar memories as our makeup melted like microwaved crayons and sweat spread to almost every inch of our clothing.

It was all worth it when Jenny, Jordan (the fiancee), and Anna (the other bride) showed up and walked downstairs. Seeing all of the love got a tearful reaction out of Jenny, which made all of the effort worth it. 

Once our scaptain Andreas, who was basically the greatest human of all time, started sailing, we all sat on the bow of the ship and gleefully enjoyed the view while periodically getting splashed with water. Andreas pointed out the different islands to us as we watched the sunset. The light eventually disappeared and we rounded a corner to see an entire twinkling city in the darkness. Photos wouldn’t capture the depth or beauty of seeing Poros from afar at night, so we just enjoyed the ride. When we sailed closer, we ohhed and awwed at all of the little buildings on the water before docking at the marina. 

One of the bridesmaids for the other bride, Faith, had a grip of steel, and held each of our hands as we walked the plank over to the dock. 

Andreas led us through the lively streets with stores and cafes on the way to his restaurant recommendation. Seeing some of the classic blue and white buildings was surreal, and the rounded white stucco stairs were adorable. The restaurant itself had a beautiful city view with trees growing through the tables. I was officially obsessed with Greece by this point. We bought gelato and baklava on the way back to the boat, surprised that the city was still open and busy past midnight.

Day 2 (Sunday)

We grabbed some breakfast in Poros, and then headed up to see the famous Poros Clocktower. The views from the clocktower were spectacular, and the flowers were some of the most vibrant that I’ve seen. It seemed like almost all of the houses and buildings had some sort of bright flower arrangement. Combined with the intricate balconies and white/blue color schemes, it felt distinctively Greek. 

We went back to the boat around midday for our journey to Ermioni. Once we arrived, we walk the short distance to the other side of the island, investigated a few pastry shops, and got splashed by the choppy water on the docks. 

Then we walked back to the souvenir shops near our boat and ate a late lunch right on the water with a much-appreciated breeze. 

It was actually Trixie’s birthday as well so after a quick break back at the boat, we went back out for a birthday dinner at Tzieris, another recommendation by Andreas. They light the water up from below at night, and there are 3 tiers of seating. The waiters, like most places we went to in Greece, went above and beyond. They pulled tables together so that we could sit nearest the water, offered to take photos of us from one level up for the best view, and literally sent someone to get a cake for Trixie because they don’t sell dessert. 

It was a wonderful night spent with fabulous people.

Day 3 (Monday)

In the morning, Andreas took us to the offices to buy ferry tickets to Hydra, and then to an amazing pastry shop a block or two away called Drougas Bakery. Thinking we could manage from there (his first mistake), he left us to find our way to the ferry directly in front of us by the time it left. After purchasing the best iced latte of my time in Greece, we went over to the ferry about 10 minutes early and were turned away even though we had tickets. After a brief argument with the tour offices, we exchanged the tickets for the next ferry (2 hours later), and notified Andreas that even though he helped us with every step of the process, we still missed the ferry. He brought the boat from the other side of the island and docked it as close to the ferry’s departing point as possible so that we could wait there. When we asked him if he was surprised that we missed the ferry, he smirked to himself and shook his head no, which we all found hilarious. 

Finally the next ferry appeared and we reached Hydra within the hour. Hydra was the largest city we had visited so far, and Andreas recommended that we didn’t skip it when that was brought up as an option. In Andreas We Trust, so there we went. Once again, he was completely right. The cobblestone, the clocktower, the stucco buildings intermixed with old stone—it was all the most breathtaking landscape so far. It was very busy, clearly a huge tourist attraction, and for good reason. We had a lovely lunch at Xeri Elia Douskos, with hot pink flowers woven through the trellis ceiling made of vines and leaves. We walked up to Lazaros Koundouriotis Mansion, with fantastic views of the city (and air conditioning!). Armed with smoothies and gyros, we window shopped, and generally enjoyed the views. Jenny tried to pet one of the donkeys at one point and startled it so much that it jerked back, which made her jump. We came, we saw, we scared donkeys. 

On the way back, some of us got yelled at by the ferry employees for trying to go to the top, even though most of our group made it up. One of Jenny’s oldest friends, Finn, sat with me below deck—both of us were lulled to sleep by the movement of the boat, but unfortunately for him, he snapped out of it and banged the back of his head on some metal paneling. Even the most luxurious vacations are not without their dangers. 

When we got back to Ermioni, we ate at Spirandreas Tavern right on the water. The only thing I hated about Greece was the prevalence of the modern locusts of the world: Cats. Cats EVERYWHERE. I maintain that my dislike of cats comes from the fact that I am incredibly allergic, but I also recognize evil when I see it. Anna also happened to be a cat enthusiast, petting even the most horrid of creatures, including one or two hissing and likely diseased cats in Hydra. I persevered, the brave survivor that I am, and we finished dinner and took a series of winding paths through the middle of the island to go see what yacht week actually looks like. Andreas had asked if we wanted to join up with them at one point and was met with uniform disgust and horror, but that doesn’t mean we’re above observing the phenomenon as if its participants were zoo animals. 

I’m not sure this was the liveliest of yacht week nights/locations, though, because it essentially consisted of 5-6 boats playing loud music, a small club with neon purple lights and a smattering of WASP-y 20-somethings bopping around, and a few obvious bars. 

We grabbed a drink at Casa Dei Bar and left yacht week behind.

Day 4 (Tuesday)

The next day actually ended up being my favorite. Grabbing a few last-minute ice coffees and pastries, we set out for Spetses. 

Spetses, to me, was just a gem. Vivid, lush flowers everywhere, pastel blue door frames on white walls, and a shopping center with cobblestone streets and back-to-back boutiques built into rounded walls. Trixie french-braided our hair, labeled them “TrixieTails,” and outlined a detailed backup career plan as an Instagram hair-influencer.

When we first arrived, we walked along the path from the dock (there’s essentially a walking path around the outer rim of the island). It also didn’t feel overly touristy, with locals populating the pebble beaches as we walked by. 

Sometime between harassing a local vendor about renting 4 ATVs (he just shrugged at us, clearly not overly concerned about making money) and getting another smoothie (light and fresh and not too sweet, I think I miss Grecian smoothies most of all), we realized that Anna’s other bridesmaid, Emma, had a bloodshot eye and intermittent weeping/sniffling. Being the absolute cutest, she said she didn’t want to disrupt any plans and she would be okay. But we don’t leave people behind with maimed eyeballs, Emma! We aren’t so different from the characters in Black Hawk Down when you think about it.

The pharmacy didn’t open until 5, so we got a late lunch on the water with all-blue chairs and tables. We stalked Andreas on Instagram and Facebook like the psychopaths we are, and then we killed time walking by the many horse-drawn carriages and the impressive Poseidonion Hotel on a wide-open area attached to a modern jetty. We wandered through the little boutiques with hand-crafted jewelry and the cutesy versions of larger chain stores like Moncler. Jordan spilled his smoothie in one of the jewelry stores, but Jenny and Trixie each bought something, so I mostly just felt bad about wasting such a good smoothie.

We finally got Emma her eye drops from the pharmacy, and Andreas joined us at Provenza for dinner. Finn devised a series of philosophic questions for us to get to know each other better, and it ended up being pretty entertaining. Highlights included a round of “what turns you on in a partner” during which one response of “bondage” was followed by Emma’s pure “family values and loyalty” and Anna’s constant references to cats when the questions were unrelated. 

The dinner was delicious and was accompanied by some good-natured ribbing by the waiter about the sheer volume of food we ordered. C’est la vieeee, om nom nom.

We grabbed drinks afterward and Andreas left for the boat (there was some drama with a larger cruise ship and the president of the marina). After about an hour, we walked back the direction we came, and Andreas had already moved the yacht, resulting in one of my favorite moments of all time. We literally wove our way through drunken partygoers (the “youths,” as Finn calls them) dancing in the nightclub and outdoor area underneath Bikini, and stepped off the side of the club into Andreas’ motorized dingy, waving and zipping away to the yacht under the cover of night like celebrities on sabbatical. 

Thinking nothing could top that day, we dropped anchor (even though I contributed 0% to any and all manual sailing tasks, I’m going to go ahead and claim the sailor-by-proxy status that allows me to say things like “we dropped anchor”) in a bay for the night. Lying on the deck and staring at the stars with the city lights in the distance, seeing one of my favorite people in the world get the exact trip she wanted, I didn’t think it could get any better than that moment. And then, I kid you not, we saw shooting stars. Anna stepped on the moment just a tad with an explanation of how shooting stars are actually space trash, but honestly, our entire group happy and laughing as we watched the sky only added to the magic of the day.

Day 5 (Wednesday)

The next day was our full day at sea. We did a good deal of swimming, part of which required some manual blowing up of floats. I ended up with an angel float with a gimpy wing, Jenny had an engagement ring float with a rock about eight times the size of her head, and Trixie had a massive peacock float that took the better part of an hour to inflate (“he’s shy”). Since Andreas’ one failing on the trip was finding Trixie a billionaire Greek boyfriend named Stavros, we passed the name on to the peacock. 

I also have to say, I’m not much of an “ocean water” sort of person. There are sharks and alligators and seaweed and trash galore where we are from, but Greece is a different thing entirely. The water is so pure and clear that it looks fake—they don’t have sharks or alligators or jellyfish. I honestly could not believe how much I loved swimming in ocean water in Greece.

We then headed to a different bay (“Love Bay”) near Poros. As we were sailing, Andreas calmly pointed out a pod of dolphins. Losing our ever-loving minds, we went shrieking to the bow and taped them jumping out of the water from afar. As we sailed in the area, they ended up swimming alongside our boat, jumping out of the water and even swimming under it and spinning around. Before we left the US, Jenny had jokingly demanded that as MOH, I needed to make sure she saw dolphins on the trip. YOU’RE WELCOME. 

While I think the dolphins were always going to be the highlight of the day, Andreas found a cave for Jenny, Jordan, Anna, and Finn to explore. Finn, Jordan, and Anna’s majestic dives were followed by a little sploot from Jenny. Unexplored caves aren’t really my scene, so I stayed on the boat with Trixie, Faith, Emma, and Andreas in a supportive capacity.

And by supportive, I mean we left them for a bit and when we returned, we realized they had to tread water the whole time because the cave floor was covered in urchins. Free gym, you’re welcome.

After collecting the cave explorers, we dropped anchor in the the bay. There was a boat that apparently had dropped anchor incorrectly which affected where we could drop anchor, resulting in an extremely entertaining yelling match between Andreas and the people on the other boat. Andreas was in the process of calmly and intelligently detailing the mechanics of anchor-dropping for us when he broke into a yelling match with the other boat, pushed his glasses up, and gave what I can only describe as a shark-eyed glare, and then calmly finished what he was saying to us. 

At one point, Jordan and Jenny decided to go investigate a small beach on the side of some rocks. I was offered a ride on Jenny’s stand-up paddle board like the first-class citizen I am, and Trixie swam along. While I provided excellent services as a rudder, I was rewarded by a slow-motion crash into some shallow rocks covered in urchins. Well, it may have been less of a crash than an incredibly slow light bump into rocks. Still—covered in urchins! Another day, another brave survival. 

Once we had our fill of swimming and narrowly surviving a harrowing urchin attack, we went back to the boat and Finn began cooking a series of delicious dishes for dinner with Faith assisting. There was spicy spaghetti, salad, some sort of bruschetta situation, and fancy pita. Once again, I assumed a supportive role and participated by eating the food. After dinner, Jenny, Jordan, and Anna opened mason jars full of all of their friends’ memories and read them out loud. When I told them that I would email them the memories and they didn’t have to keep the paper notes, Jordan said some things are okay digitally, but this was touching enough that he wanted the physical reminder. Don’t mind me while I cry forever. 

Later that night, Andreas went for a late-night swim in the dead of night, prompting Anna to get in, followed by Trixie, and then finally followed by me. I think I’ve come a long way from not wanting to touch ocean water to swimming in the sea at 3am and talking about whale’s mating habits and having a blast.

Day 6 (Thursday)

I woke up on Thursday to the smell of fresh coffee. Finn, thank all the gods in the sky, had put hot water and instant coffee out for us. I typically chain-drink coffee, so after more than 24 hours without, coffee was a medical necessity. 

As we all sat on the deck, relaxed, and sipped coffee with the sparkling water around us, I took the opportunity to capture the moment. Our surroundings still felt a little surreal, almost too beautiful to accept as reality. 

We dropped anchor at Moni, an absolutely breathtaking beach and island. Andreas, once again proving that he is the GOAT, arranged us on the boat, physically rowed out in the dingy for the proper angles, and spent the better portion of half an hour getting the perfect poses and lighting, furiously paddling back when he started to drift. I’d like to think we aren’t the most vain group he’s ever had, but he seemed to like us, so we must have had a few redeeming qualities. 

After making friends with a man and his dog who rode on our paddle board for a bit, we went to shore, Jenny and Jordan followed a peacock and Finn and I walked to the breathtaking overlook where you can see clear blue bays below and the other islands staggered on the horizon. The overlook is only about a 2-3 minute walk from the beach bar and well worth the time to check it out.

After we finished at Moni, we went to Aegina, land of the pistachio. 

We were finally successful at finding ATVs, and when we asked what time we had to be back, we were told in 1 hour…or two hours…or 5 hours…or whatever. Taking the cue, we just told them we would be back before they closed. We took the map of the island offered to us and set off. As Trixie started asking where to turn, I realized that I was the de facto navigator since we were in front. Quickly realizing that the map had no street names, I pulled out my iPhone, set the address of our first stop, the Temple of Aphiaia, and thanked god for Verizon Travel-Pass.

We got to the temple a few minutes too late (!!!), but you can actually see the temple pretty well from the gate around it. After that, we drove to the Monastery of Saint Nektarios. We couldn’t go in, but it was beautiful from the outside and the drive there on the ATVs was stunning. 

Then we drove around Perdika, a beautiful area on the water. There were lots of beaches and overlooks, though we took a wrong turn down a side street at one point. This elderly lady came running out of her house yelling at us in Greek and standing in front of the ATVs. Two of the ATVs couldn’t reverse, so we were trying to go forward to turn around, but I don’t think she understood. I think she was trying to help, but we ended up kind of scooting her out of the way by nudging forward incrementally on the ATVs. We appreciated the spirit, in any case, and then flew back down the highway to return the ATVs between the prespecified 0 and 6 hours. 

We had dinner at Dromaki, our final dinner with Andreas (still over here crying forever). This place is clearly 5 star dining and it’s so close to the water that the floor is just sand. Faith made me proud and sweet-talked the waiter into giving us free dessert for the birthdays that the group had. 

Day 7 (Friday)

We went out and grabbed a quick breakfast on Aegina at Coiffures, a breakfast-lunch cafe with Victorian décor. Unsurprisingly, it was phenomenal. 

Then Andreas told us he had a surprise for us, and took us to a beach populated by ocean-drinking goats. Excited to go explore, we set out with a few people swimming, Jenny and Jordan on a paddle board, and me, Faith, and Emma on a second paddle board. As we got closer, we realized that the entire ocean floor by the beach was covered in urchins. While the rest of the team continued to look for a way onto the beach and Faith adopted a can-do attitude, I immediately took a “nope nope nope” approach and turned us right around. Bai. 

After everyone else gave up on the urchin-infested beach and joined us back on the boat, Andreas told us about our real surprise: dragging us on the buoys behind the boat. Yes please!

First up was Jenny and Jordan. While Jenny looked like a majestic mermaid flying above the water, Jordan looked like he was being waterboarded. While we recorded him and laughed hysterically as he flopped around, Andreas, with his characteristic responsibility and patience, tried to instruct Jordan that “the important thing is to keep your head out of the water!” On cue, Jordan immediate flipped underwater, scrambling for his grip and gasping as he popped back up. Again, we could barely hear Andreas’ helpful instructions over our own cackling (#FriendshipGoals).

Instant karma hit soon enough, and all of us experienced a variation of Jordan’s experience. While it may not have looked pretty, it was an amazing send-off from Andreas and we were all already nostalgic about the trip as we finished up.

Sadly, Andreas had to take us back to dock in Athens for the night, and worst of all, leave us to go scaptain for a new crew. He hugged us all goodbye, had a last drink with us, and promised to take good care of Stavros. Some birds have to fly free. 

Based on local recommendations, we finished our night with a fancy dinner at Ellados Eikones, a modern tavern with charming curb appeal and live Greek music.

Day 8 (Saturday)

We left the boat for good in the early am and said our goodbyes since Jenny, Jordan, Finn, and I were staying to explore Athens and everyone else was leaving for the airport. We had all gotten very close and still keep in touch (and periodically harass Andreas as well). Best crew ever. 

We actually arrived at the Airbnb in Athens as the previous occupants (several elderly Canadians) were leaving. They were very annoyed that Jenny had spoken with the owner and the owner had allowed us to store our luggage early. In what I considered the ultimate act of restraint, Jenny politely made conversation instead of telling them it sounded like a personal problem. We disengaged from them and got a cute breakfast around the corner with fresh fruit smoothies and brunch. The whole area was extremely adorable with artisan pop-ups encasing cobblestone streets, and decorative trees and cafes behind them. 

When we actually went up to the apartment, it was so ridiculously cute. The Canadians had left a list of complaints so dramatic that we made fun of it for a bit before heading out to see the Parthenon. 

It was 100 degrees outside so Jenny and I stopped at a smoothie shop but the smoothies were made almost entirely of Greek yogurt, which wasn’t exactly the thirst-quenching beverage I had in mind. Still, we stopped for a few pictures with the Parthenon in the distance. 

The Parthenon itself is so high that there was a blissfully nice breeze every now and then. It was absolutely packed, but I’m so glad we did it. They clearly respect and preserve their history in Greece and it was wonderful to experience it with Jenny, Jordan, and Finn. Jenny and Jordan have always have such a love for adventure, an intelligent curiosity about history and culture, and an appreciation for how lucky and valuable these experiences are that you just can’t but enjoy the infectious enthusiasm. Now that I’ve met Finn, I also definitely include him in that description. We grabbed a few photos before a top-heavy woman in tight bicycle shorts bent over and removed a bit of grandeur of the moment.

Once we were finished, we briefly stopped for some frozen lemonades, which was exactly what I needed. Afterwards, we went in search of AC, and decided on the Acropolis Museum. My feet were killing me by this point, but the displays were so beautiful that we all kept going. The first floor is covered in glass, and you can see straight down into the ruins of an ancient community. We asked an attendant how to get down to that level (there is a separate outdoor entrance), and went down to investigate.

You can actually see the colors on the mosaic floors of what used to be someone’s home, the layout of the bath houses, and multiple community centers. We ended up seeing a brief video explaining the history of the excavation, and it turns out they built the museum on top of the ruins to be able to display it appropriately. The excavation and preparation went from 1997-2019, and had just opened. We couldn’t believe we had stumbled onto such a find. 

After finishing at the museum and feeling pretty successful for the day, we ate a few gyros and walked back to the Airbnb. We relaxed and watched a movie before going back out to pick up groceries and pastries for Jordan’s birthday. I couldn’t believe how cheap the pastry place was, full of fresh bread and brightly-decorated desserts. I think we paid around $9 for 5 items. The groceries were also incredibly inexpensive—I’ve never seen a candy bar for $0.19 before. 

We got dinner to-go (gyros and stuffed peppers), and went up to the rooftop deck to view the Parthenon at sunset. We recapped all the amazing parts about the trip and all of the reasons Finn and I love Jenny and Jordan. With some people you just know instantly that they’re your people. 

Drinking wine on top of a building with a clear view of the acropolis as it began to light up for the night, I couldn’t help but think about how lucky I am to see these marvels of the world but how infinitely luckier I am to be in the lives of the people I love.