Trip Reports

Since starting this website, I’ve documented my Greece trips with (mostly) daily blog posts. You can find each one linked at the top of the page under the Trip Reports menu heading. I’ve summarised each one below.

1. 1. 2017 Cyclades Tour: Andros, Tinos, Mykonos, Naxos, Paros, Ios, Santorini & Crete

Back in 2017, I embarked on my very first island-hopping adventure, and what a whirlwind it was! Over 18 days, I packed in an ambitious number of islands—probably more than I should have—but the journey began with a bang. The first three stops—Andros, Tinos, and Mykonos—were an unforgettable sprint with my friend Ed. With only a few days to spare, we crammed in as much as possible, spending just one action-packed night each on Tinos and Mykonos. It was a fast-paced, unforgettable start to an epic trip!

2. 2. Mini Cyclades 2018: Mykonos (including Delos), Naxos (twice) and Koufonissi

In 2018, I had the chance to return to Greece with my friend Ed, though, as before, he could only join me for the first four days. I made the most of his short stay, and after he left, I extended my adventure for another unforgettable week. Flying straight into Mykonos from the UK, we dove headfirst into the Cyclades. From there, we explored the charm of Naxos before Ed headed home, leaving me to continue solo to the dreamy island of Koufonissi.

A bit of last-minute planning led me back to Naxos for a few more nights, followed by a ferry ride to Mykonos to catch my flight home. While the trip was fantastic, I can’t help but wish I’d mixed it up a bit—Paros would have been the perfect alternative for those final days. Still, it was another incredible chapter of island-hopping in Greece!

3. 3. Amorgos 2019: Mykonos, Naxos and Amorgos

Does this trip qualify as “island-hopping”? That depends on how you define it—technically, we only stayed overnight on Amorgos! Our journey began with a flight into Mykonos (convenience wins again), followed by a brief stop on Naxos to catch the connecting ferry. So yes, we did set foot on three islands, even if two of them were fleeting visits!

Though it was my shortest Greek getaway, having Ed along for the entire trip was a refreshing change. We split our time on Amorgos between three nights in Aegiali and two in Katapola, fully immersing ourselves in the island’s charm. This adventure also marked a shift in timing for me—setting off at the end of May 2019, earlier than I usually travel. The result? A quieter island, with pleasantly mild sunshine, and perfect weather for hiking. Amorgos may not have been hot, but it was an absolute gem to explore!

4. 4. Cyclades 2019: Santorini, Folegandros, Naxos and Mykonos

If you haven’t guessed by now, I’m a little obsessed with the Cyclades! The ease of island-hopping there was too tempting to resist, so just weeks after my trip to Amorgos, I was back—but this time with my girlfriend instead of Ed. With less focus on hiking and more on relaxation, it turned into a completely different kind of adventure.

We kicked things off with three nights in Santorini, which I enjoyed far more than my first visit in 2017—having company made all the difference. From there, we ventured to a new gem, Folegandros, for another three nights. The charming accommodations, incredible food, and peaceful vibe made it a highlight for both of us.

The final stretch took us to Naxos for six nights, which was as fantastic as ever. Sadly, the trip ended on a sour note when bad weather over Gatwick delayed our flight home, forcing us to spend an unplanned night on Mykonos. But even with the hiccup, it was a memorable and refreshing getaway!

5. 5. Western Cyclades 2020: Milos, Sifnos, Serifos, Syros and Andros

Despite the challenges of travel restrictions during the COVID-19 pandemic, I was fortunate enough to squeeze in a 16-day adventure to Greece in early September 2020. This was yet another Cycladic escape, but with a twist—aside from Andros, every island I visited was completely new to me.

The journey began in Athens, where I took my very first internal Greek flight to Milos—a game-changer that was so much faster and easier than the ferry from Piraeus. From there, I hopped to Sifnos, which quickly became my favourite Greek island, followed by the rugged beauty of Serifos and the elegant charm of Syros.

I travelled solo for most of the trip, soaking in the unique vibe of each destination, before reuniting with Ed on Andros for a relaxed final few days. It was a trip full of new discoveries and a much-needed escape during a turbulent year.

6. 6. Greek Odyssey 2021: Crete, Karpathos, Rhodes, Tilos, Kos, Amorgos, Naxos, Ios, Sikinos and Sifnos

After years of honing my island-hopping skills with various short and medium-length trips, I finally took the leap: I quit my full-time job to embark on an extended adventure through Greece. What followed was a 73-day odyssey that began on Crete, wound through the Dodecanese, and—naturally—brought me back to the Cyclades.

While I revisited some familiar favourites, this trip was all about new discoveries. I explored the rugged beauty of Karpathos, the serene charm of Tilos, the lively energy of Kos, and the quiet allure of Sikinos. I also ventured into parts of Crete I’d never seen before, uncovering hidden gems along the way.

It was an unforgettable journey, one that fueled my wanderlust and inspired an even longer adventure in 2022. Greece truly has a way of drawing you back for more!

7. 7. Greek Odyssey 2022: Mainland Greece (Peloponnese), Paros, Astypalea, Kos, Amorgos, Ios, Crete, Aegina, Agistri, Athens and Sifnos (yes, again!)

While parts of this trip echoed the previous year—return visits to Kos, Amorgos, Ios, and Sifnos—it was packed with exciting new experiences that made it truly unforgettable. For the first time, I ventured into mainland Greece, exploring the wonders of the Peloponnese. From Kalamata to the medieval charm of Mystras, the dramatic landscapes of Mount Taygetus, the fairytale-like Monemvasia, and the turquoise waters of Elafonisos, every stop was a revelation.

The adventure didn’t stop there. I added three new islands to my list—Astypalea, Aegina, and Agistri—and finally ticked Athens off my bucket list, diving into the iconic city centre and its ancient history.

Ending the journey on Sifnos felt like coming full circle, but this time with a special twist: my girlfriend joined me in Athens and visited my favourite island for the first time. It was the perfect finale of an incredible trip.

8. 8. Sifnos 2023: Sifnos

After years of raving about how much I love Sifnos, my friend and travel companion Ed finally decided he had to see it for himself. So, in late June 2023, we set off on a trip to explore my favorite Greek island together. We spent five incredible nights discovering the island’s hidden gems, from stunning beaches to charming villages, and I even ventured down hiking trails I hadn’t experienced before. It was the perfect opportunity to share my love for Sifnos with Ed, and we made unforgettable memories along the way.

9. 9. Santorini, Milos and Kimolos 2024: Santorini, Milos and Kimolos

In May 2024, I set out on a quick but purposeful trip to Greece, aiming to create fresh content for this website and my growing GreeceTravelGuide YouTube channel. Crafting a practical and budget-friendly itinerary wasn’t easy, but as detailed in the ‘trip planning’ posts that kick off this series, I pieced together an exciting and efficient plan I couldn’t wait to execute.

The adventure focused on two iconic islands: Santorini and Milos. Although neither was new to me, I hadn’t yet produced island guide videos for them, and their immense popularity made them perfect additions to my channel. While plotting the Milos itinerary, I noticed an irresistible opportunity—visiting nearby Kimolos! And just like that, the trip evolved into a three-island escapade packed into a compact timeline. I couldn’t wait to bring these stunning destinations to life for my audience!

10. 10. Ios 2024: Ios

In July 2024, with a free week and Greece calling my name, I faced the ultimate question: where to go? Limited flight options and sky-high prices narrowed my choices, but the cheapest routes—surprisingly—to Santorini and Mykonos gave me a perfect excuse to revisit a favourite.

After ruling out other islands I’d explored in recent years, Ios emerged as the clear winner. Having spent 12 relaxing nights there last summer, I knew exactly what to expect—a laid-back escape. This time, I’ll fully document the trip for my Greek Adventures series. The twist? Flying back from Mykonos instead of Santorini, thanks to a cheaper return ticket. Another island-hopping adventure awaits!

11. 11. Mykonos and the Lesser Cyclades 2025: Mykonos, Naxos, Donousa, Koufonisia and Iraklia

Just a few weeks into 2025 and plans for my next island-hopping trip are already taking shape. I’ve been wanting to visit some of the smaller islands surrounding Naxos ever since I missed out on seeing them in 2021.

This trip begins with three nights on Mykonos. While it’s not my favourite island, I’ve also never really spent time exploring it and this felt like the right opportunity to see if there’s more to it than overpriced hotels and fancy beach clubs. I’ll then head to the much quieter islands of Donousa, Koufonisia and Iraklia before one final night on Naxos.