Estimated reading time: 11 minutes
There are a few places on this Earth that offer an opportunity so captivating that you’ll want to stay forever. If only to experience the joys and delights that each new experience has to offer.
Island hopping, the dream holiday, the type of vacation that lets you feel like you visited ten destinations instead of one. Moving from one island to the next, indulging in the vibrancy of one and soaking in the relaxation of another. Of the few places where this dream is possible, Heraklion Crete is one of the best. The ideal place to stay—and the one I always return to between ferry rides—is Lato Boutique Hotel, just a 10-minute stroll from the port. Its comfort, style, and sea views make it the perfect harbor between adventures.
The islands surrounding Crete are laid out in such a systematic way that it would almost be silly not to take a visit to some of them. From Heraklion, you can travel to some of them and be back for supper. But there would be almost zero fun in that, so I planned my trip wisely. Whether it was for a whistle-stop day trip, one night, or a few idle days, I was ready to embark upon a seafaring adventure, and the islands were calling.
Heraklion to Santorini – Blissful Views & Epic Sunsets
Duration: 2 hrs | Ideal for: Day trip or overnight
After a delicious seafood meal had had an early return to the sea, I made sure to remember to pack my seasickness wristbands in my trusty 40l backpack that would see me through my array of ferry trips. They might well be a placebo, but if using them meant the contents of my stomach would stay put, I would be happy to wear a dozen on each arm. They seemed to work a charm on the ferry over to Santorini, and I merely had to hold back excitement as we docked into the port.
It wouldn’t be right to travel on an ‘island-hopping adventure’ in Crete and miss out on Santorini and the beautiful coastal town of Oia (pronounced “ee-a”). Many people may not have heard of Oia, but they will most probably recognize the quaint snow-white buildings and blue-domed church roofs of Agios Spyridonas and Anastaseos that mark this coastal paradise as unique. Hailed as one of the world’s best honeymoon destinations, I was curious to discover for myself what made Santorini so special, and it wasn’t long before I found out.
There wasn’t a single thing that made Santorini stand out from the crowd. There were a million. A dozen ways I wanted to shout from the rooftops about romantic restaurants with seafood, local wine varieties and well-organized wineries to visit, the art galleries, the Greek gold jewelry shops, the spaghetti street food, and the glass bottom cruise to the volcano. A thousand ways I marveled at the rugged scenery and unique beaches formed and sculpted by a volcanic eruption now long past.
Seeking the famed sunset on my first evening, I perched on the ramparts of a building behind the church to enjoy the show. The last of the sun’s rays warmed my back and set a golden glow over the sea. I watched a million ways the sunlight danced on the ocean at sunset, creating the most remarkable scene that blazed into vibrant color, lasting until the giant red ball finally dipped completely under the horizon. As the temperature dropped, so did the breeze, and I felt almost as if all the air had been sucked out of the world and left nothing but stillness in its wake. It was all part of the magic as I witnessed the last of the color seep out of the sky. To be replaced with stars that quietly popped into life among the dark blanket. If your trip to Santorini doesn’t end in such spectacular fashion, that’s surely just one of the reasons to return to this astonishing place.
Santorini is the only island destination close to Crete where you can go and come back on the same day. It is only 2 hours on the ferry with a 7-hour stay on the island, though if you want to truly relax and enjoy the sunset it’s better to stay overnight. You‘ll have the chance to hike from Fira to Oia…along the rim of a caldera! Read more about Santorini in this article.
Naxos, Myconos, Ios, or Siros?
The Aegean sea is packed with mesmerizing islands, including Paros and Naxos. Both have that truly laid-back vibe, beautiful beaches, and are a stone’s throw away from each other, so I literally had to flip a coin to choose one over the other this time, and leave something to look forward to on my next trip.
Heraklion to Naxos: A Peaceful Contrast
Duration : 3hrs
Naxos is the kind of place you wish you could find on every street corner. A place of good food, beautiful nature, and a sort of sleepy atmosphere that calls up the sentiment of ‘the good life. Naxos almost feels like it’s not part of Greece at all. The view of the island as I approached was reminiscent of Mont Saint-Michel in France, the white houses looking like a tiny kingdom. Everywhere I went I was followed by the unique smells and delightful aromas that permeated the air, such as oregano, rosemary, and lavender. Local herbs were a pinnacle of the love and passion injected into every dish. I didn’t resist the taste of the island’s famous gruyere – traded from antiquity – and the citron liqueur made from the leaves of citron trees.
One of my many plans was to discover the gate-like palatial ruins of the Portara, an unfinished Apollo temple that gazes over Naxos. Part of the fun was getting to cross the narrow neck of land that leads between the mainland and the harbor. I was getting splashed left and right by the punishing waves as they smashed into the narrow causeway, and with every new wave, I caught a case of giggles before I stepped finally into the entrance at the huge gates. I had fun hopping in and out of the framed doorway to take selfies on my tripod, before retiring and picking my way carefully back down through the ruins and taking a dip in a natural swimming pool I had spotted on the way up the path.
Naxos has a plethora of great things to do. Hike the Zas mount or the Apano Kastro, visit its picturesque villages, windsurf at Agios Prokopios beach. I’d heard word on the wind of an ideal paradise in the South West. So I made the effort of taking a bus from Chora to reach Aliko beach. When it comes to beaches, I’m down for any kind. Some people aren’t a fan of the pebbly kind, but I love them. There’s nothing better than the gentle massage that you get from the tiny rocks under your feet, and it’s so much easier to avoid getting sand stuck in all the places where the sun doesn’t shine. Though I had to admit, the perfect white sand of Aliko, backed by an aquamarine ocean that carved a perfect bay was just divine. The lush Cedar forest and tiny church that resembled a cute little marshmallow only added to my pleasures as I wandered around with a grin like a child seeing the sun for the first time.
Heraklion to Mykonos: Party & Glamour
Duration: 4 hrs (faster in high season)
As I was merely a hop skip and a ferry away, it wouldn’t be right to head to go on an island trip without discovering Mykonos. The 4 hour trip from Heraklion to Mykonos gave me time to refresh my expectations and prepare for the wild island.
If Naxos was the head side of the coin, Myconos would be tails. Though in the landscape these islands seem similar, with gorgeous beaches and picturesque rugged landscapes, the culture on the land couldn’t be any more different. I’d passed from the cheap, laid-back attitude and walks on beaches like Agios Prokopios that lasted to the end of time on Naxos, to the wild and vibrant realms of Myconos.
As a perpetual solo-traveler, I often find myself dining alone in restaurants, but something like that seems almost illegal in a place like Myconos. I had been on the island only a brief time and had followed the captivating smells to a local restaurant serving anything and everything that hailed from the sea. Before I knew it I was laughing merrily and sharing shots of raki with a group of people I had never met before, but am since sad to never see again.
One of my favorite parts of traveling is getting to feel like ‘family’ with strangers. To be invited into a life I’m not familiar with, to feel at home in places and lives so different from my own. Myconos was one of these places. After a few shots of raki, my mind becomes pretty hazy, but I recall the taste of kopanisti which was new to me; a hot, salty, and peppery cheese with protected designation of origin. I’m pretty sure I polished off the whole thing, dipping in crisp flatbreads and amusing my new friends at my terrible pronunciation of Greek foods like ‘loukoumades’. This is where memories were paused to start again the next day! I was at the ‘Island of the winds’ and among the world’s richest tourists. Everyone was stylish and everything was built on luxury and simplicity.
Take a walk on Matogiannia pebble-street and you’ll see what I mean. If you have time visit the windmills, the Little Venice, or even hop on a ferry to Delos island (30min sail and 90 min of guided tour).
When it comes to Greece, the laid back lifestyle is always of utmost importance, and as I gazed into the starry night, laid out with a blanket on the beach on my second night on this welcoming island, I felt thankful that I had at least had one more day to explore and discover the fabulous architecture, roam the streets full of local shops and treasures, and perhaps one or two more of the vibrant beach bars. Slow travel is life for me.
Heraklion to Ios: Sunset & Seven Beaches
Duration: 2hrs & 45 min
An island of two faces, Ios is a tiny, hilly island halfway between Naxos and Santorini. A place that seems like stepping into a perpetual spring break during the busy season, and a provincial Greek paradise any other time. From July to September the island is full of revelers seeking out the best bars and the wildest nights. I was in a whirlwind of excitement..and had 24 hours to exploit this place. What’s best than a morning boat tour in seven beaches (!) and watch the sunset from Panagia Gremniotissa as night began to fall? The lights of the city would pop into life and with a great exuberant roar, and the island was alive! It was fun to let my mind loose for a single night, hopping from place to place testing cocktails and titbits. In the morning, I was ready for my hazy return and a few lazy days back in Heraklion.
Tip: If you stay more than a day take a day trip to Sikinos island too.
Heraklion to Syros: Art, History & Neoclassical Charm
Duration: 6hrs
If there’s one island that somehow manages to pack the best of the Greek experience all into one, it’s Siros. The pastel-hued villas on Syros are just one of the things that set this island apart. The sweeping shades of color on Ermoupoli Hill glisten under the Aegean sun as soon as you reach the port. I almost felt like I must have dozed off on the ferry and unexpectedly turned up on the Amalfi coast in Italy!
You can tell that this is a place that once attracted such finery, the sophisticated landscape is bursting with museums, art centers, and impeccably good restaurants, and yet it’s still cheaper and quieter than Santorini and Mykonos. I had a blast wandering around the two towns (one Orthodox and one Catholic) of Siros and soaking up the local Cycladic culture. Marveling at neoclassical buildings such as the Plateia Miaouli and the stunning Apollo Theatre. It gave me a welcome reminder of the sheer amount of history that is alive and well on the Greek Islands.
Move over Santorini, Siros has an iconic church of its own. The blue dome of Agios Nikolaos Church is almost more lovely than the one in Oia as it contrasts perfectly with the pale yellow walls that seem to rise strikingly straight up out of the cliff rock. My photography eye was twitching as I peered up at the dome from Asteria Beach. I made a bee-line for the welcoming water to capture a striking shot with my underwater casing. Half church, half ocean, all beauty. It’s funny, the ocean was pretty freezing and I waded into my waist to get the shot, but the excitement meant I hardly noticed at all and the rush of adrenaline I got from the opportunity was second to none – it’s the kind of thing I live for.
Tip 1 – Syros is famous for its loukoumia sweets and SanMihalis cheese. Ah! And Markos Vamvakaris, the father of Rempetiko music!
Tip 2 – Arrive on Sunday, return to Heraklion on Monday, or go on Friday and come back on Saturday.
Heraklion to Tinos: Faith, Food & Surf
Duration: 6hrs
The first thing I noticed about the enchanting island of Tinos as my boat pulled into view of the small island in the Cyclades was the imposing church at the top of the hill across the port. Saint Mary’s church. The most famous symbol of the Greek Orthodox religion after Ayia Sofia in Istanbul. I was impressed by the contemplation of the faithful who entered with tears in their eyes. I was also impressed by the view of the marble stairs that were carved in the middle from the steps of millions of people who had stepped on it. Entering the church one will also notice the decorations of millions of ‘tamata’ (offers of gratitude from believers for the miracles that occurred after a pray). Following this experience…rest was ordinary.
The pure blue of the sea seemed to dance all across the island, reflecting from the little square windows and giving everything the feeling of tranquility. Of course, the window shutters are actually painted blue, but the effect was quite mesmerizing on this sleepy Sunday.
In Tinos, it was all about the food (the island of foodies they say), hiking, surfing, and wild beauty.
The first thing on my agenda was a bite to eat. Tinos is 6 hours from Heraklion and I’d worked up an appetite. I found a sweet little cafe and sat with a coffee and enjoyed a local dish of sea bass fillet with chickpeas & Tinos beans, and artichoke pie, under the shade of the sycamore trees and a view of the blooming purple wisteria.
‘Panagia tis Tinou’
Every time I visit a new place, It almost immediately becomes a new favorite, fueled by some quirky cultural significance or a general sense of awe. In Tinos, it was the strange and beautiful Peristerones! As you reach the layered hills on a hike through the flourishing landscape of Tinos, these buildings seem to pop up all over the place. The whitewashed limestone Dovecotes are actually housing built for the many local dove and pigeon colonies, but the structures themselves are covered in lithographs and intricate detailing. I admired hundreds of them as I hiked through the layered plains, occasionally catching sight of a grand eruption of life as the birds tore from the structures and took to the skies in majestic flight.
The hiking paths on Tinos became a fast favorite as I didn’t know what to expect, and after every turn and over every crest I found little delights. Fascinating ruins, fountains, pretty windmills, chapels, and of course the elegant Peristerones dotted infinitely among the green valleys. I also definitely suggest the Chora – Ktikados – Kionia trail.
The morning after, I felt rejuvenated, as though the mountain air had rushed through me and opened up every limb ready to greet a new day. It was just as well, because I was once again about to try surfing, and I needed all the strength I could get. I rocked up pumped and ready to meet my peers at surf school on Kolymbithra Beach in the South of Tinos. It was a moderately windy day and the cresting waves were reaching a modest 4 or 5 feet at their peak, perfect I thought. As a short lady, the thought of battling a wave higher than me was a little terrifying. By noon, I was spent, having managed to stand up a grand total of once, and felt equally refreshed and exhausted and laid out on the sand in my wetsuit gazing into the clear blue sky.
Being a castaway on an island as beautiful as this sounded like the kind of bargain I would be more than happy to make, but being a Crete veteran at this point, I know it’s smart to leave a few days on the mainland at the end of my trip in case of schedule changes. Alas, I spotted the recognizable shape of the ferry careening towards me that evening, and I sighed. I had to leave paradise after all. But, all that meant is that I would have to come back soon.
Tip – If you stay longer, try a day trip to Andros island. It is only a 90min sail!Back to Heraklion, Crete –
Where It All Begins
As my journey drew to a close, I found myself back in Heraklion, the steady anchor to all my drifting adventures. Each island had offered something unique—sunsets, flavors, friendships, thrills—but it was the return to familiarity that made the experience feel complete. Settling once more into Lato Boutique Hotel, with its calming view of the Cretan Sea and its comforting rhythm of city life just outside the door, I felt a quiet joy. It wasn’t just a place to stay—it was a gentle transition between the dreamlike islands and the grounded beauty of Crete. And like the tide, I knew I’d be back again soon.
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