Greece is a dream destination where whitewashed villages spill down volcanic cliffs, sunsets paint the sky in hues of pink and gold, and the food is as divine as the scenery. When I set out on my 16-night island-hopping adventure, I was ready for all of it—the gorgeous Cycladic islands, vibrant culture, rich history, and of course, the mouthwatering Mediterranean cuisine. My journey took me to Santorini, Naxos, Paros, Milos, and finally, the bustling city of Athens. Whether you’re planning a romantic getaway, a solo trip, or a family vacation, this itinerary covers all the must-see spots.

Table Of Contents

1. Santorini: A Postcard-Perfect Greek Island
2. Naxos: The Underrated Gem of the Cyclades
3. Paros: A Blend of Tradition and Trendiness
4. Milos: A Rugged Paradise Full of Hidden Gems
5. Athens: A Cultural and Historical Finale
🛏️ Recommended Stays for Your Cycladic Island-Hopping Adventure
Final Tips for Island Hopping in Greece
Final Takeaways

Our Travel Route

We started our journey by flying from Toronto Pearson International Airport (YYZ) to Athens International Airport (ATH). From Athens, we booked a separate flight to Santorini, where our island-hopping adventure began. To travel between the islands, we used Ferryhopper to book our ferry rides in advance—highly recommended if you’re traveling in August, Greece’s high tourist season.

Greece Travel Itinerary Overview

Flight: YYZ ➡️ ATH
Flight: ATH ➡️ Santorini
Ferry: Santorini ➡️ Naxos
Ferry: Naxos ➡️ Paros
Ferry: Paros ➡️ Milos
Ferry: Milos ➡️ Piraeus (Athens)

⛴️ Tip! Book ferry tickets at least one month in advance through Ferryhopper to avoid sold-out routes—especially during peak season. We used the platform ourselves and loved how easy it was to compare prices and schedules.

👉 Start planning your Greek island-hopping adventure with Ferryhopper—our go-to for reliable, user-friendly ferry bookings.

1. Santorini: A Postcard-Perfect Greek Island

Santorini is one of those places that feels almost too famous — the kind of destination you’ve seen in a hundred photos before you even land. I wasn’t sure if it would live up to the hype… but it really did. The views were unreal, the cliffs dramatic, and every corner looked like it belonged in a glossy travel magazine.

But what surprised me was how much more there was beyond the blue domes and sunset selfies. There were peaceful villages, hidden beaches, incredible food, and a vibe that felt both romantic and raw at the same time. It was beautiful, yes — but also layered, lively, and so worth the five nights we gave it.

Where We Stayed: Hotel Sunshine (5 Nights)

We spent five nights in Kamari, a charming village known for its relaxed vibe, black sand beaches, and crystal-clear waters. Staying away from the crowded tourist hubs of Oia and Fira allowed us to enjoy a more peaceful experience while still being close enough to explore the popular spots and saved us a lot of money!

Our hotel, Hotel Sunshine, was a perfect choice, located right on the beachfront with stunning sunrise views every morning. The staff were friendly and helpful, making our stay even more enjoyable. Plus, the free sun loungers were a welcome bonus.

🩴 Tip! Bring water shoes—the black sand heats up quickly under the scorching Greek sun!

Exploring Santorini: Iconic Views, Hidden Gems & Nightlife

Oia’s Dreamy Sunsets: We kicked off our Santorini adventure with a visit to Oia, and yes — it really is that stunning. The views over the caldera cliffs, the whitewashed buildings, and the famous blue-domed churches are everything you’d hope for (and everything Instagram promised). But here’s the thing: Oia gets packed. We made sure to arrive early to wander the narrow paths and soak in the scenery before the crowds rolled in with their tripods and selfie sticks.

We spent the morning exploring the winding streets, browsing little boutiques, and stopping to take in the panoramic views around every corner. For lunch, we had an incredible meal at Strogili — a charming spot with terrace seating, great service, and a bottle of local Assyrtiko wine that we’re still thinking about. The food was fresh and flavourful, and the view was the kind that makes you put your phone down and just be in it.

If you’re planning to catch the sunset in Oia, bring patience and maybe a drink. It’s beautiful, but the crowds are intense — shoulder-to-shoulder at times. We preferred the early hours for a more peaceful experience, but either way, it’s a moment that feels like a dream.

Fira’s Authentic Vibe: Compared to the polished postcard perfection of Oia, Fira felt more lived-in, local, and energetic — and we loved it for that. It’s the bustling heart of Santorini, with narrow streets that wind through a mix of family-run shops, cafés, and boutiques. It felt like a place where real life was happening — not just staged for photos.

We spent our day exploring at a slower pace, popping into small galleries, grabbing iced coffees, and people-watching from shaded patios. In the evening, we made our way to PK Cocktail Bar, one of the best spots in town for sunset views over the caldera. We had a front-row seat with cocktails in hand, watching the sky turn pink and gold — a moment that somehow felt both glamorous and grounding.

Later that night, we went to The Greek Wedding Show — and honestly, it was a blast. Think live music, dancing, traditional Greek storytelling, and yes… actual plate smashing. It was lively, a little cheesy in the best way, and a great way to experience the island’s spirit beyond the beaches and views. Fira may not be as quiet as other towns, but it has soul — and that made it unforgettable. 👉 Book tickets to The Greek Wedding Show in Santorini here

Kamari’s Laid-back Atmosphere: During our downtime, we found ourselves drawn to the relaxed, easygoing vibe of Kamari — a beach town that feels low-key but still has everything you need. The black volcanic sand gives the beach a bold, dramatic look, and while the water wasn’t always calm, it was refreshing and made for some fun (occasionally splashy) swims.

What we really loved was the beachfront promenade. It’s lined with cozy tavernas, cafés, and cocktail bars that start buzzing as the sun goes down. We’d wander along the water, stop for a glass of wine or a casual dinner, and just enjoy the laid-back rhythm of the town. Kamari isn’t flashy, but that’s what makes it easy to love — it’s the kind of place where you can truly relax and just take it all in, waves and all.

Where To Eat in Santorini: Culinary Highlights

Captain’s Corner: We loved this cozy taverna so much, we came back a second time — and honestly, I’d go again in a heartbeat. It’s tucked away in Kamari, slightly off the main strip, which makes it feel like a local secret. The food is classic Greek comfort: perfectly grilled meats, fresh seafood, creamy tzatziki, and crisp Greek salads with tomatoes that actually taste like tomatoes. The staff is warm and welcoming, and the vibe is relaxed — it’s the kind of place where you settle in and linger over a carafe of house wine.

Almira Restaurant: Located on Kamari Beach, Almira offers a delightful selection of Mediterranean and Greek dishes, with an emphasis on fresh seafood. The beachfront setting provides a serene atmosphere for a relaxing meal.

Metaxi Mas: This was one of the most memorable meals of our trip. Located on a hill in the village of Exo Gonia, Metaxi Mas delivers both on flavour and views. The dishes are elevated versions of traditional Greek fare — things like fennel pie, smoked pork with vinsanto sauce, and grilled octopus so tender it basically melts. The view over the Aegean is dreamy, especially at sunset, and the atmosphere feels special without being stuffy. Make a reservation in advance — this place books up quickly for a reason.

Strogili: Located in Oia, this restaurant is all about the view. Grab a seat on the rooftop terrace and prepare for a front-row seat to Santorini’s iconic sunset. The menu features traditional Greek cuisine with a modern twist — think moussaka, fresh seafood pasta, and local wines. It’s a great spot for a romantic dinner or just a chill evening with epic scenery. It’s a bit more touristy than the others, but the view and atmosphere more than make up for it.
Kokkalo Restaurant: Located on the main road of Firostefani, Kokkalo serves authentic Greek cuisine in a welcoming atmosphere. It’s an ideal spot for those looking to savour traditional dishes while enjoying views of the surrounding area.

🚏 Tips for Santorini Travellers

Stay in Kamari: It’s ideal for food and bars without the heavy tourist crowds of Oia or Fira. The bus ride from Kamari to Fira takes about 15 minutes (€1.60), and it’s another 15 minutes from Fira to Oia for the same price.
Use Public Transport: The local buses are convenient and affordable, especially if you’re traveling between Kamari, Fira, and Oia.
Dining Out: Eating out is often cheaper than buying groceries, so indulge in the local cuisine!

Local Wine Tip: At grocery stores, you can fill plastic bottles with red, white, or rosé wine from large containers—affordable and fun!
Beach Note: Santorini’s beaches are beautiful, but they’re not ideal for swimming. If a beach holiday is what you’re after, consider visiting Milos or Naxos as well.
Airport & Transportation: Santorini’s airport is just a 15-minute drive from Kamari, which we arranged through our hotel for convenience.
Tourist Crowds: Before heading out, check the cruise ship schedule here to avoid the busiest days when large groups of tourists arrive.

If you want a blend of beautiful landscapes, cultural experiences, and fantastic food, Santorini should definitely be on your Greek island-hopping itinerary.

2. Naxos: The Underrated Gem of the Cyclades

Naxos felt like the kind of place that doesn’t need to shout to get your attention. It’s not overly curated or crowded — just naturally beautiful, quietly charming, and full of depth. From ancient ruins to mountain villages, sandy beaches to slow meals in the sun, it offered this really balanced mix of everything I love about travelling.

It’s a place that invites you to take your time, explore without an agenda, and see what you stumble into. Whether we were wandering through town, driving past goats on mountain roads, or watching the sunset with a glass of wine, it all felt refreshingly unhurried — and genuinely memorable.

Where We Stayed: Cozy & Convenient in Agios Georgios (2 Nights)

We spent two nights in a cozy Airbnb located in the Agios Georgios area. The location was perfect—just a 10-minute walk from the port, bus, and taxi stations, and within walking distance of top attractions like the Temple of Apollo and the Venetian Castle. 👉 Book your tour of the Venetian Castle in Naxos here

The neighbourhood was well-equipped with essential amenities, including a supermarket and a laundry facility, making it an ideal base for exploring Naxos.

Exploring Naxos: Beaches, Villages & Historic Sites

Agios Prokopios Beach: One of the best beaches on the island, Agios Prokopios is all about soft golden sand, clear turquoise water, and plenty of space to stretch out. It’s organized but not overly crowded, with sunbeds, beach bars, and restaurants lining the shore. It’s super easy to get to from Naxos Town, and the nearby village has a chill, laid-back vibe — perfect for a beach day that turns into dinner and drinks.
Temple of Apollo (Portara Gate): You’ve probably seen this in every photo of Naxos—and for good reason. The Portara is a massive marble doorway from an unfinished 6th-century BC temple, perched dramatically on a small islet just off Naxos Town. It’s connected by a short walkway, making it an easy (and unforgettable) sunset stroll. The views are stunning, the breeze is perfection, and the vibes? Pure Greek mythology meets golden hour magic.

Vallindras Distillery (Halki): While in the village of Halki, stop by this historic distillery that’s been producing citron liqueur for generations. A quick, free tour includes a tasting—and you can snag a bottle to take home (or “for home,” let’s be honest).
Plaka Beach: Plaka is one of Naxos’ longest and most beautiful beaches — think wide stretches of soft sand and calm, crystal-clear water that’s perfect for swimming. It’s a little quieter than some of the island’s busier spots, but still has enough tavernas and beach bars to keep you well-fed and hydrated. You can find both organized sunbed areas and more untouched stretches if you want to spread out with just a towel and a good book.

Agios Georgios Beach: Just steps from Naxos Town, Agios Georgios is the most convenient beach on the island — and it’s actually really lovely. The sand is soft, the water is calm and shallow (perfect for swimming), and there are tons of cafes, beach bars, and hotels right nearby. It’s a great option if you want a beach day without going far, or if you’re traveling with kids and want something easy and relaxed.
Chora (Naxos Town): Chora, the capital of Naxos, is the kind of place where you want to wander with no plan. The old town is full of narrow, winding alleys, white-washed houses, and hidden staircases that lead to tiny shops, bougainvillea-covered cafés, and locals going about their day. At the top, the Venetian Castle gives you a glimpse into the island’s layered history, while the Portara Gate, the massive marble doorway overlooking the sea, is perfect at sunset. It’s a mix of ancient ruins, everyday life, and that classic Cycladic charm — all in one place.

Mountain Villages: Renting a scooter and heading into the hills was one of the highlights of our time in Naxos. The mountain villages — like Filoti, Apeiranthos, and Halki — gave us a totally different side of the island. No crowds, no beach bars, just quiet stone streets, traditional tavernas, and glimpses of real, everyday life.
Filoti is built amphitheatrically on the slopes of Mount Zas and has a lively little main square where we stopped for coffee under a huge old plane tree.
Apeiranthos felt almost like a mountain fairy tale — marble-paved alleys, Venetian architecture, and a proud local spirit that you can feel as you walk around.
Halki is smaller but full of charm, with local shops selling olive oil, citrus liqueur (Kitron), and handmade textiles. We wandered slowly, stopped for lunch, and just soaked it all in.

If you want a break from the coast, the villages are where you’ll find the heart of Naxos.

Where To Eat in Naxos

Boulamatsis: A must-visit in Naxos Town, especially if you can grab a seat upstairs for the sunset view over the port. The menu is full of Greek favorites — grilled meats, fresh seafood, and a few house specials — all served in a laid-back, friendly setting. We came for the view but stayed for the food (and maybe a second carafe of wine).
To Elliniko: This is one of those places where everything just feels done right — the food, the service, the atmosphere. It’s Greek cuisine with a modern twist, tucked away from the tourist crowds. We loved the stuffed zucchini flowers and slow-cooked lamb, but honestly, it was hard to choose.
Lithos: A charming, cozy taverna in the heart of Naxos Town, perfect for a slower evening. The dishes here feel like home cooking — simple, traditional, and made with care. It’s the kind of spot where you want to linger over dinner and let the night unfold.
Amvrosia (Filoti): Tucked into the mountain village of Filoti, Amvrosia was one of our favourite meals on the island. The menu leans traditional — hearty stews, grilled meats, creamy fava, and house-made desserts. The setting is quiet and authentic, with the kind of warm, welcoming service that turns lunch into a lingering afternoon. A great reward after exploring the hilltop villages nearby.

Waffle House (Naxos Town): If you’re even thinking about dessert, this place is a no-brainer. Famous for its homemade ice cream and waffles, it’s an institution on the island. There’s usually a line, but it moves fast — and trust me, it’s worth the wait. Go for the pistachio or lemon yogurt flavours, or do it right and get it all on a fresh waffle.
Paradiso Taverna (Agia Anna Beach): Right on the sand at Agia Anna Beach, this laid-back taverna is perfect for a post-swim lunch or sunset dinner with your toes in the sand. The seafood is super fresh, and their grilled octopus and Greek salads hit all the right notes. Add a glass of chilled local white wine and you’re golden.
Saint Anna Winery (near Agios Arsenios): A small, family-run winery offering tastings of organic Naxian wines in a peaceful countryside setting. It’s low-key, scenic, and the perfect spot to unwind and try something local. You can pair your wine with cheeses, olives, and little bites — and buy a bottle (or two) to take home.

🛵 Tips for Naxos Travellers

Scooter Rental: Renting a scooter is the best way to explore Naxos at your own pace.
Dining Hours: Greeks typically eat lunch between 1:30 p.m. and 3:00 p.m., and dinner after 9:00 p.m.
🍷 Wine Tip: Try local wines like Assyrtiko and Moschofilero with seafood.

3. Paros: A Blend of Tradition and Trendiness

Paros hit that sweet spot between relaxed and lively. It had all the things I love in a Greek island — beautiful beaches, charming villages, great food — but with a little more breathing room and a little less scene. It felt stylish without trying too hard.

There’s a calm confidence to Paros. You can wander through traditional towns like Lefkes, sip wine by the sea in Naousa, or hop on a boat to a neighbouring island — all in the same day. It’s the kind of place where you could do a lot, but don’t feel like you have to. And that balance made it one of my favourite stops.

Where We Stayed: The Charm of Naousa (3 Nights)

We spent three nights in an Airbnb in the Naousa area, one of the most picturesque fishing villages on the island. Naousa’s charming streets, seaside restaurants, and lively atmosphere made it the perfect base for our stay, with easy access to both beaches and nightlife.

Exploring Paros: Villages, Beaches & Wine

Exploring Naousa: We loved wandering the maze-like streets of Naousa — whitewashed walls, pops of blue shutters, and bougainvillea spilling from balconies at every turn. The harbor area is picture-perfect, with boats bobbing in the water and seafood restaurants tucked along the edge. It has that rare mix of charm and energy — where you can sip wine at a quiet taverna one minute, then stumble into a lively bar the next. We browsed little boutiques, stopped for gelato, and stayed out way later than planned. If you’re looking for that postcard-perfect Greek town with a side of fun, Naousa is it.

Beach Hopping: We swam at Kolimbithres Beach, famous for its unique rock formations and clear waters. We also enjoyed the quieter Faragas Beach for a relaxing afternoon and ventured to Marcello Beach, known for its soft white sand and excellent service.
Wine Tasting in Paros: We spent a slow, sunny afternoon at Moraitis Winery — and it was one of those experiences that makes you fall a little deeper in love with a place. Located just outside Naousa, this family-run vineyard has been producing wine since 1910, and you can feel that history in every glass. The tasting was relaxed and welcoming, with pours of crisp whites, bold reds, and the island’s signature Monemvasia grape. We sipped, we snacked, we learned about Paros’ wine traditions, and we left with a bottle (okay, maybe two). It’s a lovely stop whether you’re a full-on wine nerd or just appreciate a good glass in a beautiful setting.

Visiting Villages: We took a day to explore the inland villages of Lefkes, Prodromos, and Marpissa — and it was honestly one of the most peaceful parts of our trip. Lefkes was the standout, with its winding marble alleys, traditional Cycladic architecture, and little cafés that invite you to slow down and just be. Prodromos and Marpissa were smaller, but full of charm — quiet corners, local life, and beautiful walking paths connecting them all. If you want to see a more local, lived-in side of Paros, this is it.

Piso Livadi: This little port town is the definition of low-key. It has a small beach, a few great tavernas right on the water, and just the right amount of bustle without feeling busy. We grabbed a late lunch here after exploring the villages, and it was the perfect place to unwind and watch the boats bob in the bay.
Day Trip to Antiparos: We loved Antiparos. It’s a quick ferry ride from Paros, but feels like a total escape. The main town is charming, walkable, and full of cute shops and cafés. We explored the Venetian Castle, dipped in quiet beaches, and even visited the Antiparos Cave, which is surprisingly impressive (and refreshingly cool!). If you’re craving a slower pace and fewer crowds, Antiparos is a gem.

Where To Eat in Paros

Siparos Seaside Restaurant: This was one of our favourite meals on the island. Right on the water just outside of Naousa, Siparos feels a little upscale but still relaxed. The seafood is incredibly fresh — we had grilled octopus and sea bass that were chef’s kiss — and the sunset view adds a serious wow factor. It’s a great spot for a special dinner or slow lunch by the sea. Reservations recommended if you want a front-row seat to the view.
Markakis Restaurant (Piso Livadi): This traditional taverna in quiet Piso Livadi served one of our most comforting meals. Everything felt homemade — from the slow-cooked lamb to the tangy tzatziki. It’s unpretentious, welcoming, and right by the harbor so you can sip wine while watching the fishing boats come in. A great stop if you’re exploring the southeast side of the island.
Safran Restaurant: This one totally surprised us — in the best way. Safran takes traditional Greek flavors and gives them a modern, creative twist. The sea bream was perfectly cooked, the watermelon salad was refreshing and unique, and the tiramisu (yes, tiramisu!) was one of the best we’ve had anywhere. Chic but approachable, it’s the kind of place you remember long after the trip ends.

💃🏻 Tips for Paros Travellers

Explore Naousa: Stay in or near Naousa if you want easy access to lively nightlife and excellent dining options.
Visit Antiparos: Make sure to take a day trip to Antiparos for a quieter, more authentic Greek island experience.

Rent a Vehicle: To explore the various beaches and villages with ease, renting a scooter or ATV is highly recommended.

If you’re looking for a destination that offers a balanced mix of relaxation, vibrant nightlife, stunning beaches, and charming villages, Paros is a must-add to your Greek island-hopping itinerary.

4. Milos: A Rugged Paradise Full of Hidden Gems

Milos was the island that surprised me the most — in the best possible way. It felt raw and wild in all the right ways, with lunar-like landscapes, secluded beaches, and a real sense of discovery. It doesn’t have the glitz of some of the better-known islands, but it more than makes up for it with character, charm, and a coastline that’s absolutely unreal.

Every day felt like an adventure — driving down dirt roads to find hidden coves, stumbling into tiny fishing villages, or jumping off rocks into turquoise water. Milos felt undiscovered without being hard to navigate, and authentic without trying too hard. It was unpolished, a little rugged, and completely unforgettable.

Where We Stayed: Cozy Airbnb Experience (3 Nights)

We spent three nights in an Airbnb in Milos, fully immersing ourselves in the island’s rugged beauty and charm. Milos is renowned for its stunning landscapes, pristine beaches, and colourful villages, making it a unique and adventurous destination.

Exploring Milos: Breathtaking Beaches, Villages & Sunset Spots

Sarakiniko Beach: We kicked off our visit to Milos with a trip to Sarakiniko Beach, famous for its otherworldly white rock formations and crystal-clear waters. Arriving early is essential since there are no umbrellas or beach chairs, just a small canteen. The lunar-like landscape is nothing short of magical.

Kleftiko Beach: One of the most famous spots on Milos, Kleftiko is only accessible by boat or hiking. We opted for a sailing tour around the island, which offered the perfect view of the stunning cliffs and vibrant blue waters. We booked with Horizon Yachts, a company with excellent reviews, and it turned out to be one of the highlights of our trip! The experience of cruising through the pristine waters and marvelling at the natural beauty of Kleftiko was truly unforgettable. 👉 Book your Kleftiko Beach boat tour here
Plaka Village: Exploring Plaka, the old capital of Milos, was an unexpected highlight. Its narrow stone streets wind between whitewashed houses, blue doors, and tucked-away shops that beg you to slow down and peek inside. The town has a laid-back but lively energy — filled with small cafés, rooftop bars, and friendly locals chatting in the shade. We wandered aimlessly, caught glimpses of the sea between alleyways, and finished the evening with a drink overlooking the island at sunset. It’s the kind of place that feels timeless.
Klima Village: Klima is tiny, colourful, and right on the water — and it’s exactly as dreamy as it looks in the photos. The syrmata (traditional fishermen’s houses) are painted in bright colors and sit right at the edge of the Aegean, so close you could almost dip your toes from the doorstep. It’s quiet, peaceful, and a perfect place to catch golden hour. We didn’t stay long, but it was one of those spots that lingers in your memory — simple, beautiful, and completely unique to Milos.

Where To Eat in Milos

Yankos Souvlaki: If you’re craving something quick, casual, and incredibly good, Yankos is your go-to. It’s Greek street food at its finest — juicy souvlaki, crispy fries, fluffy pita, and flavourful sauces that make the whole thing messy in the best way. Perfect for a beach-day lunch or a late-night bite after exploring Plaka.
Enalion Restaurant: Right on the waterfront in Pollonia, Enalion gave us fresh seafood with a view — the kind where you watch the boats float by while digging into grilled octopus and shrimp saganaki. It felt a little elevated but still relaxed, and the staff made it feel like a special occasion without being too formal. Definitely a great dinner spot to catch the golden hour glow.
Nostos: Nostos lives up to its name — a cozy, welcoming spot where seafood takes centre stage. Everything tasted like it was caught that morning (because it probably was), and the friendly staff helped us pick the perfect wine to pair with our meal. It’s tucked just off the harbor in Adamas and has a low-key atmosphere that’s ideal after a long day of exploring.
Archontoula: Set right in the heart of charming Plaka, Archontoula is one of those restaurants that feels like a local favourite and a traveler’s find. The menu is full of authentic Greek recipes — think moussaka, lamb with lemon potatoes, and melt-in-your-mouth cheese pies. We came for the food, stayed for the relaxed courtyard setting, and left feeling full and happy.
Aggeliki: This little dessert shop in Adamas became a bit of a ritual for us. The homemade ice cream and Greek pastries were the perfect end to every night. Try the pistachio or masticha flavours — or go wild with a crepe if you’re feeling extra. There’s indoor and outdoor seating, and the place always had a nice after-dinner buzz.
HANABI Seaside Sushi: When you need a break from grilled everything (it happens!), Hanabi hits the spot. Japanese cuisine with a Cycladic twist — super fresh sashimi, creative rolls, and a front-row view of the sea in Pollonia. It was a fun change of pace and a surprisingly standout meal.

🛺 Tips for Milos Travellers

Rent an ATV: Milos is a rugged island, and an ATV is the best way to explore its rocky paths and secluded beaches. The average cost is around €35 per day.
Day Trip to Kimolos: If you have time, take a ferry ride to the nearby island of Kimolos—a short 30-minute crossing. This peaceful island offers quiet beaches and a more traditional way of life, perfect for escaping the more touristy areas of Milos.
Sun Protection: Bring sunscreen and water shoes, especially for the rockier beaches.
Boat Tours: Booking a boat tour is highly recommended to reach otherwise inaccessible spots like Kleftiko.

If you crave adventure and natural beauty, Milos will exceed your expectations. Its rugged landscapes, crystal-clear waters, and charming villages make it a must-see destination on your Greek island-hopping journey.

5. Athens: A Cultural and Historical Finale

After the islands, Athens felt like a shift — louder, busier, a little rougher around the edges — but full of energy. The history is everywhere, but so is the life around it. One minute you’re walking past ancient columns, the next you’re sipping a freddo cappuccino on a buzzing patio.

We explored the big-name sights, wandered through neighbourhoods like Plaka and Monastiraki, and stumbled across plenty of spots that weren’t on any list. The food was fantastic, the sunsets from rooftop bars were unreal, and even the chaos had its charm.

Athens has grit, but it also has heart. And by the end, it had won me over.

Where We Stayed: Hotel Lozenge (3 Nights)

We spent three nights at Hotel Lozenge, perfectly located in the heart of Athens. Its central location made it easy to explore the city’s historical wonders and vibrant neighbourhoods. The hotel’s modern amenities and proximity to key attractions made our stay in Athens comfortable and convenient.

Exploring Athens: Ancient Sites & Modern Charm

Acropolis & Parthenon: Our Athens adventure began with a visit to the Acropolis, where we marvelled at iconic structures like the Parthenon, Propylaea, Erechtheion, and the Temple of Athena Nike. Arriving early helped us avoid the crowds and the heat, enhancing the experience of this awe-inspiring landmark. 👉 Book your Acropolis and Parthenon tour here

Theatre of Dionysus: Located on the southern side of the Acropolis, this ancient theatre is one of the oldest in the world. It was fascinating to imagine the grand performances that took place here.
Monastiraki & Plaka: We wandered through the bustling streets of Monastiraki and Plaka, indulging in Greek cuisine at local tavernas. A highlight was Anafiotika, a charming neighbourhood within Plaka known for its narrow, winding streets and picturesque views.
Shopping in Athens: We strolled along Ermou Street from Monastiraki to Syntagma Square, passing chic boutiques on Voukourestiou Street that led to the upscale Kolonaki neighbourhood.
Mount Lycabettus: To end the day, we took the funicular to Mount Lycabettus and enjoyed breathtaking panoramic views of Athens during sunset.

Must-Visit Spots in Athens

Hellenic Parliament & Changing of the Guard: Watching the Changing of the Guard ceremony in front of the Hellenic Parliament at Syntagma Square was a highlight. The guards, known as Evzones, wear traditional uniforms and perform a slow, highly stylized routine that’s both symbolic and surprisingly mesmerizing. It happens every hour, and it’s well worth timing your visit to see it — a perfect mix of pageantry and history right in the city center.
Temple of Olympian Zeus: Even in ruins, this temple is massive. Once one of the largest temples in ancient Greece, it’s easy to imagine how impressive it must have been in its heyday. The Corinthian columns are towering and dramatic, and it’s just a short walk from the Acropolis, making it a perfect add-on for your ancient Athens itinerary.
Panathenaic Stadium: The birthplace of the modern Olympic Games, this all-marble stadium is both beautiful and historic. We did the audio tour and learned so much about its evolution — from ancient competitions to its modern-day role. You can even stand on the medal podium or run on the track (no pressure, though).
Monastiraki Flea Market: A lively, colorful maze of shops and stalls, Monastiraki is where you go for people-watching, treasure hunting, and last-minute souvenirs. From handmade jewelry and antiques to quirky T-shirts and Greek sandals, it’s a little chaotic — but in a fun way. Don’t skip the food stalls either — grab some koulouri (sesame bread rings) or loukoumades (Greek donuts) while you browse.
National Garden: Need a break from the heat and hustle? The National Garden is a peaceful green space right in the middle of Athens, perfect for a quiet stroll or shady break. It’s lush, well-maintained, and fullasis in the city centre, perfect for a peaceful stroll and a break from the bustling streets.

Where To Eat in Athens

Tzitzikas kai Mermigas: A cozy, stylish spot that somehow manages to feel both traditional and fresh. The menu is packed with classic Greek dishes — think fava, moussaka, and perfectly grilled meats — served with creative touches. It’s a great place to try a little of everything and feel like you’ve been invited to someone’s family table (someone with very good taste).
O Thanasis: If you’re after souvlaki, this is the place. Beloved by locals and tourists alike, O Thanasis is known for its fast service, tender meat, and unbeatable value. The vibe is casual, the plates are piled high, and the flavors are on point. Pro tip: sit outside and do some top-tier people watching while you eat.

Little Kook: More than just a café — it’s a full-blown fairytale explosion. Every corner is decorated to the max with seasonal themes (think Alice in Wonderland meets Halloween meets Christmas — all at once). The desserts are as over-the-top as the decor, with huge slices of cake, whimsical drinks, and sugar everywhere. It’s a must for photos, sweet tooths, and anyone who loves a little magic.
Dos Gardenias: Craving something a little different? This lively spot brings Latin energy to central Athens, with delicious cocktails, Cuban-inspired bites, and salsa music that just might pull you out of your seat. Come for dinner, stay for the dancing — or at least for a mojito under the fairy lights.
Couleur Locale: Hidden in plain sight near Monastiraki, this rooftop bistro is the perfect combo of cool and casual. Their cocktails are solid, the food is Mediterranean with a twist, and the view of the Acropolis at sunset? Unreal. Come for a chill evening and stay as the city lights flicker on.
360 Cocktail Bar: A bit trendier and buzzier than Couleur Locale, 360 is all about the panoramic views and sleek vibes. Whether you’re sipping a craft cocktail or grabbing a late-night bite, you’ll be surrounded by one of the best views in Athens — especially when the Parthenon starts to glow. Great for date night or one last drink before heading back to your hotel.

🎟️ Tips for Athens Travellers

Buy Tickets in Advance: To avoid long lines at popular sites like the Acropolis, it’s best to purchase your tickets online before your visit. The Athens: Acropolis & Up to 5 Archaeological Sites Combo Pass is a great option—it gives you skip-the-line access to major landmarks like the Parthenon, Ancient Agora, Roman Agora, Temple of Olympian Zeus, and more. It’s convenient, cost-effective, and saves valuable time, especially during peak season. 👉 Book your Athens Combo Pass here
Wear Comfortable Shoes: Athens involves a lot of walking, especially around historical sites.
Plan for Hot Weather: During the summer months, temperatures can get very high, so stay hydrated, bring a hat and wear sunscreen.

Athens offers a fascinating blend of ancient history and modern charm, making it the perfect place to wrap up your Greek island-hopping journey.

🛏️ Recommended Stays for Your Cycladic Island-Hopping Adventure

Not sure where to stay during your Greek island escape? Here are some highly rated, handpicked hotel recommendations—a mix of luxury, boutique, and budget-friendly options—for each stop along your journey: Santorini, Naxos, Paros, Milos, and Athens.

Santorini – Recommended Hotels (Kamari Beach Area)

If you’re looking for a more relaxed (and budget-friendlier!) base in Santorini, Kamari is a fantastic option with easy beach access, great restaurants, and a more local feel.

💎 Cavo Bianco Boutique Hotel & Spa: Sleek and stylish, just minutes from the beach. Spa vibes, two pools, and modern Cycladic décor.
🌿 La Bellezza Eco Boutique Hotel: Chic suites with private jacuzzis, breakfast by the pool, and a peaceful vibe just off Kamari’s main drag.
💸 Nissia Beach Apartments & Suites: Right on the beach with a pool, cute interiors, and excellent value for money.

Naxos – Recommended Hotels

Naxos is laid-back but full of character, with beautiful beaches and a charming old town. Whether you’re after luxury by the sea or a central base to explore the island, these hotel picks offer great value and comfort without compromising on style.

💎 18 Grapes Boutique Hotel (Agios Prokopios): Chic and modern, just steps from one of the island’s best beaches.
🌿 Argo Boutique Hotel (Naxos Town): Stylish, great location, and ideal for exploring both town and beach.
💸 Ikaros Studios & Apartments (Naxos Town): Affordable, clean, and comes with a pool and big-hearted hospitality.

Paros – Recommended Hotels

Paros strikes that perfect balance between postcard-perfect charm and chilled-out Greek island life. These hotels are great for relaxing in Naoussa, soaking up beachside vibes, or staying close to Parikia’s ferry and nightlife scene.

💎 Parilio, a Member of Design Hotels (Naoussa): Elegant, minimalist, and surrounded by Paros’s dreamy landscapes.
🌿 Hotel Senia (Naoussa): Infinity pool, sea views, and walkable to Naoussa’s charming tavernas.
💸 Siroco’s Rooms and Studios (Parikia): Friendly and budget-friendly with a homey feel and great location.

Milos – Recommended Hotels

Milos is all about dreamy cliffs, volcanic beaches, and small village feels. These stays offer a mix of secluded luxury, beachfront comfort, and budget-friendly charm to suit different travel styles—whether you’re there to unwind or explore every cove.

💎 Milos Cove (Komia): Remote cliffside luxury with private pools and dramatic Aegean views.
🌿 Artemis Deluxe Rooms (Paleochori Beach): Beachfront boho-boutique dream with modern comforts.
💸 Hotel Glaronissia Rooms & Suites (Pollonia): Charming and affordable base in a peaceful fishing village.

Athens – Recommended Hotels

Athens makes a strong first (and last) impression. From rooftop views of the Acropolis to eco-boutique gems near the Plaka, these hotel options are great for kicking off your adventure or winding it down in style – without blowing the budget.

💎 Electra Metropolis Athens: Rooftop pool, Acropolis views, and steps from Plaka. Total city chic.
🌿 COCO-MAT Athens BC: Eco-boutique vibes with plush bedding and a rooftop bar that delivers big views.
💸 City Circus Athens: Quirky hostel-meets-hotel in the vibrant Psirri neighbuorhood—budget-friendly with tons of personality.

Final Tips for Island Hopping in Greece

As you wrap up your Greek island-hopping adventure, here are some essential tips to keep in mind to make the most of your journey:

Book Ferries in Advance: Booking your ferry rides through Ferryhopper at least a month ahead is highly recommended if you’re traveling during the busy summer months (July and August). It allows you to compare ferry schedules and prices easily, ensuring a smooth travel experience.
Packing Essentials: Pack light, breathable clothing for the hot summer days, but don’t forget a light jacket for cooler evenings, especially if you’re taking evening ferries. Also, bring water shoes for rocky beaches and plenty of sunscreen to stay protected.
Voltage & Portable Charger: Greece uses Type C and Type F plugs (230V, 50Hz). Bring a universal adapter and a portable charger to keep your devices powered throughout your journey.
Local Food: Indulge in the local cuisine! Every island has its own specialties, so make sure to try dishes like fresh seafood, traditional Greek salads, moussaka, and souvlaki. Also, don’t miss tasting the local wines or ouzo.
Travel Insurance: It’s always a good idea to have travel insurance that covers health, cancellations, and lost luggage—especially when island hopping.
Transportation: Rent scooters or ATVs where possible, especially on islands like Milos and Naxos, to explore the scenic routes and hidden gems at your own pace.
Accommodation Booking: Book your stays in advance during high season to secure the best spots at reasonable prices.
Respect Local Culture: While visiting churches, dress modestly. Also, remember that Greeks typically eat lunch between 1:30 p.m. and 3:00 p.m., and dinner after 9:00 p.m.
Pro tip for fellow snackers: Greece has a surprisingly elite chip game. Oregano, tzatziki, paprika—don’t skip the kiosk taste-test.

Final Takeaways

Exploring the Cyclades was a mesmerizing experience. From the postcard-perfect beauty of Santorini to the rugged landscapes of Milos, the charming villages of Paros, and the authentic charm of Naxos, each island left us with unforgettable memories. Athens provided the perfect finale, blending rich history with modern flair.

If you’re planning a Greek island-hopping adventure, this itinerary will guide you to the very best of what Greece has to offer. Enjoy every moment of your journey!

Have you visited Greece or is it still on your travel bucket list? Let me know your favourite spots or what you’re most excited to see in the comments below! And if you found this guide helpful, don’t forget to share it with your fellow travel enthusiasts. 🇬🇷💕

P.S.
If island hopping through Greece stole your heart, wait until you dive into my 17-day adventure through Türkiye! Think magical hot air balloon rides in Cappadocia, coastal gems like Kaş and Fethiye, and the bustling beauty of Istanbul. This trip was packed with history, culture, beaches, and more epic views than my camera could handle.
👉 Exploring Türkiye: A Dream 17-Day Adventure

Island Hopping in Greece: A Perfect 16-Night Cycladic Adventure