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ISLAND HOPPING IN GREECE: SANTORINI & MILOS
We embarked on an unforgettable island-hopping journey through Greece. With its crystal-clear waters, charming villages, and breathtaking sunsets, the Cyclades were calling—and we answered. We decided to explore two of its most stunning islands: Santorini and Milos.
Our trip lasted 10 days in total, and we carefully split our time between the two destinations to soak in their unique vibes. Santorini, with its iconic white-washed buildings and dramatic caldera views, offered a romantic and picturesque escape. Milos, on the other hand, surprised us with its raw beauty, colorful rock formations, and hidden beaches that felt like secret treasures.
How we divided our days between Santorini and Milos? You’ll find that just below
SUMMARY OF OUR 10-DAY ROUTE
Day 1: Arrival at Santorini
Day 2-3: Exploring Santorini
Day 4: Ferry to Milos
Day 5-9: Exploring Milos
Day 10: Heading Home
FULL ITINERARY OF SANTORINI & MILOS
Day 1: Arrival in Santorini
We landed in Santorini early in the morning, giving us a full day to start soaking in the island’s magic. For our stay, we chose a hotel within walking distance of Fira, the island’s lively capital. Instead of staying in the famous village of Oia, we opted for Fira—and looking back, it was the right decision. Oia may be iconic, but it’s also much pricier and often overcrowded, which isn’t quite our vibe.
Fira turned out to be a fantastic choice: vibrant, full of character, and packed with great restaurants and cozy spots to explore. After settling into our hotel and taking a moment to relax, we headed out to discover the town.
We ended our first day with a delicious dinner perched on the edge of the village, overlooking the sea. As we enjoyed our meal, the sun dipped below the horizon, painting the sky with warm hues—a perfect start to our Greek island adventure.
Day 2: Exploring Oia at a Relaxed Pace
After a full first day, we decided to take things a bit slower on Day 2. We spent the morning unwinding at our hotel, soaking in the peaceful atmosphere before heading out in the afternoon to explore Oia.
Getting around Santorini is surprisingly easy—public transport is well organized, and from Fira, it’s a smooth and scenic bus ride to Oia. As soon as we arrived, it felt like stepping into a postcard: whitewashed houses cascading down the cliffs, set against the deep blue of the Aegean Sea. It’s exactly the image most people have in mind when they think of Santorini.
Oia is perfect for a leisurely stroll, grabbing a bite to eat, or enjoying a refreshing drink with a view. Just be prepared—prices here are noticeably higher than in other parts of the island. Don’t expect to find a Greek salad for €5!
As evening approached, the crowds began to swell. Even though we were visiting in September, outside the peak season, the village became packed with people eager to catch the famous Oia sunset. For us, it was a bit too much. We preferred the more relaxed vibe back in Fira, where the sunsets are just as stunning, and you can enjoy them without the shoulder-to-shoulder crowds.
Day 3: Quad Adventure Across Santorini
On Day 3, we decided to explore Santorini in true island style—by renting a quad bike for the entire day. It gave us the freedom to roam beyond the tourist hotspots and discover the island’s hidden gems.
We started our journey heading south, where the landscape opens up to dramatic cliffs, quiet villages, and panoramic views that are simply breathtaking. Riding through the winding roads with the sea glistening in the distance was an experience in itself—every turn revealed a new postcard-worthy scene.
In the afternoon, we made our way east, where the vibe shifts to a more laid-back beach atmosphere. This part of the island is dotted with beach bars, many of which come with their own swimming pools—perfect for a refreshing break.
Day 4: Ferry to Milos & Settling In
This morning, we boarded the ferry from Santorini to Milos, a journey that takes about 2 to 3 hours. By midday, we arrived on this beautiful and more tranquil island, ready to begin the second chapter of our Greek adventure.
For our stay in Milos, we chose a slightly different approach: instead of staying in one place, we booked two different accommodations to experience more of the island’s charm. Our first hotel was located near Adamas, the main port town, while the second was in the peaceful village of Pollonia. Although Milos isn’t very large and you could easily stay in one spot and rent a car to explore, we liked the idea of switching locations for a bit of variety.
Want to know exactly what we did each day, where we went, and what we loved most? Read on in our detailed Milos article—we’ve got all the highlights waiting for you there!
Days 5: Boat Tour to Kleftikos & Poliegos
On day 5, we embarked on a stunning boat tour — best booked from the charming village of Adamantas, as most excursions depart from here. The journey takes you to Kleftikos and Poliegos, two breathtaking parts of Milos that are inaccessible by land.
As you sail across the crystal-clear blue waters, the boat makes several stops for refreshing swims and snorkeling. You'll explore hidden coves, dramatic rock formations, and sea caves that look like something out of a dream. To top it all off, a delicious lunch is served on board, making the experience both scenic and satisfying.
Day 6: Exploring Plaka, Milos
Day 6 marked our final day staying in Adamas. In the late afternoon, we hopped on public transport and headed to Plaka, the largest town on Milos. While Plaka isn’t big enough to fill an entire day, it’s perfect for a few hours of wandering.
We strolled through the charming streets, soaking in the cozy atmosphere and traditional Cycladic architecture. The town has a peaceful vibe, with whitewashed houses, colorful doors, and narrow alleys that invite you to explore.
We ended the day with a magical sunset at the church of Plaka, perched high above the sea. The view was absolutely breathtaking — a perfect farewell to our time in Adamas.
Day 7: Moving to Pollonia
On day 7, we left Adamas and moved to Pollonia, a peaceful seaside village on the northeastern tip of Milos. If you're curious about where we stayed — check out our full article on Milos. The hotel was truly worth it!
This day was all about settling in and exploring Pollonia at a slower pace. We took time to enjoy the surroundings, soak up the calm atmosphere, and get to know the hotel. Pollonia has a laid-back charm, with waterfront tavernas, small beaches, and a cozy vibe that invites you to unwind.
Day 8 & 9: Quad Adventure Across Milos
On days 8 and 9, we rented a quad bike — the ultimate way to explore every corner of Milos! With the freedom to roam, we made countless stops, from tiny villages to hidden beaches, discovering places that are hard to reach by public transport.
The quad gave us the flexibility to chase views, take spontaneous detours, and soak in the island’s diverse landscapes at our own pace. Whether it was a scenic lookout, a quiet bay, or a local taverna, we stopped wherever curiosity led us.
For all the details — including our favorite spots and tips — check out our full Milos article. It’s packed with insights from this two-day adventure!
Day 10: Heading Home
On our final day, we flew back home in the afternoon. Milos has a tiny airport, so don’t expect to see large international planes taking off here. Instead, we boarded a small propeller plane to Athens—a fun experience in itself—and from there, caught our flight back home.