Santorini and Milos in 8 days

General advice: try to visit the Greek islands in June or September to avoid the crowds in July and August. Also, the temperatures are very high during the peak months of the summer and it would be more unpleasant to do sightseeing.

A very important tip is… do not book the ferries on the same days that you have booked flights. Both ferries we took were not on time and one of the days it was so windy that the ferries didn’t even work between a few islands.

Santorini: we stayed in Santorini the first night and the last two nights of the trip. The first night we stayed in Oia and the last 2 nights in Firostefani. I really liked the location of Firostefani and it seemed to have less tourists than the other towns but also has caldera views and nice hotels with private swimming pools on the balconies. Oia is like the most romantic and famous of all the towns, the problem is that is super busy and it is much more expensive that any other of the towns in the island.

The recommended hotels are “Exclusive Plan Suites” at Firostefani, and If you want to stay in Oia “Armenaki” is a great option as well. Both hotels offer private swimming pools/ jacuzzi on the room and caldera views.

Milos: in Milos we stayed in Plaka for 4 nights. In Milos I would recommend staying on the northern part of the island as the majority of the things to see are in that area. I really liked Plaka and I would stay there again because the location is good and the town is so pretty! I would recommend to stay at “Halara Studios” and choose the room with private balcony and sea view. Another option is to stay at Adamas that is not a very pretty town but has a lot of options for restaurants and bars.

Day 1: Oia – Santorini

From London you can fly directly to Santorini. After landing, we went directly to our hotel and spent some time chilling at our room swimming pool while watching the sunset. The typical thing to do is to go the Oia Castle to watch the sunset from there however given the amount of people that congregate at such small place, the experience is extremely uncomfortable. We were in Oia at the end of September and still there were so many people that we did not even try to go to the castle. In my opinion, you can also watch a beautiful sunset from numerous streets and small allies around Oia without the need of going to the castle.

After that we have a very nice dinner at a beautiful place called “Karma”. The atmosphere is really nice, and you definitely have to book in advance.

Day 2: Oia – ferry to Milos

I would recommend exploring Oia in the morning when it is a bit calmer. There were still some people around and definitely I can say that this is the most touristic town of the island, but it is still nice to walk around the narrow streets, seeing the blue domes, and go up to the castle to enjoy the fabulous view.

After the stroll, we took the ferry to Milos. You only have to be 30 minutes before departure at the port as the ports are quite small. We booked our ferries with the company Seajets, they are quite fast compared to other ferry company options and it took us a bit more than 2hours. The only bad thing is that this ferry is only for passengers and you cannot take vehicles with you. Other ferry companies that do carry vehicles are Dionisios Solomos or Blue Star Chios, however the trip in this case takes between 4 and 5 hours and only operates a couple of days per week. Therefore, my advice is that you book the ferry tickets at the very beginning of planning your trip and book the rest if the trip around it.

Once we arrived at Milos Port, we rented a car via Rentalcars with AutoUnion and everything went smoothly. One tip is to definitely take a small car and nothing fancy, the roads are really narrow and many times not even 2 cars fit in!

We drove directly to our rental apartment in Plaka and watched the sunset from our room that had beautiful views! Plaka is a very well-known place to watch the sunset

Day 3: Milos beaches

First day in Milos we spend it exploring the beaches of the north area of the island.

• Firopotamos: the beach is inside a small bay where many fishermen live and fish. It is a very cute beach and for me my favourite! It was not crowded at all and it was great to relax.

• Mandrakia: this is not a beach a such, but it is a very nice village to visit and have lunch by the sea. You have to go to the only restaurant there “Medusa” – they are specialists in grilled food and both meat and fish were delicious.

• Sarakiniko beach: this beach is the most particular one of Milos. It is the most photographed spot of the island and is also considered as one of the most beautiful Greek beaches. Its particular landscape is very impressive and surely unforgettable: long horizontal rocks bent over the sea; those rocks are eroded by time and salt water and have small and huge hollows all over them. The entire landscape formed by the volcanic rocks doesn't show any signs of vegetation and is coloured entirely in a bright white, which makes an interesting contrast with the deep blue and turquoise of the surrounding waters. This amazing scenery gives one the impression of standing on the surface of the moon.

• Papafragas Caves: we tried to get here but it seemed almost impossible, the area is surrounded by a massive fence and danger signs therefore we didn’t go down as it seemed really dangerous! Instead, what you can do is to go to nearby Alogomandra beach which also has a beautiful cave.

• Pollonia: a charming fishing village, built around a pretty inlet. The church of the village, Agia Paraskevi, stands on a small peninsula, above Pollonia, and is visible from every part of the village. It has a beach of very easy access so perfect for families. Also, a very good spot to have a drink while overlooking the beach.

For dinner I would recommend “Diporto” that is a traditional Greek tavern in Plaka. “Avli” is also a good option in Plaka but always has a massive queue and you cannot book in advance.

Day 4: Boat day

One of the most typical things to do in Milos is to do a boat tour in particular to explore the south of the island that is inaccessible by car. If you are not a big fan of boats, you can rent a 4x4 for a day and explore that way the most inaccessible spots.

For the boats there are numerous options on how to do it. We rented a small boat just for us on the south of the island and rent it for half a day. Many people choose to do a cruise around the full island that usually starts in Adamantas and takes a full day, however we saw some incredible crowded ones that didn’t see very pleasant. If you book a shared one, check out what is the maximum of people that they take.

The main spots to visit with the boat are Kleftiko and Tsigrado both on the south. Tsigrado is a famous small beach that you can only access by going down a very steep rope and stair… it seemed like a very uncomfortable experience so better to just see it from the boat.

After returning the boat, we spent sometime chilling at Fyriplaka Beach that was super nice and relaxing and quite well protected from the wind. The last stop is at Thiorichia beach where the old sulfur mine of the island is located that ceased to operate in the 1960’s. The little wagons and rails from the side of the mountain to the small port, the stone buildings and the rusty tools will take you back to another era.

For dinner, we went to “Nostos” in Adamantas to try the great seafood and fish. Very nice location and fantastic place.

Day 5: Ancient Theatre and Klima

During our last day we visited the most famous places of the island. First, we went to the Ancient Theatre located on a rocky slope, near the catacombs stands the ancient theatre of Milos that Romans built during the Hellenistic period. The entrance is for free and something that you shouldn’t miss. We also visited the catacombs, but I would suggest to skip them as they didn’t cause a great impression (very small and pricey).

After that, we went to visit the beautiful fisher town of Klima that is just below the theatre. Klima was amazing, directly in the sea the colourful houses are very picturesque and the couple of shops here very cute. You can stop here for a drink or to have lunch at “Astakas”.

We actually decided to have just a drink at Klima and go for a souvlaki at ‘Spirtoni’ and it was really good! The location is fantastic and so relax for lunch.

After we visited Plathiena, a lovely beach on the northern side of Milos which is very close to Plaka. A bit secluded and not very well-known so it provides a nice place to relax.

A very famous place to go for dinner is “O!Hamos!”. Prepare to wait but it will be worth it! Traditional Greek and simple dishes that will leave you impressed.

Day 6: Milos – Santorini

Early in the morning we departed Milos (wondering already when we should go back) to go back to Santorini for a couple of days before ending our trip.

When we arrived to Santorini (this time we were staying at Firostefani) we went to the hotel first and then walked to Fira to pick up our car at the rental car place. We booked the car in advance with Rentalcars at Cars 4 Rent, the service was very good but the car was in a very bad condition… there are many options on where to rent in Fira but I would try to book in advance as the island is not cheap and because it is so touristic the prices are inflated.

After picking up the car, we went for a wine tasting to “Santo Wines”, one of the most famous places for wine tasting in Santorini. The views are incredible, and it is a very renowned place to watch the sunset. Another option for sunset is to go to Akitrori Lighthouse.

We also visited Imerovigli that is the highest point on the island. It is a nice town, but it felt more quiet and it didn’t have many shops etc, there were mainly hotels and restaurants/ bars. If you don’t have much time to visit the island, I think you can skip this spot.

I really liked the vibe of the restaurants in Firostefani and how many options we had just around the corner from the hotel. The first night we went to “Pirouni”, a restaurant with a fabulous view over the caldera and great food! I really enjoyed the prawns. After dinner you can go for ice cream to “3 Bambini bar gelateria”.

Day 7: Pyrgos, Emporio and Megalochori

One of the best things to do in my opinion, is to visit the towns that are in the inside part of the island.

• Pyrgos: it is the place where we saw most tourists out of the 3. Pyrgos sits on the slopes of Mount Profitis Ilias and has 360 views of the entire island of Santorini. Away from the busy and sometimes crowded towns of Fira and Oia, Pyrgos showcases the very best of Santorini. It is a very well-preserved village with the medieval castles, blue domed churches, and whitewashed cave houses.

• Emporio: it is just beautiful. The colours were different here, more beige and oranges instead of white and blue like the other towns of the island. The most incredible part was the cave houses which were completely unique and special!

• Megalochori: I fell in love with this town! It was definitely my favourite! First of all, we had the best lunch of the whole trip here at “Geromanolis”, we ordered the fish of the day and ohhhh my god! It was so good! After that we went for a wine tasting to “Gavalas Winery”, the wines were super good and the place felt very authentic and only 16EUR pp. If I could only choose one, I would choose this wine tasting over Santo wines. After that we had a walk around the town and went into a great handmade leather shop.

For dinner, we went to “Kokkalo” and it was again super good. This restaurant is more specialised in meats and you should definitely try the gyros… they were amazing!

Day 8: Ammoudi Bay

On our last day we decided to go to Ammoudi Bay. It is a nice bay on the lower side of Oia. We went by car as we didn’t fancy doing the 300 steps down when we were staying in Oia. To be honest it would have been better to do this while we were in Oia instead of coming back the last day (it is a 20 minute drive from Firostefani). The bay is full of nice restaurants but the most recommended one is “Ammoudi Fish Tavern”.

Finally, we had a walk around Firostefani before heading back to the airport.