Santorini, Milos and Kimolos 2024: Trip Planning

Introduction

In early April, I decided to plan my first Greece trip of 2024. Keen to obtain new content for my growing YouTube channel and take any opportunity to return to my favourite country, I sat down at the computer to design an itinerary for a short 4- or 5-day visit in the middle of May. This post explains my trip planning process and how I ended up choosing Santorini and Milos.

Finding Flights

One of the trickiest parts of booking short Greece trips is finding affordable flights to convenient destinations. I first considered a return trip via Athens, the capital city, which has by far the most regular connections with the UK. The flights weren’t cheap, though; plus, travelling via the mainland would require at least two ferries or internal flights.

I began looking at direct flights to the Greek Islands. Being early in the tourist season, flights to most islands were only available once or twice a week, making it hard to devise an itinerary for four or five nights as I didn’t want to go over budget or take too much time off work. Of all the islands I could fly to, Santorini had the cheapest inbound flight from the UK, but the return flight was expensive and didn’t fit in with my timescales either.

When I first thought about taking this trip, I had assumed there would only be time to visit a single island. As it became clear I could make the flights work better by travelling out and back via a different Greek airport; I realised that adding a second island could be viable. My natural instinct towards a slower and more relaxed itinerary had to be suppressed: this was mostly a research and content-gathering trip, not a holiday. (I have at least one Greek holiday planned for later in the year, so watch this space…)

Having settled on Santorini as my arrival airport, I looked for a route that would take me to another destination that needed an island guide, allowing me to fly home directly or providing an easy connection for a return flight.

North of Santorini lies Ios, Paros, and Naxos. These are all fantastic islands and among my favourites to visit, but I’ve seen each of them several times and made recent comprehensive videos for them, so I quickly discounted them. Mykonos, slightly further north, is an island that I’m reluctant to promote as, despite its popularity, I don’t think it represents a positive image of Greece or the reasons why I love the country so much. I will return at some point, but it isn’t high on my list for now.

There aren’t many options east or south of Santorini. Amorgos, to the northeast, I’ve already produced a video for, and it wouldn’t be an easy island to travel home from. Astypalea, east of Santorini, is lovely, but again, I ticked it off my YouTube list in 2022. Crete is the only island to the south and is far too vast to tackle in a few days. It’s also my most visited Greek island and has been featured in various videos.

The only remaining heading was west (or specifically northwest), covering the islands of Sikinos, Folegandros and Milos. Sikinos I also visited in 2022 and made a video about it. I’ve only visited Folegandros once in 2019, and it was a strong contender as it hasn’t been featured in an island guide yet. However, when I looked at ferry options for returning to the mainland to fly home, I couldn’t find one that matched a flight time without wasting a night on the mainland.

As you can see, this left me with Milos. Although I visited in 2020 and featured it in a video I made following that trip, it wasn’t much of an island guide. Milos also has a domestic airport, meaning I would have a choice of taking a ferry or flight back to the mainland for my international flight home. I’d found my islands for the trip.

Refining the Itinerary

Having identified Santorini and Milos as the islands I would be visiting, it was time to narrow down the itinerary and ensure it was viable before I booked my flights and accommodation. I found a cheap easyJet flight to Santorini that arrives mid-afternoon on a Wednesday and a reasonably priced return flight from Athens late the following Monday evening, giving me 5 nights to split across both islands.

The only ferry from Santorini to Milos is Seajets’ Super Jet, which runs daily at 15:00, arriving on Milos just after 17:00. I could either take this on Friday or Saturday – the latter giving me 3 nights on Santorini and 2 on Milos. As the ferry arrives quite late in the afternoon, though, this would only give me one full day on Milos (the Sunday) plus some of the Monday morning before my departure. I decided that the Friday ferry makes more sense as I’m confident I can squeeze a lot of sightseeing on Santorini into one full day, plus the afternoon I arrive and the morning I depart.

So far, my itinerary looks like this. I’ll add more details on how I’ll spend my time on each island further down:

1. A Wednesday morning flight departing at 07:30, arriving in Santorini at 13:50.
2. Wednesday afternoon/evening to explore Santorini.
3. Thursday, a full day exploring Santorini.
4. On Friday morning, explore Santorini, leave the hotel midday, and take the 15:00 ferry to Milos.
5. Arrive at Milos at 17:05 in the evening to explore Milos.
6. Saturday and Sunday are full days to explore Milos.
7. Monday morning, explore Milos before departure.

To get back to Athens for my flight home, I had the choice of another Seajets ferry departing at 12:50 and reaching Piraeus at 16:15 or an internal flight departing at 16:50 and arriving in Athens airport at 17:30. My easyJet flight home isn’t until 21:30 that evening, so either option was viable and would get me to the airport in plenty of time. I chose the internal flight, as it’s cheaper (€48 including luggage versus €78.70 for the ferry) and saves me travelling from Piraeus back to the airport. It also gives me a few extra hours on Milos as I wouldn’t need to be at the airport until around 3pm.

Exploring Santorini

Despite its worldwide popularity, Santorini is quite a small island and, based on my experience, doesn’t have many sightseeing opportunities. Most people come for the iconic caldera views and the impressive sunsets and barely explore the rest of the island. That said, there are a few key things to see in Santorini, and I plan to include as many of the following as I can:

• A visit to Akrotiri for the archaeological site
• Red Beach, walkable from Akrotiri
• The caldera views from Fira/Firostefani
• Oia sunset
• A winery tour
• A visit to the volcanic beaches of Kamari and/or Perissa
• Ancient Thera
• A boat trip to one of the caldera islands

I obviously won’t be able to cover every aspect of the island in two days, but the above should give potential visitors a sense of what’s available. Putting these into my previous itinerary, I’m hoping it will fit something like this:

1. Wednesday (arrival day) afternoon: Take a bus to Perissa Beach, then back to Fira and a bus to Oia for the sunset.
2. Thursday: Take the morning bus to Akrotiri and walk to Red Beach. Then, take the bus back to Fira, take another bus to Kamari, and walk to Ancient Thera. Finally, take a bus for the Winery Tour. Dinner in Fira and sunset Caldera views.
3. Friday morning: Spend some more time exploring Fira (museums, etc.), then take the bus to the ferry port for an afternoon departure to Milos.

Thursday will be a packed schedule, but as I’ve seen the archaeological museum at Akrotiri before, I’ll probably just get some exterior video, head straight for Red Beach and try to get the next available bus back to Fira for a connecting bus to Kamari. I also walked up to Ancient Thera during my brief stop in Santorini last year, but sadly, the site was closed, so I’m familiar with the walk and looking forward to seeing it properly.

A boat trip is the only thing I’ve not tried to fit into my itinerary, as I’m not sure there’s enough time. I need to research the cost and availability further before deciding whether to include it.

Exploring Milos

On my last visit to Milos in 2020, I saw a good amount of the island and recorded some usable video footage, but I’m still excited to see it again. In particular, it was very windy last time, and Sarakiniko Beach was deserted and too rough for swimming or using my drone. Hopefully, it will be calmer this time, and I can enjoy the unique and dramatic landscape more.

I’ll probably hire a car or quad bike again and visit most of the villages on the eastern side, namely Klima, Plaka, Tripiti, Firopotamos, Mandrakia and Pollonia. My base will be in the port town of Adamantas, where I can explore it at leisure. I’ll also try to include some other beaches, such as Tsigrado and Firiplaka, but I may not venture all the way west to the Monastery of St John Siderianos as it’s a long trip, and I have some recordings of it from my previous visit. This should allow me to finish most sightseeing with a day of car/ATV hire. On my other full day, in addition to exploring closer to my hotel, I’m also honing in on a plan to visit the nearby island of Kimolos.

Kimolos

The idea of hopping over to Milos’ smaller neighbour came to me quite late. I realised I had an entire second day on Milos and not much sightseeing to fill it with, then stumbled upon the opportunity of visiting Kimolos when I spotted a link for the ferry company on the bus timetable website. The boat service, detailed here: https://kimolos-link.gr/en/dromologia-osia-methodia/, indicates five crossings spaced well throughout the day when I’m on Milos, and I figured it would be an exciting way to spend the day and another Greek island to check off my list. I quickly began planning how to get to the island and back to my hotel in the port town of Adamantas.

The first challenge will be getting to Pollonia to catch the ferry, as the bus timetable (https://milosbuses.com/timetable-apr-29-12-may/?lang=en) indicates there are only two buses for this route, one early morning at 6:45 and the last returning at 14:30, which is much earlier than I would like. Even if I take the first ferry from Pollonia at 9:45, which arrives on Kimolos at 10:10, I would have to catch the 13:00 boat back to Pollonia as the next one isn’t until 16:00. This would only give me 2 hours 50 minutes on the island, which isn’t that much time. Although Kimolos is small, it would take several hours to see places on foot, and I discovered that it doesn’t have a bus service. Enter the helpful folks over on the TripAdvisor Greece Forums…

I asked how best to get around on Kimolos without public transport and was told it’s best to use a bicycle or e-bike. It’s possible to hire one on Milos and take it across on the ferry, which solves my transportation issue once I get to the island. However, it didn’t immediately address the issue with the bus timetable until I learned that e-bikes can be rented from Adamantas and that it’s only 10 kilometres from the port town across to Pollonia–perfectly manageable on a bicycle, especially one with battery power!

Armed with this knowledge, my new plan for my time on Milos is to hire a car or quad bike for the day I want to explore Milos and an e-bike for my Kimolos day. I’ll ride to Pollonia in time to catch the first ferry across, explore as much of the island as possible, and then take the ferry back to Milos.

Which day I choose to hire the vehicle will probably be decided once I arrive, so the itinerary for Saturday and Sunday could be reversed, but I’m aiming for this as a rough plan:

1. Arrive on Milos at 5pm Friday. Check into the hotel and explore a bit of Adamantas. It looks like the local bus service isn’t running at full capacity in May and stops at 18:30, so I’ll most likely have dinner near the hotel.
2. If hiring a vehicle on Saturday, explore the island as described above, with lunch probably in Pollonia and dinner in Tripiti or Plaka.
3. On Sunday, I plan to hire an e-bike and ride across to Pollonia before catching the 9:45 ferry to Kimolos. I’ll explore as much of the island as possible, then catch the 16:00 ferry back, arriving in Pollonia at 16:25. I’ll cycle back to Adamantas, which should take around 30 minutes. I’ll return the rental bike and have dinner in the port town close to the hotel.
4. Monday morning, have a relaxed morning near the hotel, then get packed and ready to catch my ferry or flight back to the mainland before returning to the UK.

Summary

As you can imagine, I’m thrilled to return to my favourite country earlier in the year than ever. I can’t wait to see what late Spring is like and how much greener and fresher it will seem. I may post more details on the itinerary again, but if not, you can check back here for a link to the blog that I’ll update as the trip unfolds.

Yammas!