Introduction
When I plan a trip to Greece, flights are always the starting point. They’re usually the biggest expense, and more often than not, they end up shaping the entire itinerary—where I go, how long I stay, and even the order of the trip.
As much as I’d love to pick an island first and build everything around it, the reality is a bit more practical. I’m limited by what’s available from UK airports (within a reasonable distance of my home address), and—just as importantly—what’s actually affordable. It’s always a balance between chasing new experiences and working within those constraints.
Understanding my Options
A bit of time browsing airline websites quickly brought up a familiar option: Mykonos. Once again, flights were reasonably priced and would drop me straight into my favourite part of Greece—the Cyclades.
But there was a catch.
I’d used Mykonos as my arrival and departure point just last year, and by now I’ve visited all of the nearby islands—some multiple times. While it made sense on paper, it didn’t exactly spark much excitement when it came to planning the trip itself.
I tried to make it work by looking at Athens flights instead, with the idea of building a more linear itinerary—starting on the mainland and finishing on Mykonos, or the other way around. There are still a few Cycladic islands I haven’t explored yet, like Kea and Kythnos, and I’ve only scratched the surface of Tinos, so I wasn’t ready to rule out the island group entirely.
On paper, it looked promising. In reality, it quickly fell apart.
Ferry connections between Kea, Kythnos and the surrounding islands—especially in May—were limited and infrequent. To make my usual style of 3–4 night stays work, I needed reliable, regular routes. Without them, the whole plan became too restrictive.
Then, while checking ferry routes from Mykonos, I spotted something unexpected: a connection to Ikaria.
Ikaria had always been on my radar, but I had no idea it was accessible from Mykonos. That immediately caught my attention.
I started reworking my itinerary around it—fly into Mykonos, ferry to Ikaria, and build from there. It felt like a fresh direction and, for a moment, I thought I’d cracked it.
But the onward journey proved tricky. Heading back west would mean retracing my steps via Mykonos, and the ferry options weren’t frequent enough to make that practical. Even if I did, I’d likely end up somewhere like Tinos… and then straight back to Mykonos to fly home.
Convenient, yes—but not exactly exciting.
Fixing the First Island Itinerary
At that point, I took a step back and started again.
I knew I wanted to visit Ikaria—and ideally pair it with another new island. Mykonos might have been the obvious entry point, but was it really the best option?
Looking more closely at the logistics, I realised I’d likely need to overnight on Mykonos just to make the ferry connection. Having already spent time there last May, that felt like a wasted day.
Then I noticed something I’d overlooked before: Ikaria has its own airport.
That changed everything.
A quick check of Athens flights showed I could leave early from the UK, arrive late morning, and comfortably catch a same-day domestic flight to Ikaria. The connection time—landing at 11:20 and departing at 16:45—was longer than necessary, but actually worked in my favour.
With the new Entry/Exit System (EES) now in place, and this being my first trip to Europe since its introduction, having extra time for passport checks and registration felt like a sensible buffer.
Suddenly, the plan felt much more straightforward—and much more appealing.
From Ikaria… to Where?
Rather than backtracking into the Cyclades, I started looking east. A quick glance at the map brought Samos into focus—another island I’d never visited, but one that had been quietly sitting on my list for a while.
It seemed like a natural pairing.
The only concern was getting home. But then I came across something that felt like perfect timing: Samos has an international airport, and Jet2 had just announced a new direct route to Manchester for 2026!
At that point, everything clicked into place.
If the flights lined up—and the price was reasonable—I had my route.
The Final Plan Confirmed
Here’s how the itinerary came together:
- An early easyJet flight from Manchester to Athens on Sunday 17th May, arriving late morning (£142 including cabin baggage)
- A few hours to spare at Athens Airport (with free food and drink courtesy of the Sky Express internal flight below)
- A late afternoon Sky Express flight to Ikaria (€96 including checked bag, seat selection, fast-track security and lounge access)
- Five nights on Ikaria
- Ferry from Ikaria to Samos with Dodekanisos Pride (€21, departing 16:25 and arriving 18:00)
- Four nights on Samos
- A midday return flight from Samos to Manchester with Jet2 on Tuesday 26th May (€128 including baggage)
Picking Accommodation and Where to Stay
With the route locked in, the next step was deciding where to stay on each island.
This is something I usually don’t have to think too much about—I tend to revisit places I already know. But with two completely new islands, it meant starting from scratch.
Ikaria
After some research (and a bit of help from ChatGPT—useful, as long as you sense-check it), three locations stood out:
- Agios Kirykos – the island’s capital and main port, close to the airport
- Evdilos – a central hub on the north coast
- Armenistis – a smaller, more scenic village further west
Agios Kirykos seemed more functional than atmospheric, so I ruled that out fairly quickly. Evdilos and Armenistis were a tougher choice, but in the end, Armenistis sounded like the better balance of charm, good food options, and access to the rest of the island.
For accommodation, I chose Pension Galini. At €67 per night (including breakfast), it’s slightly more than I paid on Mykonos last year—but with consistently strong reviews, it felt like good value.
Samos
On Samos, I narrowed it down to two options:
- Pythagoreio – a lively harbour town near the airport
- Kokkari – a smaller, picturesque village on the north coast
This time, I leaned towards a quieter, more relaxed base—so Kokkari it was.
Finding accommodation took a bit more effort, especially balancing price, location, reviews, and parking. Eventually, I settled on Kate Apartments, on the western side of the village but still within easy walking distance of the centre.
Car Hire
I’d usually rely on public transport to keep costs down—Greek island buses are generally cheap, reliable, and easy to use.
But both Ikaria and Samos are relatively large islands, and from what I’ve read, bus services are fairly limited. With only five and four days on each island, I want the flexibility to explore properly without being restricted by timetables.
So for this trip, I’ll be hiring a car on both islands—picking up at the airport in Ikaria and dropping off at the port, then doing the same in reverse on Samos.
Summary
I’m still fine-tuning the day-to-day plans for each island, so I’ll be sharing a more detailed itinerary in a follow-up post soon.
For now, the foundations are in place—and I’m genuinely excited about this one. Two completely new islands (numbers 35 and 36, if I’m counting correctly), a route I’ve never done before, and plenty of opportunities for new content along the way.
I’ll be documenting the whole trip here on the blog, as well as over on YouTube (check out Greece Travel Guide)—so if you want to follow the journey as it unfolds, there’s plenty more to come.
