Introduction
When planning trips to Greece, I usually start by looking at flights since they’re often one of the biggest expenses. The destinations and dates of available flights heavily influence when and how long I travel. For this trip, I wanted to visit some smaller islands around Naxos, and the quickest way to get there was by flying into Mykonos. After checking various websites, I discovered that EasyJet offers flights from Manchester to Mykonos. However, in May, there were only two weekly flights—on Wednesdays and Saturdays. This meant I could plan for either a trip of one week, about ten days, or two weeks.
Fixing the Itinerary
Initially, I considered a ten-day itinerary, but it quickly became clear that visiting at least two or three of the smaller Cycladic Islands within that timeframe would be a stretch. The flight will arrive late to Mykonos, requiring an overnight stay before I can start exploring. With these factors in mind, I decided on a two-week itinerary. This gave me enough time to visit the islands I wanted and allowed me to extend my Mykonos stay to two or three nights. While Mykonos isn’t one of my favourite islands, visiting early in the season, when it’s less crowded and expensive, seemed like a good opportunity to explore and create an island guide for others.

Next, I started working out possible routes for the trip. One suggestion I found online was to travel counterclockwise around Naxos, starting with Iraklia, then moving on to Schinoussa, Koufonisia, and Donousa, before looping back to Mykonos via Naxos. However, after playing around with ferry schedules and deciding on at least three nights per island, the counterclockwise route didn’t work. One stop required either just two nights or an extended stay of five nights to fit ferry connections. Reversing the itinerary worked much better.
Ultimately, my plan became this: start with three nights on Mykonos, then take a ferry to Donousa via Naxos (as there’s no direct ferry). I’ll spend four nights on Donousa, which might be excessive since it’s a small island, but it allows ample time to explore. From Donousa, I’ll head to Koufonisia for three nights. I debated skipping Koufonisia since I’d been there in 2018, but it’s been a while, and the island has become more popular. I’m curious to see how it has changed and plan to gather updated footage for an island guide.

Cutting it Down
Initially, I wanted to visit Schinoussa after Koufonisia, but even with a two-week itinerary, it wasn’t feasible to include four islands on top of Mykonos. After seeking advice online, I decided to skip Schinoussa as it’s reportedly less interesting compared to the others. Instead, I’ll go directly to Iraklia for three nights. Iraklia is quite small, so three nights should be plenty of time to explore. I could extend my stay to four nights and then take a ferry back to Mykonos on the day of my flight home. However, I opted for a different approach.
The Journey Back
Instead, I’ll spend one night on Naxos on the way back. This gives me a chance to revisit Naxos briefly and gather updated footage, as much of my existing content is getting a bit outdated. After that, I’ll take an afternoon ferry to Mykonos for a late flight home.

And that’s the rough itinerary! I’m hoping it’s a well-balanced schedule that gives me time to explore new and familiar islands without feeling rushed.