How to plan your trip

Planning a trip to the Cyclades Islands can be both exciting and a little daunting, but with a few key steps, I managed to create an itinerary that was cost-effective, efficient, and enjoyable. Here’s how I went about it:

Start with a Map

I began by looking at a map of the Cyclades and circling all the islands we wanted to visit. This helped to visualise the geography and work out possible travel routes. It also made it easier to see which islands could be grouped together logically based on ferry connections.

Choose Arrival and Departure Points

We decided to fly into Santorini and fly home from Mykonos, as both islands have international airports. This made travel much simpler and more cost-effective than flying into a smaller or private airport, and meant we didn’t need to backtrack at the end of the trip. I used Skyscanner to find our flights, and booked direct with the airline.

Experiment with Ferry Routes

Once our flights were booked, I used Ferryhopper to explore ferry routes and dates. Determine how long you wish to stay on each island, and play around with different dates/times to find the most affordable and time-efficient options.

This involved some trial and error - I rearranged the order of the islands and occasionally substituted one for another when the routes didn’t work well or weren’t cost-effective.

Book Ferries in Advance

After finalising our island-hopping route, I booked all of the ferry tickets ahead of time. Doing this in advance gave me peace of mind, particularly as we were travelling in shoulder season. It also helped to plan check-in/check-out times at accommodation and avoid long waits.

Research and Compare Accommodation

For each island, I used Airbnb, Hotels.com, and Booking.com to research places to stay. I also checked the local hotel websites, as sometimes booking directly was cheaper.

It’s important to consider the location and how accessible the accommodation is. Depending on where you’re staying, you may need to hire a car or quad bike to get around - especially if you’re staying outside of the main town or near remote beaches.

Top tip: Airbnb often offers more flexible cancellation policies, but booking direct through a local site can be significantly cheaper - so it’s worth comparing both before booking.

Vehicle Hire: Don’t Stress About Booking in Advance

I didn’t pre-book any vehicle hire in advance - instead, we waited until we arrived on each island, or the day prior. This was just as cost-effective and allowed us to see what was available and assess the area before committing.

We hired a car or quad bike on three out of the five islands we visited. On the others, we relied on public transport and walking, which worked well for smaller islands or when staying centrally.

These simple steps made planning our Cyclades adventure much easier. With a bit of flexibility and research, you can build your own smooth, affordable island-hopping itinerary too.

Whether you’re after beautiful beaches, traditional villages, or unforgettable sunsets, the Cyclades have something for everyone - and planning the journey is all part of the fun.

You can find a guide to each of the islands I visited at the bottom of this post.

highlights from each island

Santorini - Exploring the island by quad bike was a highlight - it gave us the freedom to see quieter spots like Imerovigli, which had some of the most stunning views we found anywhere on the island. Oia lived up to the hype for sunset, and dinner at Theofanis Food Experience was one of our favorite meals.

Paros - Naoussa stood out with its charm and lively atmosphere. We had a great lunch at Pita Frank, then indulged in dessert at 32 Agosto. One of the most fun parts of our stay was catching a ferry to Antiparos - a simple but rewarding day trip with a totally different vibe.

Tinos - Tinos ended up being our favorite island for food. The variety and freshness really stood out, with influences from different cultures. A morning stroll along the waterfront followed by breakfast at The Roosters made for a perfect start to the day.

Naxos - We rented a quad bike again here, which let us discover hidden spots like Hawaii Beach - quiet, remote, and beautiful. Sunset at the Portara, the ancient marble doorway of the Temple of Apollo, was another highlight.

Mykonos - Driving around Mykonos wasn’t ideal, but it was worth it to reach beaches and villages outside of the main town. Sunset in Little Venice was a standout moment - the colours reflecting off the buildings were incredible. Ornos and Panormos Bay were both great places to relax after exploring.

how long to spend on each island

Santorini - 3 days is ideal to enjoy the main sights without rushing.

Paros - Paros is diverse, so 3 days lets you enjoy both villages and beaches. If time allows, then a 1/2 day in Antiparos is worth the visit.

Tinos - Tinos is less touristy, but 2 full days is enough unless you’re deep into rural culture or hiking.

Naxos - Naxos is big with lots of variety. 3 days is perfect to enjoy beaches, history, and mountain villages.

Mykonos - If you’re into nightlife and beach clubs, then you may want longer. If not, 3 days would be enough.

where did we stay?

Santorini - We opted to stay at Terra Vecchia Suites in Fira, as we wanted to be close to the centre but not right in the heart of the action and busy tourist areas. Our apartment was just a short 10-minute walk from the town centre, which made it easy to explore, yet far enough to enjoy some downtime after a busy day exploring. Our apartment was newly renovated and felt like a private sanctuary. It came with thoughtful amenities including a private hot tub, daily housekeeping, on-site parking, and a very attentive host who went out of their way to make our stay as comfortable as possible. It was the perfect blend of convenience, comfort, and tranquility. I highly recommended staying here if you're looking to stay near Fira without being caught in the chaos.

Paros - We stayed at Play Paros Hotel, perfectly located on the beautiful Livadia Beach and just a short walk from the heart of Parikia, including the port and bus terminal. The location couldn’t have been more convenient - close enough to explore the town’s shops, tavernas, and local beaches on foot, yet tucked just outside the busy main square, offering a peaceful escape from the noise and crowds. The hotel offers stunning beach views and features a private pool surrounded by sun loungers - the perfect spot to relax and unwind after a day of exploring the island.

Tinos - We chose to stay at an Airbnb just a few meters from the port and the city centre, and the location couldn’t have been more convenient. It was less than a two-minute walk to the port, and just as close to both the main bus terminal and the heart of town. The main selling point of this apartment was the private outdoor space, a peaceful courtyard with lemon trees and a cosy seating area. It gave us a quiet retreat right in the middle of town, which was perfect for relaxing after a day of exploring.

Naxos - We chose to stay in an Airbnb nestled in a quiet neighbourhood on the edge of Naxos Town. Just a short walk from the port, the apartment sat perched at the top of a hill, offering stunning views over the harbour and the sea. It struck the perfect balance, close enough to town to enjoy its vibrant cafés, tavernas, and shops, yet far enough removed to escape the daily hustle and bustle.

Mykonos - We stayed at the Regency Villa: Sunset Suites, which we booked through Airbnb, and it was everything we could have asked for and more. This newly renovated luxury accommodation is situated just a short drive from central Mykonos, within a small, private complex of only six suites, offering a peaceful and exclusive atmosphere.

getting around

Santorini - We chose a 450L C-Force quad bike from Super Moto, and it turned out to be the perfect choice for two people. It was extremely comfortable, easy to drive, and came equipped with a secure lockbox on the back, which was ideal for storing helmets and personal items while sightseeing.

Paros - Parikia itself is very walkable, but if you’re planning to visit other towns like Naoussa or Lefkes, you’ll need to drive or take public transport. While there are plenty of options to rent a car or motorbike on the island, we didn’t feel it was necessary for our trip as public transport worked well for us. 

Tinos - Chora is very walkable, but if you want to explore other villages like Pyrgos, Volax, or Panormos, you’ll need to rent a car, scooter, or use the island’s public buses.

Naxos - We hired a 450L C-Force quad bike from Mike’s Bikes & Cars and it was the perfect choice for two people - comfortable, easy to handle, and equipped with a secure lockbox for helmets and personal items while sightseeing.

Mykonos - We rented a car during our stay from Assimomitis, which gave us full freedom to explore at our own pace. The car was comfortable, easy to drive, and perfect for navigating both the town’s narrow streets and the scenic coastal roads. We booked our rental ahead of time online, and the pickup process at the port was smooth and hassle-free. We paid around €40 per day for a Kia Picanto (plus fuel). The rental included pick up and drop off from the port/airport which was really convenient and saved us additional expenses.