Hey there, fellow travelers and digital nomads! If you’re planning a Greek island adventure, whether it’s a quick 7- to 14-day holiday or you are traveling Greece for a little longer, we’ve got the perfect Greek (Cyclades) Island Hopping itinerary for you. Having lived the digital nomad life ourselves, we know a thing or two about balancing work and wanderlust, especially in a place as captivating as the Greek Islands.
Our Greek Odyssey: A Month in Naxos
Let’s start with the laid-back vibes of Naxos. We actually spent a month there, soaking up its undeniable charm while juggling our online gigs. For those in the digital nomad community, Naxos is a gem, offering not just stunning views but also decent internet, but confirm the connectivity and speed with your hosts or whoever you are renting from ahead of time. It’s an island that caters wonderfully to both the wandering spirit and the working laptop.
Like I said, we spent a month here, but if you are just on vacation, I would still start your first 1-3 days here, depending on how much time you have and how you like to travel. Naxos is also the largest island of the Cyclades and very central for getting to most places.
Now if you know 100% you want to go to Mykonos then maybe you start there before heading to Naxos (it just makes sense if you are coming from Athens). You can also add in a day at Koufonisia, Paros, or both since they are both close to Naxos.
Next cruise to Santorini for a couple of days to get our fix of those jaw-dropping sunsets. And for the grand finale? It’s a toss-up between Mykonos and Milos. Mykonos promises a whirlwind of glitz and energy, while Milos offers a chill, nature-kissed escape. Decisions, decisions! Anyway, here’s the schedule with duration & ferry estimates.
Island Schedule From Athens
Athens Kick-Off (optional)
- You’ll probably fly into Athens, so if you have the time, it makes sense to spend a day or two visiting ancient ruins, learning about Greek mythology, eating all the great food, and exploring the coolest neighborhoods. Check out our 2-Day Athens Itinerary for some inspiration. And for my fellow digital nomads, here’s our guide to Athens for Digital Nomads to find the best spots to work and chill.
Athens to Naxos
- Duration: 3.5 to 5 hours for conventional ferries, and about 4 hours for high-speed ferries.
- Cost: €42.00 – €145.00 (approx. $44 – $153).
- Naxos is my favorite island of the cyclades.It is the largest of the Cyclades, known for its impressive mountainous landscapes & hikes, ancient ruins, and long sandy beaches, delicious local food, cute downtown.
Naxos to Koufonisia (Day Trip)
- Duration: 35 minutes to 2.5 hours depending on the vessel type.
- Cost: Starting at €8 (approx. $8.40).
- Note: The earliest ferry usually departs at 08:45 and arrives in Koufonisia around 10:15. The last scheduled trip is at 14:00, reaching Koufonisi at 16:35.
Naxos to Paros (Stay 1 Day or Day Trip)
- Duration: Around 35 to 50 minutes.
- Cost: €11.30 – €59.70 (approx. $12 – $63).
- Popular for its traditional villages, beautiful beaches, and active nightlife.
Paros or Naxos to Santorini
- Duration: 1h 25m to 3h 45m.
- Cost: €32.50 – €118.50 (approx. $34 – $125).
- Famous for its stunning sunsets, white-washed buildings, and blue-domed churches, wineries and underwater volcanoes.
Santorini to Mykonos
- Duration: 2 to 3.5 hours.
- Cost: €67.00 – €156.70 (approx. $71 – $165).
- Known for its cosmopolitan atmosphere, vibrant nightlife, beautiful beaches, and windsurfing
- Honestly we went to Mykonos instead of Milos and if I did it again I would go to Milos instead, but that is because I am not a big partier and all about the moonscape beaches. A lot of people go to Mykonos and love it, just all personal preference. This article has some good pictures and insights on all 3 (Mykonos, Santorini, and Milos)
OR Santorini to Milos
- Duration: A bit further than Mykonos (estimated about 5 hours ferry)
- Cost: Varies based on ferry but likely similar to other routes in terms of duration and slightly lower in cost compared to Santorini to Mykonos.
- Renowned for its unique volcanic landscapes and beautiful beaches, such as Sarakiniko.
This itinerary allows for in-depth exploration of Naxos with two enriching day trips to Koufonisia and Paros, followed by visits to Santorini and either Mykonos or Milos. The ferry times and costs are estimates and may vary, so it’s recommended to check the latest schedules and prices closer to your travel dates for the most accurate information.
Option to add Hydra
Start in Athens as planned, but go from Athens to Hydra instead. Hydra is not in the cyclades, but offers a unique and enriching experience, contrasting the bustling Cycladic islands with the serene, vehicle-free environment of Hydra. It’s a chance to witness a different side of Greek island life, characterized by its relaxed pace and artistic atmosphere.
- Athens to Hydra: Catch a ferry from Athens (Piraeus) to Hydra. The trip takes about 1.5 to 2 hours.
- Hydra Stay: Spend a day or two in Hydra, exploring its car-free streets, art galleries, and waterfront cafes.
- Hydra to Athens and onward to the Cyclades: Return to Athens and then continue to your original Cycladic itinerary (Naxos, Paros, Santorini, and either Mykonos or Milos).
Things to Consider
A quick tip though: ferry schedules and prices are kinda like the tide – they change. So, do yourself a favor and double-check those details closer to your departure. We want our adventure to be seamless, right?
- Booking in Advance: Especially during high season, ferry routes between popular destinations can sell out. Booking a month in advance is recommended.
- Travel Time vs Cost: Faster ferries are more expensive but save time. Slower ferries offer a more budget-friendly option but take longer. The travel times can vary drastically so be sure to check your options
- Ferryhopper is a good palace to look if you want to see all options.
- However if you know wish ferry you are taking you can book direct as well. We traveled on: Blue Star Ferries, known for their spacious and comfortable vessels, are perfect for longer, more relaxed journeys across the islands. Seajets has high-speed catamarans and ferries. Also, Golden Star Ferries offers both conventional and high-speed options. There are more than those 3, those are just the ones we took.
- Exploring Each Island: This itinerary provides a brief glimpse of each island. If you prefer a more relaxed pace or want to explore an island more thoroughly, consider skipping one of the destinations.
This itinerary is your gateway to a fantastic Greek island experience. It’s tried and tested by yours truly – a couple of digital nomads who’ve turned the world into our office. Whether you’re working remotely or just escaping for a much-needed break, these islands offer the perfect mix of adventure, relaxation, and awe-inspiring beauty.
Happy travels, and don’t forget to share your experiences with us. Let’s keep exploring this incredible world together, one island at a time!
