If you are looking for the ultimate Greek island hopping guide, you have come to the right place. Few trips we have ever taken have matched the Greek islands for sheer beauty, incredible food, warm water and the kind of days that feel almost too good to be real. We have done island hopping in both Greece and Croatia — and we run our own boutique sailing trip called Voyage out of Athens, Split, Sardinia and the British Virgin Islands — so we know a thing or two about making the most of island life. This is everything you need to plan your own Cyclades island hopping adventure.
OUR GREEK ISLAND HOPPING ROUTE
Our route through the Cyclades looked like this:
- Athens — fly in, spend time exploring the city before heading to the islands
- Santorini — flew from Athens (45 minutes, far faster than the 5–8 hour ferry)
- Tinos — a brief stop between islands; beautiful and quiet, not yet a major tourist destination
- Mykonos — ferried from Santorini (roughly 2 hours)
- Athens — ferried back from Mykonos (roughly 3.5 hours)
From Athens we went straight into Yacht Week Greece with a group of friends. Before all of that happened though, Seth proposed in Athens after we returned from Mykonos — so this trip holds a very special place in our hearts. We highly recommend ending a Cyclades island hopping trip back in Athens. The city deserves far more time than most people give it, and apparently it is also a great place to get engaged.
Pro-tip: Book all inter-island ferries through Ferryhopper well in advance. Summer routes fill up fast and on-the-day tickets for popular crossings like Santorini to Mykonos are often unavailable.
SANTORINI (WE RECOMMEND AT LEAST 4 DAYS)
We spent three days in Santorini and it was not enough. We do not say that lightly — we packed in a lot — but Santorini rewards slow travel. Here is how we spent our time, and what we would do differently. We based ourselves near Fira, which we highly recommend. Fira is central, walkable, full of great restaurants and bars, and has views over the caldera that genuinely compete with anything in the more famous Oia. It is also better positioned for getting around the island.
THE CALDERA BOAT TOUR
The single best thing we did in Santorini — possibly one of the best days of all our travels — was the caldera boat tour. You sail out around the volcanic caldera, swim in the geothermal hot springs, and stop at a small fishing village for lunch. At that lunch stop we had the best grilled octopus of our entire lives. Perfectly charred, tender all the way through, dressed with good olive oil and lemon. We still talk about it years later. Book your boat tour in advance — spots go quickly in summer and this is the one activity in Santorini you cannot afford to miss.
Pro-tip: The small towns you stop at on the boat tour are far more authentic and relaxed than Oia or Fira. Eat everything put in front of you. Order the octopus.
THE ATV DAY
Renting an ATV and driving around Santorini is one of the most fun days we have had anywhere in Europe. The island is small enough to cover in a single day and the roads take you through all the major sights — Oia, Akrotiri, the black sand beaches at Perissa and Perivolos, the lighthouse, the wineries. Stop wherever you want, for as long as you want, with no tour guide and no schedule. We paid roughly €50–70 for the day depending on season. Book your ATV rental in advance — they go fast.
Pro-tip: Start early to beat the heat and get to Oia before the crowds arrive. The village is magical at 8am and completely overwhelming by 11am.
SKIP THE OIA SUNSET CROWDS — WATCH FROM FIRA INSTEAD
Everyone tells you to watch the Santorini sunset from Oia. The Oia sunset is indeed beautiful. But the sunset from Fira is equally stunning and the crowd is a fraction of the size. We found a spot right in Fira overlooking the caldera, ordered drinks, and watched the sun drop behind the volcanic rim. We liked it better than Oia. You can actually move, breathe, and enjoy it. The caldera catching the last golden light is extraordinary. Find yourself a good terrace bar in Fira, settle in early, and enjoy one of the most memorable sunsets of your life without the shoulder-to-shoulder crowds.
A CRITICAL WARNING ABOUT THE SANTORINI FERRY PORT
The ferry port in Santorini — Athinios Port — is one of the most chaotic ports we have ever experienced anywhere in the world. Multiple ferries depart at similar times. Signage is poor. Announcements are unclear. It is genuinely not obvious which boat is going where. We got on the right ferry but it was stressful. Our advice: arrive early, have your ticket on your phone, find a crew member and ask them directly which boat is yours. Do not follow the crowds. They might be boarding a different ferry entirely.
MYKONOS (WE RECOMMEND AT LEAST 3 NIGHTS)
We spent two nights in Mykonos and wished we had more. We arrived needing rest — we were leaving for Yacht Week Greece just days later — so we kept things relatively low key. Even on a quiet setting, Mykonos delivered completely.
THE WINDMILLS AND LITTLE VENICE
Two things you absolutely cannot skip in Mykonos. The windmills sit on a hill overlooking the town and are the iconic image of the island — visit in late afternoon when the light turns golden. Little Venice is a row of colourful buildings built directly over the water, with bars and cafes where you can sit with your feet almost hanging over the Aegean. It is one of the most picturesque spots in all of Greece. Go at sunset with a drink in hand.
THE BEACHES
Psarou is our recommendation for a relaxed, upscale beach day. Paradise Beach is the party scene. We went to Psarou, had a wonderful lazy afternoon, and came back completely recharged. If you have more time, Super Paradise and Elia are also worth the trip.
THE CLUB SCENE
If you are going to Mykonos to experience the clubs — and it is absolutely worth it — give yourself more than two nights. The clubs here are world class, the energy is unlike anywhere else in Europe, and the scene starts late. We ran out of time, which remains our one genuine regret from the trip. If you have the flexibility, stay a third or fourth night and do it properly.
GREEK ISLAND HOPPING TIPS FROM EXPERIENCE
BOOK FERRIES EARLY. Use Ferryhopper to compare routes and times, and book as soon as your dates are confirmed. The Santorini to Mykonos route in summer sells out well in advance.
FLY ATHENS TO SANTORINI. The ferry from Athens to Santorini takes 5–8 hours depending on the boat. The flight takes 45 minutes. Unless you have time to spare, fly. The island-to-island legs are short enough to enjoy by boat.
RENT AN ATV OR SCOOTER ON EACH ISLAND. Both Santorini and Mykonos are small enough to cover by ATV in a day. It is the most flexible, most fun, and most affordable way to see everything.
GIVE EACH ISLAND MORE TIME THAN YOU THINK. We gave Santorini three days and Mykonos two. Both felt short. Four days in Santorini and three in Mykonos would be the move.
CONSIDER ADDING A SAILING CHARTER. If you want to take your Greek island hopping to the next level, sailing is the way to do it. We run our own boutique sailing trip, Voyage, out of Athens, Split, Sardinia and the British Virgin Islands — there is truly no better way to see the Greek islands than from the water.
GET AN ESIM BEFORE YOU LEAVE. Saily is our go-to eSIM for Greece and anywhere in Europe — use code THEJETLAGJOURNEY25 for 25% off. We also love Airalo (code JLJ10 for 10% off) as a great alternative.
DON’T FORGET ETIAS. From Q4 2026, American travelers will need to apply for ETIAS before visiting Greece and the rest of the Schengen Area. Read our complete ETIAS guide for everything you need to know — it only takes 10 minutes and costs €20.
Frequently asked questions about Greek island hopping
What is the best Greek island hopping route for first-timers?
Athens, Santorini and Mykonos is the classic Cyclades route and the one we recommend for first-timers. It combines ancient history, dramatic volcanic scenery and the best of the Aegean in a single trip. Budget at least 10 days minimum.
How do you get between the Greek islands?
By ferry for island-to-island legs — book through Ferryhopper in advance. We recommend flying from Athens directly to Santorini (45 minutes) rather than taking the 5–8 hour ferry, then ferrying between islands from there.
How many days do you need for a Greek island hopping trip?
We spent three days in Santorini and two in Mykonos and both felt short. Budget four days per island minimum, plus a couple of days in Athens at the start or end. Two weeks gives you a much more relaxed and complete experience.
Is the Santorini ferry port really that chaotic?
Yes — it is the most disorganised port we have encountered in all of our travels. Multiple ferries depart simultaneously with poor signage and unclear announcements. Arrive early and ask crew directly which boat is yours.
Is Greek island hopping better than Croatia island hopping?
We have done both and love them for different reasons. Greece is more dramatic — the volcanic scenery, the food, the history. Croatia is lush and green with incredible national parks and a buzzing sailing culture. We run Voyage sailing trips in both and would recommend doing each at least once.
