We Plan, You Play
Greek Island Hopping, Planned Around You
Your islands, your pace, your boat. We handle the ferries, the transfers and the 6am port chaos so you never once have to look at a timetable.
Greek island hopping means travelling between several Greek islands on one trip, moving by ferry or by boat and staying a few nights on each. Planned for you rather than bought off a shelf, it means a route built for your dates alone, with no group and no fixed departure.
- How long: most island hopping trips run 8 to 14 days.
- How many islands: two to four, starting and ending in Athens.
- What we book: the ferries, the hotels, the transfers and the guides.
- While you travel: a real person in Athens on WhatsApp, for the whole trip.
Here is the thing nobody tells you. The islands are the easy part.
Greece has around 6,000 islands and islets, only a couple of hundred of them inhabited, and every single one is beautiful. The hard part is the joins.
- Which ferry actually runs in May.
- Which port is on the other side of the island from the town.
- Why the wind cancelled your boat when it is 32 degrees and there is not a cloud in the sky.
That is the part we do.
Three Ways To Do It
Group tours
Fixed dates, fixed islands, a coach and forty other people. Cheapest of the three, and you see what the itinerary sees.
Do it yourself
Total freedom, and roughly eleven hours of ferry research per island. Fine if you enjoy that, and genuinely a lot of people do.
Planned for you by us
Your route, your dates, your pace. We do the eleven hours, hold the bookings before they sell out, and answer the phone when the ferry is cancelled.
How It Works
Tell us the shape of the trip
How long, what time of year, and what you actually want. Beaches, ruins, food, sailing, quiet, or all of it in the wrong order.
We propose a route
Islands that connect properly, in a sequence that works with the ferry schedules rather than against them.
You change it
Everybody changes it. That is the point of the word custom.
We book everything
Ferries, hotels, transfers, guides, and the restaurants worth booking ahead.
You travel, we stay on
WhatsApp, Greek time, from the airport transfer to the flight home.
Choosing Your Islands
The most common planning mistake is picking islands from photographs rather than from a map. The Ionian and the Cyclades do not connect. There is no ferry between the two groups at all, so getting from one to the other means crossing the mainland, usually via Athens, and that eats two days.
| Island group | Character | Best for | Getting around |
|---|---|---|---|
| CycladesSantorini, Mykonos, Naxos, Paros, Milos, Folegandros | Whitewashed, dramatic, the postcard | First trips, island hopping proper | Excellent connections, the natural hopping ground |
| SaronicHydra, Spetses, Aegina, Poros | Green, close, understated | Short trips, add-ons to Athens | One to two hours from Athens, easy |
| DodecaneseRhodes, Symi, Kos, Patmos | Medieval, Ottoman, layered | History, quieter beaches | Good within the group |
| IonianCorfu, Kefalonia, Zakynthos, Paxos | Lush, Venetian, Italian adjacent | Green landscapes, sailing | Good within the group, a separate world from the Cyclades |
| SporadesSkiathos, Skopelos, Alonnisos | Pine forest to the waterline | Beaches, families, quiet | Compact and easy |
| CreteAn entire country pretending to be an island | Mountains, gorges, four separate cities | Two weeks on its own | A trip in itself, not a hop |
Our honest advice: pick one group. Better to know two islands properly than to rush through four.
Three Routes We Build Often
Sample structures. Every one of them gets rewritten for the people travelling.
The classic
Athens to Naxos to Santorini
Three days of Athens, five on Naxos for beaches, mountain villages and the best food in the Cyclades, then Santorini for the caldera and the flight home. Naxos first is deliberate. Santorini after Naxos feels spectacular, while Naxos after Santorini feels like a downgrade it does not deserve.
The quiet one
Athens to Paros to Milos to Folegandros
For people who have seen the postcards and want the other thing. Milos for the volcanic coastline and beaches you reach by boat, Folegandros for a clifftop village and almost nothing else. Fewer sailings, so the sequencing has to be exact.
Under sail
Athens, then a private catamaran through the Cyclades
Skipper, crew, and a route decided by the wind and your mood. Beaches with no road access, no ports, no luggage moves. The most expensive way to do it and the one people talk about for years.
What We Handle
Book Greek island ferry bookings and private catamaran charters in the Greek islands through us, along with hotels and villas across Greece, private airport and port transfers in Greece and car rental in Greece. If the trip is bigger than the islands, start with bespoke Greece travel planning instead.
Getting The Ferries Right
Ferries are what turn a list of islands into a trip that holds together. Here is what we know, and what we build every route around.
Two ports serve Athens
Piraeus is the big one. Rafina is closer to the airport and sails year round to Andros, Tinos and Mykonos, adding high speed routes to Paros, Naxos, Ios and Santorini across the summer. It is consistently overlooked.
The Meltemi is real
The northerly summer wind peaks in July and August and cancels sailings on clear, hot days. High speed catamarans are usually the first to be pulled, because they are lighter.
High speed costs roughly double and saves roughly half
In windy weeks the slow ferry is the reliable one.
Ports are not towns
Santorini's port sits at the bottom of the caldera cliff. Allow real time.
Book ferries before hotels in high season
Hotels have flexibility. The 2pm sailing to Folegandros does not.
Never connect a same day flight to a same day sailing in August
One delay and there is no seat on the next one.
All of it is baked into the routes we build. Less glamorous than the photographs, and it is the reason the trip works.
When To Go
| Period | Weather | Crowds | Ferries | Verdict |
|---|---|---|---|---|
| April and May | Warm, sea still cold | Quiet | Reduced schedules | Best value, though some places are not yet open |
| June | Excellent | Building | Full schedules | Arguably the sweet spot |
| July and August | Hot | Peak | Full, with Meltemi cancellations | Book months ahead |
| September | Excellent, sea at its warmest | Thinning | Full into mid month | Our favourite |
| October | Mild, variable | Quiet | Winding down | Lovely, but watch the schedules |
| November to March | Cool, wet | Empty | Skeleton service | Athens yes, island hopping no |
Island Hopping FAQs
Two or three for a ten day trip. Four is possible and usually a mistake.
- Every island change costs the better part of a day: checkout, port, sailing, transfer, check in.
- Three islands in ten days: means roughly three full days on each.
- Four islands in ten days: means you unpack four times and swim twice.
For July and August, four to six months. For May, June and September, two to three.
- Ferries release on operator schedules: not a fixed date, and the good sailings go first.
- Catamaran charters for August: are often gone by February.
- Small islands have few beds: Folegandros and Symi sell out early.
- Off season: a few weeks ahead is genuinely fine.
Yes, with the right islands. Naxos and Paros are the two we recommend most for families.
- Shallow, sheltered beaches: and short transfer times.
- Enough to do on a rainy day: which does happen in shoulder season.
- Fewer, shorter ferry legs: build in more nights per island.
- Santorini: is spectacular and involves a great many steps.
Yes, and it happens constantly.
- Send us the flight dates and airports: and we build the route around them.
- Arrival and departure airports: do not have to match.
- Flying home from Santorini or Mykonos: rather than back through Athens often saves a day.
It depends entirely on the island.
- Naxos, Paros, Milos and Crete: yes, the good parts are inland or down a track.
- Santorini: no, and parking is a blood sport.
- Hydra: no, there are no cars on the island at all.
- Mykonos: it depends where you stay.
You message us and we sort it out. That is most of what the 24/7 support is for.
- We rebook the sailing: or find the flight.
- We hold your hotel: and move the transfer.
- You do not queue at a ferry desk: in a language you do not read.
It depends on the islands, the season and the hotels, which is a real answer rather than an evasion.
- The route drives the cost more than the length: Santorini in August and Naxos in May are different trips financially.
- Private catamaran charters: are the top end by a distance.
- Tell us a budget: and we will tell you honestly what it buys.
- No fixed packages: so nothing is priced for someone who is not you.
Ready When You Are
Tell us roughly when, roughly how long, and what you want out of it. We will come back with a route, and if it is wrong, tell us and we will change it. That is the whole job.
We are Monobrow Holidays Greece, licensed by the Greek Tourism Authority (EOT 0206Ε60000378300), based in Athens. Thanasis has been building trips here for over thirty years. Theo answers the WhatsApp.