Private Multi-Island Routes Across the Cyclades and Beyond
The Greek islands are not one destination. They are a collection of entirely different worlds, each with its own character, color, and rhythm. Whitewashed villages spilling down volcanic cliffs. Coves that see fewer than a dozen visitors a day. Harbors where fishing boats dock beside centuries-old windmills.
Since 2010, we have been building private Greek island hopping packages for travelers who want more than a postcard, whether you are planning a luxury vacation, a honeymoon, or a multi-day journey across the Aegean with family or friends. You move between islands by sea, with a planned itinerary, private transfers at every port, and a team in Athens that knows each connection.
No group bus. No fixed departure times. No compromises. Just you and an archipelago waiting to be explored.
Why Choose Private Island Hopping in Greece?
The difference between a standard package holiday and private island hopping in Greece is the ability to set your own pace:
- Fully private: your group, your itinerary, never combined with strangers
- Custom-built routes: choose your islands based on your interests and travel dates
- Logistics handled: ferries, private boats, transfers, and accommodation are all pre-arranged
- Local team on the islands: drivers and guides who know the best tavernas, quiet beaches, and off-season openings
- Flexible pacing: slow mornings, long lunches, late sunsets, all planned around your rhythm
- Accommodation at every level: boutique hotels, cave suites, and clifftop villas chosen for your trip
Explore Our Most Popular Island Hopping Packages
What's Included in Your Package
- Fully personalized multi-island itinerary built around your travel style
- All inter-island transfers: ferry tickets, private boat charters, or seaplane on request
- Private airport and port transfers on each island
- Hotels booked by us or shortlisted for you, always from properties our team knows
- Direct support from our Athens office throughout your trip
- Activity suggestions: boat tours, winery visits, archaeological sites, cooking classes
- Full refund on cancellations made 40 days or more before departure
Who Plans Your Island Hopping Route
Every package is planned in our Athens office. Eleni answers your first request and works through the island order, the number of nights, and the crossings with you. Lia and Fotini, our operations team, then book and confirm every ferry, hotel, and transfer between islands.
On the islands, the handover is personal. Loukas runs our transfers on Santorini, Stelios meets our guests on Paros and stays with them through the day, Evangelia does the same in Rhodes, and Maria guides the visit to Knossos when Crete is part of your route.
How Many Islands Should I Visit?
The sweet spot for most travelers is 3 to 4 islands over 7 to 10 days, enough to feel each island's personality without spending half your vacation on a ferry. We plan a minimum of two nights per island, because every island change costs roughly half a day once you count checkout, the port, and the crossing. A 7-day Greek island hopping itinerary typically covers Mykonos, Paros, and Santorini. A 10-day itinerary opens the door to Milos, Naxos, or Crete alongside the Cyclades classics. For ferry timing between islands, see our island hopping guide.
When is the best season for island hopping?
May, June, and September offer warm seas, open attractions, and far fewer crowds than July and August. October offers excellent value, although ferry frequency drops toward the end of the month.
Which Islands Can I Include?
Island hopping in Greece goes well beyond the Cyclades. Our packages reach the Dodecanese, the green Ionian islands, and the unspoiled North Aegean. If you are still deciding on the best Greek islands to visit, the answer depends on what you are looking for: Santorini and Mykonos for the iconic experience, Milos and Paros for something quieter, Crete for history and food. Cyclades island hopping is the most popular starting point for first-time visitors, and we will tell you exactly which combination suits your travel style.
What Our Guests Say
“I took ‘16 Days Tour in Greek Islands & Athens’. It started in Athens, then Kafalonia, Mykonos, Santorini, Crete and ended in Athens. … The trip organization, the tours, the hotels, the transfer, everything was super. The tours within the islands were very well organized and on time. I can not tell which island I liked more, each one has its own flavor. … My travel agent Dimitra, was very easily approachable, either by direct call or via whatsup. … I highly recommend Private Tours Greece for everyone thinking of visiting the wonderful country named Greece.”
majedaha, TripAdvisor
“We communicated back and forth for many months with Mrs. Dmitria to create this customized trip. Throughout all the communications, Mrs. Dmitria was very patient and flexible. She worked with us to make many changes to the itinerary until it was something that met our group's needs in terms of budget and covering the places we wanted to see. … In addition, the tour guides she booked for us were also great.”
RealityCheck3, TripAdvisor
“Our family traveled to the mainland as well as two of the Greek islands with Private tours Greece. Can’t say enough about our driver/guide George who for six of those days went above and beyond what was expected. Every drivers and local guides were on time and delivered very good service. We had one bad stay at one of the hotels and Dimitra took over and found us new accommodations. They answered all my questions during the planning stage very quickly and with professionalism. Well done!”
Stephan B, TripAdvisor
Read all our reviews on TripAdvisor
Frequently Asked Questions
What is the best island hopping route for a first trip to Greece?
For most first-time visitors, we recommend the Classic Cyclades route: Athens, Mykonos, Paros, and Santorini over 7 to 10 days. It combines the energy of Mykonos, the easy pace of Paros, and the caldera of Santorini, with manageable ferry crossings between each island.
Do you offer honeymoon island hopping packages?
Yes, and it is one of our most requested trips. Our honeymoon island hopping itineraries are built around privacy and romance: cave suites with caldera views in Santorini, a private sunset cruise in Mykonos, a table for two at a harbor taverna in Hydra. Every detail is arranged in advance so you arrive as guests, not planners.
Do I need to book ferries myself?
No. Ferry tickets, schedules, port transfers, and luggage logistics are handled entirely by us. You simply arrive at the port at the time we provide. For ports and crossing times, see our guide to getting from Athens to the Greek islands.
Can I add a private boat charter between islands?
Yes, and we recommend it for certain routes. Sailing from Mykonos to Delos or from Milos to Folegandros privately is an entirely different experience from the ferry.
What is your cancellation policy?
Cancellations made 40 days or more before departure receive a full refund. Cancellations made 19 days or less before departure are subject to full cancellation charges, although we can issue a travel credit toward a future trip on request. Between 20 and 39 days, the charge depends on the ferry, flight, and hotel bookings already committed on your behalf, and we confirm the exact figure in writing before you decide.
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