21 Days Sailing Itinerary

Itinerary for sailing in Greece - Greek island hopping

Below you can find some great ideas and itineraries maps for a three weeks island hopping cruise to the Cyclades:

Plan a Three-Week Greek Islands Voyage with Confidence

Long-range island hopping routes designed for flexibility, comfort, and real Aegean sailing conditions

Use this 21-day guide to compare route families, estimate pacing, and choose the island mix that best matches your group.

Choosing the best destination for your vacations in Greece can be a challenge since all the Greek islands are simply amazing. Why limit your holiday to just one or two islands when you can enjoy an island-hopping cruise on board your private yacht and explore a dozen?

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Note: Itinerary is subject to weather conditions.
In calm to moderate weather we can take the itinerary you like best from the options below. However, if strong winds are announced, the program will be adjusted to ensure a safe sail and anchorage at a sheltered harbor. The final itinerary is always set on board after checking the weather forecast.

The sailing time can be minimized (for extra time swimming and exploring the islands) by excluding the furthest away islands.

Greece offers an incredible diversity of islands that will fully satisfy even the most demanding visitor: the cosmopolitan Mykonos, the romantic Santorini, the magical Paros, the undiscovered Folegandros, the party island of Ios, the beautiful Naxos, and the pristine Small Cyclades just to name a few. A sailing cruise ensures a relaxing, personalized tour of the best Greek islands with a customizable itinerary.

1-2 Week Private Sailing Holidays in Greece

If your plan may shift from 21 days to a shorter premium itinerary, this page helps compare the classic one-week and two-week charter structure with full pricing clarity.

A practical reference for travelers designing a longer private yacht charter in Greece around flights, weather windows, and preferred islands.

7-14 Day Private Cruise - Details & Prices

3-5 Day Flexible Sailing Add-Ons

Need a compact route extension before or after your three-week charter? These short private sailings are ideal for custom trip building.

Useful for guests combining a long Cyclades crossing with a short private sailing segment in Greece.

3-5 Day Sailing Options - View Details

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21 Days Routes in the Greek Islands

Extended Cyclades and Aegean route families from Paros or Athens departure points

Select an island below to view its photo album and compare the rhythm of each route architecture.

Departure from Cyclades base

- sailing around the Cyclades and Dodecanese islands -
Mykonos, Santorini, Paros, Naxos, Kos, Nisiros, Astypalea, Amorgos and many more

Mykonos Naxos Small Cyclades Santorini Ios Amorgos Folegandros Milos Kimolos island Paros Syros Tinos Astypalea Kos Nisiros Anafi Patmos

Sailing Itineraries if you depart from Athens

- sailing around the Saronic islands and Cyclades -
Mykonos, Santorini, Poros, Epidaurus, Kea, Kythnos, Milos, Amorgos and others

Kea Syros Tinos Mykonos Naxos Small Cyclades Santorini Amorgos Ios Folegandros Milos Kimolos island Sifnos Serifos

mooring in the bay, access to shore by dinghy

Kythnos Poros

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However, this is just a suggestion.

We can set the program and itinerary according to your wishes and interests (within the realm of a sailboat and the time you plan to spend on board). The sailing time can be minimized (for extra time swimming and exploring the islands) by taking away the furthest away islands.

Note: In calm to moderate weather we can visit the destinations you like best. However, if strong winds are announced any of the days, the exact itinerary is subject to weather conditions and will be adjusted so that the overnight will be spent at a sheltered harbor.

Let us plan for you the perfect route around the Greek Islands for that unforgettable sailing holiday.

Owner-Operated Excellence Since 2012

Blue Water Sailing Greece is a boutique charter company founded and managed directly by owners Adriana and Radu. With over 14 years of professional sailing experience in the Cyclades and Saronic islands, we provide expert skippered vacations on our private yachts, Freedom and Albatross. Our deep local knowledge and owner-direct service ensure safe, authentic, and personalized Greek island adventures for families, couples, and groups of friends seeking a private getaway.

Contact Us

By email at:

info@sailboatchartergreece.com

— or —

sailboatchartergreece@gmail.com

By phone / WhatsApp:

+30 6933 218 799

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