14 Days Sailing Itinerary

Two week itinerary Greek islands. Best sailing in Greece two weeks itinerary

Build a Balanced 14-Day Greek Islands Cruise

Two-week route design that blends iconic Cyclades highlights with quieter island stops

Use this page to compare realistic two-week itineraries and choose the route logic that fits your group, pace, and weather priorities.

Choosing the best itinerary for your two week vacations in Greece can be a challenge since all the Greek islands are simply amazing. So why limit your holiday to just one or two of the Greek islands when you can get a two weeks island hoping cruise on board your private yacht so you can explore 13-14 Greek islands during the 14 days spent on board? For details on two weeks private sailing cruise please see: skippered sailing holidays

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.

Below you can find some great ideas and itineraries maps for a two weeks (14 days) island hopping cruise to the Cyclades and Aegean sea.

Select an island below to view its photo album.

Private 7-14 Day Sailing Packages

Planning two weeks but comparing alternatives? This guide provides a clear view of our core private sailing structures and what each duration unlocks.

Helpful if you want to shape a custom private yacht holiday in Greece around fixed travel dates.

7-14 Day Cruise Options - View Details

Short Sailing Segments (3-5 Days)

If your two-week plan includes land travel, these short private sailings work as elegant pre- or post-charter add-ons.

Great for combining a full itinerary with a focused short sailing escape in Greece.

3-5 Day Sailing Add-Ons

14 Days Routes in the Greek Islands

Two departure strategies with strong flexibility across Cyclades and nearby island groups

Select an island below to open the photo album and compare how each route family can be paced.

Sailing Itineraries from Paros

- sailing around the Cyclades islands -
Mykonos, Santorini, Paros, Naxos, Milos, Ios and many more

Mykonos Naxos Small Cyclades Santorini Ios Folegandros Milos Kimolos island Sifnos Serifos mooring in the bay, access to shore by dinghy Paros Syros Tinos

Sailing Itineraries if you depart from Athens

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

Kea Syros Tinos Mykonos Naxos Small Cyclades Santorini Ios Sifnos Serifos mooring in the bay, access to shore by dinghy Kythnos Poros Ancient Epidaurus

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 any of the days, the exact itinerary and program will be changed to adjust to weather conditions for a safe sail and anchorage at a sheltered harbor/bay.
The final itinerary is always set on board after checking the weather forecast.

Meal Options for 14-Day Cruises

During a two-week sailing itinerary, the most comfortable rhythm is a mix of simple onboard meals and evening dining ashore. Most guests enjoy easy breakfasts and light lunches onboard, then discover local tavernas for dinner at each overnight stop.

Provisioning remains straightforward: local markets and mini-markets are available across the islands, so restocking fresh Mediterranean ingredients is easy throughout the trip.

This format offers flexibility, strong value, and a more authentic island experience, while keeping onboard logistics simple and relaxed over a longer route.

Let us plan for you the perfect route in Greece for an unforgettable two week intineary in the Greek islands.

Greece offers and 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 islands of Ios , the beautiful Naxos , the pristine Small Cyclades just to name a few. A sailing cruise will ensure you a relaxing, personalized tour to the best Greek islands with a customizable itinerary.

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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