Our Best Greek Sailing Itineraries

For Those Who Love Relaxing Sailing, Enjoy the Warm Sea and Sun, and Explore Archaeological and Historical Sites

Why Sail In Greece and Where Are The Best Greek Sailing Itineraries

SailCheckers regularly asked us why we love sailing in Greece so much and ask for more about the best Greek sailing itineraries.

Before the more practical reasons for explaining our best Greek sailing itineraries, let’s marvel at the allure of Greek Mythology, the stomping ground of Poseidon, of Hercules, Lysander, and other great Hellenic heroes.

The ancient history of the Greek civilisation bursts forth at every turn with ancient ruins and dramatic temples. Spend your time gazing and contemplating of the wonder the philosophers with ideas that frame our modern world. Add the deep iridescent colours of the waters of the Ionian, Aegean, Cyclades and other hidden gems, for those thinking with their heart, there are many reasons to visit and choose one of our best Greek sailing itineraries.

Backing up the stunning waters are the numerous Blue flags you will find on Greek beaches with wonderful swimming and snorkelling opportunities, and with 1,431 to choose from, it will take you a little time to enjoy them all! The Greek weather offers over 250 days of sunshine each year and with access to 5 stunningly different sailing areas, each with their wind pattern, you are sure to find perfect sailing conditions and best Greek sailing itineraries for everyone.

We Review the Best Greek Sailing Itineraries

Five Amazing Areas to Sail – Each With Their Own Character and Sailing Conditions

shipwreck beach in Zante on an ionian sailing itinerary
white houses in Rhodes next to the ocean
colourful. houses and boats moored in the Sporades
a marina and harbour with colorful houses greek sailing itineraries

Why Not Ask For a Consultation and Get Our Experienced Greek Office to help you decide which is the best Greek sailing itineraries for you.

Best Greek Sailing Itineraries – All You Need to Know

We have created a mini Greece sailing guide with all the information you need to know including the best Greek sailing itineraries.

Wherever your start your sailing holiday in Greece, you will find superb sailing conditions in stunning surroundings, reliable winds, pristine seas, excellent food, a sunny Mediterranean climate and a welcome to match.

Our Best Greek Sailing Itineraries

Our Top 5 Best Greek Sailing Itineraries

Our Highlights. The beautiful and exotic Greek Islands lure droves of tourists every year for some of the best Greek sailing itineraries, making them one of the world’s top travel destinations. Amazing beaches, ancient ruins, excellent cuisine, colourful harbours, breathtaking views and even active volcanoes the Greek islands have it all.

Santorini. Part of the Cyclades group, Santorini is the jewel. It is considered by many the most picturesque islands. Lying in the South Of Greece, is can be a little tricky to access, or, put more accurately, harder to get home if the wind starts to blow form the north.

Mykonos. Also part of the Cyclades, Mykonos features a modern, cosmopolitan society blended with traditional whitewashed houses and maze-like streets.

SailChecker Tip: Enjoy a meal in Little Venice.

Rhodes. Located in the Aegean Sea near the coast of Turkey, Rhodes is the capital and largest island of the Dodecanese archipelago, popular for its great beaches and historical significance.

Corfu. The northernmost of Greece’s Ionian Islands, Corfu was controlled by many foreign powers, notably the Venetians and British, which is reflected in its culture and the architecture on the island. Sporades also will offer you amazing experiences with their crystal clear waters and their natural beauty

Ionian Islands

Ionian Islands

Ionian Islands. Home to the legendary “Odysseus”, the Ionian Sea consists of 7 main islands (also known as the “Heptanese”), but during your sailing adventures, you’ll find many smaller islands to explore.

Greek sailing Itineraries. What is interesting about an Ionian sailing itinerary is the contrast between the places you’ll get to visit. From the cosmopolitan and proud representative of the Venetian culture and architecture Corfu town to the breathtaking combination of blue and green hues in Lakka bay to the traditional fishing villages, one thing is for certain. You’ll be going home with more than a handful of stories and experiences to share, which makes it one of our best Greek sailing itineraries.

Best Greek Sailing Itineraries - Ionian Islands

Places To Discover. The Ionian islands are some of our favourite islands to visit, which is why we have included them in our best Greek sailing itineraries list. Some of the best islands to visit are listed below.

  • Corfu
  • Paxos
  • Parga, Mainland
  • Sivota, Mainland
  • Meganisi Island
  • Kefalonia
  • Ithaca
  • Kalamos Island

Dodecanese Islands

Dodecanese Islands

Islands. The Dodecanese islands consist of 15 larger islands and over 150 smaller islands, located in the Southeastern Aegean Sea. Within this collection of islands, only 26 are inhabited. The Dodecanese islands cover an area of 1,048 square miles, which makes it one of our best Greek sailing itineraries.

Greek Sailing Itineraries. The Dodecanese is one of our favourite best Greek sailing itineraries, and it’s easy to discover why these islands are often referred to as the ‘sunniest corner of Greece’, thanks to their crystal clear turquoise waters, sandy and stone beaches, stunning archaeological landmarks, and traditional settlements. There are also unique Byzantine and medieval monuments which cover a large number of the islands.

Best Greek Sailing Itineraries - Dodecanese Islands

Places To Discover. The Dodecanese islands are some of our favourite islands to visit, which is why we have included them in our best Greek sailing itineraries list. Some of the best islands to visit are listed below.

  • Rhodes
  • Symi Island
  • Nisiros Island
  • Kos
  • Astypalaia
  • Tilos
  • Halki
  • Kalymnos
  • Leros Island

Saronic Islands

Saronic Islands

Saronic. The Saronic Gulf is formed by two of the most prominent peninsulas in the Aegean Sea. In between the areas of Attica and Argolis, the gulf offers a number of islands worth visiting and the steadily-blowing Meltemi winds, (especially during July and August, however, not forbiddingly strong as they can get in the Cyclades). The area is also home to a variety of wildlife, including friendly short-beaked common dolphins and fin whales. History and relaxation meld together in this land of the Greek gods.

Greek Sailing Itineraries. The Saronic Gulf is one of our best Greek sailing itineraries for intermediate sailors. Involving medium winds (Force 2-5) and hidden coves excellent for taking off an afternoon and enjoying the Greek way of life, we offer seven days of history and delightful beaches ready for exploration.

Best Greek Sailing Itineraries - Saronic Islands

Places To Discover. The Saronic islands are some of our favourite islands to visit, which is why we have included them in our best Greek sailing itineraries list. Some of the best islands to visit are listed below.

  • Poros
  • Tselevinia
  • Dokos
  • Heli Beach
  • Spetses Island
  • Hydra
  • Kanakia
  • Aigina

Sporades

Sporades

Sporades. The Sporades consist of 24 islands in the Aegean Sea. 4 of these islands are completely free of human residents – you’ll only find gorgeous scenery and empty beaches. Much of the area is considered a national park, and guests are encouraged to explore the area while leaving things carefully preserved behind them. The largest and most populated island is Skopelos, which has several villages and an opportunity to experience island life.

Greek Sailing Itineraries. The archipelago is also home to several historic sites. Once the home of neolithic peoples to members of the Ottoman Empire, you’ll find sunken cities, ruins, and almost-forgotten monasteries ready to visit and discover. The Sporades offer a bit of adventure and a chance to rest from modern life. This is a slightly more challenging of our best Greek sailing itineraries for those with a few sailing trips already under their belt (Level 3).

Best Greek Sailing Itineraries - Sporades

Places To Discover. The Sporades islands are some of our favourite islands to visit, which is why we have included them in our best Greek sailing itineraries list. Some of the best islands to visit are listed below.

  • Skiathos
  • Nishida Adelfi
  • Skantzura
  • Patitiri
  • Milia
  • Kira Panagia
  • Plantitis
  • Skopelos
  • Tsougria

All Around Greece

Greek Meze

Mezedes. Most visitors are aware of Mezze well before they arrive on these shores. Yet it remains one of the most Greek of culinary traditions enjoyed by locals and visitors alike, a must try on one of our best Greek sailing itineraries.

Lunch Aboard. You can find plenty of “mezedes” around Greece, both fish and meat version. Best of all, prepare your own for the most typical of Greek lunches aboard.

Wine Tasting

Greek wine is much-maligned the world over, yet there’s so much more to Greek wine than adodgy retsina. If you do get the opportunity, you should visit at least one vineyard during your stay.

SailChecker Tip: The image is from a traditional winery in Samos, why not drop by where you will be made very welcome.

You can find traditional, family-held wineries all around the greek islands.

Our Best Greek Sailing Itineraries

Amazing Sailing Experiences

Our Amazing Customers


  • Great family vacation.

    I didn't think sailing with my family would be so much fun...

    Sailing for the first time.

    Alex
    Alex USA

  • I recommendate them !

    Everything went smooth, the paper processing, special requests and the specs of tht check-in procedure. Boat was also in good shape, so no complaints and a worry free holiday...

    We had a great experience with booking through sailchecker.

    <read more>
    Dick USA

  • Great service from Kate.

    Informative and looked for the best value for our family. Very good customer service on this side and in Greece. Great boat and skipper...

    Fantastic holiday from start to finish.

    <read more>
    Angela United Kingdom

  • Very professional outfit!

    They were very responsive and very quick to answer questions via email and instant chat. They had extensive knowledge of the area...

    We will most definitely use their services for our next bareboat sailing vacation.

    <read more>
    Kirsten W.
    Kirsten W. USA

  • Sail checker were professional from start to finish - we wouldn’t book through anyone else!

    Sailchecker were professional from start to finish - and were awesome dealing with a problem! Our first Yacht had serious issues and sail checker helped us to resolve it...

    They are easy to deal with, straightforward and honest and I would recommend them to anyone planning a charter holiday.

    <read more>
    Kat, H.
    Kat, H. UK

  • Coronavirus pandemic support has been brilliant!

    During the Coronavirus pandemic, Kate and her colleagues at Sailchecker have performed brilliantly. They have been considerate and highly efficient in re-organising our Turkey charter and also provided lots of assistance in getting our Yacht Security Deposit insurance policy transferred to match our revised charter dates.

    Truly worthy of a 5 star rating!

    <read more>
    Alan, R.
    Alan, R. UK

  • Sailing is the perfect family holiday.

    Would I go sailing again? OMG yes! Sailing is the perfect family holiday. Boys loved the activities, I enjoy relaxing as well...

    Sailchecker.com arranged a sailing cruise her family of 2 sons, daughter & hubby in the BVI with their own.

    Anne
    Anne USA

  •  Thank you sooo much!

    It was sail in the day… party at night. We couldn't have wanted a better skipper or a Spring Break!  Good times...

    Arranged for 6 friends to sail Spring Break in the British Virgin Islands for under $500 each.

    Tim
    Tim USA

  • We had an absolute blast !!

    All bookings and confirmations was always accurate with no delays. Our boat was also fabulously maintained and the Skipper new the area extremely well...

    Everything was down to the tee.

    <read more>
    Pieter Van R.
    Pieter Van R. Netherlands
SailChecker Yacht Charter and Sailing Worldwide Logo TrustPilot 4.9/5 Stars

Rated 4.9 out of 5 based on 160 reviews on Trustpilot

Got a Burning Question About Best Greek Sailing Itineraries?

We’re Happy to Answer Any Yacht Charter & Sailing Question

Leave us a quick question here, or call your local office, the numbers are located in the footer below. When not arrange a call back?

girl at desk at yacht charter show

Leave a Comment

Start typing and press Enter to search