The Best Greece Sailing Itineraries for Island Hopping

If you’ve never visited Greece before, it might be easy to overlook the fact that there’s more to the nation’s stunning beach scenes and ancient streets than what you’ll find on the mainland (and even on some of the bigger islands). Greece sailing itineraries, therefore, give you the chance to enjoy more of the area’s hidden gems and most memorable adventures.

If you’re completely new to Greece sailing itineraries but want to get the most out of your holiday before you head home, this guide is the perfect launchpad for some fantastic adventures ahead. Remember, of course, that the sailing itineraries we list here are just hypothetical - you might be able to build your own, or you could follow the direction of a cruise or tour operator.

Regardless, you should always make sure that you have an eSIM for Greece loaded up in your phone if you intend to travel around some of the islands’ hidden spots. Keep in mind you won’t always be able to get 5G in remote spots, but at least you won’t have to worry about hunting around for WiFi or running up high bills with your home network carrier!

Greece sailing itineraries explained

Greece sailing itineraries are set routes and excursions that explore some of the best-loved island spots around the area, saving travellers time and effort on having to keep flying or booking ferries out to and fro. Consider itineraries as rather like a cruise, however, you don’t have to stay on board or even book with the same companies - you might want to build your own journeys!

Overall, visitors to Greece prefer sailing itineraries that cross the Cyclades (around Mykonos), the Ionian Islands, and the Dodecanese. Generally, you’ll find these itineraries are recommended during milder months, though many people do still opt to sail out and explore the islands in the summer. That’s entirely up to you - be aware that it can get extremely hot out around the islands, even with that famous Mediterranean breeze!

Best sailing itineraries in Greece

For this guide, we’ve explored a few recommended Greece sailing itineraries that take you around the Cyclades, Ionian Islands, and Dodecanese. Again, much like with the information we share in our general Greece itinerary guide, you’re free to take these recommendations at face value and to add them into your existing plans as and where you see fit.

Cyclades sailing itinerary

Cyclades trips are great for first-time visitors and those who might only be travelling for a few days. For example, some expert travellers recommend taking a route from Athens to Mykonos on day one, then Mykonos to Paros on day two, before finishing with a trip from Paros to Santorini. This is a great way to take in the history of Athens while enjoying the beach scenes and street scenes of Mykonos and Paros.

Alternatively, some set sailing itinerary providers recommend longer trips around Milos, Sifnos, Kythnos, and Serifos, ideal if you want to take time swimming in the crystal blue waters.

Ionian Islands sailing itinerary

Sailing around the Ionian Islands is a great way to explore some of the islands’ best-loved Venetian architecture, and if you’re not too keen on choppier waters, these itineraries tend to be some of the more stable on the water, regardless of the time of year.

We’d personally recommend itineraries for these islands if you’re more fixed on taking in natural scenery than modern amenities, though it’s always best to charter a boat with a skipper if you can.

In terms of what you can and should take in with these Greece sailing itineraries, Boataround suggests taking at least seven days to explore Lefkas, Fraxia, Sivota, Paliouras, Vathi, Fiscardo, and more. This might sound like a lot to pack in, but be reassured that the distances between your destinations are nice and short.

Dodecanese sailing itinerary

The Dodecanese Islands are home to some of Greece’s most incredible rocky landscapes, with a major highlight being Rhodes, where the Colossus once stood - and, there are tons of traditional festivals, castles, tavernas, and more to explore and enjoy.

One thing that most sailing enthusiasts around Greece agree on is that the Dodecanese route is often one of the more challenging, particularly compared to the Ionian itinerary. That said, difficulty while travelling can also boil down to weather conditions, so be prepared to check for wind (and even rain - it does come down occasionally in Greece!). Boarding with a skipper will take stress off your shoulders.

In terms of the best Greece sailing itineraries that take you around the Dodecanese, we recommend following Yachtico’s lead. The experts offer a seven-day adventure starting and ending in Rhodes Town, but taking in Symi, Kos, Nisyros, Tilos, and Chalki along the way.

How long Greece sailing itineraries last

Greece sailing itineraries vary in terms of length, largely dependent on how many places you’d like to visit while on route. For example, some sailing companies recommend at least seven days of travelling to enjoy the best of the Ionian or Dodecanese routes, but you can easily do the Cyclades trip in fewer. It’s always worth researching what sailing firms and fellow travellers around Greece recommend, both for ideas and for your safety!

Best time of year for sailing in Greece

Even though you might be tempted to sail in the summer, it’s between June and August when you’re most likely to be prone to dry winds from the north, meaning sailing is likely to be choppier around this time. 

To optimise sailing for the best conditions and to save money on travel and accommodation, we always recommend travelling in spring or even fall/autumn, depending on what you’d like to see and do.

Tips for planning a sailing trip in Greece

Now you know what Greece sailing itineraries mostly involve, let’s run through a few final tips to help you prepare to set sail around the islands.

• Research the best food to try in Greece before you go! There will be lots of authentic cuisine to enjoy across your island hopping, so it makes sense to learn more about the different flavours and styles used in Greek cooking before you sail.
• Plan accommodation ahead of time for each of the stopping points in your itinerary - unless you travel with a company, which may be able to help you make bookings.
• Choose a route ideal for your experience if you’re sailing a vessel yourself (Ionian Islands for beginners, for example).
• Set up an eSIM for Europe, if not Greece, so that your devices will automatically connect to the best-available networks, and you won’t have to worry about finding new WiFi spots.
• Be sure to pack relatively light and only take the essentials - clothing, sun protection, footwear, and any medication you need.
• Plan your meals ahead of time in coordination with where you’re planning to land and visit. TripAdvisor is your friend!
• Consider using a water bottle to refill to save on waste when you disembark and explore new islands.

Following Greece sailing itineraries is a great way to explore some of the region’s best-kept secrets (which really deserve sharing). Use this guide as a leaping-off point and set sail as soon as the weather’s right!