Santorini Sailing in 2019

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Updated: May 4, 2019

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Greek Island Sailing Holidays to Santorini, Mykonos, and Athens.

Greek Island Sailing Tours: Private and semi-private charters that travel through the Greek islands.

Important: Read my page on Santorini Boat Tours if you want information about day trip tours around Santorini.

What are the best sailing tours in the Greek islands and Santorini?

There are two types of sailing tours for Santorini: day trips from Santorini through the caldera and week-long sailing tours of the Greek islands that include a stop in Santorini. On this page, I’ll discuss the 2nd kind, sailing tours that include Santorini as well as other Greek islands, usually Mykonos. These are basically chartered yachts for small groups of 8 or less that visit multiple islands in Greece. (If you want a private yacht charter of the Greek islands then just book all 8 spots on the boat.)

As I’ve said many times on this site, visiting Santorini on a cruise is not ideal. You only get to spend a few hours on Santorini and those hours are when your entire ship is also touring the island – you don’t get to see the magic of what makes Santorini so special. And you don’t get to stay overnight and see the island in the morning when it can feel almost deserted – even in high season.

But sailing tours are different. On the sailing trips I list below, you meander around the Greek islands and make stops in a number of different places that are wonderfully off the beaten path. And you start or finish your trip in Santorini so you get to spend 1 or more nights on the island to see how it really is. (No cruises start or finish in Santorini, so if you did want to see it on your own that’s a separate trip to the island – probably from Athens.)

The Best Sailing Holidays for Santorini and The Greek Islands

All of these sailing tours are with G Adventures – a fantastic company that offers unique boat tours of the Greek islands on 15m charter yachts. A skipper/captain/tour-guide is on the boat the entire trip. There is a kitchen and 3 bathrooms, safety vests, and snorkeling equipment. Some meals onboard, some on land. These tours sell out quickly so book as early as possible. Dates vary by tour but most start in late April or early May and run until mid or late October.

1. Santorini to Mykonos – 8 Days, $1072, Starts Sun, Tue, Wed, or Sat. An awesome 8 day tour of the Cycladic islands that starts in Santorini and takes in Folegandros (great for hiking), Sifnos (untouristy with wonderful beaches), Ios (the best beaches in Greece), Antiparos (tiny island with great beaches), Paros (beautiful), Naxos (mix of history, local culture, and beaches). This on a real sailboat that sleeps about 8 so it’s a very small group. The itinerary is flexible and stops are made wherever guests show the most interest.
2. Mykonos to Santorini – 8 Days, $1087, Starts Sun, Tue, Wed, Fri, or Sat. The tour begins in Mykonos and sails through the Greek islands to Santorini. Essentially, the same tour as above but in the opposite direction. Personally, I would rather start in Mykonos and sail into the Santorini caldera to end the tour – but obviously, there isn’t a huge difference. There are international flights to both Mykonos and Santorini so as far as coordinating travel, that shouldn’t be an issue.
3. Athens to Santorini – 15 Days, $2137, Starts Sun, Tue, Wed, or Sat. This one begins in Athens (which deserves a day or two to explore) and finishes in Santorini 14 nights later. Along the way you’ll stop in Mykonos, Naxos, Paros, Antiparos, Ios, Sifnos, and Folegandros – similar to the above trips only you have more time to wander and explore. There are also Santorini to Athens sailing tours.
4. Mykonos to Athens – 8 Days, $929, Starts Sun, Mon, Wed, or Sat. On the surface, this doesn’t sound as compelling (what? no Santorini?). But remember, you can visit any islands you want before the tour begins. Fly directly to Santorini, spend a few days there, then take the direct ferry from Santorini to Mykonos and begin your sailing tour. Finish in Athens and fly home from there. Perfect! The islands you visit on this tour are less touristy (and have fewer idyllic beaches): Kythnos, Kea, Aegina, Hydra, and Syros. There are also Athens to Mykonos yacht sailings.
5. Santorini to Santorini – 10 days, $1387, Starts all 7 days. This one begins and ends with Santorini which makes planning easier and gives you one more chance to see this magical island. On the flip side, you do re-trace your steps, so for most people, I would recommend a tour that starts and concludes at different destinations – but it’s still a great trip.

Sailing around the Greek Islands with small group on a small boat.

Life on board a sailing yacht through the Greek islands. Eat on deck and jump and swim at private beaches around the Greek islands.

Sailboat with kitchen and bathrooms in Greek Islands.

The kitchen and dining area below deck. Every yacht is a little different but the basic layout is the same.

Private bedroom on Santorini yacht.

There are sleeping spots for 8 guests on most of the G Adventure sailboats (though group sizes do differ depending on the tour).

Layout of sailboat in Greece wtih bathroom, bedroom, kitchen, and area to sun tan and swim.

The layout and cabins on the upper and lower decks aboard the G Adventure yachts.

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6 Questions and Comments

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  1. Santorini Day Trip to Folegandros

    Hi Dave! Do you know if there are any day tours to Folegandros? I know there are ferries that can take you there, but Sea Jets has terrible reviews, it worries me they will cancel our ferry back to Santorini, leaving us in Folegandros searching for a room to spend the night at. Any advice will help.

    Thank you in advance.

    1. Santorini Dave The Hotel Expert

      I don’t specifically know of any day trips to Folegandros but even if I did they would very likely use the public ferries for transportation so if they were cancelled you’re in the same boat (literally).

  2. Greek Island Yacht Cruise

    Hi, The G Adventure Sailing Holiday is great except we are 2 couples and some of us need slighly more upscale ship or catamaran. We would like to be 4 people on a boat or a boat with up to 75 people for 5-6 day Island hopping.
    Then we would spend 3 nights in Santorini and 2 nights in Athens. Can you suggest a few yachting charter companies or small cruse similar to G-Adventure.
    Thank you, JB

    1. Santorini Dave The Hotel Expert

      Sorry, I’m not up to date on the current crop of chartered yachts. I know they’re out there but can’t recommend any specific ones. My one bit of advice is that the more people on the ship the less enjoyable they usually are. Smaller is better when it comes to cruises of the Greek islands.

  3. Getting To Santorini for Chartered Yacht

    What is the best (easiest) way to get to Santorini from Rome? Should we fly to Athens and then ferry to Santorini? Tour is scheduled to start in early July and itinerary will be Santorini to Athens.

    1. Santorini Dave The Hotel Expert

      Since you’ll be returning to Athens at the end of your sailing tour there’s no need to stop on your way to Santorini, so best to fly directly from Rome to Santorini. There should be plenty of direct flights in July. If they are sold out then fly via Athens and get the next flight to Santorini without going into the city.

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