What are the best sailing tours in the Greek islands and Santorini?
There are 2 types of sailing tours in and around 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. If you want a completely private yacht charter then just book all 8 spots on the boat.
As I’ve said many times on this site, visiting Santorini on a cruise sucks. Don’t do it. 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, $1429, 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, $1399, 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, $2629, 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, $1399, 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 sailing.
5. Santorini to Santorini – 10 days, $1799, 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.