Meet one of our local contacts in Greece—Theo of Santosails in Santorini, sharing unique yachting experiences he offers to TLTB members and what he enjoys most about his day to day on this breathtaking island.

In the hope that visitors will be able to return to Greece in July, we recently chatted to our friend, Theo, the owner of Santosails in Santorini, to check what sailing cruises he will be offering our clients this summer. Theo has been waiting for his new catamaran (which was in lockdown at Athens port until very recently) to be brought back home to Santorini, and has some wonderful experiences to offer guests to the island.

Santorini Greece Luxury Travel Book Rental Villa
Santorini Greece Luxury Travel Book Rental Villa Sailing Boat
Private Sailing Cruise

These include a 5 hour Private Day Sailing Cruise into the famous Caldera, and a visit to the Red and White beaches with their hidden caves, allowing for optional snorkelling and swimming time. The cruise will also take in the old ports of Fira and Oia (Ammoudi).

A particularly tempting cruise, bearing in mind the spectacular Santorini sunsets, is the 5 hour Private Sunset Cruise, which leaves from Oia, and takes in Thirassia island, the Caldera and Fira.

Other suggestions include a longer (10 hour) Island Hopping Tour, which will take you to the islands of Ios and Anafi.

All Theo’s tours include round trip transportation from your villa, a freshly prepared Greek barbecue meal on board, drinks (soft drinks, wine, beer and water), and use of snorkelling equipment and towels.We asked Theo some questions about Santosails, which he has just set up this year, having had years of working for other sailing companies. With his genuine enthusiasm for his work, guests can expect a very professional and friendly service!

Santorini Greece Luxury Travel Book Rental Villa Sailing Boat
Santorini Greece Luxury Travel Book Rental Villa Sailing Boat

When asked what he enjoys most about his work, Theo had a stock answer:”When you do what you love, you will not work a day in your life.”

We can vouch for the fact that his enthusiasm for his sailing cruises is contagious!

Theo also talked about the most challenging and rewarding parts of his work: “To satisfy all guests according to their needs or wishes. The rewarding part is when they leave the cruise with a big smile, and at the end we have become friends.”

He also mentioned: “Santorini is the most safe and beautiful island in the world with its unique scenery created by the volcanic eruptions through the centuries. Concerning security and safety, the level of crime on the island is almost zero, which is also unique. The island offers wonderful food and luxury accommodation, as well as the Aegean Sea within the Caldera, where we sail, so our guests can see all the beauty, including the hidden beaches, and the epic sunsets.”

Santorini Greece Luxury Travel Book Rental Villa Sailing Boat
Santorini Greece Luxury Travel Book Rental Villa Sailing Boat Mykonos

Theo also offers sailing charters on his catamaran, for guests who want to try another experience after their villa holiday on the island. For anyone interested in this option, the minimum stay is 3 nights, and suggested itineraries can include the Cycladic islands of Ios, Naxos, Paros and Mykonos, each with a very different vibe, and all very beautiful. Breakfasts and lunches are provided on board, as well as drinks, snorkelling equipment and towels.


We offer many villas on the island, catering for small, romantic honeymoons, through to large groups. One of our favourites is the beautiful Villa Eros.

The accommodation is on two separate levels, so the villa can be rented with 2 or 5 bedrooms, depending on the size of the group.

To say that it is in a beautiful location is an understatement – its position in Imerovigli village on the highest point of the Caldera ensures breathtaking panoramic views across the Caldera to the Aegean Sea. Guests here will also experience the magnificent Santorini sunsets.

Santorini Greece Luxury Travel Book Rental Villa Sailing Boat Mykonos Villa Eros
Villa Eros
Santorini Greece Luxury Travel Book Rental Villa Sailing Boat Mykonos Villa Eros

On the large terrace, there is also a heated swimming pool, an outdoor jacuzzi, and dining and sitting areas both in and out of the shade. In addition, the villa offers an amazing venue for a small wedding, or to enjoy some pampering while on holiday (the manager here is also a yoga instructor and masseur).

Better yet, starting from July 1 until November 14, 2020 Villa Eros is on special offer. With flexible booking terms and conditions, depending on availability, there’s a new 24 hours free window between stays to be able to apply the specific government recommendations for cleaning and disinfecting the villa (applying also during stays).

Separate booking is possible during high season, for the entire villa (up to 10 guests), plus the smaller option with private pool (up to 4 guests). Minimum stay 3 nights, including daily breakfast, cleaning, and transfer on both arrival and departure.

For more details on the property and offer, be sure to get in touch!

Santorini Greece Luxury Travel Book Rental Villa Sailing Boat Mykonos Villa Eros

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