Santorini (Island)
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Sailboat rental in Santorini (Island), Greece with captain

9 boats available in Santorini (Island)
-5%
Jeanneau Sun Odyssey 49
5.0 (3 reviews)
Vlychada
Our yacht Sun Odyssey 49 successfully combines contemporary style and harmony, all while respecting the heritage of designing company. This sailboat from 49 feet has revolutionized cruising: she is the only sailboat in their category to feature movement about the deck without obstacle. Life on board has never been so simple and comfortable. We do 2 half-day cruises per day, visiting all the highlights of Santorini: Red & White beach, lighthouse, Volcano and Caldera. Seafood BBQ meal is served o...
Sailboat
Captain mandatory
8 pers.
4 cabins
2004
48 ft
Flexible Cancellation
from $1 081,96
Trehandiri
Vlychada
Embark on board the Kymatia, an amazing Trehandiri to discover the region of Vlychada. This sailboat was built in 1999 to ensure complete comfort and performance at sea. The boat has 3 fully-equipped cabins and a capacity of 7 people. With an overall length of 15 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Vlychada For your comfort, Kymatia has 2 toilets with a shower It has the following equipment: Outboard engine, Bow thruste...
Sailboat
Captain mandatory
7 pers.
3 cabins
1999
49 ft
from $911,12
More Boats More 55
5.0 (1 reviews)
Emporeío
Half Day Private cruise! € 500.00 ! The price is for up to 4 passengers ! For each extra passenger € 90 to max 22 people. --------------------------------------------------------------------- Full Day Private Cruise! € 1400.00 ! The price is for up to 8 passengers ! For each extra passenger up to 22 people, an additional 100 euros per person ! -------------------------------------------------------------------------------------------- We depart from the port of Vlichada and make our way to the...
Sailboat
Captain mandatory
22 pers.
1974
48 ft
from $512,51
-5%
Bénéteau Oceanis 361 Clipper
5.0 (2 reviews)
Emporeío
Immerse yourself in a relaxing and completely unique sailing experience. Enjoy the breathtaking scenery around Caldera and Volcano of Santorini. Take a swim in the waters of some of Santorinis most famous and beautiful beaches - whilst enjoying traditional dishes and the best of local wines and beer. Choose from morning or sunset cruises; or choose an overnight stay, anchoring at idyllic beauty spots, and enjoy the smooth lapping of the waves for a calming sleep at sea. Awake revitalised and...
Sailboat
Captain mandatory
7 pers.
3 cabins
2003
35 ft
from $671,95
Ocean Yachts Ocean Star 51.2
Oía
5 Hours tours around the caldera of Santorini with full meal and drinks.
Sailboat
Captain mandatory
10 pers.
3 cabins
2008
51 ft
from $1 594,46
Hanse 470 E
5.0 (1 reviews)
Mesariá
Our Hanse yacht 470E, a sailing yacht available for skippered charters throughout Greece. The boat has been refitted in 2022 and is kept in excellent condition. Our boat offers space for 8 guests who can sleep in 3 cabins plus 2 in dinning area ,there are two bathrooms they can use. The boat is perfect for two families or groups of friends as it can perfectly fit 7 guests plus your skipper. The boat is only available to charter with a captain who will take you to the most amazing secret spots...
Sailboat
Captain mandatory
7 pers.
3 cabins
2012
47 ft
from $439,62
Hanse 470
Vlychada
We offer for rent a Hanse 470 of 2010 departing from Vlychada. Ianira is a sailboat perfectly adapted for all rentals. This sailboat is very pleasant to handle for a week cruise or more. The boat has 3 fully-equipped cabins and a capacity of 8 people. With an overall length of 14 meters, it will be your best ally to spend an exceptional vacation on the water in the surroundings of Vlychada For your comfort, Ianira has 2 toilets with a shower It has the following equipment: Auto-pilot, Out...
Sailboat
Captain mandatory
8 pers.
3 cabins
2012
47 ft
from $389,50
Bénéteau Oceanis 46.1
Vlychada
Easy to sail, easy-going and fast! The Oceanis 46.1 boasts all the features of a large cruising yacht, with a rare balance between elegance, usable space and performance. Her stepped hull opens up an incredible amount of space inside and yet her seakeeping performance is still impressive. A large number of clever customizable fittings make her easy to sail and pleasantly comfortable. Important booking notice: The rates for both the half-day and full day cruises are for up to four (4) passeng...
Sailboat
Captain mandatory
6 pers.
5 cabins
2022
48 ft
from $1 822,24
Schooner Traditional Boat
5.0 (1 reviews)
Vlychada
TRADITIONAL SAILBOAT Adonis The Adonis represents a traditional type of boat with its unique style and charm. Equipped up to the highest safety standards, with a bar at the stern (back side of the boat) where you can find anything from water for your hike on the volcano to a snack to refuel upon descending. There is enough space for everyone to chill under the shade of the upper deck. As a part of each tour, we offer you round-trip transfers, snorkelling gear and towels, a freshly prepared BBQ...
Sailboat
Captain optional
60 pers.
5 cabins
2020
39 ft
from $2 277,80
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The reviews from our users about their rental

Umberto
Umberto
Traveled in July 2025 · 2 people · 1 day
Everything went perfectly, a private two days, sailing and discovering beautiful bays, with an experience sailor. She understood our group needs, took us in away from crowded Santorini bays, using all the time at disposal. Full of initiatives and good service including fishing and cooking fresh fishes. This is her boat, it makes a lot of difference in her dedication to ensure you enjoy at the maximum.
Casimiro A.
Casimiro A.
Traveled in August 2022 · 7 people · 1 days
I sailed with Christos and Mariangela around Santorini on 26/8/22. It was really a great great experience. Christos and Mariangela were very patient, provided with plenty of valuable information, did stop just to let the little child who was with us to jump in the water at his command, and provided a delicious meal (be careful: they cooked for an entire army :)!). 10+ - go for it! Thanks!
Scott
Scott
Traveled in July 2022 · 4 people · 1 days
We had a wonderful time on our charter today. The captain and 2nd were both incredibly gracious and attentive. Lunch was simple but tasted great and they accommodated two vegetarians in our group. The only improvement could be if the boat has a kayak or SUP. Thanks for a great time.

Is a Sailboat with a captain the right choice for Santorini (Island), Greece?

Choosing the right Sailboat with a captain will ensure a smooth and enjoyable trip. The waterways of Santorini (Island), Greece offer many opportunities for exploration and relaxation. Some Sailboats are ideal for group excursions, while others offer a more private experience. A well-equipped Sailboat allows for maximum enjoyment and comfort. With many options available, there is always a perfect fit for any type of adventure.

Renting a Sailboat with a captain in Santorini (Island), Greece, how does it work?

Whether you're looking for a Sailboat with a captain for a family day out or for some activity on the water, you can book online in just a few minutes.

Price to rent a Sailboat with a captain in Santorini (Island), Greece?

The price of renting a Sailboat in Santorini (Island), Greece is influenced by several aspects, such as the Sailboat’s capacity, features, and the time of year. Peak-season rentals tend to be more expensive than off-season bookings.

Starting at $390,64, you can access the lowest prices for Sailboats rentals. For a more typical experience, you can expect to pay an average of $1 342,76 per day.

How many people can board a Sailboat?

The rental offer in Santorini (Island), Greece allows you to find Sailboats that can accommodate up to 60 people. Dividing the rental price by the number of people makes your outing much more affordable.

What is the best time of year to rent a Sailboat with a captain in Santorini (Island), Greece?

The best months for a Sailboat rental in Santorini (Island), Greece are between June - August when the weather is warm and sunny. The water temperature during this time averages around 24–28°C, making it ideal for swimming, snorkeling, and other water activities. If you prefer a more peaceful experience, the shoulder seasons in May and September offers great conditions with fewer visitors. The weather is still pleasant, and rental options may be more affordable. Whatever the season, Santorini (Island), Greece offers an unforgettable boating adventure.

Top places to go boating in Santorini (Island), Greece

One of the best places to go boating in Santorini (Island), Greece is Oia, Caldera, Fira.. It offers excellent conditions and a great atmosphere for a day on the water. Exploring Santorini (Island), Greece by Sailboat is a fantastic way to discover its beauty.

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