Heraklion
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Sailboat rental in Heraklion, Greece with captain

13 boats available in Heraklion
Jeanneau Sun Shine 38
5.0 (20 reviews)
Heraklion
Discover the largest island in Greece by boat! Charter this Sun Shine 38 sailing yacht for 9 people! Our beautiful and well cared for Jeanneau Sunshine 38, based in Heraklion, Crete, Greece, available for day trips to Dia island and nearby beaches, and also for multi days cruises to the Cyclades islands (Santorini, Paros, Milos etc.) and the Dodecanese (Astypalaia. Rodos, etc.) Under sail, Sun Shine 38 has excellent directional stability. The yacht's steering allows not one degree of deflection...
Sailboat
Captain mandatory
9 pers.
3 cabins
1989
37 ft
Top owner
Instant booking
from $214,90
-5%
Bénéteau Luxury Full Day (8,5 h) Trips to Dia island
3.0 (1 reviews)
Heraklion
PRIVATE FULL DAY TRIP TO DIA ISLAND or TO AGIA PELAGIA BAY ON A LUXURIOUS SAILING YACHT - Full - Day Trip / Duration: 8.5 h / Starts at: 9:30 or 10:00 or 10:30 (flexible) - Full - Day Trip + Sunset Views / Duration: 8.5 h / Starts at: 11:30 or 12:00 or 12:30 (flexible) *The sailboat can host up to 16 guests. The price displayed refers to groups up to 10 guests. * For groups from 11 to 14 guests there is an extra charge of 230 euros (in total - not per guest). * For groups from 15 to 16 guests...
Sailboat
Captain mandatory
16 pers.
5 cabins
2017
50 ft
Top owner
from $940,90
Elan Half Day (5,5 h) Trips to Dia island
4.6 (7 reviews)
Heraklion
PRIVATE LUXURY MORNING TRIPS TO DIA ISLAND * From April 1 to August 31: Duration 5.5 h / Starts at 9:30 * From September 1 to October 15: Duration 5.5 h / Starts at 9:00 * From October 16 to November 15: Duration 5.5 h / Starts at 11:00 PRIVATE LUXURY SUNSET TRIPS TO DIA ISLAND * From April 1 to August 31: Duration 5.5 h / Starts at 15:30 * From September 1 to October 15: Duration 5.5 h / Starts at 15:00 * From October 16 to November 15: Duration 5.5 h / Starts at 11:00 *The sailboat can host...
Sailboat
Captain mandatory
16 pers.
5 cabins
2012
53 ft
Top owner
from $615,65
-5%
Bénéteau Half Day (5,5 h) Trips to Dia island
5.0 (1 reviews)
Heraklion
PRIVATE LUXURY MORNING TRIPS TO DIA ISLAND * From April 1 to August 31: Duration 5.5 h / Starts at 9:30 * From September 1 to October 15: Duration 5.5 h / Starts at 9:00 * From October 16 to November 15: Duration 5.5 h / Starts at 11:00 PRIVATE LUXURY SUNSET TRIPS TO DIA ISLAND * From April 1 to August 31: Duration 5.5 h / Starts at 15:30 * From September 1 to October 15: Duration 5.5 h / Starts at 15:00 * From October 16 to November 15: Duration 5.5 h / Starts at 11:00 *The sailboat can host...
Sailboat
Captain mandatory
16 pers.
5 cabins
2017
50 ft
Top owner
from $615,65
-20%
Bénéteau Oceanis 43
4.5 (4 reviews)
Heraklion
Experience Luxury Sailing in Heraklion | Premium All-Inclusive Yacht Charter Discover the crystal-clear waters of Crete aboard our prestigious Oceanis 43 sailing yacht. Offering an unmatched blend of luxury, comfort, and authentic Cretan hospitality. EXCLUSIVE CHARTER OPTIONS: • Half-Day Experience - Morning Cruise: (Contact information hidden) Sunset Cruise: (Contact information hidden) • Full-Day Journey: (Contact information hidden) ️ GOURMET CULINARY EXPERIENCE Full-Day Charter Include...
Sailboat
Captain mandatory
10 pers.
4 cabins
2016
43 ft
from $548,28
Elan Full Day Trips (8,5 h) to Dia island
5.0 (1 reviews)
Heraklion
PRIVATE FULL DAY TRIP TO DIA ISLAND or TO AGIA PELAGIA BAY ON A LUXURIOUS SAILING YACHT - Full - Day Trip / Duration: 8.5 h / Starts at: 9:30 or 10:00 or 10:30 (flexible) - Full - Day Trip + Sunset Views / Duration: 8.5 h / Starts at: 11:30 or 12:00 or 12:30 (flexible) *The sailboat can host up to 16 guests. The price displayed refers to groups up to 10 guests. * For groups from 11 to 14 guests there is an extra charge of 230 euros (in total - not per guest). * For groups from 15 to 16 guests...
Sailboat
Captain mandatory
16 pers.
5 cabins
2012
53 ft
Top owner
from $940,90
Hanse 470 E
5.0 (1 reviews)
Heraklion
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 $348,48
Gibert Marine Gib Sea 334
5.0 (1 reviews)
Heraklion
The boat is available to Charter from her base in Crete or Santorini Cyclades islands Greece. Our skippered yacht charter packages are a great way for a family or group of friends/colleagues to get out for a sailing adventure, with the confidence and security of having a professional skipper on hand to ensure everyone has a safe and enjoyable time. These trips are suitable for everyone. Her large cockpit provides a perfect place to operate weekly charter or daily trip. I invite you to cont...
Sailboat
Captain mandatory
6 pers.
2 cabins
2005
35 ft
from $232,32
Bavaria 44
Heraklion
Perfect getaway in Crete for families and friends with up to 10 pax: half-day (4.5hours) abroad a classic 44-foot sailing yacht from Heraklion to explore the Aegean Sea and anchor in the bays of Dia Island or Agia Pelagia for swimming, snorkeling and relaxing. Transfer (not included, extra per person) is provided from the coastal area between Fodele and Malia. Important notes: the price is for 4.5 hour cruise Time slots: 09:00 to 13:30 or 16:30-21:00* *(15:00-19:30 till 14-apr & from 01-oct be...
Sailboat
Captain mandatory
8 pers.
4 cabins
2003
45 ft
from $580,80
Hanse 430 E
Heraklion
Private Full Day Trip (6 hours) from Heraklion to Dia Island Discover the unique destination of Dia island while traveling private in style and comfort aboard our luxury sailing boat. Feel the breeze of Cretan sea, swim and dive into the crystal clear waters, explore the ruins of an ancient port, take a walk on the island or just relax on deck and enjoy the summer sun, while in the meantime tasting a delicious meal, served during your journey with us. Whether travelling with friends, family or...
Sailboat
Captain mandatory
10 pers.
3 cabins
2007
43 ft
from $604,03
Hanse 470
Heraklion
We offer for rent a Hanse 470 of 2010 departing from Heraklion Municipality. 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 Heraklion Municipality This Hanse 470 is equipped with 2 heads with...
Sailboat
Captain mandatory
8 pers.
3 cabins
2012
47 ft
from $397,27
Here are all the boats in the vicinity

These boats available around Heraklion, may also be of interest to you!

Bavaria 50 Cruiser
5.0 (1 reviews)
Gouves
Come see what we're all about Embark on an unforgettable sailing journey from the harbor of Gouves, where you'll be warmly greeted by our experienced captain and crew. As we set sail, we'll glide across the serene Greek blue sea, basking in the refreshing sea breeze that offers respite from the summer heat. Throughout the voyage, our attentive staff will be at your service, offering refreshing drinks and providing fishing equipment for those eager to try their hand at angling while we sail. As...
Sailboat
Captain mandatory
14 pers.
5 cabins
2026
48 ft
from $1 045,44
Elan Impression 45
Chersonisos
Yacht Charter Live the experience of the Cretan Sea and feel the superb performance under sail, skippered or not, on an half or full day cruise, on a multi day trip, on a sunset cruise or create your own dreamy trip. For those of you who would like to charter independently, there’s bareboat sailing. If you don’t have the relevant qualifications you might like a skippered charter. If there is a desire for a luxurious cruise sailing we can arrange a Skippered charter where you can be served by a p...
Sailboat
Captain mandatory
10 pers.
4 cabins
2017
49 ft
from $871,20
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Reviews from our users about their rental

Edward
Edward
Traveled in September 2025 · 4 people · 2 days
We had a really great time with Giannis on the sailboat Christina. Giannis (John) is a true gentleman and accom4plished sailor, he took very good care of us during our 3 day trip and showed us some amazing places, we also had the pleasure of his cooking as we opted for half board. We had plenty of sailing but also time to stop for a snorkel and to enjoy a delicious meal. He is well able to sail the boat single handed but is also very patient and will explain things and let you play a part. He has many years of sailing experience and knows both the boat and waters around Crete VERY well. Our safety and comfort were always priority for him and I recommend him entirely. Giannis is great company, he will tell you all about life on Crete (he is also an olive farmer and if you are lucky you will get to sample his olive oil and fresh produce) but he will also take himself off with his book and give you some family time. Thankyou Giannis for a truly wonderful and unforgetable experience!
Valdis
Valdis
Traveled in August 2024 · 4 people · 1 day
John is an amazing captain with exciting personality, perfect english language and amazing cooking skills. A true host and story teller. We felt like at home on his yacht. Yacht is very clean, gear for water activies is in great sizes and types. We had fantastic time :) GREAT Thanks!
Chris
Chris
Traveled in August 2024 · 3 people · 1 day
John is an amazing host. He is social and knows how to dose it. He knows the best spots. Is flexible. And he prepared great meals to add to the whole experience. We charted plenty of boats around the globe. This one goes in the top 3. Highly recommended
Jennifer
Jennifer
Traveled in August 2023 · 7 people · 1 days
We had a wonderful time with the wonderful skipper and host who went out of their way to accommodate us. As hosts go we could not have asked for someone more attentive and both he and the skipper were amazing. We had a delicious meal cooked by them and a fantastic time for our birthday celebration - they even provided a cake for the occasion. We would definitely recommend using them.
Edward
Edward
Traveled in July 2023 · 5 people · 1 days
Thank you for the lovely day - not only did we get master sailors, we got excellent chefs, DJs and all kinds of insights on the area. Well done gentlemen!
Martijn
Martijn
Traveled in April 2023 · 3 people · 6 days
Yannis is an excellent host and sailor. He has a keen eye for when to be present. He has excellent knowledge of Crete and of the world in general. The trip was adjusted day to day to the group’s needs and wants. The boat and equipment are older, but very well taken care of and clean. All in all I would definitely recommend Yannis to take you out on a trip short or long.
Juha
Juha
Traveled in October 2022 · 12 people · 1 days
Giannis and his team were very accommodating, even though we contacted them very late for a boat tour for the same day. They were very flexible in terms of timing too. The boat was in a great condition and the service was very hospitable. All in all it was a great experience and we had a lot of fun. Big recommendations!
Ellie
Ellie
Traveled in September 2022 · 4 people · 1 days
We had the most amazing time on the boat! The boat was In great condition and full use of the activities like the paddle board and snorkelling gear. Our skipper Theodore was so lovely and the food was incredible! Would highly recommend, a great day!

Is a Sailboat with a captain the right choice for Heraklion, Greece?

Exploring Heraklion, Greece from the water is an unforgettable experience. The combination of beautiful scenery and open spaces creates the perfect setting for any journey. Whether you are looking for a peaceful cruise or a more thrilling ride, the right Sailboat with a captain will add to the adventure. Comfortable seating, easy handling, and reliable performance make the journey even better. Every trip on the water brings discoveries and special moments.

How to book a Sailboat with a captain in Heraklion, Greece?

Search for a Sailboat with a captain in Heraklion, Greece using the various filters available. Once you find a Sailboat that suits your needs, you can directly contact the owner to confirm the rental.

Budget to rent a Sailboat with a captain in Heraklion, Greece

Sailboat rental rates in Heraklion, Greece fluctuate depending on the size, the time of year, and the length of the rental. Additional equipment and optional services may also affect the final price.

In Heraklion, Greece, listings start at $232,32, while the average rental price is $1 008,27.

Renting a Sailboat: for how many people?

The Sailboat's passenger capacity depends on its size and load capacity. The Sailboats available in Heraklion, Greece offer a maximum capacity between 6 and 16 people.

What are the best months to rent a Sailboat with a captain in Heraklion, Greece?

The best time to rent a Sailboat with a captain in Heraklion, Greece depends on weather conditions, water temperature, and tourist activity. The peak season usually runs between June - August, with warm temperatures and ideal boating conditions. During this time, the average water temperature is around 22–25°C, making it perfect for swimming and water activities. If you prefer a quieter experience with fewer crowds, the shoulder seasons in May and September are a great alternative. The weather remains pleasant, and rental prices may be lower. Whichever time you choose to rent, Heraklion, Greece offers breathtaking views and a fantastic boating experience.

Where to sail in Heraklion, Greece?

One of the best places to go boating in Heraklion, Greece is Heraklion Archaeological Museum, Knossos Palace, Heraklion Port. It offers excellent conditions and a great atmosphere for a day on the water. Exploring Heraklion, Greece by Sailboat is a fantastic way to discover its beauty.

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