Under sail · CRETE SAILING TOURS

8 Crete Sailing Tours Worth Booking

8 sailing trips  ·  seats from $35 each

Every harbour in Crete has a skipper selling seats. These 8 are the ones to choose, with prices and times laid out.

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island is best enjoyed from the water
Crete Sailing Tours, Greece Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Crete, Sailing Tours with Drinks in Greece, Sailing Tours with Lunch, Sailing Tours with Lunch in Crete, Sailing Tours with Lunch in Greece, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

1.Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Top of the fleet

Choose a shared half-day sail to Dia Island, a private yacht trip, or a one-hour coastal cruise from Heraklion. The Dia route includes lunch, unlimited water, soft drinks and local wine, plus snorkeling, paddleboards, and optional fishing. Crew members may include Stavroula, Dennis, Mido, or Miso.

“A very choppy crossing to the island. Very well handled by the skipper though The boat was comfortable and safety was well looked after Food was very good. Would have been nice to have beer as an option perhaps Time went very quickly”

Check sailing dates →Read the whole sail review

Heraklion: Private Half-Day Sailing Trip to Dia Island - Saint George Bay and the best two hours of the trip
Crete Sailing Tours, Greece Sailing Tours, Half-Day, Sailing Tours, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

2.Heraklion: Private Half-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 466 reviews · 4.5 hours

Spend 4.5 hours on a private sailing boat from Heraklion to Dia Island, with a two-person crew, unlimited drinks, fruit, snorkeling gear, fishing equipment, and paddleboards. You will anchor in Saint George Bay for swimming and lunch. Optional hotel transfers and onboard meals cost extra.

“We had a great time. If we ever get back to Crete we will do it again.”

Check sailing dates →Read the whole sail review

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - Gramvousa combines a swim with a castle visit
Catamaran Sailing Trips, Catamaran Sailing Trips in Crete, Catamaran Sailing Trips in Greece, Crete Sailing Tours, Greece Sailing Tours, Sailing Tours, Tour Reviews

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

3.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

★★★★★★★★★★5.0 · 116 reviews · 7 hours 30 minutes (approx.) · from $235Best loved

Spend 7.5 hours sailing from Kissamos to Balos Lagoon and Gramvousa Island aboard a modern catamaran limited to 22 people. Crew members such as Dimitri, Yannis, and Jessica provide drinks, Greek snacks, a Mediterranean lunch, snorkeling gear, and paddleboards. The early departure helps you reach the beaches before the largest ferries.

“We booked three boat tours with DanEri Yachts during our stay in Crete, and this one was hands down the best! No doubt Balos and Gramvousa were breathtaking, with crystal-clear waters perfect for swimming, but what truly set this tour apart was the exceptional service and the crew's genuine hospitality. Jessica made one of the best meals we had on the island, and her partner made sure we were always comfortable, bringing drinks to wherever we were relaxing on the boat and frequently checking in to see if we needed anything. It was easily one of the highlights of our week in Crete—if not the best!”

Check sailing dates →Read the whole sail review

Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024) - Finding a quiet cove on Dia Island
Catamaran Sailing Trips, Catamaran Sailing Trips in Crete, Catamaran Sailing Trips in Greece, Crete Sailing Tours, Greece Sailing Tours, Sailing Tours, Sailing Tours with Lunch, Sailing Tours with Lunch in Crete, Sailing Tours with Lunch in Greece, Tour Reviews

Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

4.Catamaran Sailing to Dia with Lunch in Heraklion, Crete(EST 2024)

★★★★★★★★★★5.0 · 64 reviews · from $142

Spend about five and a half hours sailing from Heraklion to Dia Island aboard a new Lagoon 46 catamaran. Swim in a quiet cove, snorkel, use the included SUP boards, enjoy a freshly prepared Cretan pasta lunch, and return with fruit, soft drinks, water, wine, and beer included.

“Captain and crew were awesome. It was an incredible day on and in the water. Our lunch was delicious. Highly recommend this excursion.”

Check sailing dates →Read the whole sail review

Kissamos: Balos and Gramvousa Private Sailing Trip with Meal - Leaving Kissamos Port for Balos Lagoon
Crete Sailing Tours, Greece Sailing Tours, Private Sailing Charters, Private Sailing Charters in Crete, Private Sailing Charters in Greece, Sailing Tours, Sailing Tours with Lunch, Sailing Tours with Lunch in Crete, Sailing Tours with Lunch in Greece, Tour Reviews

Kissamos: Balos and Gramvousa Private Sailing Trip with Meal

5.Kissamos: Balos and Gramvousa Private Sailing Trip with Meal

★★★★★★★★★★4.8 · 41 reviews · 8 hours

Join skipper and crew aboard Izabela, the sailboat with the grey bimini, for an eight-hour private cruise from Kissamos. You’ll spend about two hours at Balos, eat a Cretan lunch with wine and beer, then swim and hike to Gramvousa’s Venetian fortress. The boat carries snorkeling gear, a covered cabin, dining area, and bathroom with shower.

“We loved our whole day! The boat was perfect for our group of 7 people. Both Gramvousa and Balos was amazing the water is so clear and calm. George was amazing, we helped ourselves to drinks and lunch was delicious. George allowed us the perfect amount of time to swim, explore and relax. Facilities were great also.”

Check sailing dates →Read the whole sail review

Private Sailing Cruise, Balos and Gramvousa with meal and drinks. - Two hours around Balos Lagoon
Crete Sailing Tours, Greece Sailing Tours, Private Sailing Charters, Private Sailing Charters in Crete, Private Sailing Charters in Greece, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Crete, Sailing Tours with Drinks in Greece, Sailing Tours with Lunch, Sailing Tours with Lunch in Crete, Sailing Tours with Lunch in Greece, Tour Reviews

Private Sailing Cruise, Balos and Gramvousa with meal and drinks.

6.Private Sailing Cruise, Balos and Gramvousa with meal and drinks.

★★★★★★★★★★5.0 · 38 reviews · 8 hours (approx.)

Set out from Kissamos at 10:00 a.m. aboard the sailing boat Izabela for Balos Lagoon and Gramvousa. Your skipper, such as Christopher or George, chooses safe swim spots and shares local insight. Expect a Cretan lunch, beer, wine, soft drinks, snorkeling gear, beach umbrellas, and time to explore the fortress.

“The scipers where very polite and served us everything we needed. The sailing vessel was bigger then expected and in really good conditions. It was clean and we had two rooms ans two bathrooms to our hand. The two spots we went to where amazing and had a stunning view! All in all totaly worth the money!!!”

Check sailing dates →Read the whole sail review

Private Sailing Cruise from Heraklion to Dia Island - Reaching Dia Island’s quiet southern bays
Crete Sailing Tours, Greece Sailing Tours, Private Sailing Charters, Private Sailing Charters in Crete, Private Sailing Charters in Greece, Sailing Tours, Tour Reviews

Private Sailing Cruise from Heraklion to Dia Island

7.Private Sailing Cruise from Heraklion to Dia Island

★★★★★★★★★★5.0 · 22 reviews · 6 hours (approx.)

Spend about six hours sailing privately from Heraklion to Dia Island with Captain Greg and Dimitrius. Swim in clear water, use the paddleboard and snorkeling gear, explore a former Minoan harbor area, and enjoy fruit, snacks, drinks, and a meal aboard a comfortable boat.

“After careful consideration, the captain and first mate rescheduled our tour to a day with wasn't windy and cold - it was amazing! Their thoughtfuness to do this really shone, and the half-day tour was the perfect relaxing end to our Greek vacation. Both were such gracious hosts to make this a great experience... and the food was delicious!”

Check sailing dates →Read the whole sail review

From Chania: Fully Private Sailing Cruise with Meal & Drinks - Ai Giannis and the old fortifications of Souda Bay
Crete Sailing Tours, Greece Sailing Tours, Private Sailing Charters, Private Sailing Charters in Crete, Private Sailing Charters in Greece, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Crete, Sailing Tours with Drinks in Greece, Sailing Tours with Lunch, Sailing Tours with Lunch in Crete, Sailing Tours with Lunch in Greece, Tour Reviews

From Chania: Fully Private Sailing Cruise with Meal & Drinks

8.From Chania: Fully Private Sailing Cruise with Meal & Drinks

★★★★★★★★★★5.0 · 18 reviews · 7 hours

Sail east from Souda Bay on the private yacht Be Happy with skipper Nikos and a hostess, stopping at Ai Giannis and quiet coves near Karga and Drapano. You can swim, snorkel, try sailing under supervision, and eat a fresh Cretan three-course lunch with wine and beer. The seven-hour trip costs $883 for up to four people.

“The best tour ever! Nikos & Alex were amazing and cooked us the best meal! If you’re in Crete this is the best tour you could reserve. The boat was clean, very new & the food was greek and delicious!”

Check sailing dates →Read the whole sail review

Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
Scroll to Top

Explore sailing

Pick a boat, a coast or a time of day.

Kinds of sail

Catamaran tripsTall shipsYacht chartersPrivate chartersLessons

Time of day

Golden-hour sailsDinner sailsParty sailsTwo-hour sailsFull-day sails

On board

Drinks on boardLunch at anchorSwim stopsSnorkel sails

Out at sea

Island hoppingWhales and dolphinsNile feluccasEvery sailing trip