Crete Sailing Trips


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15 Best Crete Sailing Trips Worldwide

The best days on the water.

The 15 most popular crete sailing trips. What each sail costs, how long you are on the water, and which crews run it well.

15 Best Crete Sailing Trips Worldwide

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Picking the right option: shared half-day, private, or 1-hour coastal
Crete, Crete Sailing Trips, Cruises & Boat Tours, Island-Hopping Sails, Lunch Experiences, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Picking the right option: shared half-day, private, or 1-hour coastal
Crete, Crete Sailing Trips, Cruises & Boat Tours, Island-Hopping Sails, Lunch Experiences, Sailing, Tall Ships & Sailing Boats, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

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

Sail from Heraklion to Dia Island for snorkeling, unlimited drinks, and lunch on a yacht, with easy pickup options available.

★ 4.9

“I loved the sailing trip and the time we had to swim. The skipper and first mate were friendly and professional. The meal was healthy and delicious. The crew provided a quick safety talk, rules of the vessel, and tips for a successful sailing trip. This was a great afternoon that I was sad to…”

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Heraklion: Private Half-Day Sailing Trip to Dia Island - Private sailing from Heraklion: what you really buy with your money
Crete, Crete Sailing Trips, Cruises & Boat Tours, Half-Day, Island-Hopping Sails, Private, Private Sailing Charters, Sailing, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - From Kissamos dock to open water: what the morning feels like
Crete, Crete Sailing Trips, Cruises & Boat Tours, Lunch Experiences, Sailing, Tour Reviews

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

4.From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

Sail from Kissamos to Balos Lagoon and Gramvousa Island with a fresh on-board Cretan lunch, swimming stops, and castle views.

★ 4.9

“Family of four adults. We loved the private atmosphere of the tour. The scenery was amazing and the lunch simply delicious. Having never sailed before, we felt very safe with the Captain, Vasilis and his first mate, Katarina. They were both personable and accommodating when we requested to change dates. Thank you Falarnasa Sailing for…”

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Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Loutro village: boat access, small-street wandering, and sea views
Crete, Crete Sailing Trips, Cruises & Boat Tours, Sailing, Tour Reviews

Sailing trip to the Top Coasts of Crete, Daily/Multi-day

Dia island : Small Group Sailing Trip to Dia Island with Lunch - Dia wildlife spotting: dolphins, monk seals, falcons, and wild goats
Crete, Crete Sailing Trips, Cruises & Boat Tours, Island-Hopping Sails, Lunch Experiences, Sailing, Small-Group Sails, Tour Reviews

Dia island : Small Group Sailing Trip to Dia Island with Lunch

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - From Kissamos dock to open water: what the morning feels like
Crete, Crete Sailing Trips, Cruises & Boat Tours, Lunch Experiences, Sailing, Tour Reviews

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

7.From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

Sail from Kissamos to Balos and Gramvousa with real sailing, deck-cooked Cretan lunch, and snorkel time in clear lagoon waters.

★ 4.8

“We were onboard the very pampering Electra Yacht. The whole experience was perfect. the skipper and assistant are very professional, attentive and very nice, pleasant and gave great Service! The food (traditional food, fruit, beer) was very tasty, the background music. Balos and Gramvousa are must see locations. It wasnt cheap but still good value…”

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Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated! - Onboard setup: showers, WiFi, and the gear list that changes the day
Catamaran Cruises, Crete, Crete Sailing Trips, Cruises & Boat Tours, Drinking Tours, Island-Hopping Sails, Lunch Experiences, Party & Music Cruises, Sailing, Tour Reviews, VIP

Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

8.Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated!

Luxury catamaran to Dia Island with open bar, seafood lunch, snorkel/SUP gear, and a small-group vibe in Crete.

★ 5.0

“The best caramaran in the port and I'm sure is the crew. Amazing captain, chef and assistant. Beautiful and tasteful food, with dinner and snacks before and after. Everything is thought of, even SUPs and snorkel equipments. Captain anchored us in the best spot in the bay, close to the shore. Amazing experience, would reccomend…”

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Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - The one-hour sail out: what you’ll notice on the water
Crete, Crete Sailing Trips, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Sailing, Snorkel Sailing Trips, Snorkeling, Sunset Sails, Tour Reviews

Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

9.Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

Sail from Heraklion to Dia Island for swimming, snorkeling, lunch, and optional sunset sailing, with pickup options and small-group comfort.

★ 5.0

“This was a truly fantastic experience that my wife and I enjoyed thoroughly! First, we appreciated all the communication before the day of our trip, with all the practical information regarding the trip, which made the preparations and planning simple and easy. We felt the duration of 4.5 hours worked very well. The trip itself…”

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Heraklion: Private Full-Day Sailing Trip to Dia Island - Your boat, your crew, and the gear you’ll use
Crete, Crete Sailing Trips, Cruises & Boat Tours, Full-Day, Island-Hopping Sails, Private, Private Sailing Charters, Sailing, Tour Reviews

Heraklion: Private Full-Day Sailing Trip to Dia Island

10.Heraklion: Private Full-Day Sailing Trip to Dia Island

Private 6.5-hour sailing from Heraklion to Dia Island with snorkeling, fishing gear, paddleboards, unlimited drinks, and optional lunch.

★ 4.9

“Our sailing trip to Dia Island was an unforgettable experience! From the moment we stepped aboard, the crew made us feel right at home. They were exceptionally accommodating, ensuring that every detail was perfect for our family. The boat was well-maintained, and the journey was smooth and scenic. We were able to relax, swim in…”

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Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Dia Island Time: Snorkel, SUP, Fishing, and the Flamingo Float
Catamaran Cruises, Crete, Crete Sailing Trips, Cruises & Boat Tours, Drinking Tours, Island-Hopping Sails, Lunch Experiences, Party & Music Cruises, Sailing, Small-Group Sails, Tour Reviews

Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

11.Dia Island Catamaran – Premium Lunch, Open Bar, Small Group

Small-group catamaran to Dia Island from Heraklion with snorkeling, SUP, and a premium onboard lunch plus an open bar.

★ 5.0

“We had a great day with George and Alexandra. This is basically a ride to Dia island off Heraklion where you anchor and pass the day swimming and sunbathing. Out at 10:00 back by 16:00. The food was ok. This trip is what you make it and depends on the other members of the group.…”

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Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - The 8:30am start: how you avoid the big-boat scramble
Catamaran Cruises, Crete, Crete Sailing Trips, Cruises & Boat Tours, Sailing, Tour Reviews, VIP

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

12.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

Luxury catamaran from Kissamos to Balos Lagoon and Gramvousa. Snorkel, SUP, skip crowds, and enjoy lunch plus unlimited drinks.

★ 5.0

“Catamaran ride to 2 beaches. The day was beautiful as well as the beaches. You could visit these beaches by ferry but would recommend this better. We were a small group which made it special. Lunch was served and it was delicious. Mussels, salad, chicken, bread and orzo with seafood. Also plenty of beer and…”

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Sailing Trips with Cretan Sailing - The First Big Stop: St. George Bay and the BBQ Moment
Crete, Crete Sailing Trips, Cruises & Boat Tours, Sailing, Tour Reviews

Sailing Trips with Cretan Sailing

13.Sailing Trips with Cretan Sailing

Traditional boat cruise from Hersonissos with two swim stops, snorkeling gear, and BBQ lunch on Crete, Greece.

★ 4.0

“Experience is great, we had 2 stops, first one just to swim and second one with different places you could swim to and different activities. Me as a not strong swimmer was given a floatie so could fully participate. We chose to do snorkeling at second stop, it is just the goggles they give but…”

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Sailing Cruises Chania - Setting sail around the Gulf of Chania (without feeling rushed)
Crete, Crete Sailing Trips, Cruises & Boat Tours, Sailing, Tour Reviews

Sailing Cruises Chania

14.Sailing Cruises Chania

Sail Chania’s gulf on a private cruise with swim stops, snorkeling gear, Cretan snacks, and possible Kri Kri goat sightings.

★ 5.0

“We had an amazing time!! The crew was wonderful and took good care of us! I highly recommend - you won’t be disappointed!!”

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Panormo: Luxury Catamaran Cruise with Lunch & Open Bar - The catamaran comfort: shade, sunbeds, and the practical extras
Catamaran Cruises, Crete, Crete Sailing Trips, Cruises & Boat Tours, Drinking Tours, Lunch Experiences, Party & Music Cruises, Sailing, Tour Reviews, VIP

Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

15.Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

Luxury catamaran cruise from Panormo with brunch, SUP and snorkeling, Mediterranean lunch, open bar, small-group vibe, and sea views.

★ 5.0

“We had the most amazing boat day. From start to finish the crew were amazing, we had so much fun. We went as a family with 4 young children and we felt very safe.”

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More Crete Sailing Trips Worldwide

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The sailing ports worth the trip, grouped by the sea they sit on.