Under sail · CRETE SAILING TRIPS

Sailing in Crete: The 15 Best Trips to Book

39 sailings  ·  from $35 a head

Crete is long, and the good sailing splits between the Kissamos boats out to Balos and the Dia Island runs off Heraklion. The 15 below cover both ends, with departure times and what lunch aboard includes.

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Meeting the skipper at Heraklion Port
Crete Sailing Trips, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Lunch Experiences, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Tour Reviews

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1h to 6h 30m · from $35Our pick

Sail from Heraklion to Dia Island for swimming, lunch, drinks, and Crete views, with shared, private, and one-hour cruise choices.

“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 availability →Read our full review

Heraklion: Private Half-Day Sailing Trip to Dia Island - Saint George Bay and the waters of Dia
Crete Sailing Trips, Greece Sailing Trips, Half-Day, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Private Sailing Charters, Private Sailing Charters in Crete, Tour Reviews

Heraklion: Private Half-Day Sailing Trip to Dia Island

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch - Leaving Kissamos on a Small Sailboat
Crete Sailing Trips, Greece Sailing Trips, Lunch Experiences, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Swim Stop & Beach Sailing Trips, Tour Reviews

From Kissamos: Balos Gramvousa Sailing Cruise with Lunch

Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Loutro: A Village with No Road In
Crete Sailing Trips, Greece Sailing Trips, Tour Reviews

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

Dia island : Small Group Sailing Trip to Dia Island with Lunch - Agios Georgios or Panagia: the main swimming stop
Crete Sailing Trips, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Lunch Experiences, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Semi-Private Sailing Cruises, Semi-Private Sailing Cruises in Crete, Tour Reviews

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

5.Small Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★5.0 · 162 reviews · 4 hours 30 minutes (approx.) · from $72

Review of Crete’s small-group sailing trip to Dia Island, with snorkeling, SUP, lunch, wildlife, hotel pickup, and practical booking advice.

“- Captain and staff including pick up driver were really nice - water is really clear - boat is clean - captain brought a sea urchin to show to everyone. That was cute. BUT - the Equipment is the worst snorkeling Equipment We ever had on such a trip - at first they just had 8 snorkels for 12 ppl. So the Captain handed me his private one. That one was good. Later he found some more and said i have to change. Then i had to Deal with the rubish everyone had. Water came with EVERY breath. I didnt make it 2 meters of the boat on second attempt.…”

Check availability →Read our full review

Luxury Catamaran Cruise, Dia Island –Open Bar & Lunch -Top Rated! - Three hours in Dia’s peaceful bay
Catamaran Cruises, Catamaran Cruises in Crete, Crete Sailing Trips, Drinking Tours, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Lunch Experiences, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Tour Reviews

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

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

★★★★★★★★★★5.0 · 143 reviews · 5 hours 30 minutes (approx.) · from $145

Review of Crete’s luxury Dia Island catamaran cruise, with seafood lunch, open bar, snorkeling, SUPs, and practical booking advice.

“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 to anyone.”

Check availability →Read our full review

Sailing Trip to Dia with Snorkeling, Dining & Sunset Option - St. George’s Bay gives you time to slow down
Crete Sailing Trips, Dining Experiences, Dinner Experiences, Evening Experiences, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Sailing & Snorkeling Trips, Sunset Sailing Cruises, Tour Reviews

Sailing Trip to Dia with Snorkeling, Dining & Sunset Option

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

★★★★★★★★★★5.0 · 142 reviews · 4 hours 30 minutes (approx.) · from $36

Sail from Heraklion to Dia Island for snorkeling, a fresh onboard meal, Cretan wine, and an optional sunset return.

“It was just beautiful. From pickup to drop-off, everything just worked out. The shuttle was very punctual, even a little early at the hotel, so we could start on time at the harbor. Alexandra and Markos were warm and inviting. They explained everything well and took care of everything we needed. The sailing trip was beautiful despite the very calm sea, and Markos did his best so that we could at least sail a little with the power of the wind. When we arrived at the island, there were explanations and assistance for the activities. We were very impressed by Markos' patience and calmness when he helped a fellow traveler…”

Check availability →Read our full review

Heraklion: Private Full-Day Sailing Trip to Dia Island - What makes Dia Island worth the crossing
Crete Sailing Trips, Full-Day, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Private Sailing Charters, Private Sailing Charters in Crete, Tour Reviews

Heraklion: Private Full-Day Sailing Trip to Dia Island

Dia Island Catamaran – Premium Lunch, Open Bar, Small Group - Boarding in Heraklion and Sailing Past Rocca a Mare
Catamaran Cruises, Catamaran Cruises in Crete, Crete Sailing Trips, Drinking Tours, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Lunch Experiences, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Semi-Private Sailing Cruises, Semi-Private Sailing Cruises in Crete, Tour Reviews

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

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos - Starting from Kissamos with a smooth setup
Catamaran Cruises, Catamaran Cruises in Crete, Crete Sailing Trips, Greece Sailing Trips, Swim Stop & Beach Sailing Trips, Tour Reviews

Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

10.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Review of the Balos and Gramvousa luxury catamaran cruise from Kissamos, with food, timing, swimming stops, costs, and practical tips.

“The whole day was amazing! Staff were great and so friendly. Food was delicious and lots of it. Loved doing the smaller boat tour, we were able to beat the crowds from the big ship to both spots and we enjoy before all the people arrived. Beer and wine included. 100% recommend”

Check availability →Read our full review

Sailing Trips with Cretan Sailing - Stalis: a second chance to swim and see fish
Crete Sailing Trips, Greece Sailing Trips, Tour Reviews

Sailing Trips with Cretan Sailing

11.Sailing Trips with Cretan Sailing

★★★★★★★★★★4.0 · 99 reviews · 4 hours (approx.) · from $54

Review of Cretan Sailing from Hersonissos, with swim stops, BBQ lunch, snorkeling, costs, crowd tips, and practical booking advice.

“Although the trip itself was very nice and enjoyful, it was way too expensive for what we got. The sailing and jumping from the boat into the clear blue water at 2 spots was very nice, but lunch was very poor, and eventually we felt like we paid way too much for this kind of tour.”

Check availability →Read our full review

Sailing Cruises Chania - Swimming and snorkeling near the Island of Ag
Crete Sailing Trips, Greece Sailing Trips, Tour Reviews

Sailing Cruises Chania

12.Sailing Cruises Chania

★★★★★★★★★★5.0 · 93 reviews · 4 to 7 hours (approx.) · from $437

Review of Sailing Cruises Chania, a private Crete yacht trip with swimming, snorkeling, Cretan food, an open bar, and coastal views.

“Yannis and Kostas were so awesome. They taylores our sail to our interests. We loved that we got to put the sails up and turn off the engine and enjoy a peaceful day. I highly recommend them for a beautiful sailing experience.”

Check availability →Read our full review

Panormo: Luxury Catamaran Cruise with Lunch & Open Bar - The 100-minute sail along Crete’s north coast
Catamaran Cruises, Catamaran Cruises in Crete, Crete Sailing Trips, Drinking Tours, Greece Sailing Trips, Lunch Experiences, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Tour Reviews

Panormo: Luxury Catamaran Cruise with Lunch & Open Bar

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

★★★★★★★★★★5.0 · 80 reviews · 6 hours 30 minutes (approx.) · from $174

Review of Crete’s Panormo luxury catamaran cruise, with breakfast, swimming, SUP, snorkeling, Mediterranean lunch, and an open bar.

“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.”

Check availability →Read our full review

Rethymno Catamaran Cruise: Healthy Lunch & Open Bar - Sailing north along Crete’s coast
Catamaran Cruises, Catamaran Cruises in Crete, Crete Sailing Trips, Drinking Tours, Greece Sailing Trips, Lunch Experiences, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Sailing Trips with Lunch & BBQ, Sailing Trips with Lunch in Crete, Tour Reviews

Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

14.Rethymno Catamaran Cruise: Healthy Lunch & Open Bar

★★★★★★★★★★4.5 · 79 reviews · 6 hours 30 minutes (approx.) · from $174

Review of Rethymno’s 6.5-hour catamaran cruise, with healthy Cretan meals, open bar, swimming, SUP, snorkeling, and practical tips.

“Amazing trip all round. Superb crew, fantastic food. Nothing to fault at all. An incredibly relaxing day with a wonderful small group (8) of people. We enjoyed this so much and would do every day if we could! Would highly recommend.”

Check availability →Read our full review

Sailing Trip to Dia Island - All Inclusive - Three hours around Dia Island
Crete Sailing Trips, Greece Sailing Trips, Island Hopping Sailing Trips, Island Hopping Sailing Trips in Crete, Sailing Trips with an Open Bar, Sailing Trips with an Open Bar in Crete, Tour Reviews

Sailing Trip to Dia Island – All Inclusive

15.Sailing Trip to Dia Island – All Inclusive

★★★★★★★★★★5.0 · 67 reviews · 6 to 8 hours (approx.) · from $90

Review of Crete’s all-inclusive sailing trip to Dia Island, with seafood lunch, drinks, snorkeling, paddleboarding, timing, value, and practical tips.

“A great day out! George and Niko were incrediblley friendly and I feel like we became fast friends through the day. The water was cool but clear as crystal, easy to see the fish! The sun was great at drying us off upon leaving the ocean for a fresh made meal which we enjoyed with our new found friends (including the other visitors) on the boat. The island is practically untouched and has only a few buildings. Stunning views all round, throughout the whole trip...”

Check availability →Read our full review

Scroll to Top

Explore Greek sailing

Pick an island, a boat, or a kind of day aboard.