Where to Sail: the 6 Best Sailing Trips in Crete

1.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Our pick

Sail from Heraklion to Dia Island on a shared yacht trip with lunch, local wine, soft drinks, snorkeling gear, paddleboards, and optional fishing. You get about four to six hours on the water, with crew such as Stavroula, Dennis, or Mido. Private and one-hour coastal options are also available.

“The activity was very well organised (10/10) as well as the pick up and drop off service.”

Check availability →Read our full review

2.Private Half-Day Sailing Trip to Dia Island

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

You’ll sail from Heraklion with a two-person English or Greek-speaking crew to Dia Island’s Gulf of Saint George, once explored by Jacques Yves Cousteau. Expect a private boat for up to eight, clear water for swimming and snorkeling, fishing gear, paddleboards, fruit, wine, soft drinks, and about 2.5 hours at anchor. Hotel transfers and full meals cost extra.

“Sailing trip was great, guides gave a lot of explanation concerning the boat, island and history.”

Check availability →Read our full review

3.Balos Gramvousa Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 257 reviews · 7.5 hours · from $229

Sail from Kissamos to Balos Lagoon and Gramvousa Island aboard a small shared or private boat with an experienced skipper. Swim, snorkel, hike to Gramvousa Castle, and enjoy a fresh Cretan lunch with drinks, fruit, and shaded deck seating. Guides such as Vasilis, Katarina, Jo, and Luis help make the day personal and relaxed.

“Vasilis and Katarina were amazing and we loved it! Delicious lunch and gorgeous views. We felt safe and enjoyed the ride. Definitely would recommend.”

Check availability →Read our full review

4.Private Full-Day Sailing Trip to Dia Island

★★★★★★★★★★4.9 · 140 reviews · 6.5 hours

Sail privately from Heraklion to Dia Island with a two-person crew, stopping at Saint George Bay for swimming, snorkeling, fishing, and paddleboarding. You get fruit, unlimited water, soft drinks, and local white wine. Boats include options such as the Elan 37, and hotel transfers and onboard meals cost extra.

“We told the guides we were more interested in sailing than the excursions and they accommodated our request. The Elan 37 is a fun boat and she sailed well even in light winds. The lunch was delicious and we enjoyed it in an idyllic bay on Dia island. The captain and first mate were vey kind and helpful with our two kids. I highly recommend this excursion and will book again if we return to Crete.”

Check availability →Read our full review

5.Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos

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

Sail from Kissamos to Balos Lagoon and Gramvousa on a small catamaran limited to 22 people. Swim, snorkel, paddleboard, and enjoy Greek snacks, a Mediterranean lunch, drinks, and attentive crew such as Dimitri, Yannis, and Jessica. The early start helps you reach both stops before the large ferries arrive.

“Dimitri, Yanni and Jessica were amazing during our tour. It was an amazing day with my husband and two teens. Thank you!!”

Check availability →Read our full review

6.Balos and Gramvousa Private Sailing Trip with Meal

★★★★★★★★★★4.8 · 41 reviews · 8 hours

Spend eight hours aboard the Izabela, a private sailing boat from Kissamos Port to Balos Lagoon and Imeri Gramvousa. Swim, snorkel, hike to a Venetian fortress, and eat Cretan food with wine, beer, soft drinks, and fruit. George, Christopher, Alex, and the crew are noted for friendly service and careful timing.

“Highly recommend for a small group of friends! We debated driving to Balos vs boating and we were so grateful we chose this experience. We stopped at Gramvousa island first and hiked to the top for beautiful views and photo opportunities of Balos. Then had a delicious lunch and swim. Short trip over to Balos where we spent a couple hours enjoying the beach. We walked to the main shore and greeted the goats. It felt like perfect amounts of time allotted to each stop, we never felt rushed and we enjoyed the experience to the fullest. One tip- take a Gravol before you set sail, the way there was…”

Check availability →Read our full review