GREECE

The 15 Best Greek Sailing Trips

72 sailing trips  ·  from $35 a head

Greek water is clear enough to see your anchor and the Aegean wind is stronger than the brochures admit. These 15 cover Crete, the Cyclades and the Saronic, priced and timed, with a note on what the meltemi cancels.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - The one-hour sail toward protected Dia
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch - Sarakiniko and Glaronissia from the sea
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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

Santorini: Sailing Catamaran Cruise with BBQ and Drinks - Palea Kameni and the Santorini volcano
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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island’s clear water and quiet cove
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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

4.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Best value

Review of Crete’s Dia Island sailing trip from Heraklion, with yacht views, swimming, snorkeling, lunch, drinks, costs, and practical tips.

“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”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Hotel pickup makes the port connection easy
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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach brings the first clear-water swim
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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

6.Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

★★★★★★★★★★4.8 · 851 reviews · 5 - 10 hours · from $69

Review of Corfu’s Gouvia sailing trip, with small groups, clear-water swims, cliff jumping, snacks, drinks, and Blue Cave views.

“Fantastic day out!! Definitely would recommend booking! We had booked for a hen party with 11 girls and we had the best time! Ari, our skipper, was second to none and joined in on the fun, taking pictures and tailoring our stops to suit us. we had plenty of time on each stop to jump in, swim or to stay on board and enjoy a drink. We were able to buy alcohol on-board and the prices were very reasonable! Ari made us a light lunch also which was perfect! 10/10 would recommend!!!”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - The one-hour sail to Dia Island
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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

7.Sailing Cruise to Dia Island with Drinks and Meal

★★★★★★★★★★4.9 · 778 reviews · 6 hours · from $106

Review of Sailing Grace’s six-hour cruise from Heraklion to Dia Island, with swimming, snorkeling, SUP, lunch, drinks, and sunset views.

“This was truly an incredible day! So relaxing in such a beautiful place. They made lunch on the boat and it was amazing. Swimming, walking the beach and soaking up the sun on the deck - absolute perfection.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling - What Dia Island offers once you arrive
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Heraklion: Dia Island Sailing Cruise with Snorkeling

8.Dia Island Sailing Cruise with Snorkeling

★★★★★★★★★★4.7 · 742 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island for swimming, snorkeling, paddleboarding, Greek food, wine, and clear-water bays.

“A beautiful day, great weather, calm sea. Crew were kind and great to talk with. Really enjoyed snorkelling, the water was magical!”

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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch - Cape Vani and the volcanic west coast
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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch

Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Delos: one and a half hours among ancient stones
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Shared Mykonos Sail Cruise to Delos and Rhenia Islands

10.Shared Mykonos Sail Cruise to Delos and Rhenia Islands

★★★★★★★★★★5.0 · 705 reviews · 6 hours (approx.) · from $151Top rated

Review of Mykonos sailing to Delos and Rhenia, with ruins, swimming, snorkeling, barbecue lunch, drinks, costs, and practical tips.

“The sailing trip to Delos and Renia was maybe our favorite activity of our time in Mykonos. It was a good mix of relaxation and activity — enjoying a relaxing drink and lunch on the boat, exploring on our own in Delos, and a refreshing swim at Renia. I would have liked a little bit more time on Delos, but other than that, it was perfect. Staff/crew was very attentive to the needs of all passengers.”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Starting at the Yacht in Mykonos
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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

11.Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks

★★★★★★★★★★4.5 · 608 reviews · 6 hours (approx.) · from $145

Sail from Mykonos to Rhenia and Delos for swimming, lunch, Greek ruins, wine, and a guided island tour in six hours.

“The experience was incredible and genuinely memorable. The onboard crew were excellent, attentive, and responsive to our needs. Communication before the trip was clear, especially when they let us know our morning cruise was moved to the afternoon due to wind conditions. The food was a bit too carb-heavy for my preference. It included pasta, salad, bread, and cheese, served family style with other passengers. Drinks were complimentary but needed to be requested directly from the crew. The biggest issue was time management, or more accurately, the lack of clarity around how long we had at each stop. We spent a lot of time at Rhenia, which was enjoyable, but…”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks - Sailing past Indian Head Mountain and the lighthouse
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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

12.Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

★★★★★★★★★★5.0 · 560 reviews · 5 hours (approx.) · from $145

Sail Santorini’s caldera, swim at volcanic springs, enjoy a Greek BBQ, and sip unlimited drinks on this five-hour catamaran cruise.

“Me and my husband had done this tour exactly 10 years ago when we were still dating. This was our first international trip and it was a highlight of our holiday! So…we decided to do it again 10 years later and take some then and now photos! It was great and everything we remember. It was also amazing to get out of the crowds. We hope to see you in another 10 years!!!”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Leaving Heraklion for Dia Island
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Sailing Cruise to Dia Island with Meal and Water Activities - The Bay of Saint George and Dia’s unusual past
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Sailing Cruise to Dia Island with Meal and Water Activities

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Dia Island and the quiet waters of Saint George Bay
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

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