Where to Sail in Greece: 15 Top Trips

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Dia Island from a protected bay

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Top of the fleet

Sail from Heraklion’s Venetian Harbour to protected Dia Island aboard a yacht limited to 14 people. You’ll swim, snorkel, paddleboard, and enjoy shrimp linguini, Greek salad, Cretan appetizers, and unlimited drinks. English-speaking crew members may include Mariana, Manos, Sofia, Giannis, or Captain Petros, with morning and sunset departures available.

“This was a top notch experience: I strongly recommend this sunset boat trip!”

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Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

2.Adamas: Milos & Polyaigos Full-Day Sailboat Tour with Lunch

★★★★★★★★★★4.9 · 1,646 reviews · 10 hours · from $147

Spend 10 hours circling Milos and visiting Polyaigos, with swim stops at Gerakas and Kleftiko, snorkel gear, lunch, snacks, and drinks included. Guides such as Dora, Niki, and Alexandra share island stories, while the crew adjusts the route when wind makes the northern coast rough.

“Best trip we have ever been on! The boat was amazing, the food was amazing (we were fed fresh yummy food multiple times and there was unlimited drinks). Our tour guide Dora was amazing, very friendly and knowledgeable about the tour stops. She made the tour great! Couldn’t recommend enough, she even taught us traditional Greek dances - amazing vibes and very fun. The tour stops were amazing, 3 amazing places to swim. Kleftiko is a must visit, swimming into the caves is a highlight! - 10/10 would recommend, worth the money!”

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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

3.Santorini: Sailing Catamaran Cruise with BBQ and Drinks

★★★★★★★★★★4.7 · 1,452 reviews · 5 hours · from $117

You’ll cruise Santorini aboard a luxury catamaran with an English or Greek-speaking crew, stopping at Red Beach, Mesa Pigadia, Palea Kameni, and the hot springs. Expect three swim stops, snorkeling gear, towels, a BBQ, wine, soft drinks, and sunset views. Maria, Neta, and Liz are among the crew members praised for warm, attentive service.

“This was excellent!!!! We wished there was an all day option. The crew on board, our driver, the people answering all my crazy questions on WhatsApp, were fantastic. They were even able accommodate a vegan diet which we were so thankful for as well. This is a top notch company and it shows. For anyone visiting Santorini looking for a great cruise look no further.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

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

★★★★★★★★★★4.8 · 1,405 reviews · 1 hour - 390 minutes · from $35Lowest fare aboard

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”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

5.Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $95

Spend about five hours sailing from Ammoudi or Athinios, with hotel pickup, swims near the volcano, Red Beach and White Beach, plus a BBQ buffet, Santorinian wine, soft drinks and music. The later departure may include sunset views toward Oia. Expect a lively boat with up to 55 passengers, shade, restrooms and snorkeling gear.

“Not sure this was the right trip for us. Didn't know was a party catamaran. However the company running this do have a more semi private opinion The BBQ was very good, actually enjoyed it and the crew was very good too Just the experience was not enough. A bit more could have been better The snorkeling equipment was not clean”

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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

From Gouvia Marina, sail northeast on a small yacht with an English or Greek-speaking skipper. Swim at Barbati and Gialiskari, try a supervised cliff jump, explore a blue cave, and enjoy sandwiches, fruit, and soft drinks. Boats hold up to 12 people, with private trips available. Bring snorkel gear, towels, and sunscreen.

“We absolutely loved this boat trip, very chilled and relaxed and beautiful views, our guide (Ari) was brilliant and fun too😁”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

7.Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

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

Join Sailing Grace for a six-hour cruise from Heraklion to Dia Island. You’ll sail with an English or Greek-speaking crew, hear island legends, swim, snorkel, fish, paddleboard, and eat a Mediterranean meal onboard. Hotel pickup is available, and afternoon departures can include a sunset return.

“We had an amazing trip to Dia island with Stelios and Celia! We decided to try the full day trip over the half day and are so glad we did. Definitely pay the bit more if you can! The pickup from our hotel was right from the door and on time, we were welcomed on board at the harbour and at the island had a chance to try snorkelling and SUP for the first time. Lunch was prepared while we swam and we had plenty of chance to sunbathe without feeling under pressure to do anything to a schedule. The whole experience was so relaxing, we felt like welcomed guests…”

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Heraklion: Dia Island Sailing Cruise with Snorkeling

8.Heraklion: Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion’s old Venetian harbor to uninhabited Dia Island with a small crew of up to 18 people. Ernesto and George are among the crew members you may meet. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks plus either seafood pasta or a lighter half-day meal.

“Despite the 40 min delay by transit authority that required us to divvy out passengers into several boats, they added 30 min on the end. The boat ride was refreshing and had a nice ship on the catamaran prepared by the skipper, wonderful views, about 30 min of swimming, snorkeling. The snorkeling equipment wasnt great and not much underwater sealife , so dont plan on itlooking like the Caribbean. The captain, Station was fun and full of stories”

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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch

9.Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch

★★★★★★★★★★4.8 · 713 reviews · 8 hours · from $170

Spend eight hours sailing west from Adamas with Excellent Yachting, stopping at Kalogries, Kleftiko, and Agios Dimitrios. The crew provides snorkeling gear, underwater photos, a RIB cave tour, breakfast snacks, Greek lunch, and drinks. Captains such as Giannis and guides including Christos, Dionysis, and the two Georges add island stories and plenty of good humor.

“Great value for money and the guides are full of laughs. Great day great company, I would highly recommend”

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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 $151Best loved

Spend about six hours aboard a spacious gulet from Agios Ioannis, sailing to UNESCO-listed Delos and the clear swimming waters of Rhenia. You can explore Delos on your own or prebook a guided tour, then enjoy a BBQ buffet, drinks, snorkeling gear, and attentive crew care. Hotel transfers cost extra.

“The experience was amazing, once in a lifetime. We are so happy we decided to book this tour. The crew and food were excellent!”

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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

Spend about six hours sailing from Mykonos to Rhenia and Delos. Swim from the yacht in clear Aegean water, use the free snorkel gear, eat lunch with wine and soft drinks, then tour Delos with a licensed English-speaking guide. The group can reach 35 people, though yacht size and numbers vary.

“Thld was the highlight of our trip--swimming in the Mediterranean Sea with my son. The crew of Chris, Thanos and The Captain (I don't want to butcher his name) was incredibly hospitable with our 3 yr old. The only very minor complaint was the extended 2 hrs stay on Delos given the heat, but that's just Greece. The whine was minor, and my child just hung at the boat. Hopefully you are as lucky as us and we were with 2 other amazing families that we really enjoyed sharing the boat with......the other boat looked miserable based on the demanding and rude guests at check-in (lol & dodged that boat).…”

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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

Spend about five hours on a catamaran sailing Santorini’s caldera, with hotel pickup, swim stops at Red or White Beach, warm volcanic springs, a Greek BBQ, and unlimited beer, wine, and soft drinks. Morning departures leave Vlichada Marina, while afternoon sailings begin near Akrotiri and may include sunset views.

“Great half day event with excellent crew. Definitely must do in Santorini! Two stops for swimming, dinner and sunset - everyhting was just perfect. Me and my kids enjoyed this trip.”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

13.Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.7 · 529 reviews · 4.5 - 7 hours · from $82

Sail from Heraklion to uninhabited Dia Island with a small crew of 10 to 18 people. You can snorkel, paddleboard, swim, eat Greek food, and watch the sunset from a catamaran. Half-day and full-day options are available, with hotel pickup offered from selected areas.

“We had a wonderful time! There were a lot of people on the boat but it didn’t feel crowded. The cove where we anchored was lovely — our only complaint was that a party boat anchored nearby and played loud (bad) house music the whole time. It made the experience slightly less idyllic, but we tuned it out eventually, food was delicious, guides were friendly and cooked a delicious dinner, and the sunset was dreamy. A perfect way to spend our afternoon/evening in Heraklion!”

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Sailing Cruise to Dia Island with Meal and Water Activities

14.Sailing Cruise to Dia Island with Meal and Water Activities

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $96

Sail from Heraklion to uninhabited Dia Island aboard a yacht or catamaran with a maximum of 14 people. Swim in a protected cove, snorkel, paddleboard, fish, and enjoy shrimp linguine, Greek salad, fruit, beer, wine, and soft drinks. Pickup is available across much of Crete.

“Wonderful experience. The crew was great and the food was so fresh and delicious. Perfect day trip !”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

15.Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 517 reviews · 6 hours · from $100

Sail six nautical miles from Heraklion to Dia Island with a maximum of 10 people. Captains George, Panos, and Vaso bring local stories and easygoing Cretan hospitality, while you swim, snorkel, paddleboard, fish, and eat shrimp or vegetarian pasta with unlimited drinks.

“George and Marco were friendly and informative and made the trip very enjoyable. We spent a good amount of time snorkelling using the equipment they provided and enjoyed a nice lunch of pasta, salad and fruit. It’s a small group of 10 so the boat isn’t overcrowded and you get to know the people well. Highly recommend”

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