GREECE SAILING TOURS

15 Greek Sailings Worth the Crossing

223 sailings  ·  from $35 a head

Crete runs day boats out to Dia, Milos sails the Polyaigos coast and the Cyclades hop islands when the meltemi allows. The 15 below are compared on the crossing, the swim stops and which months the wind cancels.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Why 14 people changes the feel of the cruise
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Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

1.Dia Island Sailboat Cruise with Swimming and Meal

★★★★★★★★★★4.8 · 2,579 reviews · 5.5 hours · from $95Our pick

Sail from Heraklion’s Old Venetian Harbour to Dia Island aboard a small yacht with up to 14 people. You’ll swim, snorkel, paddleboard, and eat shrimp linguini, Greek salad, and Cretan appetizers. English-speaking crew members such as Mariana, Manos, Sofia, Giannis, and Captain Petros have earned warm praise for friendly service, with afternoon trips offering sunset views.

“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”

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

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

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

Spend a full day circling Milos and visiting Polyaigos, with swim stops at remote bays, snorkeling at Kleftiko, and lunch served aboard. Guides such as Dora, Nikki, and Alexandra share island stories and keep the mood lively. Three boats carry up to 25 people each. The route can change with the weather.

“Nikki was an amazing tour guide! Mariana who worked onboard as well and helped with our food and drinks was also such a gem. We had a great time and saw the most amazing spots of Milos. Kleftiko was definitely the highlight of our day, it felt like a dream swimming in the most crystal clear waters of Milos. Highly recommend this if you are in Milos, the only way you can see all the beaches that are only accessible by boat.”

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Santorini: Sailing Catamaran Cruise with BBQ and Drinks - Pickup from Thera and the run to Vlychada Port
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Santorini: Sailing Catamaran Cruise with BBQ and Drinks

3.Sailing Catamaran Cruise with BBQ and Drinks

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

Spend five hours aboard a luxury catamaran from Vlychada, with hotel pickup, three swim stops, Red and White Beach views, the hot springs, volcano, and a BBQ at Mesa Pigadia. English and Greek crew members, including Maria and Neta on some departures, serve wine, soft drinks, and optional premium drinks.

“This is my second time on this tour, with the same company, and I still recommend them. Safe, fun, informative, with a great lunch and plenty of time to swim and relax while listening to music and coasting on the water.”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - Dia Island: clear water and limited time ashore
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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

Sail from Heraklion with an English-speaking crew to Dia Island for swimming, snorkeling, paddleboarding, fishing, lunch, and unlimited drinks. Shared trips include the meal, while private cruises let you add one. Stavroula, Dennis, and other crew members are praised for friendly, careful service. A one-hour coastal option skips Dia and water activities.

“Nice shorter activity 4 hr, Friendly crew! Good lunch with plenty of water and wine! Beautiful day! ❤️🥂”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks - Hot springs near the volcano
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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 on a spacious Santorini catamaran, with hotel pickup, caldera views, hot springs, Red Beach, White Beach, swimming, snorkeling, and a BBQ meal. Complimentary water, soft drinks, and Santorinian Nychteru wine are included. The later sailing aims for sunset near Oia, though the final viewing point can change.

“Overall it was ok. The food was good along with the views. Music was load and it could’ve been shorter. Those looking for a quiet ride around seeing the sites this is not for you.”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks - Barbati Beach and 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

Cruise from Gouvia Marina along Corfu’s northeast coast aboard Ikaria or Eros 2, with a skipper such as Ari, Savvas, or Thassos. You’ll stop at Barbati Beach, Gialiskari, and a blue cave for swimming, snorkeling, and optional cliff jumping. Sandwiches, fruit, and soft drinks are included, while snorkeling gear and alcoholic drinks cost extra.

“This trip was a highlight of our holiday. Our skipper was friendly and informative . The boat was great with plenty of shade but also lots of space up front for sun lovers. Sandwiches and fruit were provided at one of the swimming stops and soft drinks were included. There was plenty of time for swimming at each of the 3 stops. I would do this trip again when next in Corfu.”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Arriving at Dia Island’s clear-water cove
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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

Sail from Heraklion’s Old Venetian Harbor to Dia Island with a certified crew, often including Captain Nick, Stelios, Celia, Kristina, or Iorgu. Swim, snorkel, fish, paddleboard, hike, and eat a fresh lunch onboard. Choose hotel pickup or meet beside Marina Café, and consider an afternoon departure for sunset.

“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 - Arriving at Dia’s clear-water bays
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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 with a professional crew to Dia Island, about an hour offshore. Swim in clear bays, use the included snorkeling and paddleboard gear, and enjoy drinks with either seafood pasta and Greek salad or a lighter half-day meal. Ernesto and George are among the crew members praised for their care and stories.

“Thank you for the nice sailing trip to Dia Island. We had a really great time, the staff has been super nice and caring! We had some nice food and our glutenfree and vegan wishes were considered. We would really recommend this trip and would love to come again one day.”

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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch - Leaving Adamas with the Bears and fishing villages
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Adamas: Kleftiko Sailing Day Trip with Snorkeling and Lunch

9.Kleftiko Sailing Day Trip with Snorkeling and Lunch

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

Spend eight hours sailing west from Adamas aboard a spacious yacht with a small group of up to 26 people. Swim at Kalogries and Agios Dimitrios, explore Kleftiko by snorkel gear and RIB, and enjoy Greek food, drinks, and underwater photos from the crew. Guides speak English, Greek, and Italian.

“The crew were amazing! So positive and happy! The food was excellent! Swimming and snorkeling were so much fun. We had to take a different route due to weather so I was disappointed we did not get to see caves.”

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Shared Mykonos Sail Cruise to Delos and Rhenia Islands - Sailing toward Delos, Greece’s ancient island center
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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

Spend about six hours sailing from Agios Ioannis to Delos and Rhenia aboard a spacious gulet with a friendly crew, including Dimitri and Thomas on some departures. Explore Delos for 90 minutes, swim and snorkel in clear water, and enjoy a buffet of grilled meats, vegetables, Greek salad, tzatziki, rice, fruit, and drinks.

“This is a must do / from the pick up to the drop off. It was perfectly executed. I’ve done a lot of boat tours at various destinations and this was by far the best. The crew -Dimitri and Thomas - were stand-up. They helped my mom who had some mobility issues throughout the day. Additionally, they were so patient and helpful with all of the guests. The captain was a class act. We loved the swimming spots -my kids enjoyed the day immensely. The lunch was the best lunch I have had yet in Mykonos, which says a lot.”

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Mykonos Sail Cruise to Rhenia, Guided Tour of Delos, Lunch&Drinks - Swimming off the yacht at Rhenia
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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 on a six-hour yacht trip with an English-speaking guide, lunch, wine, soft drinks, Wi-Fi, and snorkeling gear. Swim from the yacht in a clear Rhenia cove, then explore Apollo’s legendary birthplace with a licensed guide. Delos admission and optional transfers cost extra.

“Overall, the experience was great. The Delos tour was a little long - especially given the temperature. The guide was very knowledgeable though. The time swimming at Rhenia was lovely. The water was so clear and refreshing. There were 14 people on our boat, which was too many to be comfortable. The crew was professional and provided great service.”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks - Sailing past the lighthouse and Indian Head Mountain
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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 aboard a catamaran sailing around Santorini’s caldera. Swim near the Red and White Beaches, visit Palea and Nea Kameni, soak in volcanic hot springs, and enjoy a Greek BBQ with unlimited beer, wine, and soft drinks. Hotel pickup and drop-off are included.

“Great trip! Food was fantastic and service was amazing! Would highly recommend doing this excursion!”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Leaving Heraklion for an hour at sea
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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

13.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 up to 18 people. Swim, snorkel near an old Minoan port, use the paddleboard, and enjoy Greek food onboard. Full-day trips include salad, tzatziki, and seafood pasta, while half-day trips include tomato pasta. Crew members such as Andreas and George add local stories and friendly help.

“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 - Three hours for swimming, snorkeling, and paddleboarding
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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 about three hours in a sheltered bay for swimming, snorkeling, paddleboarding, fishing, and sunbathing. Lunch, fruit, Greek appetizers, beer, wine, soft drinks, and equipment are included. The boat carries up to 14 people, though some departures may use a larger catamaran.

“Great day out ,everything was perfect from start to finish.If your coming to Crete on holiday don’t miss out on this trip”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Meeting at Heraklion Port or using the minivan transfer
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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

15.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 provide local stories, swimming time, SUP boards, snorkeling gear, fishing equipment, lunch, and unlimited drinks. Optional minivan pickup makes this a practical half-day escape from much of Crete’s north coast.

“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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Newest in Greece Sailing Tours

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