Top 15 Sailing Trips in Greece

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

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

Review of Crete’s Dia Island sailing cruise from Heraklion, with swimming, snorkeling, paddleboarding, a Greek meal, drinks, and sunset options.

“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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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

2.Sailboat Cruise to Dia Island with Drinks & Lunch

★★★★★★★★★★4.9 · 1,287 reviews · from $90

Sail from Heraklion to Dia Island for swimming, snorkeling, lunch, unlimited drinks, and relaxed yacht time on Crete’s clear waters.

“I loved the sailing trip and the time we had to swim. The skipper and first mate were friendly and professional. The meal was healthy and delicious. The crew provided a quick safety talk, rules of the vessel, and tips for a successful sailing trip. This was a great afternoon that I was sad to see end.”

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Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

3.Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer

★★★★★★★★★★5.0 · 1,170 reviews · 5 hours (approx.) · from $133Top rated

Review of Santorini’s five-hour luxury catamaran cruise with swimming, snorkeling, Greek BBQ, drinks, hot springs, and sunset views.

“Such a fun tour. Swimming in the hot springs was a unique experience and the waters around the island were so clear it. Got to see a lot of fish. The food was also super delicious!”

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Sunset Sailing Catamaran Cruise in Santorini with BBQ and Drinks

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

★★★★★★★★★★4.5 · 1,105 reviews · 5 hours (approx.) · from $96

Review of Santorini’s 5-hour sunset catamaran cruise with swimming, hot springs, BBQ, drinks, hotel pickup, and practical booking tips.

“Sunset tour was absolutely amazing. Stopped at a couple of places to snorkel and the water was so clear you could see down 30’. Food was good and plenty of it. Met very nice people and the whole boat had a great time listening to music and dancing. Sunset was fantastic as pretty much all sunsets in Santorini are.”

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Gouvia: Corfu Island Sailing Trip with Snack and Soft Drinks

5.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, three swim stops, cliff jumping, snorkeling, snacks, and Blue Cave views.

“Good trip, captain was really nice and it was great if we would sail out ⛵️”

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Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

6.Sailing Cruise to Dia Island with Drinks and Meal

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

Sail from Heraklion to Dia Island for swimming, snorkeling, SUP, Greek food, drinks, and sunset views on a six-hour yacht cruise.

“This was a fabulous trip. The staff were very friendly and committed to making sure everyone had a good time. They boat was fantastic and their were enough activities to keen everyone entertained during the cruise. Food was fantastic too. Highly recommend this tour to anyone in Heraklion for the day.”

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Heraklion: Dia Island Sailing Cruise with Snorkeling

7.Dia Island Sailing Cruise with Snorkeling

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

Review of the Heraklion to Dia Island sailing cruise, with snorkeling, paddleboarding, meals, drinks, crew details, costs, and practical tips.

“The crew was super friendly. Even the weather condition was not the best, the travel went quite smooth. The bays are there just amazing. Only dis thing was, I was expecting to swim in more spots (we did 2), but the places we swam was fantastic 🥰 The food was not great but it tastes good since you became super hungry 😁”

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Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

8.Sailing Catamaran Cruise in Santorini with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 568 reviews · 5 hours (approx.) · from $96

Review of Santorini’s 5-hour catamaran cruise with hotel transfers, swimming, snorkeling, BBQ lunch, wine, and volcano views.

“Such a fabulous day out, everything was seamless and so relaxing. Great staff, easy return transfers, delicious food and great communication throughout. Definitely recommend for a lovely cruising day on the sea with a few stops for swimming 🙂”

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Santorini Sailing Dream Catcher with BBQ Lunch and Drinks

9.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 hot springs, enjoy a Greek BBQ, and take in Red Beach, White Beach, and sunset views.

“I went soli today and the vibe in the boat is actually amazing where you can start making friends so fast there. The crew members and the food are both amazing. The swim stops are nice as they picked good spots compared to other boats I have been to”

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Sailing Cruise to Dia Island with Meal and Water Activities

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

★★★★★★★★★★4.5 · 526 reviews · 5 hours 30 minutes (approx.) · from $97

Sail from Heraklion to Dia Island for swimming, snorkeling, paddleboarding, a Cretan lunch, drinks, and a relaxed small-group day at sea.

“Very confusing figuring out who the contact people were, ours wasn't very friendly and hard to understand..boat MUCH smaller than pic and NO island, stuck in windy spot w/ warm beer and little rooom.”

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Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

11.Balos & Gramvousa Luxury Catamaran Sailing Cruise

★★★★★★★★★★4.9 · 516 reviews · 7 - 8.5 hours · from $229

Review of the Balos and Gramvousa luxury catamaran cruise from Kissamos, including food, stops, costs, transfers, and practical booking tips.

“Great day out on the water, great crew who looked after us all day.”

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Heraklion: Private Half-Day Sailing Trip to Dia Island

12.Private Half-Day Sailing Trip to Dia Island

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

Sail from Heraklion to Dia Island on a private yacht with swimming, snorkeling, fishing, fruit, drinks, and optional lunch.

“The guys were great! They knew what they were doing and we’re super accommodating! Definitely recommend 😁”

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Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

13.Santorini Luxury Sailing Catamaran Cruise with BBQ, Drinks and Transfer

★★★★★★★★★★4.5 · 422 reviews · 5 hours (approx.) · from $133

Review of Santorini’s 5-hour catamaran cruise with hotel transfers, Greek BBQ, open drinks, swimming, snorkeling, and caldera views.

“Attentive staff, excellent food and the chance to swim and snorkel in the Aegean Sea made for an unforgettable day.”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

14.Sailing Trip to Dia Island with Lunch & Swimming

★★★★★★★★★★4.8 · 414 reviews · from $67Best value

Review of Crete’s Dia Island sailing trip from Heraklion, with lunch, swimming, snorkeling, SUP, fishing, drinks, transport, and practical tips.

“Niko and Dmitri were brilliant! They couldn’t do enough for us and were very attentive. The food was great and the whole experience was the highlight of our trip! They were very friendly and I would give them 10/10 for the trip! Thank you guys!”

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