Category Sailing

Crete · SAILING

Sailing in Crete: The 15 Best Cruises

109 tours

Under sail the north coast opens up in a way the coach roads never manage. Most boats leave Heraklion marina in the morning for Dia Island, drop anchor in a cove for swimming and snorkelling, and cook lunch on board. Here is the fleet compared: boat size, group numbers, how much of the day is actually under sail, and what the meal amounts to.

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

Heraklion: Dia Island Sailboat Cruise with Swimming and Meal - Getting there: Cafe Marina, timing, and pickup reality

1.Heraklion: Dia Island Sailboat Cruise with Swimming and Meal

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

A 5.5-hour small-group sailing cruise from Heraklion to Dia Island, with swimming, snorkeling, paddleboarding, and a Mediterranean meal.

“Here’s a smoother, more natural version of your text: This was the last day of our trip through Crete, and we ended it in the best way possible. The cruise was incredible, the weather was perfect, and the crew and food were fantastic. It was everything I wanted and more. We were having so much fun that we didn’t even have enough time to try all the activities - which is actually a good thing!”

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Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch

Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch - The sail to Dia Island: a practical 1-hour rhythm

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal

Heraklion: Sailing Cruise to Dia Island with Drinks and Meal - Before you go: what you need to know about pickup and boarding

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

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

Sail from Heraklion to Dia Island for snorkeling, SUP, fishing, and a full onboard meal with drinks, wine, and raki.

“The most magical and romantic experience to end our trip in Crete. Hosts were delightful, the snacks and drinks were excellent, the equipment and amenities provided for snorkelling, fishing and paddle boarding were amazing! The sights on the way and from the island were incredible - recommend the evening trip for the sunset. 100/10 couldn’t recommend more! So so worth the money!”

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Heraklion: Dia Island Sailing Cruise with Snorkeling

Heraklion: Dia Island Sailing Cruise with Snorkeling - Heraklion Departure: From Old Venetian Harbor to Open Water

4.Heraklion: Dia Island Sailing Cruise with Snorkeling

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

Sail from Heraklion to uninhabited Dia Island for snorkeling, paddleboarding, and wine, plus a simple Greek meal on a small yacht.

“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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Sailing Cruise to Dia Island with Meal and Water Activities

Sailing Cruise to Dia Island with Meal and Water Activities - The Sail Out: Views, Relaxing Tempo, and Weather Sense

5.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 Dia Island for swim, snorkel, SUP, and a full lunch with wine and beer, plus time to relax aboard.

“A well run yacht, clean and tidy. Very friendly and informative crew. Plenty of time at Dia island to snorkel, paddle board and swim . Excellent food prepared by the captain and plenty of drinks to go around. Highly recommended.”

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Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise - Kissamos Morning: Welcome Drinks, Quick Safety, and a Proper Start

6.Kissamos: Balos & Gramvousa Luxury Catamaran Sailing Cruise

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

Cruise from Kissamos to Balos Lagoon and Gramvousa on a luxury catamaran with great food, open bar, and multiple swimming options.

“We had an exceptional day on our catamaran trip. The crew – Yanny, Dimitri, and Jessica – were incredibly kind and attentive, always making sure we were comfortable. They truly took care of us from start to finish. The food served on board was fresh, delicious, and of excellent quality. This activity is absolutely worth it: by choosing the catamaran, we avoided the crowds of the larger boats and enjoyed a more intimate and pleasant experience. The two beaches we visited, Balos and Grand Vousa, were simply stunning and unforgettable. A memorable experience we would highly recommend!”

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Heraklion: Private Half-Day Sailing Trip to Dia Island

Heraklion: Private Half-Day Sailing Trip to Dia Island - Your Private Boat Day, Plus a Crew That Actually Helps

Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

Rethymno: Sunset Catamaran Cruise - Sushi & Open Bar - Where You Start: Rethymno Marina, Parking, and What Happens First

8.Rethymno: Sunset Catamaran Cruise – Sushi & Open Bar

★★★★★★★★★★4.8 · 446 reviews · 3.5 hours · from $100

3.5-hour Rethymno sunset catamaran with sushi, open bar, SUP and snorkeling, plus a swim stop and pink flamingo photos.

“The crew was very experienced, communication was also great. It was a bit windy at first but the crew brought to an amazing area with quiet sea where we had a long pause and were able to swim. This little cruise was my mom’s birthday present and she was extremely happy.”

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Heraklion: Sailing Trip to Dia Island with Lunch & Swimming

Heraklion: Sailing Trip to Dia Island with Lunch & Swimming - Getting on board: Old Anchor meeting point, small group feel, and quick briefing

Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks

Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks - Welcome drink, snacks, and that first stretch of sailing

Rethymno: Sailing Catamaran Cruise with Meal & Drinks

Rethymno: Sailing Catamaran Cruise with Meal & Drinks - Boarding at Rethymno Marina and meeting the crew on Karina

Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

Heraklion: Small-Group Sailing Trip to Dia Island with Lunch - Getting on board at the Old Venetian port, then letting the crew run the show

13.Heraklion: Small-Group Sailing Trip to Dia Island with Lunch

★★★★★★★★★★4.7 · 277 reviews · 4.5 - 7 hours · from $94

Small-group yacht sail from Heraklion to Dia Island for snorkeling, falcons, and an organic lunch, with transfers and gear included.

“Absolutely amazing experience! We booked a morning sail to Dia Island to celebrate our 30th anniversary. We were a small group of six +2 crew, it was perfect. After a few days of high winds it was an exciting trip and our captain explained the sailing process along the way, he also gave information on the biodiversity of the island and some mythology. We had looked forward to the experience and it didn’t disappoint, the best value for money experience and one we can’t wait to do again! Thank you Altersail!”

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Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling - Getting from Heraklion to Dia: sailing time plus real flexibility

14.Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling

★★★★★★★★★★4.6 · 242 reviews · from $63Best value

Sunset sailing from Heraklion to Dia Island for snorkeling, paddleboarding, included food, drinks, and pickup options.

“The entire experience was wonderfully enjoyable. The guides were incredibly friendly and helpful throughout, and ensured that we got the most out of the experience. The water activities at the shores of Dia Island were great, and the atmosphere was very relaxing. The snorkelling was particularly fun, and I greatly enjoyed seeing some of the marine life swimming on the sea floor. The return home, timed to coincide with the setting of the sun was beautifully serene. Again, I cannot credit the guides, Emanuel and Constantine, enough. They were great craic.Read more”

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Sailing trip to the Top Coasts of Crete, Daily/Multi-day

Sailing trip to the Top Coasts of Crete, Daily/Multi-day - Meeting at Sfakia Port, Then Settling In