Sailing from Heraklion delivers Mediterranean magic without the tourist crowds. The standout excursion heads to Dia Island, a pristine natural reserve just offshore. For value and convenience, full-day group tours include meals, drinks, and snorkeling gear – all with expert local crews who know these waters intimately.
I especially love the intimate catamaran sunset trips, which give you the best views of Crete’s rugged northern coast without the daytime heat. For families or small groups, private charters offer flexibility and personalized attention, though they’re pricier than group options.
Check out these top-rated sailing tours from Heraklion’s harbor:
Good To Know
- Dia Island Sailing Cruise is a highly recommended tranquil adventure with activities like paddleboarding, snorkeling, and fishing.
- Full-Day Sailing Excursions to Dia Island feature stunning landscapes, professional crew, unlimited drinks, and eco-friendly routes.
- Private Sailing Adventures offer all-inclusive packages with cultural insights, cuisine, and flexible pricing starting from €790.00.
- Intimate Sunset Cruises in Rethymno provide stunning sunset views, Cretan delicacies, and complimentary beverages.
- Sailing experiences feature knowledgeable guides, emphasize safety and guest comfort, and cater to adventurers of all abilities.
Sailing Cruise to Dia Island With Meal and Water Activities
For those seeking a tranquil sailing adventure from Heraklion, the Sailing Cruise to Dia Island With Meal and Water Activities offers a delightful excursion.
This highly-rated tour boasts a 94% traveler recommendation and a Badge of Excellence. Guests can explore the uninhabited Dia Island, partake in water activities like paddleboarding and snorkeling, and relax on the yacht.
The experience includes a delicious lunch of shrimp linguini, Greek salad, Cretan appetizers, and tropical fruits. Amenities like fishing gear, alcoholic beverages, and restroom facilities ensure a comfortable journey.
With convenient pickup options and free cancellation, this sailing cruise is an excellent choice for making the most of your time in Crete.
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Dia Island: 7hrs Full Day Semiprivate Sailing in Crete
This full-day sailing excursion to the pristine Dia Island from Heraklion offers a unique opportunity to explore Crete’s stunning coastal landscapes.
With a professional, certified crew, the cruise includes a sailing experience, a delicious meal, and various water activities like snorkeling and stand-up paddleboarding.
The package provides excellent value, costing €98 per person, and has received overwhelmingly positive reviews, with 96% of customers recommending the tour.
Travelers can enjoy unlimited drinks, free transfers within 10 km of the port, and an eco-friendly route that caters to nature enthusiasts.
However, some guests have noted minor issues with beverage temperature and facility cleanliness, which the operator should address to maintain their high-quality standards.
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Sunset – Sailing Cruise on Yacht Catamaran, Rethymno, Crete
Seeking a more intimate and serene sailing experience in Crete? The sunset sailing cruise on a yacht catamaran in Rethymno may be the perfect choice.
Rated 4.6 out of 51 reviews, this activity offers a comfortable and friendly atmosphere, stunning sunset views, and a range of water activities like swimming, snorkeling, and paddleboarding.
Travelers can enjoy a selection of Cretan delicacies and complimentary beverages, including Prosecco, wine, and soft drinks.
However, those prone to seasickness may want to reconsider during rough weather conditions.
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Private Sailing Cruise to Dia Island With Meal & Water Activities
Travelers seeking a private sailing adventure to the idyllic Dia Island can embark on a memorable cruise from Heraklion, Greece.
The 5-star rated experience includes a friendly and informative crew, offering cultural insights and cuisine recommendations. The all-inclusive package features a delectable lunch, an array of beverages, and a variety of water activities like swimming, snorkeling, and stand-up paddleboarding.
Pickup is available from multiple locations, with the meeting point at Cafe Marina in Heraklion’s old Venetian port. The cruise is priced from €790.00 per group of up to 10 participants, with flexible payment options and free cancellation up to 24 hours prior.
Positive reviews highlight the excellent food, fun activities, and attentive service from the crew.
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Full-Day Luxury Sailing Escape in Crete
For those seeking a luxurious day out on the waters of Crete, the Full-Day Luxury Sailing Escape offers an unparalleled experience.
This private tour takes guests on a 5-star sailing adventure, complete with a certified skipper, snorkeling gear, and an array of gourmet meals and drinks.
Travelers can bask in the sun on comfortable mats, indulge in local wine and fresh seafood, and enjoy the stunning coastal views.
With a 5.0 overall rating from 3 reviews, this sailing excursion is a must for those looking to truly enjoy the beauty of Crete’s waters.
Pickup and transportation options make it convenient to reach the meeting point.
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SAILING Full Day Island DIA With Lunch From Heraklion
Set out on a full-day sailing adventure to the enchanting Dia Island from Heraklion, Crete. This group tour is limited to 10 passengers, ensuring an intimate experience.
Indulge in swimming, snorkeling, fishing, and hiking during your island explorations. Savor a Cretan lunch prepared by the captain, along with snacks and drinks. Free snorkeling and fishing equipment are provided on board.
The tour price starts at $101.49 per person, with optional transfer available. Meet at Cafe Marina, and confirm your pickup details at least 24 hours prior.
Reviews praise the friendly staff, beautiful views, and delicious food. Though some note overcrowding, the boat capacity aligns with legal requirements.
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Snorkeling Boat Trip With Motor Yacht
This snorkeling boat trip with a motor yacht provides an exciting opportunity to explore the waters around Heraklion, Greece.
Rated 4.5 out of 5 by previous travelers, this shared boat trip accommodates up to 15 guests and includes the use of snorkeling equipment as well as snacks, bottled water, and seasonal fruit.
The pickup location is outside your hotel or the Port of Malia, with details provided upon booking.
While not wheelchair accessible, the trip is suitable for most travelers, excluding those with serious medical conditions or pregnant women.
With a patient crew and an overall enjoyable experience, this snorkeling excursion is a great way to learn about the beauty of the Cretan coast.
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Sunset Sailing Trip to Dia & Museum of Heraklion
Travelers seeking a magical evening on the Cretan waters can enjoy a sunset sailing trip to the picturesque Dia Island.
This 4.5 to 7-hour experience, rated 4.6 out of 5 stars from 222 reviews, offers a small-group sailing adventure with snorkeling opportunities. Priced at $73.42, the cruise departs from Heraklion and includes pickup service.
Guests can enjoy breathtaking views of the island’s rugged coastline, swim in crystal-clear waters, and savor a sunset over the Aegean Sea.
After the sailing excursion, visitors can explore the renowned Heraklion Archaeological Museum, home to the world’s largest collection of Minoan artifacts.
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Private Sailing From Heraklion. 5-Hour Catamaran Trips
For travelers seeking a more exclusive sailing experience in Heraklion, a private catamaran cruise to Dia Island offers a luxurious 5-hour adventure.
Priced from $1,783.17 for up to 10 participants, the cruise includes a welcome with local snacks, a sail to Dia Island, and activities like swimming, snorkeling, fishing, and paddleboarding.
Onboard, guests can enjoy unlimited drinks, freshly prepared Mediterranean meals, and amenities like music and Wi-Fi. The catamaran is equipped with safety gear, and the experienced crew is Red Cross certified.
The cruise can be personalized for special occasions, with morning or evening departures available. Weather conditions may affect the schedule, and transfer services are offered for an additional fee.
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Private Full Day Sailing Trip From Heraklion to Dia Island
Embarking on a private full-day sailing excursion from Heraklion to the nearby Dia Island offers travelers a chance to enjoy the stunning Cretan coastline.
The 6-hour sailing trip, which includes swimming and a meal, accommodates small groups and provides pickup service. Priced at €60 per person, the experience earns a 4.8-star rating from 389 reviews.
Visitors can also opt for a 4.5-7.5 hour sailing cruise to Dia Island with snorkeling opportunities, starting at €70 per person.
Plus, a sunset sailing cruise to Dia Island with snorkeling is available, lasting 4.5-7 hours and costing €70 per person.
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Heraklion Private Catamaran Cruise to Dia
One of the premier sailing experiences in Heraklion is the private catamaran cruise to the nearby Dia Island. Priced at $1,520.94 for up to 10 participants, this 6.5-hour excursion includes a scenic sail, activities like swimming and snorkeling, and a freshly prepared Mediterranean lunch.
The cruise departs from the Marina Café in Heraklion, with an experienced crew providing safety equipment and guidance. Onboard amenities include music, Wi-Fi, and an inflatable flamingo for photos.
Families will appreciate the child-friendly features like a toy box and special meal options. With free cancellation up to 24 hours in advance, this private sailing trip offers a memorable way to explore the beautiful waters around Heraklion.
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Heraklion: Full Day Sailing to Dia With Lunch
Travelers seeking a full-day sailing adventure from Heraklion can embark on a cruise to the nearby Dia Island. This 6-hour small group tour includes pickup from select Heraklion hotels, sailing to Dia, and a delicious lunch on board.
Guests can swim, snorkel, and explore the island’s beaches and caves. With a 4.8 rating from 389 reviews, this sailing excursion provides an idyllic way to experience Crete’s stunning coastline.
The tour is priced from $62.94 per person. Booking this sailing trip allows travelers to escape the crowds and fully enjoy the natural beauty of the Aegean Sea surrounding Heraklion.
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From Heraklion: Private Sailing Trip With Hanse 470
A private sailing trip from Heraklion to Dia Island aboard a Hanse 470 yacht provides an exclusive opportunity for up to 10 guests to explore the stunning Cretan coastline.
Priced from $734.25 per group, the 6-hour excursion includes sailing, a break with wine and snorkeling, and historical narrations by the local expert captain.
Guests can relax in Saint George Bay, swim, and enjoy scenic views of the coastline.
The trip includes snorkeling equipment, music, and hotel pickup and drop-off.
With a 5/5 rating based on one review, this sailing experience is suitable for all skill levels and an excellent choice for families.
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Heraklion: Private Catamaran Dia, Sunset & Appetizers Cruise
For those seeking a more luxurious sailing experience in Heraklion, the private catamaran cruise to Dia Islands offers an enchanting sunset adventure.
Priced from $944.03 for up to 10 participants, this 3.5-hour journey includes a safety briefing, refreshments, and local snacks before setting sail.
Guests can enjoy an hour of catamaran sailing, followed by 75 minutes of activities at Dia, such as swimming, snorkeling, and SUP surfing.
The luxurious catamaran provides unlimited drinks, light snacks, and photo opportunities on an inflatable flamingo.
With an experienced crew and liability insurance, this cruise is ideal for romantic outings, family events, and memorable experiences under the Mediterranean sunset.
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From Heraklion: Private Sunset Sailing Trip With Hanse 470
The Hanse 470 yacht offers a private sunset sailing adventure from Heraklion’s Old Venetian Port, inviting guests to embark on a 6-hour excursion filled with serene sailing, refreshing water activities, and awe-inspiring views of the Cretan coastline.
Priced at $734.25 for up to 10 participants, the trip includes a sailing journey to Dia Island, where guests can swim, snorkel, and enjoy local snacks.
The itinerary also features a safety briefing, historical narrations, and the opportunity to witness the stunning sunset colors.
With an excellent yacht, outstanding local expert captain, and complimentary snorkeling equipment, this private sailing experience promises an unforgettable way to explore Heraklion’s natural beauty.
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Heraklion: Dia Island Private Sailing Cruise With Full Meal
Heraklion offers travelers a chance to experience the beauty of Dia Island through a private sailing cruise that includes a full meal.
This 6-hour small group tour provides pickup from select Heraklion hotels, transporting guests to the marina for a sailing adventure around the picturesque Dia Island.
Cruisers can swim, snorkel, and relax as they take in the stunning views of the Cretan coastline.
The highlight is a full traditional Greek meal served on board, allowing visitors to savor local flavors as they sail.
With a 4.8-star rating from 389 reviews, this Dia Island sailing cruise is an excellent way to take in Heraklion’s natural splendor.
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Heraklion: Dia Island Sailing Cruise With Snorkeling
One popular sailing experience in Heraklion is the Dia Island Sailing Cruise with Snorkeling. Priced from €70.00 per person, this 4.5 to 7.5-hour cruise departs from the Heraklion Old Venetian Harbor.
Guests sail to Dia Island, where they can swim, snorkel, and enjoy activities like paddleboarding. Lunch options include a traditional Greek meal or turkey club sandwiches, and drinks like water, soft drinks, and wine are provided.
Pickup and drop-off services are available from various locations. With an overall rating of 4.6/5 from 462 reviews, this cruise offers an exciting and educational sailing experience in Crete.
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From Heraklion: Dia Island Private Sailing Trip
Sailing from Heraklion’s Cafe Marina, this private 6-hour excursion to Dia Island offers an intimate and tailored experience for up to 10 guests.
After a scenic briefing, you’ll sail to the island’s bay, where you can swim, snorkel, and enjoy local snacks and free time.
The return trip features historical narrations of Crete’s coastline.
The price of $608.37 per group includes private trips, snacks, refreshments, and snorkeling equipment, plus hotel transfers.
Though not suitable for wheelchair users, the excursion boasts a 5/5 rating from 3 recent reviews praising the friendly skipper and well-equipped boat.
Reservations with free cancellation up to 24 hours in advance can be made online.
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From Heraklion: Sunset Private Sailing Boat Trip
This sunset private sailing boat trip from Heraklion port offers an unparalleled opportunity to explore the idyllic Dia Island.
The 6-hour excursion accommodates up to 8 guests and departs at 3 PM, returning around 9 PM. Priced from €790 per group, the trip includes swimming, snorkeling, fishing, and a Mediterranean lunch with unlimited drinks.
Participants must provide their personal details as required by Greek law.
Although the trip isn’t suitable for those with heart problems or mobility issues, it promises a relaxing and memorable experience amidst the stunning Cretan coastline at sunset.
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Heraklion: Sunset Private Sailing Trip to Dia Island
Embarking from Heraklion’s port, the sunset private sailing trip to Dia Island offers a serene and picturesque experience for up to 8 guests.
Lasting 3.5 hours, this romantic cruise features stunning views of the island’s coastline as the sun dips below the horizon. Guests can enjoy snacks and drinks while taking in the tranquil atmosphere.
With a rating of 4.8 out of 138 reviews, this activity is a popular choice for those seeking a relaxing and intimate sailing adventure.
Priced at $94.40 per person, the sunset private sailing trip to Dia Island is an excellent way to cap off a day in Heraklion.
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Sunset Sailing Trip to Dia Island – Heraklion Port, Crete
From the port of Heraklion, adventurers can embark on a captivating sunset sailing trip to the nearby Dia Island.
This 4.5 to 8-hour small group experience, certified by GetYourGuide, offers a chance to sail aboard a sailboat and soak in the breathtaking views.
Travelers can enjoy drinks and a delicious lunch while cruising towards Dia Island, where they’ll have the opportunity to swim in the crystal-clear waters.
With 4.9 out of 5 stars from 1,264 reviews, this sailing excursion is a must-do activity for those seeking to experience Crete’s stunning coastal landscapes during the golden hour.
Read our full review: Sunset Sailing Trip to Dia Island – Heraklion Port, Crete Review
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Heraklion: Sunset Sailing Cruise Dia Island With Snorkeling
The Heraklion sunset sailing cruise to Dia Island offers adventurers a captivating small group experience certified by GetYourGuide. This 4.5 to 7-hour excursion departs from Heraklion port, taking guests on a 1-hour boat ride to the nearby Dia Island.
Activities include snorkeling, paddleboarding, swimming, and beach relaxation. Meals range from Greek salad and tzatziki to pasta dishes, with a traditional raki digestif. Participants can expect ample opportunity for sunset photography and wind-powered sailing on the return trip.
Friendly and knowledgeable guides, including captains Alex and Michalis, receive high praise from previous travelers. This cruise isn’t suitable for wheelchair users, but others can enjoy the beautiful scenery, aquatic activities, and delectable cuisine.
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The Sum Up
Heraklion offers an array of sailing experiences, from day cruises to Dia Island with meals and water activities to private sunset trips along the coast. Whether you’re seeking a relaxing escape or an adventure-filled day, there’s a sailing tour in Heraklion to suit your preferences. With a variety of options available, you’re sure to find the best sailing experience to make your Crete vacation unforgettable.