Sailing from Heraklion offers some of Crete’s most rewarding day trips. The main destination is Dia Island, just north of the harbor, where crystal-clear waters and secluded coves await. These tours typically run 4.5-7 hours, combining swimming, snorkeling, and water activities with traditional Greek meals onboard.
I especially like the intimate catamaran cruises that limit groups to 12-15 passengers – they’re worth the extra cost. The best operators provide quality gear, serve fresh local food, and employ knowledgeable local crews who share insights about the region’s history and marine life.
For families and first-time sailors, the half-day tours hit the sweet spot, while full-day excursions appeal to those wanting maximum time on the water. Most tours maintain excellent ratings (4.6-4.9 stars) from past guests.
Check out these top-rated Heraklion sailing experiences:
Key Points
- Heraklion offers a variety of highly rated sailing excursions, ranging from 4.5 to 7 hours in duration, with prices starting from $74.12 per person.
- Sailing experiences include activities like swimming, snorkeling, paddleboarding, and fishing, with equipment provided and Mediterranean-inspired meals served onboard.
- Comfort cruises, Dia Island catamaran tours, full-day sailing adventures, and sunset cruises are among the diverse options available, catering to different interests.
- Personalized sailing trips with a maximum of 10 travelers provide a unique and memorable experience, with the possibility of dolphin sightings and knowledgeable guides.
- Culinary experiences on board, featuring traditional Greek meals and unlimited drinks, contribute to the culture and overall enjoyment of the sailing adventure.
Comfort Cruise – Sailing Catamaran Trips From Heraklion, Crete
For a leisurely day on the water, consider the Comfort Cruise sailing catamaran trips departing from Heraklion, Crete. Rated 4.9 out of 137 reviews, these excursions take you to the nearby Dia island, offering a range of activities like snorkeling, stand-up paddleboarding, fishing, and swimming.
The spacious catamaran accommodates up to 20 travelers and provides onboard amenities like Wi-Fi, snorkeling gear, and SUP boards. Enjoy a Mediterranean lunch with dishes like Greek salads, pasta, and desserts, complemented by alcoholic beverages for those 18 and older.
The trips depart at 9:30 am, and you’ll want to arrive 15 minutes early at the Cafe Marina meeting point. With wheelchair accessibility and a convenient cancellation policy, the Comfort Cruise is an excellent option for a relaxing day on the Cretan seas.
Read our full review: Comfort Cruise – Sailing Catamaran Trips From Heraklion, Crete Review
Book now: Check availability
Heraklion: Dia Island Catamaran Cruise With Drinks and Lunch
If you’re looking to explore the stunning Cretan seas, the Dia Island Catamaran Cruise with Drinks and Lunch is an excellent choice.
This 5.5-hour small group tour allows you to sail to the beautiful Dia Island, where you can swim, snorkel, and enjoy a delicious meal.
With pickup available, you’ll start your journey from Heraklion.
The catamaran cruise has a 4.8 rating from 68 reviews, and it’s priced at $127.05 per person.
This is a great way to experience the local culture and natural beauty of Crete while relaxing on the water.
Read our full review: Heraklion: Dia Island Catamaran Cruise With Drinks and Lunch Review
Book now: Check availability
Sailing Cruise to Dia Island With Meal and Water Activities
Embark on an enchanting sailing cruise to the captivating Dia Island, just off the coast of Heraklion, Crete. Rated 4.8 with 94% traveler recommendation, this excursion offers a delightful blend of relaxation and adventure.
Explore Crete’s stunning coastline on a yacht, enjoying activities like swimming, snorkeling, paddleboarding, and fishing. Savor a delicious lunch featuring Greek specialties, fresh fruit, and refreshing drinks.
The experience includes equipment like fishing gear, stand-up paddleboards, and snorkeling equipment. With a maximum of 10 travelers, pickup options from various locations, and flexible cancellation policies, this sailing cruise provides an unforgettable way to learn about Crete’s natural beauty and rich culture.
Read our full review: Sailing Cruise to Dia Island With Meal and Water Activities Review
Book now: Check availability
Heraklion: Sailing to Dia Island With Lunch on Catamaran
Discover the captivating Dia Island on a sailing excursion aboard a brand new catamaran, departing from Heraklion, Crete.
This 5-hour tour includes a live guide in English and Greek, and free cancellation up to 24 hours in advance.
Enjoy swimming, snorkeling, fishing, and stand-up paddleboarding, along with a traditional Cretan lunch and beverages.
The price starts from Kč 3,161 per person, with a reserve now & pay later option available.
Don’t forget to bring necessary items like sunglasses, swimwear, and sunscreen.
This experience isn’t suitable for those with pre-existing medical conditions or wheelchair users.
Unleash your adventurous spirit and explore the beauty of Dia Island on this unforgettable sailing adventure.
Read our full review: Heraklion: Sailing to Dia Island With Lunch on Catamaran Review
Book now: Check availability
Heraklion: Nature Reserve Full Day Sailing to Dia Island & Lunch
Although the weather may vary, this full-day sailing cruise to Dia Island from Heraklion offers an exceptional opportunity to learn about the natural beauty of this protected nature reserve.
With over 55 positive reviews and a 96% recommendation rate, the cruise includes a delicious meal, unlimited drinks, snorkeling equipment, and SUP boards, catering to nature lovers and eco-conscious travelers.
The professional, certified crew ensures a safe and enjoyable experience, providing first aid if needed.
Whether you’re swimming, snorkeling, or simply taking in the stunning surroundings, this sailing adventure promises a memorable day on the water.
Read our full review: Heraklion: Nature Reserve Full Day Sailing to Dia Island & Lunch Review
Book now: Check availability
Dia Island: Yoga & Sunset Sailing
After exploring the natural wonders of Dia Island on the full-day sailing cruise, you can take your experience further with a yoga session and sunset sailing adventure.
The 4.5-7 hour Sunset Sailing Cruise to Dia Island with Snorkeling offers a small-group experience with pickup available. You’ll enjoy the tranquility of the sea, take in the stunning Cretan sunset, and participate in a rejuvenating yoga session on the beach.
This unique combination of activities allows you to fully learn about the beauty of the island and leave feeling refreshed and centered. At €70 per person, this is an exceptional value for a memorable and wellness-focused sailing excursion.
Read our full review: Dia Island: Yoga & Sunset Sailing Review
Book now: Check availability
Sunset – Sailing Cruise on Yacht Catamaran, Rethymno, Crete
Set out on a captivating sunset sailing cruise aboard a luxurious yacht catamaran in Rethymno, Crete. Operated by DanEri Yachts, this 4.6-rated experience offers stunning views, complimentary drinks, and traditional Cretan bites.
Sip on Prosecco, wine, and soda as you sail into the sunset, and enjoy snorkeling or stand-up paddleboarding in the calm waters. The crew is friendly, and the catamaran can accommodate up to 30 travelers.
While the activity is wheelchair accessible and near public transportation, pregnant guests and those prone to seasickness may want to avoid it during rough weather conditions.
With a 90% recommendation rate and a Badge of Excellence, this sunset sailing cruise is a must for families, couples, and solo travelers seeking relaxation and scenic views.
Read our full review: Sunset – Sailing Cruise on Yacht Catamaran, Rethymno, Crete Review
Book now: Check availability
Heraklion: Dia Island Morning Sailing Trip With Snorkeling
Experience the serene beauty of Dia Island on an exhilarating morning sailing trip from Heraklion. For just $84.70 per person, you’ll embark on a 6-hour adventure, exploring the island’s pristine waters and vibrant marine life.
The small group size of 10 ensures an intimate and personalized experience. Sail for 75 minutes to Dia, then spend 3.5 hours swimming, snorkeling, and relaxing with local snacks.
Throughout your journey, marvel at the scenic coastline views from the sailboat. With a knowledgeable and friendly crew, you’re guaranteed an unforgettable experience.
Don’t miss this chance to discover the hidden gems of Dia Island.
Read our full review: Heraklion: Dia Island Morning Sailing Trip With Snorkeling Review
Book now: Check availability
SAILING Full Day Island DIA With Lunch From Heraklion CRETE
Get set for a full-day sailing adventure to the enchanting Dia Island from Heraklion, Crete.
Enjoy a 4.6-rated tour with a maximum of 12 travelers, priced from $101.86 per person. The tour includes a skipper, crew, snorkeling and fishing gear, snacks, drinks, and delightful Cretan cuisine.
Pickup is available from select areas, with an optional 10€ transfer fee. Relish the scenic views, swim, snorkel, and stand-up paddleboard.
Savor a pasta with seafood, Greek salad, and tzatziki. Unwind on beanbags at the beach.
While most travelers rave about the experience, be aware of potential overcrowding and food quantity issues. Confirm the start time with the local provider in advance.
Read our full review: SAILING Full Day Island DIA With Lunch From Heraklion CRETE Review
Book now: Check availability
Dia Island: Semi-Private Full Day Sailing Trip With Meal
Sail away to the enchanting Dia Island on this semi-private full-day adventure from Heraklion, Crete.
Spend 5.5 hours exploring the island’s beautiful landscapes and crystal-clear waters on a small group cruise aboard a catamaran. Enjoy a delicious meal prepared onboard as you take in the stunning scenery.
The small group size ensures a more personalized experience. With pickup available, you’ll have a hassle-free journey to and from the departure point.
Priced at Kč 3,010 per person, this experience is a fantastic way to discover the natural beauty of Dia Island and create lasting memories on the Cretan seas.
Read our full review: Dia Island: Semi-Private Full Day Sailing Trip With Meal Review
Book now: Check availability
Heraklion: Sunset Sailing Cruise Dia Island With Snorkeling
If you’re seeking a memorable way to cap off your day in Heraklion, the Sunset Sailing Cruise to Dia Island with Snorkeling is an experience not to be missed.
This 4.5-7 hour small-group excursion offers a relaxing boat ride, ample time to swim, snorkel, and paddleboard around Dia Island, and a delicious traditional Greek meal.
With a knowledgeable guide leading the way, you’ll also have the chance to witness a stunning sunset over the Aegean Sea.
Priced from $74.12 per person, this cruise includes all necessary equipment and receives excellent reviews for its safety, service, and overall enjoyment.
Read our full review: Heraklion: Sunset Sailing Cruise Dia Island With Snorkeling Review
Book now: Check availability
Dia Island: Semi Private Full Day Sailing Cruise
Spend a captivating day exploring the serene waters and hidden coves surrounding Dia Island on a semi-private full-day sailing cruise.
This 5.5-hour experience whisks you away on a small-group adventure, providing pickup from your Heraklion hotel. Sail to Dia Island, a tranquil paradise, and anchor in a secluded bay for swimming and snorkeling.
Savor a freshly prepared Greek meal on board as you take in the stunning coastal vistas. Throughout the journey, your knowledgeable captain shares insights about the island’s history and natural wonders.
With a maximum of 12 guests, you’ll enjoy an intimate and personalized sailing experience, perfect for creating lasting memories of your time in Heraklion.
Read our full review: Dia Island: Semi Private Full Day Sailing Cruise Review
Book now: Check availability
Heraklion: Sailing Cruise to Dia Island With Drinks and Meal
For a captivating sailing excursion from Heraklion, embark on a 6-hour cruise to the serene Dia Island. Priced from $95.29 per person, this tour offers a guided experience with activities like snorkeling, paddleboarding, fishing, and hiking.
Savor a Mediterranean-inspired onboard meal featuring seafood pasta, fresh salads, and local snacks, complemented by water, soft drinks, beer, wine, and traditional raki.
Marvel at the scenic sailing, potential dolphin sightings, and picturesque sunset views on the return trip. With a 4.8/5 rating based on over 200 reviews, this cruise promises an unforgettable adventure highlighted by friendly guides and the natural beauty of Dia Island.
Read our full review: Heraklion: Sailing Cruise to Dia Island With Drinks and Meal Review
Book now: Check availability
Heraklion: Dia Island Small Group Catamaran Cruise With Meal
Set out on a captivating 5.5-hour catamaran cruise from Heraklion’s Old Venetian Port to the serene Dia Island.
You’ll enjoy a safety briefing, followed by sailing, swimming, snorkeling, and paddleboarding at the island.
Savor a delectable Mediterranean meal onboard, including shrimp linguini, Greek salad, and tropical fruit, accompanied by unlimited wine, beer, and soft drinks.
The friendly crew, beautiful scenery, and opportunities to spot dolphins make this an unforgettable experience.
Priced from Kč 2,408 per person with flexible booking and free cancellation, this small group cruise offers excellent value.
Don’t miss this chance to learn about the stunning beauty of Dia Island.
Read our full review: Heraklion: Dia Island Small Group Catamaran Cruise With Meal Review
Book now: Check availability
Heraklion: Sailing Trip to Dia Island With Lunch & Swimming
Discover the serene beauty of Dia Island with this immersive sailing trip from Heraklion. Priced from $90 per person, this 6-7 hour excursion includes snorkeling, fishing, SUP paddleboarding, and swimming at the island.
You’ll enjoy a delectable Mediterranean lunch with unlimited drinks as you sail along Crete’s picturesque coastline, with the possibility of spotting dolphins. Departing from Heraklion Port or select pickup points, this small-group cruise accommodates up to 8 participants.
With a 4.8/5 rating based on 390 reviews, this sailing adventure offers excellent value and an unforgettable experience. Don’t miss the opportunity to explore Dia Island and create lasting memories on the waters around Crete.
Read our full review: Heraklion: Sailing Trip to Dia Island With Lunch & Swimming Review
Book now: Check availability
Heraklion: Sunset Catamaran Cruise With Dinner and Drinks
Indulge in a captivating sunset catamaran cruise from Heraklion, where you’ll learn about the serene beauty of the Cretan coastline.
For €125 per person, you’ll enjoy a 5-hour excursion, with activities like snorkeling, stand-up paddleboarding, and inflatable flamingo rides.
Savor a freshly cooked Mediterranean dinner, complemented by unlimited drinks, as you take in the stunning sea views.
The experienced crew will ensure your safety and comfort throughout the journey.
Explore Dia Island’s bay, and witness a breathtaking sunset at sea.
With flexible booking and cancellation policies, this cruise is the perfect way to elevate your Heraklion experience.
Read our full review: Heraklion: Sunset Catamaran Cruise With Dinner and Drinks Review
Book now: Check availability
Day Cruise From Heraklion With Catamaran & Transfer Service
Venture out from Heraklion’s bustling port on a day cruise aboard a state-of-the-art catamaran.
This 5.5-hour small-group excursion includes pickup service, taking you to explore the scenic Dia Island. Enjoy swimming and snorkeling in the island’s crystalline waters, followed by a delicious meal prepared onboard.
The catamaran cruise offers panoramic views of the Cretan coast, as you sail along the sparkling Mediterranean. With a maximum of 12 passengers, you’ll have an intimate and personalized experience.
Priced at €96.00 per person after a 20% discount, this day cruise provides an unforgettable way to experience the beauty of Heraklion’s waters.
Read our full review: Day Cruise From Heraklion With Catamaran & Transfer Service Review
Book now: Check availability
Heraklion: Sunrise Balloon Flight & Sunset Catamaran Cruise
Experience the best of Heraklion’s natural beauty with this captivating Sunrise Balloon Flight and Sunset Catamaran Cruise tour.
Soar over the breathtaking Lasithi Plateau in a hot-air balloon, then relax on a catamaran as you sail into the sunset. The 7-hour adventure starts with a 45-minute balloon flight, followed by a light breakfast and sparkling wine.
In the afternoon, board the catamaran for 3.5 hours of swimming, snorkeling, and enjoying local snacks and unlimited drinks.
With convenient hotel pickup, exceptional service, and stunning views, this tour offers incredible value.
Don’t miss the opportunity to experience the magic of Heraklion from both the sky and the sea.
Read our full review: Heraklion: Sunrise Balloon Flight & Sunset Catamaran Cruise Review
Book now: Check availability
Heraklion: Dia Island Sailing Cruise With Snorkeling
Sail away to the idyllic Dia Island on this captivating cruise from Heraklion.
This 4.5- to 7.5-hour sailing adventure offers a chance to explore the uninhabited landscape and crystal-clear waters of Dia. You’ll enjoy swimming, snorkeling, and paddleboarding, along with a traditional Greek meal and drinks.
The cruise departs from the Heraklion Old Venetian harbor, with pickup options from various locations. Rated 4.6/5 by over 460 reviewers, this small-group experience is perfect for those seeking a peaceful, immersive way to experience Crete’s stunning coastline.
Don’t miss the chance to overcome your fears and embrace the tranquility of this island paradise.
Read our full review: Heraklion: Dia Island Sailing Cruise With Snorkeling Review
Book now: Check availability
From Heraklion: Private Sailing Trip With Our Hanse 470
Our private sailing trip from Heraklion to Dia Island aboard our well-maintained Hanse 470 yacht offers an unparalleled opportunity to explore the stunning Cretan coastline.
For just $741.15 per group (up to 10 participants), you’ll enjoy 6 hours of sailing, swimming, snorkeling, and relaxation.
Highlighting the journey are the scenic views, historical narrations, and the tranquil bay of Saint George.
Our expert local captain will guide you, while providing an introduction to sailing and music on board.
With hotel pickup and drop-off included, this is an unforgettable way to experience the beauty of Heraklion from the water.
Read our full review: From Heraklion: Private Sailing Trip With Our Hanse 470 Review
Book now: Check availability
The Sum Up
Heraklion offers a variety of sailing experiences, from leisurely catamaran cruises to private sailing trips. You can explore Dia Island, enjoy water activities, and savor delicious meals on these excursions. Whether you’re seeking a relaxing day on the water or an adventure-filled sailing journey, Heraklion has something to suit your preferences. With so many options available, you’re sure to find the best sailing experience to make your trip to Crete unforgettable.