Heraklion isn’t just about ancient ruins and bustling markets—it’s also an excellent place to explore by water. With its calm, clear waters and plentiful islands like Dia, Heraklion offers some truly memorable sailing adventures. Whether you’re into snorkeling, enjoying a gourmet meal, or just relaxing with a drink in hand, there’s a tour that suits your style. We’re big fans of the Luxury Catamaran to Dia for its combination of comfort and gourmet food, or the Sunset Sailing Cruise for those craving a magical end-of-day experience. Whatever your preference, Heraklion’s waters deliver a blend of adventure and relaxation you won’t forget.
Quick Overview
Heraklion’s sailing tours cover a broad spectrum, from luxury catamarans with gourmet meals and open bars to small-group snorkeling trips and full-day excursions around Dia Island. Some tours focus on water activities like paddleboarding and snorkeling, while others emphasize scenic cruising and sunset views. Many include meals and drinks, making them perfect for a laid-back day at sea. Check out the full list below, each offering something different:
- Luxury cruises with gourmet lunch and open bar
- Family-friendly trips with snorkeling and paddleboarding
- Sunset cruises with romantic scenery
- Full-day adventures with remote beaches and wildlife spotting
1. Heraklion: Dia Island Sailboat Cruise with Swimming and Meal
At number 1, this 5.5-hour cruise on a modern, large sailing yacht offers water activities like paddleboarding and snorkeling, plus a Mediterranean meal and unlimited drinks. The route includes scenic views of Dia Island and the chance to see dolphins or even dolphins—an added thrill. The boat departs from Heraklion, with 14 drop-off locations, making it very accessible. Reviewers love the friendly crew, beautiful waters, and the sunset views. Priced at about $81, it’s excellent value for a laid-back day on the sea. Its combination of water activities, good food, and flexible drop-off points makes it ideal for travelers looking for a mix of adventure and comfort. The casual, friendly atmosphere makes it perfect for families and groups who want a memorable day at sea.
Bottom Line: A well-rounded option with great reviews, water activities, and sunset views. Best for travelers who want plenty of time in the water and a relaxed vibe.
2. Sailing Cruise to Dia Island with Meal and Water Activities
This 5.5-hour cruise is rated a perfect 5.0 based on 359 reviews and costs about $92.69. It focuses heavily on exploring Dia Island, with snorkeling, paddleboarding, and fishing included. Departure from Heraklion is smooth, with the crew sharing stories about Dia’s legends and history—like the myth of Zeus turning a monster into the island. The boat provides lunch, snacks, and drinks, making it a good value. Reviewers emphasize the friendly crew, delicious food, and crystal waters. It’s suitable for those who like hands-on water fun, as well as relaxing on deck. The included equipment for snorkeling and paddleboarding makes this a standout for active travelers.
Bottom Line: An authentic, water-focused trip perfect for those wanting to swim, snorkel, and enjoy the sea in a comfortable setting.
3. Heraklion: Sailing Trip to Dia Island with Lunch & Swimming
For around 6 hours, this tour offers a private-feel experience with max 10 guests. The sailing from Heraklion to Dia includes a delicious local lunch and unlimited drinks. The itinerary features snorkeling, fishing, and SUP paddleboarding in Dia’s secluded bay. Guests rave about the friendly local crew, who treat everyone like family, and the gorgeous scenery. The tour is ideal for small groups, couples, or families wanting a personalized experience. The boat departs from the port and the trip’s highlights include scenic views, underwater exploration, and plenty of time to relax.
Bottom Line: A perfect choice for travelers seeking a more intimate, private experience with water activities and authentic Crete hospitality.
4. Heraklion Luxury Catamaran to Dia: Gourmet Lunch & Open Bar
At number 4, this luxury 5-hour cruise offers a spacious, shaded, and sun deck-equipped catamaran with gourmet lunch prepared onboard. With unlimited wine, beer, soft drinks, and water, it’s designed for indulgence. The snorkeling gear, SUPs, and floaties are included, and guests often comment on the comfortable, high-end experience. Rated 5.0 with over 220 reviews, passengers appreciate the personalized service and gourmet food. It’s ideal for celebrating special occasions or those who prefer a relaxing, upscale experience on the water.
Bottom Line: For travelers seeking luxury combined with water activities and excellent cuisine, this cruise delivers in spades.
5. Heraklion: Luxury Sailing Catamaran Dia Island | Gourmet Menu
Rated 4.9/5, this 5.5-hour cruise aboard the EOS Yachts catamaran is a favorite among travelers. It features high-quality onboard lunch by a chef, and snorkeling, fishing, and paddleboarding are included. The route offers breathtaking views and the possibility of spotting dolphins—a real treat. The crew’s attention to detail and the luxurious setting make this perfect for couples or groups wanting a premium experience. The itinerary includes a scenic sail, time on Dia Island, and returning with sunset views.
Bottom Line: An upscale choice for those who want comfort, luxury, and a memorable scenery-filled day.
6. Heraklion: Dia Island Sailing Cruise with Snorkeling
This 4.5 to 7-hour tour at just $63 takes you on a comfortable cruise to Dia Island, with snorkeling gear provided. It’s rated 4.6/5 from nearly 500 reviews. The trip emphasizes underwater exploration, with time for swimming and relaxing in Dia’s untouched waters. The crew makes sure everyone feels safe, with lifejackets and professional guidance. The itinerary balances scenic sailing with fun in the water, and reviewers love the beautiful waters and friendly crew.
Bottom Line: A budget-friendly, flexible day that’s perfect for active travelers wanting to see Dia’s natural beauty.
7. Heraklion: Dia Catamaran Tour, Lunch, Open Bar & Snorkeling
Rated 5.0/5, this 5-hour cruise on a Lagoon 450 catamaran offers snorkeling, paddleboarding, and fishing alongside Mediterranean lunch and unlimited drinks. The small group size (no more than 20) creates a personal, friendly atmosphere. Guests praise the helpful crew and the comfortable, spacious boat. It’s ideal for those looking for a relaxed day with water fun and good food in a semi-private setting.
Bottom Line: For those who prefer a small, intimate group with plenty of water activities, this cruise is a winner.
8. Heraklion: Sailing Cruise to Dia Island with Drinks and Meal
This 4.5 to 7-hour tour offers a relaxed cruise with snorkeling, swimming, and a solid Mediterranean meal. Rated 4.8/5, it is praised for the friendly crew, good food, and scenic sailing. It’s good for travelers who want a balanced experience of water activities and onboard relaxation. The included drinks and regional food make it an all-in-one day.
Bottom Line: A dependable, versatile option ideal for those wanting a balanced mix of activities and comfort.
9. Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling
Rated 4.6/5, this sunset cruise is perfect for romantic evenings. It features snorkeling, relaxing on the boat, and enjoying the sunset over Dia Island. Travelers love the crystal waters, beach chilling, and light onboard food. It’s suited for those seeking a relaxing, scenic experience with an elegant vibe.
Bottom Line: Best for romantic travelers or groups wanting a peaceful sunset with water activities.
10. Heraklion: Dia Island Morning Sailing Trip with Snorkeling
This early-morning cruise, rated 4.9/5, is perfect for nature lovers. It’s a 6-hour trip with snorkeling and swimming in Dia’s clear waters. Reviewers find the crew friendly and the scenery stunning. It’s especially suited for early risers wanting a peaceful start to their day with plenty of water time.
Bottom Line: An excellent choice for morning explorers who want to beat the crowds and enjoy Dia’s natural beauty.
11. Heraklion: Nature Reserve Full Day Sailing to Dia Island & Lunch
This full-day trip, rated 5.0/5, offers a relaxed pace and remote beaches. It includes snorkeling, visiting lesser-known beaches, and a lunch with local wines and drinks. Limited to just 10 travelers, it suits those seeking a more intimate, scenic experience. The highlights include visiting quiet beaches and seeing Crete from the water.
Bottom Line: Ideal for quiet, scenic days away from crowds, especially if you love snorkeling and remote spots.
12. Heraklion: Dia Island Ultimate Catamaran Cruise with Meal
Rated 4.8/5, this 7-hour adventure on a luxurious catamaran features snorkeling, fishing, paddleboarding, and a tasty onboard meal. Its extensive route includes multiple stops and scenic sailing. Reviewers highlight its spacey, comfortable boat and excellent crew. The trip is perfect for travelers wanting an all-inclusive, luxury experience with plenty of water time.
Bottom Line: For those seeking luxury, extended time, and comprehensive water activities, this cruise excels.
13. Heraklion: Sunrise Balloon Flight & Sunset Catamaran Cruise
This 8-9 hour combo adventure includes a hot-air balloon ride over Lasithi Plateau and a sunset cruise to Dia Island. Rated 5/5, it’s suited for travelers looking to combine aerial views with relaxing sailing. It’s a premium experience that blends adventure with romance, especially with unlimited drinks and a Mediterranean dinner.
Bottom Line: Perfect for adventure seekers and romantics wanting a full-day of diverse experiences.
14. Dia Sailing Cruise With All-inclusive Meal And Drinks
Rated 4.8/5, this 5.5-hour tour offers authentic Mediterranean cuisine, water activities, and dolphin sightings. It includes hotel transfers, making it very convenient. The focus is on relaxation, good food, and fun, making it suitable for families and couples.
Bottom Line: An all-in-one option with meals, drinks, and water fun, ideal for a full day of leisure.
15. Rethymno: Sunset Catamaran Cruise with Wine and Snacks
Rated 4.5/5, this 3.5-hour cruise from Rethymno offers unlimited wine, soft drinks, and light snacks. It’s a semi-private experience perfect for romantic evenings, with gorgeous sunset views over the sea. Its smaller size and relaxed pace make it ideal for couples or small groups.
Bottom Line: Best suited for romantic, intimate experiences with stunning sunset scenery.
How to Choose the Best Sailing Experience in Heraklion
Picking the right tour depends on your interests, budget, and available time. If you’re after luxury and gourmet food, the Luxury Catamaran to Dia is hard to beat. For active water lovers, the Water Activities Cruise offers plenty of snorkeling, paddleboarding, and swimming. Or, if a romantic sunset is what you crave, the Sunset Sailing Cruise delivers unforgettable views.
Consider your fitness level—some tours involve more swimming or water sports— and whether you prefer a small-group experience or a larger boat. Booking early is recommended during peak summer months, especially for the popular tours like the Ultimate Catamaran Cruise.
Heraklion’s sailing options range from relaxing sunset cruises to luxury full-day adventures. Whether you want a quiet day exploring Dia’s wildlife or a gourmet cruise with wine and water sports, there’s something for all. For a laid-back day with a mix of activities and fine food, the luxury catamaran options are hard to beat. If your goal is a fun-filled water day, opt for a trip with snorkeling, paddleboarding, and swimming. Whatever you choose, these tours promise a memorable way to experience Crete from the water—so don’t wait, book early and enjoy the sea!