Heraklion, on the northern coast of Crete, is a prime spot for sailing adventures. With calm waters, reliable winds, and a stunning coastline, it’s no wonder sailors flock here. Whether you want a laid-back afternoon with a glass of wine or a full-day exploration of Dia Island, Heraklion offers something for every type of sailor. We particularly like the Heraklion: Sailing Trip to Dia Island with Lunch & Swimming, which provides a relaxed, personalized experience with snorkeling, fishing, and a tasty cretan meal. Plus, dolphins sometimes make a cameo, making every trip a bit more special.
For those craving luxury, the Heraklion Luxury Catamaran to Dia – Chef Lunch & Open Bar is a top choice, with gourmet onboard dining and unlimited drinks. And if you want a private voyage, the Heraklion: Dia Island Private Sailing Cruise with Full Meal allows you to customize your day with friends or family, enjoying the sea at your own pace. Here’s a helpful overview of the best options, each with its own charm.
1. Heraklion: Sailing Trip to Dia Island with Lunch & Swimming
At number 1 is this friendly, small-group sailing adventure that feels personal without the price tag of a private charter. The tour limits to just 10 people, making it ideal for a cozy day with fellow travelers. You’ll start with a scenic sail across the Aegean, then arrive at Dia Island, famous for its clear waters and rocky landscapes. The crew prepares a fresh Cretan meal—beer, wine, and soft drinks are unlimited—and you can snorkel, paddleboard, or fish in the secluded bay. What makes this tour stand out is the balance of relaxation and activity, plus the stories shared by a warm local crew. Guests love the “crystal-clear water,” “dolphin sightings,” and the “unforgettable vibes” of sailing back at sunset. While not the cheapest, the small group and personalized service make it good value. This trip suits travelers looking for a relaxed, authentic Crete experience with a bit of adventure.
Bottom Line: A top choice for small-group lovers wanting a relaxed, friendly atmosphere and activities like snorkeling and paddleboarding in pristine waters.
2. Heraklion Luxury Catamaran to Dia – Chef Lunch & Open Bar
Number 2 on our list is a luxurious take on sea adventures. This luxury catamaran offers plenty of space to spread out, with shaded areas and sun decks perfect for lounging. The onboard chef serves a gourmet lunch that elevates the experience, with fresh, restaurant-quality flavors. Unlimited wine, beer, and soft drinks keep everyone refreshed as you sail toward Dia Island, stopping for swimming, snorkeling, and free time on the island’s beautiful beaches. Snorkeling gear, SUP boards, and floaties are included, so you can stay active as long as you like. Many reviews highlight the “friendly crew,” “immaculate boat,” and “breathtaking views.” It’s a bit pricier but offers a more upscale experience, perfect for couples or those celebrating a special occasion.
Bottom Line: Perfect for travelers seeking a premium, all-inclusive day on the water with excellent food and plenty of space to relax.
3. Heraklion Luxury Catamaran Dia Isla -Gourmet Lunch Top Rated
Number 3 features a highly-rated luxury catamaran known for its outstanding reviews and top-notch service. This 5.5-hour cruise includes a restaurant-quality onboard lunch and options to snorkel, fish, and paddleboard. The vessel offers excellent photo opportunities and wildlife sightings—dolphins and seabirds often make an appearance. The itinerary includes a quick stop at Rocca a Mare Fortress for some sightseeing, then a leisurely trip to Dia Island, where you’ll enjoy free time for swimming and exploring. Guests praise the “stunning views,” “delicious food,” and “professional crew.” This tour is ideal for those who want a luxurious, all-inclusive day with flexible water activities and scenic sailing.
Bottom Line: Best suited for travelers wanting a gourmet experience with high comfort and the chance to see wildlife along the way.
4. Heraklion: Sunset Sailing Cruise Dia Island with Snorkeling
Number 4 offers a more romantic, laid-back experience. This sunset cruise combines a day of snorkeling, swimming, and relaxing on the beach, capped by a stunning sunset over Dia Island. The tour lasts 4.5 to 7 hours, with plenty of time on the boat to unwind, enjoy drinks, and take in the changing sky. The crew is professional, and the included food and drinks make the trip easy and enjoyable. Reviewers mention the “unforgettable sunset,” “crystal-clear waters,” and “relaxing atmosphere.” It’s a good choice for couples or anyone wanting a mellow day that ends with a memorable view.
Bottom Line: Ideal for those seeking a relaxing, romantic outing with snorkeling and sunset views.
5. Heraklion: Nature Reserve Full Day Sailing to Dia Island & Lunch
Number 5 is for the serious day-tripper. This full-day sailing trip lasts about 7 hours and limits to just 10 passengers, ensuring a quiet, personalized experience. The tour includes stops at remote beaches and nature spots, with snorkeling gear and SUP boards provided. The crew is praised for their warmth and knowledge, and the included lunch features local favorites like slouvaki. Guests report the water being “crystal clear” and the crew being “fantastic,” making this a great choice for travelers who want a slower, more immersive day on Crete’s waters. Since it’s a full-day tour, it’s best for those with flexible schedules and a love for nature.
Bottom Line: Excellent for nature lovers who want a leisurely, full-day adventure with plenty of opportunities to explore and relax.
6. Heraklion: Sunrise Balloon Flight & Sunset Catamaran Cruise
Number 6 combines two extraordinary experiences—a sunrise hot-air balloon ride and an evening sunset cruise. It’s the most comprehensive package, lasting 8-9 hours, with the balloon offering stunning aerial views over the Lasithi Plateau. After the flight, you’ll enjoy a 5-hour sunset cruise on a luxury catamaran, complete with drinks and a Mediterranean dinner. Travelers love the “romantic atmosphere,” “breathtaking views,” and “professional pilots and crew.” This tour is perfect for celebrating special occasions or anyone wanting a full day of adventure and relaxation with a guaranteed wow factor.
Bottom Line: Best suited for those seeking a unique, full-day experience combining sky-high views and sea relaxation.
7. Dia Sailing Cruise With All-inclusive Meal And Drinks
At number 7, this all-inclusive sailing offers a relaxed 5.5-hour trip with unlimited drinks and a Mediterranean menu. The boat is modern and comfortable, and the crew is known for being friendly and attentive. The itinerary includes snorkeling, swimming, and the chance to spot dolphins—if you’re lucky. Reviewers mention the “delicious food,” “helpful crew,” and “beautiful sunset.” The transportation is included, making it a fuss-free option for travelers wanting a laid-back but well-catered experience.
Bottom Line: A great choice for food lovers and those who want an easy, all-inclusive day at sea.
8. Heraklion: Dia Island Private Sailing Cruise with Full Meal
Number 8 caters to groups looking for privacy. This private cruise up to 10 people offers a flexible, personalized experience on a modern yacht. The trip includes a full meal, water activities like snorkeling and paddleboarding, and the chance to enjoy Dia Island at your own pace. Guests appreciate the “professional crew,” “delicious food,” and “dolphin sightings.” It’s ideal for celebrating a special occasion or simply enjoying a quiet, tailored day with family or friends.
Bottom Line: Best for travelers who want exclusivity and full control over their itinerary.
9. From Heraklion: Dia Island Private Sailing Trip
This small, private sailing trip is perfect for a custom experience. It lasts around 6 hours and is limited to groups of up to 10. The itinerary includes snorkeling, sightseeing, and time on Dia Island, with flexible options for swimming and exploring. Guests praise the “friendly skipper,” “spacious boat,” and “well-catered food.” It’s suited for couples or families looking for a private, intimate day at sea.
Bottom Line: Excellent for those seeking a fully tailored, intimate sailing adventure.
10. Heraklion: Sunset Private Sailing Trip to Dia island
Number 10 is a private sunset cruise perfect for a romantic escape. Lasting about 4.5 hours, it combines sailing, swimming, and enjoying the sunset from the water. The crew provides snacks and drinks, and the scenery as the sky changes color is unforgettable. Reviewers say it’s “great for couples” and “relaxing with stunning views.” It’s ideal if you want a private, intimate experience with a spectacular backdrop.
Bottom Line: Best for couples or small groups seeking a peaceful evening with sunset views.
11. Heraklion: Private Catamaran Cruise to Dia with Meal&Drinks
Number 11 offers a luxurious, private experience aboard a high-end catamaran. It includes a full meal, drinks, and opportunities for swimming, snorkeling, and paddleboarding. You can pick morning or evening departures for a personalized day. Many reviews highlight the “delicious food,” “friendly crew,” and “perfect setting for celebrations.” It’s a fantastic choice for special events with family and friends.
Bottom Line: Perfect for celebrating a special occasion in style, with full customization.
12. Heraklion: Dia Island Sailing Trip with Lunch
Finally, this sailing trip combines comfort and good value, offering a 5.5-hour experience with lunch onboard. You’ll sail in a luxury yacht, stopping for swimming, snorkeling, and exploring Dia Island. Reviewers mention the “delicious lunch,” “friendly crew,” and “beautiful waters,” making it a solid all-around choice for a relaxed day at sea.
Bottom Line: A reliable, enjoyable option for those wanting a balanced day with good food and scenic sailing.
How to Choose the Best Sailing Experience in Heraklion
When selecting your ideal sailing adventure, consider your budget, time constraints, and what kind of experience you’re after. For a luxurious day with gourmet food and unlimited drinks, the Luxury Catamaran to Dia or the private Dia Island Cruise are excellent. If you prefer a more authentic, small-group vibe, the Heraklion: Sailing Trip to Dia Island delivers a personalized experience with snorkeling and paddleboarding.
For scenic sunsets, the Sunset Sailing Cruise is unbeatable, especially for romance or relaxing evenings. Budget travelers or those wanting a full-day adventure can check out the Full Day Sailing to Dia, which includes remote beaches and nature stops.
Booking early is wise, especially in peak summer months, as these tours can fill quickly. Consider your fitness level—most trips involve swimming and snorkeling, so bring gear if you’re comfortable in the water. These options cover all tastes, from intimate private cruises to upscale day trips. Pick the one that matches your style and enjoy Crete’s beautiful sea.
With so many excellent options, your perfect sailing trip in Heraklion awaits. Whether you want a private sunset cruise or an all-day adventure with snorkeling and local food, Crete’s waters won’t disappoint. Book early, pack your sense of adventure, and get ready for a memorable day on the sea.