Crete isn’t just about ancient ruins and beautiful beaches; it’s also a fantastic place for sailing adventures. The island’s diverse coastlines, especially around Heraklion, Chania, and Kissamos, offer perfect conditions for both relaxing day trips and active excursions. Whether you’re after a luxurious private yacht, a lively group cruise, or exploring secluded coves with family or friends, Crete delivers. We love experiences like the Heraklion Sailboat Cruise to Dia Island for its blend of comfort, adventure, and excellent reviews, or the Luxury Catamaran Cruise for a more intimate, upscale day on the water. Crete’s sailing options promise memorable moments and plenty of opportunities to enjoy the sea’s beauty.
Quick Overview
On this list, you’ll find day trips and multi-day adventures, including shared and private options. The tours vary from 4-hour snorkeling trips to full-day explorations along the island’s south coast. You’ll find luxury catamarans, traditional sailing boats, and private yacht charters. Some trips include lunch onboard, others focus on snorkeling, fishing, or sunset views. Now, let’s dive into the details of these top Crete sailing experiences.
1. Heraklion: Sailboat Cruise to Dia Island with Drinks & Lunch
Starting with a classic favorite, this Sailboat Cruise to Dia Island from Heraklion blends relaxed cruising with island exploration. For around $90 per person, you get 4.5 to 6.5 hours of sailing, swimming, and snorkeling. The trip features a luxury yacht, unlimited drinks, and a onboard meal that guests consistently praise—“the food was very good,” reports one. The itinerary includes sailing along the Heraklion coast, free time on Dia Island, and a chance to swim in crystal waters. The crew, led by Captain Marco and Alexandra, are attentive, ensuring everyone relaxes and enjoys the experience. The reviews highlight the small group size, friendly atmosphere, and delicious onboard food.
Bottom Line: This tour offers excellent value, especially for those craving a mix of sailing, swimming, and good food in a friendly setting.
2. Heraklion: Private Half-Day Sailing Trip to Dia Island
Looking for something more personalized? The Private Half-Day Sailing Trip gives you a 4.5-hour cruise tailored to your group, up to six people. The focus is on luxury and flexibility—you can swim, snorkel, fish, or just relax on deck. The crew provides snorkeling gear, fresh fruit, unlimited drinks, and the option to add a full onboard meal. Guests love the friendly crew and clean boat, with one review noting, “the crew was super friendly and attentive.” The private option is ideal for celebrating special occasions or seeking a more intimate experience.
Bottom Line: Perfect for small groups wanting exclusivity, with the freedom to customize your day on the water.
3. Sailing trip to the Top Coasts of Crete, Daily/Multi-day
If you’re interested in exploring Crete’s lesser-visited southern coast, this multi-day private sailing trip from Sfakia is a standout. For around $1,147, your group visits Glyka Nera Beach, Marmara Beach with caves, and Loutro village. It’s a full-day adventure, but the real treasure is the pristine, quiet scenery away from tourist crowds. Guests rave about the non-touristy nature and the chance to sail, snorkel, and sunbathe in secluded coves. The trip includes lunch, snacks, and soft drinks, making it a comprehensive experience.
Bottom Line: Best suited for those wanting a private, multi-day exploration of Crete’s untouched southern coast with plenty of swimming and sailing.
4. From Kissamos: Balos Gramvousa Sailing Cruise with Lunch
This Balos & Gramvousa cruise is a full-day journey from Kissamos, offering a scenic sail with stops at two iconic spots. For about $190, you’ll spend 8 hours on a shared or private boat, including swimming, hiking to Gramvousa’s castle, and a traditional onboard lunch. The highlight is the opportunity to snorkel in Balos Lagoon and explore the historic fortress on Gramvousa. The reviews mention the gorgeous boat, delicious food, and the less crowded experience compared to large tour boats. The crew’s expertise helps you maximize your time at each location.
Bottom Line: An excellent choice for history enthusiasts and those seeking a full day of sightseeing, swimming, and scenic sailing.
5. Heraklion: Luxe Catamaran Sailing Cruise to Dia Island with Lunch
For a more upscale experience, this Luxe Catamaran Cruise combines comfort, style, and exclusivity. It lasts about 6.5 hours and includes breakfast, unlimited drinks, and a luxurious onboard lunch. The cruise begins with coffee and pastries, then sails along the coast to Dia Island, where guests can swim and snorkel in secluded bays. The reviews praise the small group size, beautiful boat, and the overall relaxed atmosphere. Wi-Fi onboard allows sharing your photos instantly, adding a modern touch to this classic sailing adventure.
Bottom Line: Ideal for travelers seeking a more refined, intimate day at sea with premium amenities.
6. Sailing Trip to Dia with Snorkeling, Dining & Sunset Option
This Sunset Sailing offers a compact 4.5-hour experience that’s perfect for those wanting a quick but memorable trip. It includes snorkeling, lunch, and the chance to witness the spectacular sunset over Dia Island. The reviews mention the beautiful blue waters and the friendly crew making it a relaxing and picturesque way to end your day. The boat’s small size gives a personal feel, and the snacks and drinks keep everyone happy.
Bottom Line: Best for travelers who want a short, scenic trip with sunset views and plenty of time for swimming.
7. Heraklion: Private Full-Day Sailing Trip to Dia Island
If a full-day private charter appeals to you, this Heraklion Private Full-Day Sail offers 7 hours on a luxury yacht. It’s perfect for celebrating a special occasion and includes snorkeling gear, fishing equipment, and unlimited drinks. The private boat can comfortably host up to six guests and offers the flexibility to customize your stops. Guests rave about the friendly crew and the excellent onboard meal.
Bottom Line: For those seeking ultimate privacy and a bespoke experience, this tour delivers in style and relaxation.
8. Sailing Cruises Chania
Chania’s gulf is known for its beautiful coastlines and birdlife, and this Sailing Cruise from Chania offers an immersive experience. You’ll visit Ag.Theodori island and Maharida beach, enjoying swimming, snorkeling, and traditional Cretan snacks. The 5-star reviews note the boat’s impeccable maintenance and the crew’s friendly service. The trip provides a balanced mix of relaxation and sightseeing, with time spent exploring and lounging.
Bottom Line: Great for travelers based in Chania who want a well-balanced day at sea with nature and comfort.
9. Catamaran Sailing to Dia with Lunch in Heraklion, Crete
This Catamaran Sailing to Dia combines luxury and adventure with paddleboarding, snorkeling, and a delicious onboard lunch. The 5-star reviews highlight the professional crew, beautiful boat, and the hours of fun in the water. Departing from Heraklion, it’s a perfect choice for travelers wanting a luxurious, active day on the sea.
Bottom Line: Perfect for those who want adventure, comfort, and great food in one trip.
10. Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete
This shorter but lively tour offers 4 hours of sailing with snorkeling, paddleboarding, and a tasty pasta lunch. The reviews mention great crew, beautiful waters, and the fun of riding the boat. It’s ideal for families or those with limited time who still want to enjoy a relaxing, fun-filled day.
Bottom Line: A quick, activity-rich trip suited for travelers seeking fun and flexibility.
11. Balos & Gramvousa Luxury Catamaran Sailing Cruise from Kissamos
This luxury full-day cruise from Kissamos is a top contender for cruising enthusiasts. It includes swimming, snorkeling, and a full onboard lunch. The small group and reviews praising the food and crew make it a comfortable, enjoyable experience. The stops at Balos Lagoon and Gramvousa Island are highlights, with options to explore the fortress or relax on deck.
Bottom Line: Best for travelers seeking a luxurious, all-inclusive trip with plenty of time at iconic locations.
12. Balos Shared Catamaran Cruise (small group up to 12)
This small-group cruise offers a personalized experience with limited guests. You’ll visit Balos Lagoon and Gramvousa, enjoy snorkeling, and indulge in Greek-style lunch. The reviews emphasize the friendly crew and the exclusive feel of the trip. It’s perfect for travelers who want a more intimate, less crowded experience.
Bottom Line: Ideal for those wanting a luxury feel with smaller groups and personalized attention.
13. Crete Yacht Cruises 7-Hours Private Guided Cruise in Ag. Nikolaos
This private 7-hour cruise from Agios Nikolaos combines luxury, privacy, and personalized service. Led by Captain Mike, you’ll visit beaches like Voulisma and Kolokytha, with home-cooked food and local wines. The reviews mention the delicious homemade meal and the exceptional service. It’s suited for families or couples looking for a bespoke experience tailored to their wishes.
Bottom Line: The ultimate choice for privacy and exclusivity with a focus on comfort and local flavors.
14. Dia island: Small Group Sailing Trip to Dia Island with Lunch
Limited to 12 people, this small group sailing trip emphasizes personalized service. It includes insider tips on wildlife, snorkeling, and enjoying a local organic lunch. Reviewers highlight the friendly crew and flexible itinerary. It’s best for travelers who want a less crowded, interactive experience.
Bottom Line: Great for nature lovers and those wanting a more intimate day on the water.
15. Hersonissos: Sunset Catamaran Cruise with Snacks and Drinks
Ending on a romantic note, this sunset cruise from Hersonissos lasts about 3.5 hours. It includes snacks, drinks, and stops at Malia and St. Georg Bay. The reviews praise the friendly crew, spectacular sunset views, and relaxing atmosphere. It’s ideal for couples or anyone wanting a peaceful evening at sea with beautiful scenery.
Bottom Line: Perfect for a romantic evening or a gentle way to unwind after a busy day exploring.
How to Choose Your Perfect Crete Sailing Experience
When picking a sailing trip, consider your budget, the type of experience you want (private vs. group), and your interests—whether it’s snorkeling, sightseeing, or simply relaxing. For a luxury day with plenty of comforts, the Luxe Catamaran Cruise or the private Heraklion Full-Day are excellent. If you’re after a more active, interactive trip, the Balos & Gramvousa cruise or the small group trips offer a more personal touch. Booking early, especially in peak summer months, guarantees availability for these popular tours.
To sum it up, Crete offers a wide range of sailing experiences suited for every preference. For relaxed days with family, the Heraklion Sailboat Cruise to Dia is a reliable choice. For something more exclusive, the Private Full-Day or the Luxury Catamaran cruises provide top-tier comfort. For a blend of adventure and scenery, the Balos and Gramvousa trips stand out. No matter your choice, booking early will help you secure a spot on these unforgettable routes. Happy sailing!