Crete isn’t just about ancient ruins and olive groves; it’s also a prime spot for sailing adventures. With its clear waters, steady breeze, and a coastline dotted with coves and islands, Crete offers something for all on the water. Some trips focus on relaxed snorkeling and swimming, like the private Heraklion: Private Half-Day Sailing Trip to Dia Island, perfect for a family or romantic escape. Others, like the Kissamos Balos Gramvousa Sailing Cruise with Lunch, combine sightseeing, hiking, and swimming in iconic spots. And for those looking for a touch of luxury, the Heraklion Private Sailing Catamaran or Dia Island Catamaran Premium Lunch options offer a day of fine dining, open bars, and high-end boat comfort.
For those wanting a lively atmosphere, catamaran cruises with drinks, music, and plenty of space to relax are a favorite. Meanwhile, sunset cruises like the Dia Island Sunset Sail give you a peaceful way to end the day. Whatever your style, Crete’s sailing options promise memorable views and unique experiences on the Aegean Sea.
1. Heraklion: Private Half-Day Sailing Trip to Dia Island
At number 1, this private half-day trip offers a relaxed 4.5 hours of sailing from Heraklion to Dia Island. The tour includes swimming, snorkeling, fishing, and plenty of lounging on your own private boat. Unlimited drinks and fresh fruit keep you refreshed, and for an extra treat, you can add a full onboard meal. The trip’s flexibility makes it ideal for those who want to tailor their experience—whether it’s a quick escape or a leisurely afternoon. Reviews highlight how attentive and friendly the crew is, with one saying, “The boat was wonderful and really clean,” and another noting, “Fabulous trip.” This tour is perfect for couples or small groups looking for a private, relaxed outing on the water. Bottom line: a well-rated, flexible choice for a personalized day at sea.
2. From Kissamos: Balos Gramvousa Sailing Cruise with Lunch
This 8-hour cruise hits the spot for those wanting a full day exploring Crete’s most iconic spots. The tour departs from Kissamos and takes you to Balos Lagoon and Gramvousa Island, with options for shared or private sailing. The itinerary includes swimming, snorkeling, hiking up to the fortress on Gramvousa for panoramic views, and a traditional Cretan lunch cooked onboard. Guests love the balance of activity and relaxation, with one reviewer praising the “tasty foods, the company, and the stunning scenery.” The crew’s ability to navigate busy spots and avoid crowds adds value, especially at the popular Balos. Bottom line: a comprehensive, scenic cruise ideal for history and nature lovers with a full day free.
3. Sailing Trip to Dia with Snorkeling, Dining & Sunset Option
For around $100 per person, this 4.5-hour boutique yacht experience combines sailing, swimming, snorkeling, and a sunset cruise. The focus here is on intimacy and quality, with a well-maintained 45ft sailboat and attentive crew. Guests enjoy crystal-clear waters, sheltered bays, and Mediterranean cuisine. The sunset add-on transforms the trip into a perfect evening escape, with reviews calling it “an excellent sailing experience” and “very relaxing.” The trip is best suited for those who want a shorter, high-end experience with stunning sunset views. Bottom line: an intimate, well-reviewed option ideal for couples or small groups seeking a luxurious, scenic evening.
4. Heraklion: Private Full-Day Sailing Trip to Dia Island
This 7-hour private cruise offers a full day of sailing, including swimming, snorkeling, and fishing, with unlimited drinks and fresh fruit. It’s similar to the half-day but with more time to explore Dia and relax onboard. The itinerary includes two stops on Dia with plenty of leisure time, plus scenic sailing. Reviewers appreciate the “delicious, fresh food” and attentive crew, making it a great choice for families or small groups wanting exclusivity. The value for the all-inclusive experience is high, given the private setting and personalized service. Bottom line: a luxurious, flexible day on the water, perfect for those wanting privacy and extensive time on Dia Island.
5. Sailing Cruises Chania
Number 5 offers a flexible 4-7 hour cruise around the Gulf of Chania, starting from the Old Venetian Harbour. It features stops at Ag.Theodori Island and Maherida, both offering swimming, snorkeling, and birdwatching. The trip includes local snacks, fresh fruit, and drinks from the open bar. One reviewer calls it “the best crew we have sailed with,” highlighting the friendly service and well-maintained boat. The varied itinerary with natural and cultural sights makes this a great option for those wanting a mix of water fun and scenic cruising. Bottom line: an engaging cruise perfect for exploring Chania’s coastline with stops for wildlife and swimming.
6. Catamaran Sailing to Dia with Lunch in Heraklion, Crete
This 5.5-hour luxury catamaran trip combines comfort with fun. You’ll swim, snorkel, and paddleboard in Dia’s clear waters, with no extra charge for paddleboards. The boat’s spacious design allows for plenty of lounging while enjoying unlimited drinks and a freshly cooked Mediterranean lunch. Guests rave about the “incredible day” and “awesome crew,” with reviews praising the “beautiful and very clean” boat. The inclusion of water activities makes it suitable for families and groups wanting a relaxed yet activity-filled day. Bottom line: a high-end, activity-rich cruise with excellent reviews and all the amenities for a memorable day.
7. Sailing to Dia Island with lunch on Bavaria 51 Heraklion, Crete
For around $116, this 4-hour sailing adventure offers snorkeling, paddleboarding, and fishing, plus a delicious onboard lunch. The Bavaria 51 is known for its spacious deck and smooth sailing, making it ideal for those who want a taste of traditional sailing combined with fun water sports. Guest reviews highlight the “most delicious pasta dish” and “beautiful waters,” with the crew earning praise for their professionalism. The shorter duration makes it suitable for travelers short on time but wanting a full experience. Bottom line: a quick yet comprehensive sailing outing with good food and water activities.
8. Private luxury Escape Sailing, Snorkel and Lunch Cruise
This exclusive 5-hour private yacht experience is perfect for a quiet, personalized day. It offers snorkeling, swimming, and a multi-course Mediterranean lunch, all onboard a yacht that promises privacy and comfort. Reviews note the excellent organization and friendly staff, making it ideal for couples or small groups wanting a tailored experience. The focus on eco-pleasure and serene scenery makes it a luxurious way to see Dia Island. Bottom line: a high-end, personalized cruise suited for a romantic or special occasion.
9. Hersonissos: Catamaran Sailing Trip to Dia Island with Lunch
This 6.5-hour catamaran tour departs from Hersonissos and is designed for families and all types of travelers. It includes snorkeling, paddleboarding, swimming, plus a Mediterranean lunch with drinks. The crew’s friendliness and the boat’s spaciousness get rave reviews, with one reviewer calling it “a wonderful afternoon cruise.” The trip’s length allows plenty of time to relax and enjoy Dia’s waters. Bottom line: a family-friendly, well-reviewed, and comprehensive day on the water.
10. Dia Island Catamaran – Premium Lunch, Open Bar, Small Group
This 6.5-hour premium catamaran cruise offers an open bar, freshly prepared meal, and plenty of water activities. It’s ideal for celebrating a special occasion or just soaking up the sun in style. The small-group format ensures personalized service, with reviews praising the “friendly and attentive” staff and “super tasty food.” The addition of free WiFi and inflatable fun gear like flamingos and paddleboards keeps everyone entertained. Bottom line: a luxurious, fun-filled cruise with excellent reviews for those wanting comfort plus active options.
11. Heraklion Private Sailing Catamaran Cruise to Dia with Lunch
This private luxury trip on the Excess 11 catamaran offers a 6.5-hour day of swimming, snorkeling, and fishing, with a gourmet Mediterranean lunch. Its exclusivity makes it perfect for special occasions or travelers who want privacy, with reviews emphasizing the “amazing” crew and “beautiful boat.” The included amenities like snorkeling gear and onboard dining make it a top-tier experience. Bottom line: a premium, private adventure tailored for a small group seeking ultimate comfort.
12. Sailing trip to DIA in Heraklion, Crete
This 4-hour privately guided cruise is limited to just 10 passengers, with a focus on peaceful sailing at sunset. Featuring champagne, wine, and snacks, it’s perfect for a romantic or reflective evening on the water. The reviews mention how beautiful and well cared-for the boat and crew are, with one saying, “an amazing team.” Ideal for those wanting a quiet, intimate experience as the sun sets. Bottom line: a short, romantic sunset cruise for those seeking serenity and stunning vistas.
13. Small Group Sailing Cruise from Heraklion to Dia Island
This semi-private 6-hour cruise combines social sailing with plenty of swimming and exploring. The tour features a mix of relaxation and activity, with the chance to explore ruins, enjoy local food, and take in Dia’s natural beauty. One reviewer notes the “excellent team” and the “perfect amount of time.” It’s suited for travelers seeking a shared experience with some social interaction but still ample leisure. Bottom line: a good balance of social and relaxing, offering a semi-private feel.
14. Kissamos: Balos and Gramvousa Private Sailing Trip with Meal
Number 14 offers a private 8-hour sail to Balos and Gramvousa, with exclusive use of the boat and a homemade meal onboard. Ideal for groups wanting to avoid crowds, it includes visits to both iconic sites, swimming, snorkeling, and hiking to the Venetian fortress. Guests praise the “perfect amount of time” and the “delicious local food.” It’s best suited for groups who want complete privacy and a tailored itinerary. Bottom line: a premium, private experience emphasizing exclusivity and personalized service.
How to Choose the Best Sailing Experience in Crete
When deciding between these options, consider your budget, the amount of time you want on the water, and your interests. For private, customizable trips, options like the Heraklion Private Half-Day or the Full-Day are ideal. If you want scenic day trips with hiking and history, the Kissamos Balos Gramvousa cruise might be best. For a luxury experience with water activities and onboard dining, look into the Catamaran trips or Premium Catamaran cruise. And if a romantic sunset or small-group social cruise appeals, the sunset or Heraklion sunset tours are great options.
Booking early is wise, especially for the popular summer months. Check availability in advance and consider your preferred duration, activity level, and whether you want a private or group experience. Many tours include lunch, drinks, and water gear, so plan accordingly.
Crete’s sailing options are wide-ranging, from intimate private charters to lively group cruises. Whether you’re after a quick half-day, a full-day adventure, or a luxury yacht experience, you’ll find something to match your style. For families, couples, or groups of friends, crete’s waters promise a day of fun, relaxation, and unforgettable views—so don’t wait, book early, and set sail into the Cretan blue.