Agia Pelagia is a fantastic base for exploring Crete’s waters. Its calm bays, clear blue sea, and proximity to beautiful islands make it an ideal spot for sailing lovers. Whether you’re after a luxurious private cruise or a more active adventure, there’s something here for everyone. We’re especially fond of the Heraklion: Private sailing to Dia Island with Lunch—a perfect blend of comfort, scenery, and local flavor. Imagine relaxing onboard, snorkeling in pristine waters, and enjoying fresh organic Greek cuisine. For a more hands-on experience, the Private Heraklion Active Sailing to Hidden Beaches offers a chance to learn seamanship, explore secret coves, and swim in turquoise waters. If you prefer a bigger group and a classy yacht experience, the Heraklion: Private Sailboat Trip with Swimming, Meal & Drinks delivers a luxurious outing with plenty of space and top-notch service. Lastly, for those on a budget or seeking a romantic sunset sail, the Private Sailing Trip from Heraklion to Dia with meal & SUP combines scenic views with relaxed snorkeling and a friendly atmosphere. Whatever your style, these options promise memorable moments on Crete’s sparkling sea.
1. Heraklion: Private sailing to Dia Island with Lunch
At number 1 on our list is this highly-rated private sailing experience that combines the beauty of Dia Island with a full day of relaxation and adventure. Starting from Agia Pelagia or other pickup points, you’ll be transferred to a large, comfortable yacht staffed by a knowledgeable local crew. The focus here is on personalized service, with a 4.9/5 rating from nine reviews, emphasizing the high quality of the experience. The itinerary includes swimming and snorkeling in the crystal-clear waters of Dia, along with dolphin and marine life watching. The highlight is a freshly prepared organic lunch onboard, with traditional Greek flavors that satisfy even the most discerning palates. Passengers rave about the friendly crew and scenic sunset views on the return journey. This tour excels for those seeking a private, intimate escape with options for aquatic activities and cultural insights.
The tour’s flexibility allows for a start at various locations, making it convenient for different travel plans. The only downside might be the price—$452 per group up to 8—but for the level of comfort and exclusivity, it’s good value. If you want to combine luxury with a taste of Crete’s marine life, this trip hits all the marks.
Bottom Line: Perfect for couples or small groups wanting an exclusive, all-inclusive day on the water with great scenery and personalized service.
2. Private Heraklion Active Sailing to Hidden Beaches
Second on our list is this active sailing tour, which offers a dynamic mix of seamanship, exploration, and fun. The experience is designed for those who want more than just sitting back—learning the secrets of seamanship, discovering tucked-away beaches, and enjoying calm, turquoise waters. The itinerary includes a one-hour sail from Agia Pelagia, followed by three hours of swimming, snorkeling, and food tasting. The highlight is exploring natural rock formations and secret beaches accessible only by boat. What makes this tour stand out is its focus on exploration and participation; you get to stand up paddleboard, take photos, and enjoy a relaxed sunset sail.
This tour is ideal for active travelers, families, or anyone interested in hands-on experiences. It’s rated 5/5 based on a single review, which praises the friendly crew and the chance to explore Crete’s coastline in a more intimate way. The meal and drinks onboard add to the value, especially considering the personalized nature of the trip.
Bottom Line: Best suited for travelers who want a more involved, discovery-oriented sailing adventure with opportunities for swimming, snorkeling, and natural exploration.
3. Heraklion: Private Sailboat Trip with Swimming, Meal & Drinks
Number 3 offers a luxurious private sailboat experience on a 54-foot yacht, perfect for bigger groups up to 18 people. The focus here is on comfort, style, and a premium experience. You’ll start from Cafe Marina, where your friendly crew will guide you through a scenic 75-minute cruise to Dia Island. Along the way, you can enjoy sightseeing, wine, and the chance to snorkel or swim in clear waters. The boat is equipped with all safety gear, lifejackets, and insurance, assuring peace of mind.
This trip is ideal for those celebrating special occasions or simply seeking a more upscale sailing outing. The reviews note the professional crew and the enjoyment of scenic views. The itinerary includes a focused 3.25-hour time at Dia, allowing ample time for swimming and relaxing on board. The value is in the spacious yacht, private setting, and the included amenities.
Bottom Line: Great for groups that want a private, stylish, and relaxed sailing experience, with plenty of space and personalized service.
4. Private Sailing Trip from Heraklion to Dia with meal & SUP
Last but not least, this affordable private sailing option is perfect for individuals or couples, costing just $71 per person for a five-hour trip. Starting from Heraklion port, you’ll cruise along scenic waters, with opportunities for swimming, snorkeling, and stand-up paddleboarding. The trip includes snacks and soft drinks, making it an excellent budget-friendly choice that still offers plenty of fun and relaxation. The itinerary is straightforward: a scenic sail to Dia, a swim and photo stop, then a sunset return.
This experience is ideal for travelers who want to enjoy sailing and water activities without breaking the bank. It’s rated with reviews praising the professionalism and the relaxed atmosphere. The focus on scenic views, local snacks, and the chance to participate in the sailing makes it a good pick for couples, solo travelers, or small groups.
Bottom Line: Best for budget-conscious travelers seeking a casual, fun outing with plenty of opportunities for swimming, snorkeling, and sunset views.
How to Choose Your Perfect Sailing Experience
When deciding between these options, consider your budget, the kind of experience you want, and how much time you have. For a truly private and luxurious day, the Heraklion: Private sailing to Dia Island with Lunch delivers top comfort and exclusivity. If you’re eager for a more active, exploratory day, the Private Heraklion Active Sailing to Hidden Beaches offers hands-on participation and secret spots. For larger groups or special occasions, the Heraklion: Private Sailboat Trip with Swimming, Meal & Drinks combines style with relaxed luxury. Budget travelers or those seeking sunset romance might prefer the Private Sailing Trip from Heraklion to Dia with meal & SUP.
Think about your fitness level, your interest in water activities, and whether you want a private or shared experience. Booking early is advisable, especially in peak summer months, to secure your preferred date and boat.
Final Thoughts
Agia Pelagia offers a surprising range of sailing options. For pure luxury and privacy, the first and third tours stand out. If you’re more adventurous and want to explore hidden beaches, the second is perfect. Budget travelers or sunset lovers will enjoy the last option, with its affordability and relaxed vibe.
No matter which you choose, Crete’s waters promise a memorable experience. Each tour offers a different way to enjoy the sea—just pick one that suits your style and dive in early to secure your spot.