Greece’s crystal-clear waters, countless islands, and warm sunshine make it one of Europe’s top sailing destinations. Whether you want to glide silently past the famous white-washed buildings of Santorini, snorkel around hidden caves near Corfu, or relax aboard a private yacht in Milos, Greece offers something for all. We particularly love the Daily Sailing Tour from Skopelos in Alonissos for its combination of wildlife spotting, secluded beaches, and flexible options—plus the chance to see dolphins, seals, and turtles. For a more luxurious day at sea, the Hersonissos: Luxury Catamaran Cruise to Dia with unlimited drinks and a Mediterranean feast hits the spot. With so many options, Greece is perfect whether you’re seeking adventure, relaxation, or a bit of both.
Quick Overview
Our list covers a variety of sailing experiences: from daily group tours, private yacht rentals, to semi-private cruises, and even family-friendly options. Whether you prefer a full-day yacht adventure in Rhodes, a romantic sunset cruise in Santorini, or a family-friendly catamaran with meals on Crete, there’s something to match your style and budget. Now, let’s take a detailed look at each.
1. Daily Sailing Tour from Skopelos in Alonissos By Kardous,Thasos
At number 1, this popular day trip from Skopelos combines nature, relaxation, and potential wildlife sightings. Departing daily from Skopelos harbor, the Kardous Sailing Thasos sails to the Alonissos Marine Park, home to seals, dolphins, and turtles—which you might spot along the way. The tour offers options for group or private trips, with a maximum of 8 passengers for a more intimate experience. Highlights include swimming at heavenly beaches, paddleboarding, and snorkeling.
This trip is praised for its friendly hosts and high standards of cleanliness, with reviews mentioning the calm, relaxing atmosphere and the delightful Greek treats served onboard. The itinerary allows for 5 hours exploring the marine park and 3 hours relaxing on beaches only accessible by boat, making it ideal for those seeking a peaceful escape. The admission tickets to protected areas are included, making it good value for money.
Bottom Line: Small-group, wildlife-friendly sailing with flexible options and authentic hospitality. Best suited for those wanting a peaceful day with the chance to see marine life.
2. Hersonissos: Luxury Catamaran Cruise to Dia – Lunch & Drinks
Number 2 on our list is a luxurious day out from Crete’s Hersonissos. This 6.5-hour cruise combines comfort, stunning scenery, and delicious Mediterranean cuisine. The catamaran is spacious and well-appointed, perfect for relaxing while enjoying unlimited drinks—from soft drinks to wine and beer—served throughout the trip.
The tour includes a scenic sail to Dia Island, with opportunities for snorkeling, paddleboarding, and inflatable flamingo fun in the clear waters. The highlight is the freshly cooked Mediterranean lunch, which guests praise for its quality and variety. The itinerary also features scenic views and plenty of time for swimming and relaxing.
This experience is perfect for adults and families looking for a high-end, all-inclusive day at sea. The reviews emphasize friendly staff, gourmet food, and the spacious deck that allows plenty of room to soak in the sun.
Bottom Line: An elegant, all-inclusive cruise ideal for those who prioritize comfort, good food, and adult relaxation, with options for families as well.
3. From Naxos: Schinoussa and Iraklia Sailing Cruise with BBQ
Coming in at #3, this sailing trip from Naxos offers a blend of beach time, scenic wreck exploration, and a delicious BBQ lunch. The trip visits Iraklia and Schinoussa, two lesser-known but stunning islands, with time for swimming at sandy beaches.
A special feature is the stop at Alimia, where you can snorkel above a WWII plane wreck—a real treat for history and underwater enthusiasts alike. The itinerary includes exploring Iraklia’s quaint capital village, Agios Georgios, offering a glimpse of local life.
Guests often appreciate the casual, friendly atmosphere and the chance to combine sightseeing with swimming and snorkeling. The BBQ lunch is homemade and authentic, adding to the overall value.
Bottom Line: Perfect for travelers who want a mix of history, secluded beaches, and an authentic Greek BBQ—less crowded, more relaxed.
4. Milos: Private Yacht Tour—Kleftiko Sarakiniko Poliegos
Number 4 is a luxury private yacht experience in Milos, ideal for couples or small groups up to 16. The Open-Yacht Raptor takes you to Kleftiko caves, Sarakiniko beach, and Poliegos island—the highlights of Milos.
The tour is fully customizable, allowing you to choose stops and spend as much time as you like at each site. Guests rave about the gourmet lunch, open bar, and luxurious comfort—a real treat if you want privacy and exclusivity. The tailored itinerary makes it perfect for special occasions or those craving a personalized experience.
While the price reflects the exclusivity, this tour offers exceptional value if privacy and customization are top priorities. The top reviews highlight the professional crew and beautiful scenery.
Bottom Line: For those seeking a bespoke, luxury experience tailored to your schedule and interests, this private yacht is hard to beat.
5. Private Catamaran Cruise Mykonos Delos with Meals & SUP
Number 5 offers a half-day private cruise in Mykonos, perfect for couples, friends, or small families. This semi-private experience explores the famous Delos and Rhenia Islands, with stops that include snorkeling, paddleboarding, and beach relaxation.
Guests love the personalized service and the delicious lunch served onboard, which includes Greek specialties. The spacious deck and flexible itinerary make it great for those wanting a customized and intimate experience.
Reviews highlight the friendly crew, beautiful scenery, and the enjoyable mix of activity and relaxation. It’s a good choice if you want a luxurious yet flexible day at sea.
Bottom Line: Ideal for couples and small groups seeking a personalized, scenic cruise with excellent amenities.
6. Catamaran’s Private Tour / Mykonos
Number 6 is a private catamaran cruise in Mykonos, perfect for a boho-chic experience. With a 4-20 person capacity, it’s suitable for celebrating special occasions or just enjoying privacy. The itinerary is simple—starting and ending at Paraga Beach, giving you full control over your day.
Guests rave about the exclusive atmosphere and the flexibility to craft your perfect day on the water. The comfort and privacy make this a luxurious, yet relaxed option.
Bottom Line: For small groups seeking exclusivity and a laid-back vibe, this private cruise provides an exceptional experience.
7. Santorini Catamaran Sunset Skyline Cruise
Number 7 is a Santorini sunset cruise that offers one of Greece’s most picturesque sailing experiences. Over 5 hours, you’ll visit Red Beach, White Beach, and volcano hot springs, all while watching the sunset paint the sky.
This tour includes snorkeling, swimming, and a local onboard meal with drinks. The famous volcanic views and hot springs are spectacular at dusk, making this a romantic favorite.
Guests appreciate the comfortable boat and the stunning scenery, with reviews mentioning the magical sunset as a highlight. It’s perfect for couples celebrating something special.
Bottom Line: Best for lovers of romance and scenery, with a memorable sunset backdrop.
8. Heraklion: Catamaran Sailing to Dia island
Number 8 offers a spacious catamaran cruise departing from Heraklion to Dia Island. The 6-hour trip is suitable for families and couples alike, combining water sports, scenic sailing, and local food.
Guests praise the friendly crew, good value, and the opportunity for snorkeling and paddleboarding. The trip includes scenic views and free-riding in the protected waters of Dia’s beaches.
This experience is ideal if you want a relaxed day at sea with plenty of activity options and no fuss. The small group size and certified crew add extra comfort.
Bottom Line: A solid choice for those seeking a hassle-free, activity-rich day on the water.
9. Private Daily Sailing Cruise from Skopelos port to Alonissos
Number 9 is a private option, similar in scope to Tour #1 but available for up to 8 people. It offers flexibility and privacy for a personalized experience, sailing through the marine park to beautiful beaches only accessible by boat.
Guests appreciate the customizable itinerary and the chance to see dolphins and sea turtles. The admission to protected areas is included, making it good value for those wanting an exclusive, wildlife-rich day.
Bottom Line: Excellent for small groups wanting privacy and customization, with the bonus of wildlife sightings.
10. Mykonos Catamaran Delos Rhenia semi private cruise
Last on our list, this semi-private cruise offers about 6 hours exploring Delos and Rhenia. It’s perfect for those who want to experience the famous archaeological site and enjoy swimming and snorkeling.
Guests mention the friendly crew, the delicious onboard lunch, and the memorable scenery. The smaller group size makes it easier to relax and enjoy the trip fully.
Bottom Line: Ideal for travelers seeking a semi-private, culturally rich experience with plenty of swimming.
How to Choose Your Perfect Sailing Experience
When selecting a sailing tour in Greece, consider your budget, interest level, and group size. Want a luxury private yacht? The Milos private yacht offers indulgence and exclusivity. On a tighter budget? The Naxos sailing cruise provides a wonderful mix of beaches and history at a more affordable price.
If you prioritize family-friendly activities, the Heraklion catamaran or Naxos sailing trip could be ideal. For romantic sunsets, the Santorini sunset cruise is hard to beat. Meanwhile, those craving a personalized experience will find the private options in Milos and Mykonos particularly appealing.
Booking early is advisable, especially in peak summer months, and always check whether meals, drinks, and equipment like snorkels are included in the price.
Greece’s diverse sailing options mean you can tailor the experience to your preferences—whether you want wildlife encounters, luxury comfort, cultural exploration, or simply soaking up the sun. With so many choices, your perfect day at sea is just a booking away.