Greece isn’t just about ancient ruins and olive oil; it’s also about sailing through some of the most stunning waters in Europe. The country’s thousands of islands, rugged coastlines, and clear blue seas make it an ideal backdrop for a sailing adventure. Whether you want a peaceful day exploring hidden beaches around Skopelos, a luxurious private yacht around Milos, or a lively catamaran cruise with drinks and snorkeling—Greece offers a wide variety of options. We’re particularly fond of experiences like the Daily Sailing Tour from Skopelos in Alonissos for its approachable nature, friendly guides, and flexible options for group or private trips.
What makes Greece so special for sailing is the combination of crystal-clear waters, serene beaches accessible only by boat, and the opportunity to see wildlife like dolphins, seals, and turtles. Plus, many tours include stops at famous sites like Dia Island, Kleftiko, and the caves of Corfu, giving you a chance to explore both the coast and underwater world. No matter your budget or experience level, there’s a Greek sailing trip tailored for you.
Below, you’ll find a list of the 15 best sailing experiences in Greece, ranging from half-day private catamaran cruises in Mykonos to full-day group adventures in Crete and private yacht tours around Milos. Each one offers a different flavor of what Greece’s waters have to offer.
1. Daily Sailing Tour from Skopelos in Alonissos By Kardous,Thasos
Starting from the picturesque port of Skopelos, this daily sailing trip takes you to Alonissos and its famous marine park. With a maximum of 8 passengers on board, the tour offers both group and private options, which makes for a flexible and intimate experience. The trip features swimming at secluded beaches, paddleboarding, and snorkeling to explore the marine life, with a chance to see dolphins, seals, or turtles along the way.
The main highlight is the visit to Alonissos Marine Park, where wildlife sightings are common and the scenery is breathtaking. Passengers consistently praise the friendly hosts, Alexandra and Antonis, and the overall relaxing vibe—making it a top pick for anyone wanting a low-key, authentic day at sea. The boat is well-maintained, and the itinerary allows for plenty of time to unwind, swim, and enjoy Greek delicacies on board.
Bottom Line: A small-group, flexible adventure perfect for travelers seeking a quiet, nature-focused day with high-quality hospitality and snorkeling fun.
2. Hersonissos: Dia Catamaran Cruise with Lunch & Drinks
From the lively port of Hersonissos, this luxury catamaran cruise offers a full 6.5 to 7.5 hours of sailing, swimming, and feasting. Set sail to the uninhabited Dia Island, where the crystal waters are ideal for snorkeling, paddleboarding, or just lounging on deck. The trip includes unlimited drinks, from soft drinks to wine and beer, and a freshly prepared Mediterranean lunch that caters to both kids and adults.
The itinerary features scenic views and opportunities for scenic swimming, with the boat stopping multiple times for water activities. Guests note the comfort of the spacious deck and the attentive crew, making this a great choice for families, couples, or groups wanting a more luxurious day at sea. The departure point is Hersonissos Port, easy to access, and the trip offers excellent value given the length and inclusions.
Bottom Line: A mix of comfort, activity, and relaxation, making it ideal for those who want a full day of sailing with food and drinks included.
3. Milos: Private Yacht Tour—Kleftiko Sarakiniko Poliegos
For those seeking privacy and customization, the private yacht tour around Milos is unmatched. Up to 16 guests can enjoy this luxury day aboard the open-yacht Raptor, with the itinerary tailored to your interests. The tour includes stops at iconic spots like Kleftiko caves, Sarakiniko’s moon-like landscape, and other hidden bays.
This experience stands out for its personalized approach, allowing travelers to decide where to linger, swim, snorkel, or simply relax. The open bar and gourmet lunch add to the indulgence, while the yacht’s comfort makes it perfect for families or groups of friends. Reviews mention how the captain and crew, with years of experience, make this a truly special day.
Bottom Line: The best choice for travelers wanting a completely private, flexible, and luxurious sailing experience with top-notch amenities.
4. Private Catamaran Cruise Mykonos Delos with Meals & SUP
This half-day private catamaran offers an intimate way to explore the Delos and Rhenia Islands. The tour includes stops at Rhenia, famous for its peaceful beaches, and Delos, a UNESCO archaeological site. With snorkeling, paddleboarding, and a delicious onboard lunch, it’s perfect for those who want a mixture of cultural and water-based activities.
Guests appreciate the flexibility of a private charter, with the option to customize the itinerary and spend more time at favorite spots. The crew, led by Captain Vasilis and Emil, is praised for professionalism and hospitality. It’s a compact but comprehensive experience, ideal for families or couples craving exclusivity.
Bottom Line: An excellent choice for those wanting a personalized, relaxed day on the water with cultural and recreational highlights.
5. Private Daily Sailing Cruise from Skopelos port to Alonissos
Similar to our first pick, this private sailing trip starts from Skopelos and heads to Alonissos Marine Park. It offers the freedom to customize your day, whether you want more swimming, snorkeling, or simply relaxing onboard. The trip can also be booked as a group or private experience, with a maximum of 8 people.
On the way, you’re likely to see dolphins, and in Alonissos, explore beaches accessible only by boat. The hosts, Alexandra and Antonis, receive rave reviews for their warm hospitality and flexibility. The itinerary provides a perfect balance of adventure and downtime.
Bottom Line: Best suited for small groups or families looking for a flexible, private day at sea in Greece’s magical waters.
6. Catamaran’s Private Tour / Mykonos
For travelers after a boho-chic experience, this private catamaran in Mykonos offers a luxurious, flexible cruise for up to 20 people. Starting from Paraga Beach, guests can enjoy a full or half-day sailing adventure with stops at beaches, coves, or the iconic Delos island.
What sets this tour apart is the private experience—perfect for special occasions, romantic trips, or groups wanting total privacy. The crew ensures a tailored itinerary, and the boat’s stylish design makes for fantastic photos. The review highlights the tranquil atmosphere and personalized service.
Bottom Line: Ideal for groups seeking a stylish, private day at sea with customizable options and a touch of luxury.
7. Heraklion: Catamaran Sailing to Dia island
On the bustling island of Crete, this 6-hour catamaran trip departs from Heraklion Port, sailing to Dia Island. It offers snorkeling, paddleboarding, and a scenic cruise, with a focus on family-friendly activities. The crew provides all safety equipment, and the trip includes a local onboard meal.
Guests love the relaxed pace and the opportunity to see Dia’s remote beaches. The cruise is suitable for all ages but especially appealing to those who want a straightforward, well-organized day on the water. The reviews mention the professional crew and good value for the price of $95 per person.
Bottom Line: A reliable, fun day for families or couples wanting a simple yet enjoyable boat trip in Crete.
8. Private Catamaran Cruise in Santorini and BBQ Drinks
This private 5-hour cruise in Santorini combines stunning volcanic scenery with a delicious BBQ onboard. Swim in the volcanic Hot Springs, relax at the Red, White, and Black Beaches, and enjoy panoramic views of Thirassia Island. The private trip includes lunch, drinks, and the opportunity to take countless photos.
Guests rave about the luxury experience and the chance to swim in volcanic waters. The boat’s elegant design and attentive crew make it perfect for honeymooners or anyone celebrating a special occasion. The included hotel transfer adds convenience for a seamless day.
Bottom Line: The go-to option for a romantic, exclusive day with spectacular scenery and excellent hospitality.
9. Mykonos Catamaran Delos Rhenia semi private cruise
This semi-private cruise offers a 6-hour sail around Delos and Rhenia, including swimming, snorkeling, and onboard lunch. With a maximum of 12 people, it balances intimacy and socializing, making it popular among couples and small groups.
The highlight is the archaeological stop at Delos, a UNESCO site, combined with relaxing at Rhenia’s beaches. Reviewers mention the friendly crew and enjoyable onboard atmosphere, although the limited lunch options at sea are worth noting. It’s good value at $192 per person.
Bottom Line: A good pick for those who want a mix of cultural exploration and water fun without the crowds.
10. Aeolus Motor Yacht cruise in Paros
This 7-hour motor yacht cruise in Paros offers a relaxed way to see the Cyclades. It includes swimming at Pantheronissia, a stop at remote beaches, and a taste of authentic Greek flavors onboard. The yacht’s speed allows visiting multiple spots in one day.
Travelers mention the professional crew and the ease of enjoying the boat’s comfort, especially if you want to cover more ground quickly. It’s a good choice for active travelers who want variety and a smooth ride.
Bottom Line: Best for those seeking a swift, well-organized day with comfort and scenic stops.
11. Attica: Sailing Cruise the Attica Riviera and Swimming
Near Athens, this 6-hour sailing trip combines cultural sights with relaxation. Sail along the Attica Riviera, visit Ydrousa Island, and enjoy a private chef-prepared meal. Snorkeling and swimming are included, with the option to explore local beaches.
Reviewers praise the beautiful scenery and the high-quality onboard meal. The proximity to Athens makes it convenient for a day trip or a relaxing escape without traveling far. It’s perfect for those wanting to combine sightseeing with water fun.
Bottom Line: A practical choice for travelers wanting a scenic, culinary, and aquatic experience close to Athens.
12. Balos: Catamaran Shared Sailing Cruise with lunch and drinks
This shared 7-9 hour cruise along Crete’s coast offers swimming, hiking, and scenic cruising. Departing from Kissamos port, it features stops at the famous Balos Beach and Gramvousa, with plenty of time for snorkeling and relaxing.
Though reviews are limited, the itinerary’s focus on local snacks, lunch, and drinks combined with the scenic routes makes it a popular choice for travelers eager to see Crete’s iconic sights. It’s an active day, suited for those comfortable with a longer trip.
Bottom Line: Excellent for active travelers seeking a full day of exploring Crete’s famous beaches and caves.
13. Corfu Sunset Private Yacht Cruise
This 3-hour private cruise around Corfu offers a peaceful way to see the Venetian architecture and the beautiful coastline. It’s perfect for special occasions or romantic evenings, with stunning views of Vidos Island, Garitsa Bay, and Mon Repos.
The intimate setting makes it ideal for couples or small groups wanting a cozy, scenic experience. The cruise is customizable, and reviews note the serene atmosphere and personalized service.
Bottom Line: A top pick for a romantic sunset, or a quiet, scenic cruise with personalized touches.
14. Corfu: Private Sailing Cruise to the Caves of northeast coast
This 5-hour private tour along Corfu’s northeast coast explores stunning sea caves. It offers opportunities to swim, snorkel, and marvel at the limestone formations while sailing in calm waters. The tour is suitable for all ages, with safety equipment provided.
Reviewers mention the beauty of the caves and the peaceful pace, making it a relaxing, scenic experience. The private setting ensures a tailored trip — ideal for families or couples looking to avoid crowds.
Bottom Line: Perfect for nature lovers wanting a tranquil, scenic day exploring Corfu’s caves.
15. Daily Sailing experience between Naxos and Paros coastline
This 9-hour cruise is a comprehensive sailing adventure around Naxos and Paros. It emphasizes crystal waters, coastal scenery, and swimming spots specially chosen for their beauty. The experienced crew ensures safety and comfort throughout.
It’s a great fit for those who want to combine sightseeing with plenty of time to swim and relax. The tour’s length and focus on water activities make it great for active travelers wanting a full day at sea.
Bottom Line: A top choice for experienced sailors or travelers seeking a full, scenic day with ample swimming.
How to Choose Your Perfect Greek Sailing Experience
When selecting the right sailing trip, consider your budget, your interest in private vs. group experiences, and whether you prioritize water activities, cultural sites, or simply relaxing. For example, couples seeking romance might prefer the Corfu Sunset Private Yacht, while families might enjoy the Heraklion: Catamaran Sailing to Dia for its straightforward, kid-friendly amenities.
If you want a luxury experience with gourmet food and open bar, the Milos private yacht or the Santorini private catamaran are excellent options. For more active days full of snorkeling and hiking, the Balos shared cruise offers a comprehensive experience. Booking early and considering the season will ensure availability for your preferred dates.
Greece offers an impressive range of sailing adventures—whether you want a peaceful day exploring secluded beaches, a private luxury cruise, or a lively group outing. Two or three standout choices are the Daily Sailing Tour from Skopelos for its balance of intimacy and natural beauty, and the Milos private yacht for a truly tailored, luxurious day. No matter your style, Greece’s waters promise unforgettable memories—so book early and prepare to enjoy some of the best sailing in Europe.
