Halkidiki’s stunning coastline, characterized by crystal-clear waters, rocky coves, and lush forests, makes it a perfect playground for sailing. Unlike many destinations where you’re limited to land-based sightseeing, Halkidiki offers access to secluded beaches, hidden coves, and untouched islands that are best reached by boat. Whether you’re after a luxurious private cruise, a lively sunset sail, or a small-group adventure exploring remote coves, this region has something for every sailor. We particularly like the Day Sailing Trip in Halkidiki for its flexibility and access to locations you won’t find on your own — a true highlight for those craving authentic, off-the-beaten-path experiences.
Halkidiki is also known for its variety of tours—ranging from half-day excursions to multi-day voyages—that cater to different interests and budgets. Some tours emphasize privacy and luxury, while others focus on discovering nature and local culture. No matter your style, you’ll find options that let you enjoy the sea at your own pace. Below, we’ll explore the top sailing experiences in Halkidiki, helping you pick the perfect trip.
Quick Overview
This list includes luxury private cruises, small-group yacht trips, sunset sails, and multi-day adventures. Each offers a unique way to enjoy the Greek coastline:
– Private cruises with personalized touches
– Short, lively trips to secret bays
– Sunset tours perfect for romance
– Longer sailing trips for deeper exploration
Now, let’s set sail through the best options Halkidiki has to offer.
1. Day Sailing Trip in Halkidiki
At number 1, the Day Sailing Trip in Halkidiki offers the perfect escape from crowded beaches. For around $398.97 per person, this 7-hour tour takes you to isolated coves and hidden beaches accessible only by boat. Your professional skipper guides you through the turquoise waters of the Mediterranean, where you can swim, snorkel (gear provided), and relax onboard. The yacht features drinks, snacks, and Greek mezze, making it an ideal choice for celebrating special occasions or just unwinding in style. The itinerary includes stops at Toroneos Gulf and Porto Carras’ secret bays, ensuring you see the region’s most scenic spots.
Guests praise the tour’s relaxed atmosphere and the chance to discover areas not reachable by land. Perfect for small groups or couples who want a luxurious, personalized experience, this cruise is a fantastic way to enjoy Halkidiki’s coastline without the crowds.
Bottom Line: For a full-day escape into serene waters with excellent amenities and personalized service, this trip hits the mark.
2. 5 Hours from Kassandra: W Sithonia Coves & Islands Yacht Sailing
Number 2 on our list is the 5-hour tour, which costs about $69.96 per person. It’s ideal for those who want a taste of Halkidiki’s beauty without committing to a full day. This small-group trip from Kassandra takes you to the West Sithonia Islands, where you’ll explore secret caves and secluded coves in Porto Carras. The tour emphasizes learning about the area’s history and culture while providing plenty of opportunities for swimming and relaxing onboard.
Guests love the personalized attention from the captain and the chance to find quiet, pristine swimming spots. It’s suitable for travelers who want a shorter, intimate experience focused on authentic exploration rather than just sunbathing.
Bottom Line: A short, highly personalized trip perfect for families or groups seeking a relaxed day among unspoiled waters.
3. Private Sailing Cruise in Halkidiki, Greece
For around $460.96 per group, the Private Sailing Cruise in Halkidiki offers an exclusive experience that mimics hanging out with a local friend who owns a gorgeous boat. This [7-hour], fully customizable tour departs from Ormos Pana and explores Diaporos Island and Vourvourou Bay. Expect to visit beautiful beaches, crystal waters, and enjoy swimming and snorkeling in calm, clear seas. The yacht’s interior and deck are carefully curated for comfort, with snacks and drinks provided.
What makes this tour stand out is the luxury, privacy, and flexibility. Guests often mention the yacht’s cleanliness, the attentive crew, and the chance to create a bespoke itinerary. Ideal for couples or small groups celebrating a special occasion, this cruise delivers an intimate, high-standard experience.
Bottom Line: If privacy and customization matter most, this private cruise offers the best bang for your buck with a personal touch.
4. Half Sailing Cruise to Secret Bays
Number 4 is the Half-Day Sailing Cruise, perfect for those short on time but craving a sensory-rich experience. For approximately $338.19 per person, you’ll sail through Toroneos Gulf and visit hidden bays that are difficult to access by land. It’s a condensed version of the full-day trips, but it offers just as much excitement and scenic beauty.
Guests describe it as a “bomb full of stimuli,” with plenty of swimming, snorkeling, and relaxing onboard. This tour is well-suited for travelers who want to enjoy the sea but don’t have a full day to spare. The focus on exploring less crowded spots makes it a top pick for adventure lovers and nature seekers alike.
Bottom Line: A fantastic choice for a quick but fulfilling sailing adventure with all the scenic highlights.
5. Kassandra: West Sithonia Coves and Islets Sailboat Tour
Sailing between Kassandra and Sithonia, this 5-hour tour includes stops at Kelyfos Island and secret coves. Priced from around $68.23, it attracts those looking for a semi-VIP experience with small groups (up to 8). Highlights include snorkeling among marine life, exploring hidden beaches, and relaxing in the sun.
Guests appreciate the chill atmosphere and the friendly skipper, with reviews praising the private, less crowded feel and the chance to see the islands and coves that are inaccessible by land. It’s best suited for travelers seeking a balance of guided adventure and personal space.
Bottom Line: Great for small groups wanting an intimate, relaxed day of sailing with lots of opportunities to swim and snorkel.
6. 3 Hours Kassandra Sunset Sailing Yacht Tour
Number 6 offers a short but memorable 3-hour sunset sail, costing about $44.71 per person. Departing from Chrousso marina, you’ll cruise past beautiful coastlines and enjoy the spectacle of Halkidiki’s sunset. It’s ideal for romantics or families with children, as it combines stunning scenery with a relaxed atmosphere. Snorkeling gear is included, and refreshments like fruit and wine are provided.
Guests love watching the horizon turn fiery colors, creating a perfect backdrop for photos or a quiet moment with loved ones. The sunset experience is a quick escape into the magic of Halkidiki’s coast, without committing a full day.
Bottom Line: A budget-friendly, romantic option for sunset lovers looking for a relaxed evening at sea.
7. Halkidiki: Private Sailing Yacht Cruise Swim in Blue Waters
Costing about $94 per person, this private sailing option offers a 7-hour journey on a Bavaria 40 sailboat. It’s perfect for those wanting a personalized experience with the freedom to swim, snorkel, and explore unique spots. The itinerary includes stops in Spalathronisia and Kelyfos Island where calm, clear waters invite swimming.
Reviewers comment on the friendly captain, comfortable boat, and the beautiful coves discovered along the way. This trip is suited for groups or couples seeking a semi-private charter that combines adventure with luxury.
Bottom Line: A flexible, private option that’s great for those seeking intimacy and plenty of swimming.
8. 5 Hours from Sithonia: Sailing trip secluded coves & Islands
Number 8 is a 5-hour trip, priced at about $68.23 per person, focusing on exploring west Sithonia’s secluded coves and Porto Carras. It’s perfect for travelers who want to avoid the crowds and find quiet, untouched beaches. The tour is highly praised for its snorkeling and sailing opportunities, with Captain George often highlighted as friendly and accommodating.
Reviewers mention the beautiful coastlines and the quiet, exclusive spots visited. Ideal for those who enjoy quiet nature, snorkel gear, and sailing in calm waters.
Bottom Line: Excellent for travelers seeking serenity and a chance to explore Halkidiki’s less visited corners.
9. Halkidiki: 7 Hours Private Cruise with Sailing Boat
Number 9 is a 7-hour private cruise, priced at $802 per group. It offers a full day of exploring remote bays, hidden beaches, and crystal-clear waters. The itinerary includes stops at Spalathronisia, Lemos, and Kelyfos Island, with options to snorkel, swim, or just relax onboard. The boat’s onboard amenities include fresh fruit and local drinks, making it a luxurious escape.
Guests describe it as a “high-standard” experience with customizable stops and abundant swimming opportunities. This tour is for travelers who want privacy, comfort, and a full day of exploration with a small group or family.
Bottom Line: The best choice for those wanting a comprehensive, private day on the water with tailored options.
10. 2-Day Halkidiki Sailing Cruise
A rare opportunity, this 2-day cruise offers an immersive experience. Priced at $954.37 per person, it includes accommodation onboard, visits to unapproachable beaches, and hidden beauties. The itinerary features overnight stays and multiple stops at Porto Carras, Kelyfos, and other secluded spots. Guests can swim, snorkel, and sail during the day, with plenty of time to relax onboard.
Reviewers highlight the luxury, professional crew, and variety of destinations. It’s perfect for those with a flexible schedule seeking a multi-day adventure that combines sailing, sightseeing, and relaxation.
Bottom Line: For seasoned sailors or adventurous travelers, this two-day trip provides a comprehensive, high-end experience.
11. Sunset Sailing Cruise Halkidiki
The 3-hour sunset cruise is a romantic highlight, costing roughly $283.61 per person. It departs from Halkidiki and takes you to watch the sun dip below the horizon while enjoying music, drinks, and relaxation onboard. Snorkeling equipment is included, and a bottle of wine and fruit complement the experience.
Guests describe it as “an absolute blast” and perfect for couples or small groups wanting a peaceful, scenic evening. With its intimate setting and breathtaking views, this tour is ideal for celebrating a special occasion.
Bottom Line: An elegant, picture-perfect way to end a day with a romantic sunset at sea.
12. 3-Hour Private Sunset Sailing Experience in Halkidiki
Number 12 offers a private 3-hour sunset experience for groups up to 9 people, priced at $418.88. Departing from Porto Carras, you’ll enjoy a swim stop as the sun approaches the horizon, and sip wine while listening to music. The trip includes night sailing back, providing a unique way to see Halkidiki’s coast under starry skies.
Guests comment on the friendly crew and the memorable sunset moments. It’s suited for those who want a more personalized, romantic experience with a touch of night adventure.
Bottom Line: Perfect for intimate groups or couples seeking a romantic, private sunset sail.
13. Kassandra: Golden Hour Sailing – Private Sunset Cruise
This 3-hour private sunset cruise for groups up to 8 costs $561. It offers a breathtaking view of Halkidiki’s coast as the sun sets and provides music, wine, and fresh fruits onboard. The cruise begins from Halkidiki Sailing and takes you through the Toroneos Gulf, with plenty of time for photos and relaxing.
Guests say it creates a magical atmosphere, ideal for celebrating anniversaries or romantic getaways. The focus on privacy and comfort makes it stand out.
Bottom Line: An elegant, intimate choice for a memorable sunset experience.
14. Full Private Day Tour Sailing Experience in Halkidiki
Number 14 is a 7-hour full-day private tour, costing about $682.52 per group. It includes stops at secluded beaches, private Porto Carras beaches, and Kelyfos Island. The trip offers options to sail, swim, snorkel, or stand-up paddleboard. The crew provides local music, fresh fruit, and drinks.
Guests praise the luxury, customizable itinerary, and variety of swimming spots. This tour suits travelers who want a comprehensive, luxurious day with plenty of opportunities for adventure and relaxation alike.
Bottom Line: Best for travelers wanting a flexible, all-in-one private experience in Halkidiki.
15. 3 Hours Neos Marmaras: Day or Sunset Sailing Tour
Finally, the 3-hour tour from Neos Marmaras offers daytime or sunset options for just about $40.72 per person. It visits Kelyfos Island and focuses on small groups for a more personal experience. Reviewers love swimming in turquoise waters and the relaxed pace. The sunset version is especially popular for its unforgettable views and calm atmosphere.
This tour is perfect for families or travelers on a budget but wanting to experience Halkidiki’s coast in style.
Bottom Line: An affordable, intimate way to enjoy Halkidiki’s beauty, whether during the day or at sunset.
How to Choose Your Perfect Sailing Experience
When selecting a sailing trip in Halkidiki, consider your budget, time availability, and interests. For example, if you want a luxury private cruise with full customization, the Private Sailing Cruise is ideal. If a shorter, scenic sunset is more your style, the Sunset Sailing Cruise offers a romantic, budget-friendly option. For travelers eager to explore secluded coves without a long commitment, the Half Sailing Cruise or Secluded Covet Tour provide excellent choices.
Book early, especially in high season, to secure your preferred dates and boat type. Think about whether a full-day adventure or a shorter trip suits your style, and match your choice accordingly.
Final thoughts
Halkidiki offers an impressive range of sailing experiences suited for all tastes—whether you’re after a private luxury cruise, a fun small-group adventure, or a romantic sunset sail. For those seeking luxury and privacy, the 7-hour private cruise or the 2-day sailing stand out as top options. If you prefer a more relaxed, budget-friendly approach, the sunset tours and shorter trips provide memorable moments without stretching your schedule.
Remember, the best way to enjoy Halkidiki’s coast is to get out on the water! With so many excellent choices, you’re sure to find the perfect match. Just book early, pack your sunscreen, and get ready for some of the best sailing Greece has to offer.