Halkidiki sailing excursions and boat rides from Kassandra or Sithonia

A sailing yacht day trip to Chalkidiki, Sithonia, or Kassandra. During your 2026 summer vacation, you should take a skippered sail for the day.

Group day sailing boat trips in Kassandra or Sithonia are unique experiences that let you see the stunningly beautiful Halkidiki region while basking in the warm Aegean sun. As you sail around this historic and mythical sea, you can find amazing hidden bays, beautiful beaches, and crystal-clear turquoise waters.

Kassandra and Sithonia are two of the most beautiful peninsulas in the Halkidiki area of Macedonia. They are surrounded by the Aegean Sea’s stunning waters. Group day sailing trips let you discover the beauty and depth of these two gorgeous peninsulas, both of which have long and fascinating histories.

Visitors who want to go on a group day sailing trip in Kassandra or Sithonia must first decide what kind of sailing adventure they want to experience.

Options include:

 
• 3-hour fishing trip

 

• 3-hour sunset sail

 

• 5-hour sail from midday to afternoon

Depending on the type of trip, you may be able to find secret coves, sail through islands, explore beaches and bays, and take in stunning views. After picking what kind of trip to take, the next step is to book your spot. This can be done at our sailing tour office in Kallithea, Kassandra (at the corner of Smyrnis and Konstantinoupoleos streets) or online. Transportation is included in the price if you are staying in or near Kallithea, Pallini, Kryopigi, Polyhrono, Haniotis, Pefkochori, Paliouri, or Chrousso Beach. If you have your own rental car, you can drive yourself and save some money. Neos Marmaras does not offer airport transportation, but most hotels and resorts in the area offer shuttle service to and from the port. There are trips available for all budgets and locations.

Prices for our group sailing trips include:

 
• the captain (skipper)

 

• fuel

 

• taxes

 

• boat rental cost

 

• traveler’s insurance

 

• docking and port fees

 

• water

 

• coffee or tea

 

• and transportation (if it’s available in your area).

Once the trip is paid for and the day of sailing arrives, everyone in your group needs to make sure they are ready by bringing the right clothing, sun protection, food, drinks, and snacks. Once the boat gets moving, it’s a great time to take in the beautiful scenery, the gentle motion of the boat, and the calm, peaceful mood out on the water. Depending on the type of trip you chose, the crew will make sure guests get to paddleboard (SUP), swim, snorkel, fish, and enjoy other activities.

Sailing for a day with a group in Kassandra or Sithonia is an amazing experience that lets you see some of the most beautiful parts of Greece in total comfort. Whether you go on a standard sailing tour, a fishing trip, a sunset cruise, or a full day trip, you can explore the gorgeous bays and beaches that surround the two peninsulas in the Halkidiki region of Macedonia.

It is a truly unique experience to sail around Halkidiki’s “legs” for a day. At 10:00 a.m., 1:00 p.m., or 7:00 p.m., we set out from Neos Marmaras port, Porto Carras marina, or Hrousos pier for a sailing tour of the Toroneos Gulf.

The best thing to do in the Halkidiki area is to join a group on a sailboat.

The Chalkidiki area is a sailor’s paradise. During your 2026 summer vacation, you’ll notice a sea breeze forms every day from noon until sunset. It provides just enough wind to make sailing fun, and it’s absolutely perfect for beginners who want to enjoy the amazing feeling of gliding with the wind on the water. Out here, it’s just you and nature. The Halkidiki area features beautiful beaches and a lush pine forest that goes right down to the water’s edge. It’s the perfect escape on a typical hot summer day in Greece. So, if you plan to spend your vacation in our area, you simply must do a boat tour—a trip with a captain on one of our sailing yachts to Sithonia or Kassandra.

From Thessaloniki, you can take day sails.

It takes 1 hour and 15 minutes to drive from Thessaloniki to Neos Marmaras, which might seem like a bit of a drive, but it is well worth it. If you choose this trip, you’ll enjoy a full day that includes driving through a beautiful pine forest on your way to one of the best times you’ve ever had on the water.

It is rated as one of the best Halkidiki excursions on TripAdvisor.
We can also help you arrange a rental car or a shuttle transfer for your group.

Halkidiki day sailing – Yacht charter starting points

From Gerakini, Psakoudia, Metamorphosis, Nikiti, Akti Elias, Lagomandra, Vourvourou, Ormos Panagias, Agios Nikolaos, and Pyrgadikia, it’s an easy trip to Neos Marmaras, Sithonia, Halkidiki, Greece, where our sailing tours begin. For guests coming from the first part of Kassandra—including N. Moudania, Nea Fokea, Athitos (Afitos), Sani, Kallithea, Kriopigi, Polychrono, Haniotis, Pefkochori (formerly Kapsohora), Paliouri, Loutra Agias Paraskevis, Skioni, Possidi, Fourka, and Siviri—our boat charters use the Hrousos pier. From the southern towns on the east coast of Kassandra, you can get a complimentary ride to Kalithea.

The route of the day trip to Halkidiki from Sithonia

Our first stop is Kelyfos, which is also called Helona (meaning “turtle”). The water here is incredibly clear, making it perfect for swimming or fishing. The rocky bottom is teeming with marine life. After that, once the normal sea breeze dies down, we set sail south for Gerochristos Island and Lemos Beach. Both sides of the sandbar that connects the peninsula to the mainland are surrounded by water. You’ll often spot the boats of famous movie stars anchored off the beach. We used to be the only ones going to Angelina Jolie’s favorite beach, but now it’s a popular spot. You can eat your lunch right on the boat. After lunch, we tour the secret coves south of Neos Marmaras and stop for one last swim before heading back to Kamenos, which is one of the most beautiful beaches in Halkidiki. In this spot, the lush green trees go all the way down to the clear water.
The route could change due to weather conditions, at the captain’s discretion, or if the guests want to do something else, like eat lunch while underway to get more sailing time in.

The schedule for the day trip to Halkidiki from Kassandra.

Depending on the tour you choose, we will pick you up from the Hrousos pier at Paliouri Beach at 10:00 a.m., 1:00 p.m., or 7:00 p.m.
We head out to Spalathronisia, Laimos Beach, and the tip of Gerochristou Island. The water is warm and crystal clear—far away from the crowds of tourists.
The last stop before heading back is Kelyfos Island.

This day sailing plan is absolutely perfect for birthdays, anniversaries, or any other type of celebration you can think of.

Surprise someone you care about or a friend!
Let us know in advance, and we’ll take care of the cake, champagne, wine, or whatever else you’d like as a special treat.

Only a hat, swimsuit, beach towel, sunscreen, and sunglasses are really necessary.

Join a luxury sailing yacht for a day trip! It will be the highlight of your trip to Halkidiki.

All our boats have a minimum capacity of 8 guests, a restroom, hot water, a fully equipped kitchen, safety equipment, a radio/CD player, a Bimini top (an awning over the cockpit for shade), cockpit cushions, and paddleboards (SUP). You will have one cabin at your disposal to store your belongings, change clothes, or let the kids rest.

For private trips, call us to book directly.

To join other groups for a sailing trip, book here:

or contact us for details and last-minute offers!