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Thessaly

Sailing Trips & Tours

Our most recommended Thessaly Sailing Trips & Tours

Full Day Sailing Trip around Skiathos Island

1. Full Day Sailing Trip around Skiathos Island

Depart from the new port of Skiathos at 10:00 am and make a first stop at the small island of Arkos. There you enjoy local snacks and cool juice before the first morning swim on a unique beach. Leaving the island of Arkos, the captain sets sail and you will have the opportunity to learn about sailing, try to navigate the boat or simply sunbathe on the deck. Sometimes you can admire the friendly dolphins which  accompany the boat! Next stop is the isle of Dasia with its blue cave, where you will dive and swim like never before! Afterwards will be the perfect time for local snacks on board, accompanied by an ouzu. Sail to the west side of Skopelos island, full of beaches with clear blue waters and pine trees next to the sea and an ideal spot for yet more diving and swimming. The captain will then take you to the beach of Panormos, which is difficult to find and thus very quiet. Swim and sunbathe almost by yourself before a lunch menu consisting of Greek homemade food is served. Plenty of wine and some fruit is offered as a dessert. Later the captain sets sail towards the island of Tsougrias where you can see a spectacular sunset. There you can swim one last time and taste a sweet delight offered by the crew. Then the trip comes to an end as the boat returns to the port of Skiathos.

Volos: Pagasetic Gulf Full-Day Sailboat Experience

2. Volos: Pagasetic Gulf Full-Day Sailboat Experience

Set off for a rejuvenating day with your friends or family on a sailboat adventure from Volos. Relax on board, swim in the stunning blue waters of the Pagasetic Gulf, and explore Trikeri Island. A cocktail, snacks, snorkeling gear, and paddle-boarding gear will be provided. Leave early in the morning to visit some secluded locations in the Pagasetic Gulf, such as Tzasteni, Prassouda Island, Milina, Afissos, and many small picturesque bays. Your skipper will navigate the boat safely while your hostess prepares snacks and more. Stop at secluded beaches and dive into crystal-clear waters. Dock at Trikeri Island. Explore the island on your own or bring food to cook on the boat. For a taste of the local cuisine, check out the few tavernas serving up Greek island delicacies. After lunch, enjoy a cocktail on board and even try your hand in sailing. If weather permits, you'll have the chance to snorkel or use the stand-up paddleboard available on board. End the day with a sure-to-be magical sunset as you return to the Volos port.

From Kassandra: 7-Day Greek Island Private Sailing Adventure

3. From Kassandra: 7-Day Greek Island Private Sailing Adventure

Start from Halkidiki, from Skiathos or Skopelos. The program that follows is indicative and starts from Miraggio Hotel Spa in Kassandra or Neos Marmaras in Sithonia. 1st Day. We put the luggage and supplies on board and a short briefing about the boat and the journey is made by the captain. We open sails for the island of Kyra Panagia and enjoy the Aegean by sailing. We moor in St. Peter’s natural bay. We can swim in the crystal clear waters and stay for the night. 2nd Day. We take our morning dive and eat our breakfast. We are heading for the beaches of Alonissos. In the afternoon we moor to Steni Vala or Patitiri. Here we have the opportunity to visit the amazing Old Chora Alonnisos, with the incredible sunset. One of the most beautiful of the Aegean! 3rd Day. We raise anchor and continue for the beautiful beaches of Alonissos. Our sea route goes to Skopelos and in the afternoon we arrive and we moor in the beautiful hora of Skopelos and stay overnight. The beautiful hora of Skopelos has everything, shopping, restaurants, tavernas, bars, clubs and whatever you want. 4th Day. We wake up and after we have taken our Skopelian pies for breakfast, we open sails for the beautiful beaches on the south of the island. When we are filled with sea and sun, we moor at the afternoon for an overnight stay in the natural bay of Panormos. One of the most beautiful coves in the Aegean! Here the picturesque taverns are on the waves and the scenery is idyllic. 5th Day. We untie the cables and take the bow to Skiathos. On the way we sail and stop for a swim in the islet of Tsoukria. An amazing islet with blue-green waters, a breath away from the port of Skiathos. Early in the afternoon we moor in the town of Skiathos, where we stay for the night. The cosmopolitan Skiathos has what your heart asks! 6th Day. We raise anchor and open sails for western Skopelos and its magical bays. One beach follows the other, with the scenery to be enchanting! At the end of the day we set in N. Klima or Glossa, two beautiful ports from where you can enjoy one of the most beautiful sunsets! Here you can enjoy fresh fish with a unique view! 7th Day. After we wake up and take our morning dive, we lift the anchor and get started for our base. Enjoying the route and sailing, we reach the area of Halkidiki. We swim at to the magical bays of Porto Carras and after the sunset we set in the harbor of N. Marmaras for our last night. The next day at 9.00am remove your luggage and depart from the boat with unique memories! The schedule can be changed. Depending on weather condition and costumer’s preference, after the captain’s agreement, who must first of all take care the safety of the crew and the boat.

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What people are saying about Thessaly

Overall rating

4.7 / 5

based on 14 reviews

A lovely day sailing to Skopelos on board the Diamanti with friendly, attentive host and competent skipper. We had plenty of stops at quiet bays to swim and snorkel, lots of drinks available and snacks and fruit. We stopped for a fantastic lunch in Skopelos which was also included in the price. I would say this is a really good value trip and I’d recommend it. There were 10 of us in total, perhaps 12 might have been a bit cramped on the deck for sunbathing, but overall it was a lovely day out sailing.

Well organised left as scheduled and took our family of 5 to some amazing coves to swim and snorkel. We had an excellent lunch and the crew could not do enough for us, the sun shone and we had a memorable trip would recommend to everyone, Thank you Natalie and the Captain

It was a very nice tour to some beautiful islands around Skiathos which some of them you can only reach by boat. The crew was very experienced, very chilled and friendly and everything was very relaxed and well organized. Next time round, we will surely do it again!

Natalie and Alkimonas were the best! Definitely recommend it if you are looking for something chill and relaxing.

Great day trip out, brilliant and friendly crew and would 100% recommend to all.