Under sail · SKIATHOS SAILING TRIPS
Good skiathos sailing trips fill up weeks ahead and the settled-weather days go first. Below: the 11 to book early, what each includes and how they differ.
Review of Skiathos’s 7-hour sailing cruise with Skopelos, Mamma Mia beach, swimming stops, snorkeling, and freshly cooked Greek lunch.
“We were feeling like home Family atmosphere Very nice Greek food I highly recommand this tour”
Sail from Skiathos to Skopelos aboard Rainbow yacht, swim at Tsougria and Panormos, enjoy Greek lunch, drinks, and relaxed island views.
“Yannis, Angelica and Naya( their beautiful German Shepherd) were just so relaxed about everything. From the time we came aboard—( 12 people) till we returned to port. There was plenty of room with several bean bags on Rainbow -their yacht. The swimming spots were sensational including a cave Yannis pointed out to us. The lunchtime meal Angelica prepared was authentic & plentiful Greek meal . They provided a lovely variety of cold drinks throughout the day. And an added bonus was seeing a pod of dolphins swim up to us as we were returning. “Sailing and snow” day charters were 5 star relaxed Skiathos and outer islands sailing! You only…”
Spend eight hours sailing from Skiathos to Skopelos with swim stops, snorkeling, SUP, Greek taverna lunch, drinks, and a small-group yacht.
“Relaxed sailing, lots of drinks and snacks provided during the day, and lunch (inc water) in a Greek water-side taverna, all included in the price (you pay extra for different drinks at lunch time). Lots of swimming stops. Clear clean water. Lovely day sailing, stopping, swimming, chatting.”
Review of Skiathos Katerina Traditional Sailing, with swim stops, Greek lunch, snacks, wine, practical tips, costs, and who should book.
“Best activity in Skiathos! Captain, mate and chef went all out. Food was delicious and plenty of it. Dimitri was able to tell us about every stop and was very hospitable. Captain made every effort to keep us away from crowds including adjusting the itinerary to get ahead of the crowds”
Review of Kallisti Sailing’s Skiathos day sail, with secluded swim stops, fresh lunch, SUP, snorkeling, and practical booking tips.
“We had an unforgettable sailing trip in Skiathos with Captain Babis! ⛵️ He was super friendly, welcoming, and made us feel right at home on the boat. We saw so many beautiful places, enjoyed amazing views, and the food on board was absolutely delicious. Babis made sure everything was perfect from start to finish – it was the ideal mix of adventure, relaxation, and great company. Highly recommend this experience to anyone visiting Skiathos! 🌊✨”
Sail from Skiathos aboard Nireas for swim stops, homemade food, paddleboarding, drinks, and quiet Aegean coves.
“This was a brilliant trip - I was travelling solo but felt totally at ease and met some lovely people on board including our wonderful host Maria and sailor George. The boat is spotlessly clean and very comfortable with plenty of shade if needed. The food was plentiful and excellent quality. We made several stops in coves for swimming and snorkelling. It was all very relaxed. I thoroughly recommend this trip.”
Sail from Skiathos to Skopelos for swim stops, Greek lunch, paddleboarding, snorkeling, and a relaxed small-group day at sea.
“Amazing Skiathos Sailing Trip! Our sailing trip around Skiathos was an absolutely fantastic experience! The boat was beautiful, and the food was delicious, offering a true taste of local flavors. We immediately felt like part of a family with the incredible crew. We stopped at some stunning swimming spots with crystal-clear waters. Highly recommended for an unforgettable and relaxing day on the sea!”
Review of Skiathos’ small-group sailing day with Lalaria, Skopelos, BBQ, swimming, drinks, and attentive local hosts.
“It was a pleasure having Kostas and Aristo with us, because they are an incredible duo capable of enjoy all the crew and explore new places. We were able to see the best beaches even before all other big tours, Indeed it was fantastic making this experience alone. However, all the entraitment and the food was amazing starting in the morning till later afternoon. I would recommend this tour to anyone is willing to have good time with friends”
Review of a private Skiathos sailing trip to Tsougrias, Skopelos, Dasia cave, and Arkos with lunch, snorkeling, and swimming.
“Escursione molto bella Capitano simpaticissimo e molto competente Attenzione a chi soffre di mal di mare a guardare le previsioni perché se c’è molto vento si sente tanto il movimento su questo tipo di Barca”
Spend 7.5 hours sailing from Skiathos to Skopelos with Greek food, drinks, swimming, snorkeling, SUPs, and Captain George.
“An unforgettable day on the Argo III! Warm welcome, tasty snacks and fruits, a delicious meal in a Greek taverna, and a relaxing drink on board. The route was beautiful and we discovered amazing hidden spots. Highly recommended – perfect from start to finish!”
Review of a private Skiathos yacht cruise with swim stops, Skopelos beaches, onboard breakfast, captain-led routes, costs, and practical tips.
“This was a great activity! Katrina did a great job with communication and Captain Christos did a wonderful job making a great day for us. The boat was very comfortable and we went to some very nice spots. The food and champagne was much appreciated. Overall, it made our visit to Skiathos.”
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