10 Skiathos Sailing Trips That Earn the Fare

1.Full-Day Sailing Cruise with Lunch

★★★★★★★★★★4.9 · 307 reviews · 7 hours · from $165Number one

Join Lambros, Anastasia and George aboard the Aeolus for a seven-hour sailing day from Skiathos. Swim at Tsougria, Kastani and quiet coves, snorkel with provided gear, paddleboard, and eat a fresh Greek lunch cooked on board. Choose a shared small-group cruise or private outing, with route changes possible in poor weather.

“This was our 2nd time on this beautiful yacht. The whole experience is amazing. The time spent sailing and the quiet coves we visited were wonderful. Our hosts were incredible, the food is fabulous . This trip is not to be missed 😍”

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2.Day sailing Skiathos Skopelos with lunch on Rainbow yacht

★★★★★★★★★★5.0 · 262 reviews · 7 hours (approx.) · from $163Highest rated

Join Yannis and Angeliki aboard Rainbow yacht for a relaxed seven-hour sail from Skiathos. Swim at Tsougria, Panormos, and Skopelos beaches, enjoy Greek food cooked on board, and see Mamma Mia filming areas. Weather may shape the final stop, with Lalaria, Dasia, or Arkos possible.

“Wonderful experience, the stops are great for swimming and snorkelling . The food is lovely and plentiful, as are the drinks. We had a great day, thank you.”

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3.From Skiathos Marina: Yacht Sailing Day Trip with Lunch

★★★★★★★★★★4.8 · 180 reviews · 8 hours · from $175

Spend eight hours aboard the MARINA yacht with skipper Lambros and crew, sailing from Skiathos toward Skopelos. Breakfast, drinks, towels, snorkeling gear, fishing gear, SUP use, fruit salad, and a Greek taverna lunch are included. Expect several swim stops, changing routes when wind requires it, and a small-group feel.

“Super great day out and the crew was so kind and easy going with us! Highly recommend to anyone looking for a day trip from Skiathos”

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4.Wooden Sailboat Full- or Half-Day Trip with Meal

★★★★★★★★★★5.0 · 88 reviews · 8 hours · from $159

Spend the day aboard Katerina, a 62-foot wooden sailboat built in 1958, with captain Dimi and a friendly crew. Swim and snorkel at beaches such as Lalaria, Kastani, Panormos, Tsougria, and Arkos, then enjoy snacks, a fresh Greek meal, wine, fruit, and dessert. Choose a full-day cruise or half-day sunset sailing.

“Fantastic experience! We were well looked after throughout the day with cold drinks, snacks and bbq lunch. Beautiful swim stops.”

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5.day sailing trip with swim stops and lunch

★★★★★★★★★★4.9 · 69 reviews · 8 hours · from $157

Join Captain Babis and the Kallisti Sailing crew for an eight-hour trip between Skiathos, Skopelos, Arkos, and Tsougkrias. Swim in quiet coves, use the paddleboard and snorkel gear, and enjoy a fresh lunch with drinks aboard a spacious 46-foot sailboat. Small groups, flexible routes, and calm local know-how make this a relaxed day at sea.

“This was the best boat day I’ve ever been on! Stops were beautiful locations only accessible by boat and timing was perfect! Lunch and snacks were delicious and having drinks on board with a good playlist was a perfect plus. The best part of our day with Kallisti Sailing was Captain Mpampis and his family… they were all so helpful, friendly and accommodating. We will definitely be booking again when we come back to Skiathos!”

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6.All-Inclusive Sailing Cruise-Skiathos & Nearby Islands with Lunch

★★★★★★★★★★5.0 · 52 reviews · 7 hours (approx.) · from $156

Spend about seven hours aboard the wooden boat Nireas with Maria and Captain George, stopping at three or four coves around Skiathos and nearby islands. Swim, snorkel, paddleboard, eat a generous meal, and enjoy drinks as the route changes with the weather. The shared cruise leaves Skiathos New Port at 10 a.m. and returns there.

“A wonderful day hosted by the beautiful, hardworking Maria. She and captain George were so friendly and so obliging , the food provided was amazing, the atmosphere on board made up of a mixture of nationalities was very good and the group numbers kept to a comfortable 15 . All in all 5 star”

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7.All-Inclusive Sailing Cruise with Lunch!

★★★★★★★★★★4.9 · 51 reviews · 7 hours · from $159

Sail aboard Nireas from Skiathos New Port, with Maria and the crew guiding you to three or four swim stops around Skiathos and Skopelos. Expect snorkeling, paddleboarding, snacks, fruit, drinks, and a Greek lunch. Wind may change the route, keeping you on Skiathos for calmer water and secluded beaches.

“This is exactly what I dreamed a boat trip would be like. The boat was stunning, with a good amount of space and comfy seating. It was such a nice journey throughout with plenty of room to relax. Maria was so lovely and accommodating throughout, always asking if there was anything we needed as well as explaining where we were going and about the different islands. The food was delicious and the trip had just the right amount of people- not too crowded but just enough to have a nice little conversation with everyone which was really nice☺️ again thank you so much, me and my partner had an amazing…”

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8.All Inclusive Daily Sailing with BBQ on Board

★★★★★★★★★★5.0 · 34 reviews · 8 hours (approx.) · from $168

Join Kosta and Aristotle of Sporades Sailing for an eight-hour cruise from Skiathos. Swim at Lalaria, explore the Dasia sea cave, visit Skopelos coves, and stop at Arkos or Tsougrias. Breakfast, a BBQ lunch, drinks, fruit, and paddle-surfing activities are included for a maximum of 10 people.

“Awesome experience with Kosta and Aristo, very friendly and accommodating. The food was great too, been on many day trips but never had that much food on board. Highly recommended!”

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9.Private Sailing Trip with Lunch and Snorkeling

★★★★★★★★★★4.9 · 26 reviews · 8 hours · from $1,767 per boat

Join Captain George for an eight-hour private sailing trip from Skiathos to Tsougrias, Skopelos, and Arkos. Swim, snorkel, try stand-up paddleboarding, visit Kastani Beach and the Dasia blue sea cave, and eat lunch at a traditional taverna in Neo Klima. The boat carries up to 12 people, with snacks, coffee, soft drinks, Wi-Fi, and fruit included.

“Wonderful experience. Captain George was fantastic. Beautiful sights and had plenty of time at the swimming locations. Highly recommend. Was the highlight of our holiday.”

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10.ARGO III Skiathos Day Sailing, Breakfast, Lunch, Drinks

★★★★★★★★★★5.0 · 3 reviews · 7h 30m · from $127Cheapest deck

Join Captain George and Mairi aboard ARGO III for a 7.5-hour sailing trip from Skiathos to Skopelos. Expect breakfast, fruit, snacks, drinks, a Greek lunch, beach stops, snorkeling, paddle boards, and music, with birthday cake and champagne available for celebrations.

“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!”

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