Where to Sail: the 10 Best Skiathos Boat Trips

1.Mamma Mia Island and Beach Day Cruise

★★★★★★★★★★4.4 · 717 reviews · 7 hours · from $63Our pick

Sail from Skiathos to Skopelos aboard the Kalypso boat, stopping at Kastani, Panormos, and Milia Beach. Expect Mamma Mia music, film-location stories, swimming time, a tavern lunch stop, and an optional €16 visit to Agios Ioannis Chapel. Pickup is available from main-road bus stops outside Skiathos Town.

“Love it overall! Maybe the only negative thing was that the boat was packed and it was difficult to find a spot to sit. Everything else was great and the places that we visited were amazing!”

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2.Skopelos and Alonissos Boat Trip with Stops

★★★★★★★★★★4.8 · 543 reviews · 9 hours · from $73

Spend nine hours island-hopping from Skiathos to Skopelos and Alonissos aboard the Agios Nikolaos. Walk Skopelos Town, visit Alonissos Old Town, photograph the Blue Caves and Mamma Mia sites, then swim from the boat near Kastani Beach. Expect music, dancing, jokes, and helpful commentary from the lively crew, including the much-mentioned Kyriakos.

“It was a wonderful trip. The boat was very comfortable, the music was great. It was a well-organised very fun and very full tour. Hello-hellloooo...Kyriakos, the attendant, was the star of the boat and the trip. His narration was very humorous, his dancing was wonderful, he added great value to the tour. It was an unforgettable trip.”

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3.Sea and Sun Island Day Cruise

★★★★★★★★★★4.2 · 399 reviews · 7 - 8 hours · from $56Best value

Sail from Skiathos on the Kalypso for 7 to 8 hours, stopping at Lalaria Beach, Kastro, a lunch and swim stop, and Tsougria Island. An English-speaking guide such as Tatiana or Demetra helps explain the route. Bring swimming shoes, cash, and a towel, and expect changes if wind or rough seas affect the north coast.

“Llaria beach was such a highlight, so beautiful and a must do if visiting skiathos. We stopped at two other locations which were very nice, the lunch stop had very little to do, it would have been nice to be somewhere that potentially had some nice walks, we did have a wander around but mainly ended up looking at peoples lovely houses.”

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4.Full-Day Sailing Cruise with Lunch

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

Sail from Skiathos at 10:15 aboard Aeolus with captain Lambros, Anastasia, and George. Expect a relaxed small-group day with stops around Tsougria, Skopelos, Kastani, Argos, and Dasia, plus snorkeling, paddleboarding, swimming, and a freshly cooked Greek lunch with drinks.

“It was a lovely day, went in the sea a couple times which was gorgeous and had a delicious dinner. They had a nice level of guidance and leaving us to it which was perfect. Would definitely recommend.”

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

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

Spend eight hours aboard Marina with skipper Lambros and his crew, sailing from Skiathos toward Skopelos. Swim at Lararia, Tsougria, Kastani, Hovolo, Dasia, or Arkos when conditions allow, use the included SUP and snorkeling gear, and eat lunch at a local taverna. Breakfast, snacks, drinks, towels, fruit salad, and coffee are provided.

“It was a perfect day at sea! We stopped at two beautiful beaches, went for lunch and then went to see Lalaria even though the waves were too big to stop there, but we all really wanted to see the beach. And then we stopped for another wonderful swim. There were snacks and drinks on board and we had everything we needed. We will remember this day as one of the best days on our vacation! We would recommend to anyone who loves to sail, loves to swim in clear blue waters, hates crowded beaches and just wants a good day on the sea!”

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

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

Spend up to eight hours aboard Katerina, a 1958 wooden sailboat built by Georgios Psarros. Captain and guide Dimitri take you to hand-picked beaches for swimming and snorkeling, while an onboard chef serves Greek food, snacks, fruit, dessert, wine, water, and soft drinks. Choose a full-day cruise or a half-day sunset trip.

“The most beautiful trip of my life. We originally used the 4-hour trip, but 2 days before we were offered to go for the whole day for the same money. A huge big thank you for it, because this way we could spend our whole day on a beautiful boat tour. Secondly, I am gluten sensitive and they took care of this with incredible kindness. Speaking of the food, it was perfect. Every second hour they brought us some snacks, alcoholic and non-alcoholic drinks and water. In addition, we visited the most beautiful islands. We had about 30-45 minutes in each place, which was enough for everything, we could swim,…”

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7.Cruise to Lalaria, Kastro, and Tsougris

★★★★★★★★★★3.7 · 80 reviews · 7 hours · from $56

Spend seven hours circling Skiathos aboard Kalypso, with an English-speaking tour leader and stops at Lalaria Beach, Kastro, Katigioris or Asselinos, and Tsougris Island. You get swimming time, a look at the old capital, and a long lunch break. The schedule is scenic, but weather can change the route and Kastro time is short.

“Dobrý deň, nakoľko nebolo dobré počasie - veľmi veterno, sme neboli na Lalarii. Cesta loďou bola veľmi nebezpečná v mnohých úsekoch, bolo lepšie radšej plavbu deň predtým zrušiť. Nevideli sme to čo bolo plánované. S pozdravom Erika Nosianová”

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8.day sailing trip with swim stops and lunch

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

Join Captain Babis aboard Kallisti, a spacious 46-foot sailboat, for an eight-hour private or small-group day on the Sporades. Expect secluded coves, swim and snorkeling stops, SUP, fresh local lunch, drinks, and a relaxed sail around Skiathos, Skopelos, Arkos, and nearby islands.

“We had a truly amazing boat trip with Barbis and Marta! Both of them were incredibly friendly and welcoming, and they went out of their way to make sure everyone felt comfortable and had a great time. Even though the wind conditions weren’t ideal that day, Barbis and Marta handled everything perfectly — they adjusted the route and brought us to calmer, beautiful beaches so we could still enjoy the day to the fullest. The food that Barbis prepared on board was absolutely delicious — definitely a highlight! Throughout the trip, they constantly checked in with us, offering drinks, making sure we were doing well, sharing stories, and creating a…”

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9.All-Inclusive Sailing Cruise with Lunch!

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

Spend 10:00 a.m. to 5:00 p.m. aboard Nireas, sailing from Skiathos toward Skopelos with host Maria. Expect three or four swim stops, snorkelling, paddleboarding, Greek food, fruit, snacks, and drinks. The route changes with the wind, and on rough days the crew stays near Skiathos for calmer coves.

“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!”

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10.Boat Cruise with Dinner & Sunset Viewing

★★★★★★★★★★5.0 · 34 reviews · 7 hours · from $188

Spend seven hours with George, Giannoula, and their son on a traditional family-run cruise for up to eight people. Swim and snorkel at Tsougria, Arkos, Lalaria, and other boat-only spots, see caves and Skiathos Castle, then share homemade Greek dishes, wine, sweets, and sunset views on the way back.

“It was one of the best cruises we have been on. The family were wonderful and the food was excellent. The swimming stops were amazing and we all had so much fun on the paddle board (or off the paddle board more like!).”

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