7 Sailing Trips in Skiathos, Priced and Ranked

1.Full-Day Sailing Cruise with Lunch

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

Review of Skiathos’ seven-hour Aeolus sailing cruise, with Skopelos, Mamma Mia beach, swim stops, snorkelling, and fresh Greek lunch.

“Loved it. The ship is well appointed and well kept with plenty of space for each pair or group. The lunch was excellent! When arriving at the meeting spot, it was slightly further than the geotag in a private looking area - so just walk out there. Labros is a fount of knowledge and we should have spent more time asking questions as he knew the area, history, ecology well and was very interesting and have great travel tips for the future. Smooth, calm travel and the beaches were lovely. Surprisingly more fish when snorkelling than expected and plenty of time to swim. A highlight of our trip from Aotearoa…”

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2.Day sailing Skiathos Skopelos with lunch on Rainbow yacht

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

Sail from Skiathos to Skopelos aboard Rainbow yacht for swimming, coastal views, homemade Greek lunch, drinks, and relaxed island stops.

“Everything about this experience was absolutely perfect. Every positive review you can read is spot on. Fantastic hosts...Yannis, Angelica & Naya. Plenty of space on the boat. Food was spectacular. Mellow, relaxing vibe the entire trip. Plenty of time to swim and explore at every stop. Thanks so much for the memories, our family of 5 loved it!”

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3.Day-Sailing Tour with Lunch on Board

★★★★★★★★★★5.0 · 191 reviews · 7 hours · from $165

Spend seven hours sailing near Skiathos and Skopelos with swim stops, snorkeling, paddleboarding, fresh Greek lunch, and a small crew.

“I booked this a few weeks in advance as availability was limited. We had a fabulous day sailing to different islands around Skiathos on the beautiful sailing boat. Only 12 of us so plenty of room to move around and chilll out on bean bags. The couple running it were lovely, welcoming, chatting, friendly but the star crew member was Nyla, the German shepherd who was dolphin spotting for us (unfortunately we didn't see any that day). There were 5 swim spots where they anchored and you could jump in the crystal clear waters if you wanted. Snorkels were provided and even had a go at paddle boarding with the…”

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

★★★★★★★★★★4.6 · 95 reviews · from $137Best value

Sail from Skiathos to secluded Aegean bays, swim, snorkel, enjoy a Greek taverna lunch, and return after eight relaxed hours at sea.

“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.”

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

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

Sail Skiathos on a 62-foot wooden boat with swim stops, snorkeling, fresh Greek food, wine, and a sunset half-day option.

“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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6.day sailing trip with swim stops and lunch

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

Sail around Skiathos and Skopelos on a relaxed 8-hour trip with swim stops, SUP, snorkeling, local lunch, and Captain Babis.

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

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

Sail Skiathos and nearby islands aboard Nireas with swim stops, homemade lunch, drinks, snorkeling, paddleboard use, and a small group.

“Fantastic day out with Merry & George the captain! The boat is beautiful and very clean and tidy. The day was fabulous with lots of swim stops against beautiful Greek island backdrops!! The food was also exceptional and lovingly homemade and plenty of it!”

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