Sailing adventures in Skiathos offer the perfect mix of island exploration and authentic Greek experiences. The most practical options include half-day and full-day trips on traditional wooden boats – perfect for travelers who want to combine swimming with local cuisine. I especially appreciate the 8-hour sailing excursions, which hit the sweet spot for experiencing secluded beaches while providing enough time for water activities. The private yacht cruises, though pricier, are worth considering for families or small groups wanting flexibility and personal attention.
I’m particularly fond of the classic wooden boat tours, which deliver the most authentic Greek maritime experience, complete with fresh-caught fish and access to hidden coves you simply can’t reach by land.
Check out our carefully selected sailing tours below.
Key Points
- Wooden Sailboat Day Trips from Skiathos harbor offer a personalized experience with knowledgeable crew and explore picturesque beaches for $142.68 per person.
- Day Sailing Trip with Swim Stops is an 8-hour excursion aboard a 46-foot sailing boat with access to secluded coves and activities like paddleboarding and snorkeling.
- Day Sailing Boat Trip from Skiathos Port is an 8-hour adventure to Aegean coves with swimming, snorkeling, paddleboarding, and an authentic Greek lunch in Skopelos for $126.82 per person.
- Private Sailing Adventure from Kassandra is a 7-day customizable small-group tour visiting Skiathos, Skopelos, and Alonissos with a well-equipped yacht and an experienced skipper.
- Private Yacht Cruise Experience is a 4-hour private yacht cruise around Skiathos with personalized service, hidden cove exploration, swim stops, and sunbathing on deck for $285.35.
Skiathos: Wooden Sailboat Full- or Half-Day Trip With Meal
Departing from the main harbor of Skiathos, the wooden sailboat trip around the island offers a full- or half-day adventure.
For $142.68 per person, you’ll explore Lalaria, Kastani, Panormos, Tsougria, and Arkos beaches, with opportunities to swim, snorkel, and savor local cuisine.
The 62-foot wooden boat, built in 1958, provides comfortable amenities like a wide deck, poof cushions, and electric toilets.
Enjoy morning and afternoon snacks, a freshly-cooked lunch, dessert, fruits, and wine, all while taking in stunning views.
The knowledgeable crew ensures a personalized experience and handles any emergencies with safety gear and first-aid.
With a 4.9/5 rating, this flexible sailing tour is a must for an unforgettable day on the Aegean Sea.
Read our full review: Skiathos: Wooden Sailboat Full- or Half-Day Trip With Meal Review
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Skiathos: Day Sailing Trip With Swim Stops and Lunch
Although the island of Skiathos offers many stunning beaches, some of the best spots are only accessible by boat.
That’s where the Skiathos: Day Sailing Trip With Swim Stops and Lunch comes in. This 8-hour excursion aboard a 46-foot sailing boat lets you discover beautiful, secluded coves and swim in the clear waters of Skiathos and Skopelos.
Enjoy a delicious lunch featuring fresh, local ingredients, and learn about the region’s history and culture from the captain.
With opportunities for paddleboarding and snorkeling, as well as a comfortable, relaxing atmosphere, this sailing trip is perfect for adults, families, and groups.
And with free cancellation up to 24 hours in advance, you can book with confidence.
Read our full review: Skiathos: Day Sailing Trip With Swim Stops and Lunch Review
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From Skiathos Port: Day Sailing Boat Trip With Lunch
Escape the bustle of Skiathos Port and embark on an 8-hour sailing adventure that takes you to the stunning, secluded coves of the Aegean Sea.
Enjoy a day filled with swimming, snorkeling, and paddleboarding as you explore the crystal-clear waters.
Savor an authentic Greek lunch at a traditional taverna in Skopelos.
The highly-rated crew provides exceptional service and assistance without being overbearing.
This customizable experience offers flexibility, with free cancellation up to 24 hours in advance.
At just $126.82 per person, it’s a great value for a memorable day on the water.
Don’t miss this opportunity to create lasting memories on the beautiful Aegean Sea.
Read our full review: From Skiathos Port: Day Sailing Boat Trip With Lunch Review
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From Kassandra: 7-Day Greek Island Private Sailing Adventure
Eager to explore the captivating Greek islands at your own pace?
Set out on a 7-day private sailing adventure from Kassandra. This small-group tour allows you to customize your itinerary, visiting the highlights of Skiathos, Skopelos, and Alonissos.
Sail aboard a well-equipped yacht with an experienced skipper, enjoying the flexibility to stop for swimming, hiking, or dining at quaint seaside tavernas.
With 4.9 out of 5 stars from 18 reviews, this private sailing trip offers an intimate and authentic way to discover the Sporades islands.
Prices start from €130 per person, making it an affordable way to learn about the Greek island lifestyle.
Read our full review: From Kassandra: 7-Day Greek Island Private Sailing Adventure Review
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Skiathos: Private Yacht Cruise With Swim Stops
Set sail on a private yacht cruise around the scenic island of Skiathos and enjoy a day of swimming, relaxation, and exploration.
This 4-hour tour offers a personalized experience with a small group, allowing you to discover hidden coves and private beaches. Hop off the boat for refreshing swim stops and soak up the sun on the deck.
The private speedboat provides pickup from your location, so you can start your adventure hassle-free. With a 5-star rating, this cruise is an excellent choice for those seeking an intimate and unforgettable sailing experience in Skiathos.
Priced at $285.35, it’s a premium option that delivers exceptional value.
Read our full review: Skiathos: Private Yacht Cruise With Swim Stops Review
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The Sum Up
Skiathos offers a range of sailing experiences, from day trips to multi-day adventures. You’ll discover picturesque coves, swim in crystal-clear waters, and savor local cuisine. Whether you prefer a private yacht or a traditional wooden sailboat, you’ll find an option that suits your interests and budget. With so many choices, you’re sure to have an unforgettable sailing experience in Skiathos.