Skiathos is a sailor’s paradise. Its crystal-clear waters, hidden coves, and scenic islands make it an ideal spot for sailing adventures. Whether you’re after a relaxing day on a yacht or a traditional wooden boat experience, Skiathos offers something for all. We especially love the Rainbow yacht day sailing trip, thanks to its intimate atmosphere and personal service. Imagine cruising through the Aegean with just a small group, enjoying delicious Greek food and swimming in secluded spots. For a more comprehensive experience, the All-Inclusive Sailing Cruise takes you around several islands with plenty of swimming, snorkeling, and onboard snacks. You can read about these adventures and more below.
Quick Overview
The list below covers a variety of Skiathos sailing experiences. From luxury yacht trips with gourmet meals to traditional wooden boat excursions, there are options for every taste and budget. Want a semi-private cruise with a small group? Check out the Skiathos Semiprivate Sailing Cruise. Interested in a private yacht for a special celebration? The Private Yacht Cruise offers exclusivity and personalized attention. For those seeking a classic sailing vibe, the Wooden Sailboat Full-Day Trip provides an authentic experience. Each tour offers unique features, so read on to find the perfect fit.
1. Day sailing Skiathos Skopelos with lunch on Rainbow yacht
At number 1, the Day sailing Skiathos Skopelos with lunch on Rainbow yacht combines affordability with a touch of luxury. This 55-foot sailing boat is designed to give you a relaxed, personalized experience. The small group size ensures you’ll get plenty of attention from the crew, Yannis, Angelica, and their German Shepherd Naya, who love sharing their passion for sailing. The tour includes several swimming and snorkeling stops, allowing you to explore the beautiful waters of Skopelos and Skiathos.
What makes this tour stand out is the friendly atmosphere and excellent service. Reviewers mention how relaxed and welcoming the crew is, with comments about the “plenty of room” and “amazing food.” You’ll enjoy a seven-hour journey with a balance of sailing, swimming, and relaxing on deck. The boat’s personal touch makes it ideal for travelers who want a semi-private experience without breaking the bank. The price of around $157 per person offers good value considering the small group size and quality service.
Bottom Line: If you want a cozy, memorable sailing adventure with friendly hosts and a focus on personal service, this trip on Rainbow yacht is hard to beat.
2. From Skiathos Marina: Yacht Sailing Day Trip with Lunch
Next up is the Yacht Sailing Day Trip from Skiathos Marina, which offers an eight-hour exploration of the Aegean’s beauty. This tour is perfect if you seek a full day of sun, sea, and relaxation, with the benefit of a professional skipper and hostess guiding the way. The itinerary includes swimming, snorkeling, and even dolphin sightings, making it a lively experience. Lunch is served at a typical Greek taverna in Skopelos, allowing you to sample local flavors.
This trip is highly rated for its balanced mix of adventure and comfort. Reviewers praise the crew’s helpfulness and the chance to discover “beautiful places” that are only accessible by boat. The boat is equipped for swimming and snorkeling, and the day includes plenty of drinks and snacks. It’s a good choice for travelers wanting a comprehensive day out with all the comforts and no worries. The approximate price provides good value for the length and quality of the experience.
Bottom Line: For a full day of sailing, swimming, and authentic Greek cuisine, this trip offers a seamless mix of fun and relaxation.
3. Skiathos: Wooden Sailboat Full- or Half-Day Trip with Meal
At number 3, the Wooden Sailboat Full- or Half-Day Trip is a nod to tradition. This 62-foot wooden vessel is designed by a renowned builder, offering a more classic sailing vibe. The itinerary is flexible, letting you choose between a half-day or full-day adventure with stops at beaches like Lalaria, Kastani, and Panormos for swimming and snorkeling.
The highlight here is the authentic experience of sailing on a traditional wooden boat while enjoying a freshly-cooked meal onboard. The crew shares local stories as you relax to music, sip wine, and watch the scenery pass by. The trip’s personalized approach, with options to adapt your stops, is perfect for travelers who want a mix of sightseeing, swimming, and culinary delights. Guests mention the helpful and humorous crew, and the food gets high praise for its quality.
Priced around $152, this experience offers good value for anyone interested in a more tangible connection to Greek sailing traditions. It’s ideal if you want a mix of adventure and culture in a traditional setting.
Bottom Line: For lovers of classic wooden boats and a flexible itinerary, this trip provides an authentic, relaxed sailing experience with excellent food.
4. Skiathos: day sailing trip with swim stops and lunch
Number 4 on our list is the Day Sailing Trip with Swim Stops and Lunch. This eight-hour tour is perfect for travelers wanting a laid-back day on the water. The 46-foot boat is cozy yet comfortable, with plenty of space for swimming, snorkeling, and relaxing. Captain Babbis guides you through secret spots between Skiathos and Skopelos, making it a personalized experience.
Reviewers appreciate the boat’s cleanliness and comfort, with mention of the bean bags on deck for lounging. The trip’s simplicity and focus on swim stops make it ideal for those who prefer a more casual outing rather than a structured tour. The lunch is included, and the day is filled with opportunities to unwind and enjoy the sea.
At around $147, this trip offers straightforward value for travelers who want a relaxed, intimate sailing day with good company and scenic swimming spots.
Bottom Line: If you prefer a simple, stress-free day with comfortable boat amenities and swim stops, this trip is a solid choice.
5. Skiathos Semiprivate Sailing Cruise
Number 5 is the Skiathos Semiprivate Sailing Cruise, which caters to small groups (maximum 6). Priced at roughly $144 per person, it guarantees a personalized experience with a crew that provides attentive service. The cruise includes beautiful swimming and snorkeling spots, along with the chance to enjoy local food and the company of like-minded travelers.
Guests praise the “great day sailing” with Yanni and Captain George, highlighting the relaxed atmosphere and stunning scenery. The small group size means you get a more intimate feeling, perfect for travelers who want to avoid crowded tours. The cruise lasts around 7 hours and offers a good mix of activity and leisure.
This trip suits travelers looking for an authentic, semi-private adventure that feels exclusive but accessible. The value is high given the small group size and quality reviews.
Bottom Line: For a more intimate, personalized sailing experience, this semi-private cruise offers excellent value and a chance to connect with fellow travelers.
6. All-Inclusive Sailing Cruise-Skiathos & Nearby Islands with Lunch
Number 6 is the All-Inclusive Sailing Cruise, which explores Skiathos, Skopelos, and nearby islands. For about $145, you get seven hours of sailing, swimming, snorkeling, and paddleboarding. This tour stands out for its inclusiveness—snacks, main meals, fruits, and drinks are all provided onboard, making it ideal for travelers who want a hassle-free experience.
The itinerary includes stops at various beaches and hidden spots, especially when weather conditions are challenging. Reviews mention the crew’s friendliness and the chance to see dolphins, which adds a special touch. The equipment for paddleboarding and snorkeling is provided, giving you plenty of ways to enjoy the water.
This tour is perfect if you’re after a comprehensive day with all amenities included. It suits active travelers who want variety but also value convenience and comfort.
Bottom Line: For a full-day, all-inclusive adventure with multiple island stops, this cruise delivers a lot of value and variety.
7. ARGO III Skiathos Day Sailing, Breakfast, Lunch, Drinks
Number 7 is the ARGO III Skiathos Day Sailing. This 7.5-hour trip emphasizes a premium experience, including breakfast, lunch, and drinks. The boat offers a VIP feel, making it ideal for celebrating birthdays or special occasions. The crew provides opportunities for swimming, snorkeling, paddleboarding, and enjoying water toys.
Guests describe the trip as “changing your life for one day,” thanks to its luxurious service and the fun, lively atmosphere onboard. The experience is tailored for those who want a memorable, upscale outing with plenty of options for water activities and gourmet meals.
At approximately $142, it offers good value for those seeking a more exclusive, celebratory experience. It’s suited for travelers who want to indulge and make special memories.
Bottom Line: For a luxurious, celebration-ready sailing day with excellent food and activities, this trip is the top choice.
8. Skiathos: Private Yacht Cruise with Swim Stops
Finally, the Private Yacht Cruise offers total exclusivity. For $1,694 per group (up to 8 people), you get a 7-hour personalized cruise between Skiathos and Skopelos. The captain steers you toward idyllic beaches and swimming spots, with all needs taken care of.
Reviewers love the comfort and flexibility. The captain’s careful planning and the food and champagne onboard make it a memorable, luxurious day. It’s perfect for special occasions or travelers wanting complete privacy. The trip’s exclusivity means you can customize your stops and activities.
It’s an investment, but if you’re traveling with a small group or celebrating something special, this private cruise provides unmatched comfort and flexibility.
Bottom Line: For privacy, luxury, and customization, this private yacht cruise is an excellent choice—be sure to book early.
How to Choose Your Perfect Skiathos Sailing Experience
When deciding on the best sailing tour, consider your budget, desired level of privacy, and what you want to get out of the day. If affordability and a friendly atmosphere are your priorities, the Rainbow yacht trip (link) offers excellent value. For a full day with all amenities included, check out the All-Inclusive Sailing Cruise (link). Those seeking intimacy or celebration may prefer the Semiprivate (link) or Private Yacht options (link).
Decide if you want the charm of a traditional wooden boat (link), or a more luxurious, VIP experience (link). Book early, especially for private options, to secure your preferred date and ensure you get the best experience.
Skiathos offers a wide range of sailing adventures, whether you’re after a relaxed day with friends, a luxurious celebration, or an authentic wooden boat trip. Each experience is uniquely suited to different tastes and travel plans. Whether you choose a small, intimate cruise or a private yacht for your special occasion, you’re sure to enjoy the stunning scenery and crystal-clear waters that make Skiathos a sailing haven.