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

Introducing the All-Inclusive Sailing Cruise in Skiathos

This all-inclusive sailing cruise offers a fantastic way to experience the beauty of the Greek islands, especially Skiathos and Skopelos, from the deck of a well-maintained yacht. With a full day running from 10 a.m. to 5 p.m., this tour combines scenic swimming spots, relaxing sunbathing, and delicious food — all in a small, intimate group setting. The reviews consistently praise the friendly guides, especially Maria and Giorgio, for their helpfulness and warm hospitality, making each trip feel more like a day with friends than a typical tour.

What I particularly like about this experience is how flexible and accommodating it is, especially in adjusting to weather conditions. If the wind picks up, the crew shifts the route along the southern coast of Skiathos, which means you still get those stunning views and swim stops without battling rough waters. Also, the inclusion of snacks, a main meal, and unlimited drinks keeps everyone comfortable and energized. Plus, the chance to spot dolphins and other wildlife adds an exciting touch to the day.

One potential consideration is the group size — with a maximum of just 12 travelers, this trip feels cozy and personalized. But if you’re seeking a larger, more bustling boat, this might not be your ideal choice. Still, for those looking for a relaxed, intimate experience in a stunning setting, this cruise hits all the right notes.

Key points / Takeaways

• Small group size ensures personalized attention and a relaxed atmosphere.
• Flexible route adapts to weather, often including hidden beaches and calm swim spots.
• Excellent guides like Maria and Giorgio receive high praise for their friendliness and helpfulness.
• Multiple swim and snorkeling stops provide ample opportunity to cool off and explore the underwater world.
• All-inclusive food and drinks make it easy to relax without worrying about extra costs.
• Wildlife sightings, including dolphins, add a memorable element to the trip.

Starting from Skiathos Port: The Best Way to Begin Your Day

The tour kicks off bright and early at 9:00 a.m. from Skiathos Port, with most travelers arriving around 30 minutes prior. The meeting point at the sailing yacht Nireas, part of the PlainSailing.com fleet, is easy to find and near public transportation, which is a bonus for those relying on local transit. The crew’s friendly communication beforehand — from confirming dietary needs to explaining the day’s plan — sets the tone for a smooth adventure.

The boat itself feels more like a private yacht than a generic tour vessel, with a maximum of 12 guests. This small group size creates a cozy atmosphere, perfect for chatting with fellow travelers or simply soaking in the scenery without the noise of large crowds. The crew, especially guides Maria and Giorgio, are praised for their warmth, knowledge, and ability to make everyone feel at home.

The Itinerary: What You Can Expect

The full-day trip runs from 10:00 a.m. to 5:00 p.m., with a suggested arrival by 9:30 a.m. to get settled. The route varies depending on weather conditions — on windy days, the boat sticks close to the southern coast of Skiathos, ensuring a smoother ride. This flexibility means you often get extra time at some of the best swim spots or hidden beaches that aren’t accessible by land.

The primary focus is on swimming, snorkeling, and paddleboarding, with equipment provided onboard. Expect around 34 scenic swim stops, which might include both well-known beaches and secret coves, especially if the crew wants to avoid the wind. Several reviews highlight how these stops are carefully chosen to maximize comfort and beauty, with some lucky travelers even spotting dolphins along the way.

The food is another highlight. Snacks, a substantial main meal, fresh fruits, and unlimited water and non-alcoholic drinks are included, with moderate alcohol service (about 3-4 drinks per guest). One reviewer was especially happy to find the food “fantastic” and appreciated the relaxed, friendly atmosphere maintained by the crew.

Highlights of the Swim and Snorkel Stops

You’ll love the variety of beaches visited — some are lively and bustling, others quiet and secluded. The snorkeling gear makes it easy to explore the underwater life, and paddleboarding is a fun bonus for those wanting a bit more adventure. According to reviews, guides like Maria are not just friendly but also very informative, sharing tips and local insights that add depth to the experience.

Weather and Route Considerations

Weather plays a significant role. When the wind is strong, the crew adapts by sticking closer to the coast, which means fewer long-distance crossings and more time in protected areas. This flexibility is crucial because it ensures a safer, more comfortable experience for everyone, while still offering plenty of opportunities to relax and enjoy the scenery.

Food and Drinks: A Feast on the Water

The onboard lunch is consistently praised, with some reviewers calling it “beautiful” and “delicious.” The crew caters to dietary needs if notified in advance, including vegetarian or gluten-free options. The variety of snacks and fruits ensures you’re never hungry between swim stops, and the unlimited non-alcoholic drinks keep everyone refreshed under the sun.

Wildlife and Special Moments

Several testimonials mention the thrill of spotting dolphins, which adds an extra layer of magic to the day. The guides’ ability to spot wildlife and point out local features greatly enhances the experience, making it more than just a boat ride.

Who Is This Tour Best For?

This trip suits travelers who enjoy intimate, relaxed outings with a focus on swimming, snorkeling, and beautiful scenery. It’s perfect for those who appreciate good food, friendly guides, and a flexible itinerary that adapts to weather. The small group size and personalized service make it ideal for couples, families, or friends seeking a special day on the water away from the crowds.

Price and Value Analysis

At around $145 per person, including meals, drinks, and equipment, this tour offers excellent value given the personalized service and quality of the experience. The reviews show that many guests felt the food, guide, and overall atmosphere justified the cost. Compared to larger group tours, the small size and flexible route make you feel like a guest rather than just another ticket number, elevating the experience.

If you’re looking for a relaxed, well-organized way to explore Skiathos and nearby islands from the water, this cruise is hard to beat. The guides’ friendly approach and the quality of the included food make it stand out as a genuine, enjoyable adventure. It’s especially suited for travelers who value intimate settings, stunning scenery, and the chance to spend a day swimming in crystal-clear waters with the comfort of onboard snacks and drinks.

While weather can influence the route, the crew’s flexibility ensures you’ll still have a memorable day. Just remember to book well in advance — the tour tends to fill up about a month ahead — so you can secure your spot for a day full of sun, sea, and Greek charm.

Frequently Asked Questions

How early should I arrive for the tour?
It’s best to arrive by 9:30 a.m. to check in and settle before the 10 a.m. departure.

Where does the tour start and end?
The tour departs and returns to Skiathos Port, at the PlainSailing.com Yacht Charter dock.

What’s included in the cost?
Snacks, a main meal, fresh fruits, water, non-alcoholic drinks, snorkeling and paddleboarding equipment, and some alcohol in moderation.

Can dietary restrictions be accommodated?
Yes, if you let the crew know in advance, they can cater to vegetarian, gluten-free, or other dietary needs.

What if the weather is bad?
If weather conditions are unsuitable, the tour will be canceled or rescheduled at no extra cost, with full refunds offered.

How many people will be on the boat?
A maximum of 12 travelers ensures a small, friendly group.

Are there any hidden costs?
No, the price covers everything except optional extras or fees that you might encounter at some swim spots.

What should I bring?
Bring sun protection, a towel, a hat, and perhaps a waterproof camera; everything else — food, drinks, and equipment — are provided.

Is paddleboarding easy for beginners?
Yes, paddleboards are included and suitable for all skill levels, and guides are happy to help newcomers.

Are dolphins likely to be seen?
While wildlife sightings depend on luck, some guests have enjoyed spotting dolphins during their trip.

This sailing cruise in Skiathos offers a delightful blend of scenic beauty, comfortable amenities, and authentic Greek hospitality. It’s a perfect way to spend a day on the water, making memories that will stay with you long after you leave the Aegean.