If you’re dreaming of a day spent aboard a spacious sailboat, gliding through the sparkling waters of the Aegean, this Daytrip with Diamanti Sailing Skiathos might just be what you’re after. We haven’t done this exact trip ourselves, but based on what travelers say and the detailed itinerary, it’s a solid choice for those looking to combine sailing, swimming, and a taste of authentic Greek hospitality in one package.
What we love about this experience is how it balances activity and relaxation — with plenty of swimming stops, a lovely lunch in Skopelos, and the chance to enjoy sailing on a well-equipped boat. We also appreciate the personal touch that comes from the reviews praising the knowledgeable captain and the intimate, friendly vibe of the trip. On the flip side, it’s worth mentioning some considerations, like the potential for windy conditions that might make seasickness a concern for sensitive souls. Overall, if you’re into sea, sun, and scenic stops, this tour seems to hit the mark.
This adventure suits travelers who want more than just lounging on a beach. It’s ideal for those who love the idea of sailing, discovering hidden caves, and stopping at iconic beaches like Kastani — the one from Mamma Mia! If you’re traveling with a group or celebrating a special occasion, the private charter option could add that extra touch of exclusivity. Now, let’s break down what makes this trip a worthwhile pick, and who might want to give it a miss.
Key Points

- Beautiful Stops for Swimming and Snorkeling: Expect 4-5 refreshing stops in crystal-clear waters, perfect for cooling off and exploring marine life.
- Sailing Experience on a Spacious Boat: The Beneteau Cyclades 50.5 offers plenty of space, cushions, and pillows for relaxing while sailing.
- Signature Highlights Include Dasia Blue Seacave and Kastani Beach: Unique spots that add a special touch to your day, especially if you’re a fan of movies or nature.
- Delicious Snacks and a Local Greek Lunch: Onboard snacks, drinks, and a hearty lunch in Skopelos make the trip enjoyable and filling.
- Flexible Itinerary, Weather-Dependent: While the plan is set, expect some variation based on weather conditions, which could affect stops or sailing times.
- Private Charter Available: For groups or special occasions, you can book the boat privately, up to 12 passengers.
The Itinerary: What You Can Expect

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Morning Departure and First Swim
The trip kicks off early, with the promise of punctual departure. The first stop is at Tsougrias Islands, where the clear waters beckon for a morning swim. The reviews highlight how much travelers appreciated the calm, inviting waters — a great way to start the day.
Sailing to Skopelos and Kastani Beach
Once everyone’s refreshed, the captain will get the sails up. Crossing over to Skopelos, you’ll enjoy the sensation of being under sail as the breeze fills the boat. The highlight here is visiting Kastani Beach, famous for its role in Mamma Mia! It’s a popular photo spot, and travelers love the chance to relax on the sand or swim in the sea.
Snacks, Swims, and Snorkeling
Back on the boat, you’ll enjoy light snacks and refreshing drinks as the captain navigates to the next swimming spot. Expect another swim, and perhaps a bit of snorkeling — the water clarity gets rave reviews, giving a good chance to see marine life. As one reviewer said, it felt like a personal trip with great care taken by the crew.
More Great Tours NearbyLunch in Neo Klima, Skopelos
The tour includes a stop in Neo Klima, where a traditional Greek taverna awaits. The lunch, although drinks are not included, is described as hearty and authentic, giving you a real taste of local cuisine. The reviews mention spaces that feel personal and away from mass tourism, adding to the genuine experience.
Exploring Dasia Blue Seacave
In the afternoon, the boat stops at Dasia Seacave, known for its striking blue waters and impressive rock formations. This is a photographer’s dream and a favorite among travelers who want to soak in stunning scenery.
Final Sail and Fruit Salad
After exploring the cave, the boat heads towards Arkos Island, with plenty of time to unwind on cushions and enjoy the breeze. Before heading back to Skiathos, you’re treated to fruit salad and more drinks — a sweet, refreshing way to end the day.
End of the Day
The trip wraps up with the return sail to Skiathos harbor, typically lasting around 8 to 8.5 hours. Travelers consistently mention how the experience is well-paced, with enough variety to keep everyone engaged and relaxed.
What Makes This Tour Stand Out?

The Boat and Crew
The Beneteau Cyclades 50.5 is praised for its spaciousness, offering plenty of room for lounging — cushions and pillows ensure comfort. The captain, often described as passionate and knowledgeable, makes a significant difference. Many reviews say they felt well cared for, and the personal attention makes the trip feel special rather than commercial.
The Stops and Sights
The variety of stops — from swimming in transparent waters, visiting a famous beach, exploring a blue cave, to eating at a traditional taverna — gives this trip a well-rounded appeal. The stops are well spaced out, ensuring enough time to enjoy each without feeling rushed.
The Food and Drinks
Snacks and soft drinks onboard keep you fueled, and the included lunch in Skopelos is seen as a highlight. While drinks at the tavern are excluded, this allows flexibility to choose what suits your taste.
The Authentic, Personal Vibe
Travelers love the feeling of being on a “trip with friends,” thanks to the friendly crew. The reviews mention that it avoids mass tourism, offering a more intimate experience.
Price and Value

At $154 per person for an 8-hour sailing adventure, this trip is reasonably priced considering the inclusions — snacks, drinks, Wi-Fi, and a proper Greek lunch. The experience offers a lot of value for anyone wanting a full day out on the water, exploring multiple sites, and enjoying quality time in a beautiful setting.
Compared to similar experiences, the private option (up to 12 passengers) might be the best choice if you’re celebrating something special or traveling with a group. The personalized service and exclusive access to the boat can make it worth the extra cost.
Things to Keep in Mind
- Weather Conditions: The itinerary varies depending on weather, so be prepared for potential changes. Windy days might make this trip feel more lively but could also cause seasickness.
- Seasickness: If you tend to feel unwell on boats, consider taking precautions, especially in windy weather.
- What to Bring: Sun protection, swimwear, towels, sunglasses, and biodegradable sunscreen are essentials. Don’t forget your ID or passport and beachwear.
- Not Suitable for Wheelchair Users: The boat isn’t designed for wheelchair access, so plan accordingly.
- Drinks in the Taverna: Drinks are not included with lunch, so budget for those separately if you want wine or soft drinks.
Who Is This Tour Best For?

If you’re someone who loves the idea of sailing, swimming in clear waters, and enjoying authentic Greek cuisine, this trip offers a well-balanced day out. It’s ideal for those who appreciate a personal touch from the crew and want to see some iconic spots like Kastani Beach and Dasia Cave.
However, if you’re particularly seasick or prefer a more leisurely, land-based experience, this might not be perfect. Also, those needing wheelchair accessibility should consider other options.
Overall, it’s a fantastic choice for sea lovers, adventure seekers, or anyone wanting to explore Skiathos and Skopelos from the water with ease and comfort.
Daytrip with Diamanti Sailing Skiathos, lunch included
FAQ

Is this tour suitable for children?
While the tour is generally family-friendly, it’s best for older children comfortable with boat trips and swimming. Seasickness could be a concern for younger kids.
What is included in the price?
The tour includes the boat trip, snacks, coffee, soft drinks, lunch (excluding drinks at the tavern), and Wi-Fi onboard.
Are drinks in the tavern included?
No, drinks at the lunch stop are not included, so you can purchase what you prefer there.
How long is the trip?
The trip lasts approximately 8 to 8.5 hours, depending on weather and conditions.
Can I book a private trip?
Yes, the boat is available for private hire with a maximum of 12 passengers, perfect for special occasions.
What should I bring?
Swimwear, towels, sunglasses, sun hat, biodegradable sunscreen, ID, and beachwear are recommended.
Is the itinerary fixed?
The plan might vary due to weather, but the main stops and activities are similar, focusing on swimming, exploring caves, and enjoying local cuisine.
Is there Wi-Fi onboard?
Yes, Wi-Fi is available for guests to stay connected during the trip.
Overall, this sailing tour offers a lively, scenic, and authentic taste of the Aegean Sea, combining adventure with relaxation. If you’re eager to spend a day on the water with friendly guides, enjoy beautiful stops, and indulge in good food, it’s a trip worth considering.
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