5-Day Crewed Charter “The Discovery” – Lagoon 42 catamaran

An Authentic 5-Day Sailing Adventure in the Cyclades

Picture this: five days of sailing through Greece’s most iconic islands on a sleek Lagoon 42 catamaran, with a crew dedicated to your comfort. For $10,732 per group (up to six people), you’ll experience the beauty of Santorini, Koufonissi, Paros, Antiparos, and Ios, all from the perspective of a luxurious vessel, with the flexibility of private group travel.

What we love about this experience is how it combines the thrill of being at sea with plenty of opportunities to relax and take in some of the most breathtaking scenery Greece has to offer. The boat itself offers a comfortable and intimate setting, with three private cabins, three bathrooms, and attentive crew support. It’s perfect for travelers who want to avoid crowded tours, enjoy personalized service, and truly live the Greek island lifestyle.

One potential consideration is the fixed route—it’s subject to weather conditions and may be modified, so flexibility is key. But overall, this trip suits those looking for a luxury escape that balances adventure with comfort—ideal for couples, friends, or small families wanting a memorable, authentic experience.

You can check availability for your dates here:

Key Points

• Luxury and Comfort: A well-equipped Lagoon 42 catamaran with private cabins and crew to ensure a smooth sailing experience.
• Unrivaled Island Stops: Visit Santorini’s caldera, Koufonissi’s pristine beaches, Paros’ charming villages, Antiparos’ tranquility, and Ios’ famous beaches.
• All-Inclusive Value: Meals, linen, and fuel included, with transparent expenses managed through the APA deposit.
• Flexible and Private: Private group experience with options to cancel or reschedule with 24 hours’ notice.
• Authentic Greek Experience: Local English and Greek-speaking crew, personalized attention, and the chance to explore Greece’s most celebrated islands from a unique perspective.
• Stunning Views & Authentic Atmospheres: From Santorini’s caldera to Ios’ crystal waters, the scenery is consistently impressive.

Exploring the Sights and Experiences

Embarking at Vlychada Marina

The journey starts with a private transfer from your chosen pickup point—be it your hotel or a nearby accessible location—to Vlychada Marina. This smooth start sets the tone for a hassle-free adventure. Once onboard, you’ll meet your crew, who will take care of all the details—think of them as your personal Greek hosts.

Santorini’s Caldera and Koufonissi

Your first day is a highlight: sailing through Santorini’s famous caldera offers dramatic views of volcanic cliffs, whitewashed villages, and blue-domed churches. We loved the way the boat glides smoothly past this world-renowned scenery, offering plenty of photo opportunities without the crowds.

Koufonissi, your first island stop, is a paradise for lovers of unspoiled beaches. The island’s tranquility and natural beauty give it a feeling of being a hidden gem. Its pristine beaches and clear waters are perfect for relaxing, swimming, or just soaking up the sun. You’ll stay overnight here, giving plenty of time to explore or simply enjoy the quiet.

More Great Tours Nearby

Paros: The Charm of a Classic Greek Island

The next morning, you’ll sail to Paros, a must-see for its picturesque villages, lively harbor, and traditional atmosphere. One of the reasons many travelers love this part of the trip is the chance to see a more authentic side of Greece—away from the tourist-heavy spots. We read reviews praising its “charming streets” and “vibrant local life,” making it a perfect spot for a laid-back afternoon or evening.

Antiparos: Serene and Idyllic

Day three brings you to Antiparos, a small, white-washed island with a peaceful ambiance. Its calm, blue-green waters and simple beauty evoke the feeling of a quiet retreat. The island feels like a canvas of white with dashes of green and blue, offering calm and serenity. Optional land excursions here might include wandering the narrow streets or enjoying a quiet dinner by the water.

Ios and Manganari Beach

The fourth day is a favorite for many: sailing to Ios, home to its legendary Manganari Beach. Known for its crystal-clear waters and soft sands, it’s a spot that’s often compared to scenes from “The Big Blue.” Many reviews highlight the spectacular landscapes and the opportunity to swim in waters that seem to go on forever. Spending the night here lets you appreciate the island’s natural beauty and perhaps enjoy some local nightlife if you’re inclined.

Returning to Santorini

On the final day, the boat makes its way back to Santorini. Seeing the caldera from the water one last time is a spectacular way to end the trip. Your disembarkation is smooth, with a driver waiting to take you to your next destination or accommodation.

The Practicalities and Value

The Itinerary

This cruise covers some of Greece’s most famous islands in a manageable five-day schedule. Each stop offers a different experience—whether it’s Santorini’s iconic views, Koufonissi’s quiet beaches, or Ios’s lively sands. The route, while flexible depending on weather, is designed to maximize scenic beauty and relaxation.

What’s Included and What’s Not

The price covers transportation, crew, meals, linen, and fuel, which means you don’t need to worry about hidden costs. The APA deposit is a transparent way of managing additional expenses like mooring fees and food & drinks, and it’s refunded if unused. However, off-board activities are paid separately, so if you want to explore or do land-based excursions, you’ll need to budget for those.

The Vessel and Crew

The Lagoon 42 catamaran is praised for its modern, comfortable design. It’s a small vessel, with a maximum capacity of six passengers, making it ideal for those seeking an intimate experience. The crew, usually a skipper and a deckhand, are described as passionate and attentive, ensuring your comfort at all times. Their knowledge and friendliness add a personal touch that many reviews find memorable.

Flexibility and Booking

With options to cancel up to 24 hours in advance and a reserve-now, pay-later policy, booking this trip offers peace of mind. It’s suited for travelers with flexible plans who value personalized experiences over large group tours.

What to Bring

Essentials include a hat, swimwear, towel, camera, sunscreen, and comfortable clothes — simple items that will keep you comfortable as you enjoy the sunshine and scenery.

Deep Dive into the Experience

The Itinerary in Detail

The first day’s sail through Santorini’s caldera is often described as breathtaking. Many travelers comment on how the boat allows you to appreciate Santorini’s volcanic cliffs with a less crowded, more personal perspective. The calm waters and the gentle breeze make for a relaxing start.

Koufonissi’s beaches are often described as pristine and quiet, with many reviewers noting their “crystal waters” and “perfect swimming conditions.” The overnight stay gives you ample time to explore or simply unwind on the beach.

Paros impresses with its charming villages and lively harbors, offering a taste of authentic Greek island life. Many enjoy wandering its narrow streets, discovering local tavernas, and soaking in the relaxed atmosphere.

Antiparos is often lauded for its serene beauty. The island’s white-washed architecture and tranquil waters make for excellent photos and peaceful walks.

Ios is frequently highlighted for its spectacular beaches, especially Manganari, famous for its striking landscape and crystal waters. Reviewers mention swimming here as an unforgettable highlight.

On the final day, the return trip to Santorini provides a beautiful farewell, with views that many describe as simply stunning.

Authenticity and Personal Touches

Guests appreciate the personalized service from the crew, who often share local stories and tips. The small group size helps foster a friendly, intimate atmosphere, making it easier to connect—and relax—during the trip.

The Experience of Living on Board

The vessel’s modern amenities and the attention to detail in meal preparation mean that you’re well-cared for. Many reviews mention the quality of breakfast and the included meals, often noting that they are hearty and well-presented.

The Cost and Value

While $10,732 might seem steep at first glance, the package includes luxury accommodation, all meals, transportation, and the experience of sailing through some of Greece’s most beautiful islands. Comparing this to land-based trips combined with private transportation and guided tours, it offers a more relaxed, all-in-one experience with the added bonus of being on a yacht.

Who Is This Trip For?

This cruise is ideal for adventurous travelers who seek exclusivity and comfort. If you love the idea of waking up to new island vistas each day, enjoying personalized service, and sailing on a modern vessel, you’ll find this experience rewarding. It’s perfect for small groups, couples, or friends wanting a luxury yet authentic Greek island adventure.

However, those who prefer more active land-based exploration or are sensitive to weather changes should consider whether the fixed route and seasonal sailing conditions suit their plans.

The Sum Up

This 5-day sailing adventure through the Cyclades offers a rare blend of luxury, authentic Greek charm, and stunning scenery. You’ll get a chance to see some of the most beautiful islands from a perspective few travelers experience—on the water, with the wind in your hair and the sun on your face.

If you value personalized service, quiet beaches, and scenic sailing, this trip provides excellent value. It’s a great choice for small groups or couples who want a luxury escape with an authentic touch. While the price may seem high, the experience of sailing through Greece’s iconic islands aboard a modern, well-equipped vessel makes it worth considering.

For those who want a relaxed, intimate, and scenic Greek island adventure, this cruise checks all the boxes, promising unforgettable views and genuine moments at every turn.

FAQ

What is included in the price?
The price covers transportation from your pickup point, the skipper and deckhand, daily breakfast and one additional meal, linen and bedding, and fuel. All expenses like mooring fees and food & drinks are managed via the APA deposit.

Can I cancel or reschedule?
Yes, you can cancel up to 24 hours before the trip for a full refund. The booking also allows you to reserve now and pay later, offering flexibility if your plans are not yet firm.

How many people can fit on the vessel?
The Lagoon 42 has a maximum capacity of six passengers, making it an intimate experience with personalized attention from the crew.

Are off-board activities included?
No, all costs for off-board activities are paid separately by the customers.

What should I bring?
Bring a hat, swimwear, towel, camera, sunscreen, and comfortable clothes for sailing and exploring the islands.

Is the route fixed?
The company might modify the route depending on weather conditions or other factors, but the main stops are Santorini, Koufonissi, Paros, Antiparos, and Ios.

This 5-day cruise offers a fantastic way to explore Greece’s iconic Cyclades in comfort and style, with plenty of opportunities to enjoy beaches, local culture, and breathtaking views—all from a well-appointed yacht with attentive crew support.

You can check availability for your dates here: