If you’re dreaming of sailing through the Greek islands aboard a luxurious yacht, a 5-day crewed charter like “The Discovery” on a Lagoon 42 might just be your ideal adventure. While we haven’t personally been on this exact tour, we’ve helped many travelers weigh their options for exploring the Cyclades by sea, and this experience offers a lot to love—think stunning views, all the comforts of a well-equipped vessel, and visits to some of Greece’s most iconic islands.

What really stands out is how this trip combines comfort with adventure. The crew’s focus on making your stay smooth and enjoyable is clear, and visiting islands like Santorini, Koufonissi, Paros, Antiparos, and Ios means you’ll get both lively scenes and tranquil spots. However, it’s worth mentioning that this is a more intimate experience—so if you’re picturing a big group or family with kids, you’ll want to make sure the setup matches your needs.

For those who enjoy a mix of scenic sailing, island hopping, and relaxed luxury, this tour could fit like a glove. But it’s also good to consider your preferences for off-boat activities and how much you want to explore independently once ashore. Overall, it’s best suited for travelers craving a seamless, scenic, and stylish way to see the Cyclades islands.

Key Points

Luxurious Experience: Sail comfortably on a well-equipped Lagoon 42 catamaran with professional crew support.
Prime Island Visits: Cover Santorini, Koufonissi, Paros, Antiparos, and Ios—each offering unique sights and vibes.
All-Inclusive Feel: Breakfast and meals are included, with the crew handling the daily upkeep and meal prep.
Intimate Group Size: Limited to six guests, creating a cozy, personalized atmosphere on board.
Flexibility & Convenience: Private transfers, and the possibility to reserve with flexible payment options.
Limited Off-Boat Activities: Extra expenses for offboard activities are not included, so plan accordingly.

You can check availability for your dates here:

An In-Depth Look at the 5-Day Cyclades Yacht Cruise

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Starting Point: Vlychada Marina, Santorini

Your adventure kicks off with a private transfer from your chosen location to Vlychada Marina. This is a smart touch, removing the hassle of figuring out how to get to the boat. From there, the crew will help you settle into your cabin and get ready for the journey ahead. The boat accommodates up to six passengers across three cabins, meaning a small group for a more intimate experience.

Day 1: Santorini to Koufonissi

Sailing through Santorini’s caldera sets the tone for an awe-inspiring trip. Santorini is famous for its dramatic cliffs and sunset views, but what you’ll really love is gliding past the island’s stunning volcanic formations as you head toward Koufonissi. This tiny island is a highlight for many—its natural beauty and tranquil vibe make it an ideal first stop. Expect to spend the night here, soaking up the peaceful island atmosphere and possibly catching a sunset view from the deck.

Day 2: Koufonissi to Paros

Next, you sail to Paros, which is often described as a must-see “sea” destination in the Cyclades. Paros combines traditional charm with lively towns—perfect for those who enjoy a bit of both. During the day, you might explore the charming streets of Naoussa or Parikia, with their whitewashed buildings and lively tavernas. But most people are eager to get back on the boat and enjoy the sunset from the deck, with the gentle sea breeze and panoramic views. An authentic Greek experience awaits here, with a relaxed island vibe.

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Day 3: Paros to Antiparos

Antiparos is a smaller, quieter island, often described as a white canvas with touches of green and blue. It’s perfect if you’re into serene landscapes and unspoiled beaches. This is where you can truly unwind—taking in the calm surroundings and enjoying the simple pleasures of island life. The crew will likely prepare a meal, and you can spend your evening strolling along the shoreline or relaxing on deck, taking in the peaceful atmosphere.

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Day 4: Antiparos to Ios

Moving onto Ios adds a lively contrast. Known for its vibrant nightlife, Ios also has some of the most spectacular beaches in the Cyclades—like Manganari Beach, which many describe as one of the best on the island. You’ll have plenty of time to swim, sunbathe, and relive scenes from “The Big Blue,” thanks to the crystal-clear waters. This day balances lively scenery with the chance to relax on soft sands and soak in breathtaking views. Spending your night here means waking up to some of Greece’s most picturesque landscapes.

Day 5: Back to Santorini

The final day involves sailing back to Santorini, giving you one last chance to admire the caldera’s iconic views. After disembarking, a driver will take you to your next destination, concluding your memorable island-hopping adventure. It’s a fitting end to a trip packed with some of Greece’s most photogenic and loved islands.

What This Tour Means for Travelers

This crewed yacht provides a luxury, hassle-free way to traverse the Cyclades, with a focus on comfort and convenience. You’ll enjoy the privacy of small-group travel, with the crew taking care of meals, upkeep, and navigation. It’s perfect if you prefer a curated experience over independent sailing or large tour groups.

The itinerary hits all the highlights—Santorini’s spectacular scenery, the tranquility of Koufonissi, the charm of Paros and Antiparos, and the lively beaches of Ios. The boat’s capacity keeps it intimate, but that also means you’ll want to be comfortable sharing space with a small group. The included meals and transfers help streamline the experience, while the focus on scenic stops makes it ideal for shutterbugs and those looking to relax in beautiful surroundings.

Price & Value

At $10,732 for a group of up to six, this experience offers a good balance of luxury and exclusivity. When you consider the inclusions—meals, transfers, and the personalized attention of the crew—the price aligns with a high-end, all-in-one holiday. However, off-board activities and extras aren’t included, so if you’re into exploring more independently or trying lots of local tours, you’ll need to budget extra.

The Experience on Board

Travelers consistently praise the crew’s passion and professionalism, which makes a big difference in creating a relaxing atmosphere. The vessel’s three cabins provide enough space for everyone to unwind privately, and the well-trained crew ensures a smooth, comfortable stay. The boat itself is modern, with the capacity for maximum six guests, which fosters close connections but also preserves privacy.

Practical Tips

Pack light, breathable clothes, and swimwear—most days involve sun, sea, and relaxation.
Bring a hat, sunscreen, and a camera to capture the stunning views.
Prepare for some sea days, so be comfortable with boat travel.
Off-boat activities are at your expense, so plan for extra costs if you want to explore islands more thoroughly.

Who Should Consider This Tour?

This experience is most suited for travelers looking for a luxurious, intimate sailing adventure with the convenience of a crew taking care of all logistics. It’s ideal for couples, small groups of friends, or even solo travelers who enjoy meeting like-minded explorers. If you’re after a lively party atmosphere, this might be a bit subdued—though Ios does bring some energy, so you can balance relaxing days with lively nights.

It’s also a good fit for those who value stunning scenery and seamless travel without the hassle of planning every detail themselves. Keep in mind, if you are looking for extensive off-board activities or traveling with young children, you might want to check other options or consider whether the boat’s size and schedule fit your needs.

Frequently Asked Questions

How many passengers can the vessel accommodate?
The Lagoon 42 has three cabins and can hold up to six guests comfortably, making it perfect for small groups seeking privacy and intimacy.

What’s included in the price?
The price covers transportation from your chosen pick-up point, a skipper and deck hand, daily breakfast, one additional meal, linen and bedding, and all expenses like fuel, taxes, and mooring fees covered by the APA deposit.

Are meals provided?
Yes, breakfast and one other meal (either lunch or dinner) are included. The crew handles meal prep, so you’ll enjoy fresh, delicious food during your trip.

Can I customize the route or activities?
The route can be modified due to weather or other conditions, but generally, the itinerary is set to include the key islands. Offboard activities are at your expense, so additional sightseeing or tours will need to be arranged separately.

Is there a cancellation policy?
Yes, you can cancel free of charge up to 24 hours before the trip, which offers good flexibility should your plans change unexpectedly.

What should I bring?
Pack a hat, swimwear, towel, camera, sunscreen, and comfortable clothes suitable for a warm, sunny climate. Don’t forget your sense of adventure!

Is this experience suitable for children or families?
The tour is designed for private groups and is not specifically marketed as family-friendly, especially considering the boat’s small size and the nature of sailing. It’s best suited for adult travelers or groups comfortable with boat travel.

Ready to Book?

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

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Final Thoughts

If you’re craving a taste of the Greek islands with a touch of luxury, this 5-day crewed sail offers a pretty compelling way to experience the Cyclades. It combines scenic beauty, comfort, and the chance to share a small-group adventure with like-minded travelers. While it’s not inexpensive, the inclusions and focus on high-quality service make it worth considering for a special occasion or a memorable escape.

The trip’s real strength lies in its balance—beautiful islands, comfortable sailing, and an intimate setting. It’s best suited for those who enjoy relaxed, scenic holidays with a dash of adventure, but don’t want to give up creature comforts. If you’re someone who appreciates stunning views, good company, and a hassle-free experience, this could be just what you’re looking for.