Island Hopping: Santorini Catamaran Charter Cruise with a skipper

Discover the magic of Greece with a private seven-day catamaran cruise around Santorini and beyond. For just over $8,500 per group (up to 10 people), you can enjoy a tailored sailing experience, exploring iconic islands, swimming in crystal waters, and relaxing in your own private cabin. The journey includes a professional skipper, hostess, and all the comforts of private accommodation, making it a luxurious yet authentic way to see the Greek islands.

What we love most about this experience is how customizable it is — you decide where to go, whether it’s the volcanic islands, secluded beaches, or famous hotspots. Plus, the reviews highlight the crew’s attentiveness and the incredible views, both of which elevate this from a typical boat trip to a memorable voyage. The only consideration? The price might be steep for some, but the privacy, flexibility, and quality of service often justify the cost. It’s perfect for couples, friends, or families who want a private, high-end sailing adventure without the rush of larger tours.

This tour is ideal for travelers seeking a luxurious, personalized experience with the freedom to craft their own island-hopping route. If you value private cabins with en suite bathrooms, attentive service, and the chance to explore at your own pace, then this cruise will suit you perfectly. It’s also a great choice if you’ve already seen the main sights of Santorini and want a more intimate, comfortable way to discover lesser-known spots.

This experience made our article of We Rank Santorini’s 15 Top Sailing Experiences.

Key Points

• Customizable Route: You choose your destinations, offering flexibility unlike pre-set tours.
• Private Accommodation: Stay overnight in comfortable cabins with private bathrooms, adding a touch of luxury.
• All-Inclusive Service: Skipper, hostess, linens, towels, snorkeling gear, and safety equipment are included, ensuring a hassle-free trip.
• Excellent Crew: Consistently praised for their friendliness, attentiveness, and professionalism.
• Spectacular Views: Expect breathtaking scenery, with many reviews mentioning the stunning ocean and island vistas.
• Value for Luxury: While pricey, the private, tailored experience often receives high praise for its quality and personalized service.

In-Depth Review: A Truly Personal Sailing Journey in Greece

The Experience You Can Expect

This seven-day Island Hopping cruise offers more than just a day at sea; it’s a chance to craft your ideal Greek island visit aboard a Lagoon Catamaran. Starting from Santorini or another Greek island (with an extra cost), you can create a route that suits your interests — whether exploring famous spots or discovering hidden gems.

What makes this experience stand out is the total customization. Unlike traditional tours with fixed itineraries, you tell your skipper which islands or beaches you want to explore. You might hop from Santorini to nearby islands like Thirassia or plan longer stays at special spots. The flexibility is perfect for those who prefer to go off the beaten path or spend more time swimming and relaxing.

Detailed Itinerary Breakdown

The tour’s itinerary is designed to be flexible, with each “stop” essentially a day in one location, allowing you to set your pace and priorities. For example, many guests love the chance to visit the Greek islands, enjoy swimming in the sea, and snorkel with provided equipment. The first day typically involves setting sail from Santorini (or another port). The subsequent days are spent exploring various islands, with reviews mentioning spectacular views and friendly crew making every stop enjoyable.

The final day usually involves returning to your starting point, but the route is adaptable. With the skipper and hostess onboard, you can enjoy a luxurious and private experience, with your own cabins that include four private bathrooms. It’s a treat to sleep in your room after days of exploring, and the reviews rave about the comfortable cabins and linens.

What the Crew Adds to Your Experience

A recurring theme in reviews is how knowledgeable, friendly, and attentive the crew is. Reviewers frequently mention crew members by name, praising their hospitality, local knowledge, and ability to make everyone feel special. One reviewer even says, “Never in my life have I met someone like Peter,” highlighting how certain crew members can make the experience memorable.

The crew’s focus on safety, comfort, and fun creates a relaxed atmosphere where you can truly unwind. Snorkeling gear, safety equipment, and a dinghy boat are included, so you can get close to the water and explore without worry.

The Value of This Experience

While the price of $8,558.73 might seem high compared to group tours, the private, customizable nature of this cruise offers significant value. You’re paying for privacy, flexibility, and a high level of service. Many reviews mention the quality of food, the attentiveness of staff, and the breathtaking scenery as making it worth the cost.

Guests often comment on the informative and fun crew, who make stops educational and lively, adding depth to what could otherwise be a simple boat ride. The inclusion of linens, towels, snorkeling gear, and private bathrooms enhances comfort and convenience, making the trip feel like a true escape.

Practical Tips for Travelers

• Arrive prepared: Bring sunscreen, swimsuits, sunglasses, and a windbreaker — the weather can change, and you’ll want to be comfortable.
• Consider the weather: The tour is weather-dependent — poor conditions could lead to cancellations with full refunds or rescheduling.
• Bring your own drinks and snacks: Food and drinks are not included, so plan accordingly if you want to indulge.
• Book early: The popularity and limited group size mean this experience can fill up quickly, especially during peak season.
• Think about the overnight stay: If you love the idea of sleeping onboard, the private cabins provide a truly immersive experience.

Who Is This Tour Best For?

This private sailing cruise is perfect for those who want full control over their island-hopping experience. It’s ideal for couples, friends, or families who value privacy, comfort, and personalized service. If you’ve already seen the main sights of Santorini and are craving a quieter, more relaxed way to explore the Greek islands, this is a superb choice.

It suits travelers who don’t mind a premium price for a more luxurious, intimate, and flexible experience. The reviews indicate that people who appreciate friendly, knowledgeable guides and stunning scenery will find this trip particularly rewarding. If you love snorkeling, swimming, and dining onboard with excellent service, this cruise offers a top-tier experience.

FAQ

How many days does the cruise last?
The cruise lasts about 7 days, giving you plenty of time to explore different islands and relax onboard in style.

Are meals included in the price?
No, all meals and drinks are not included, so you’ll need to bring your own or arrange that separately. However, guests often rave about the crew’s hospitality and the opportunity to enjoy your own cuisine onboard.

What is the group size?
The cruise is private, accommodating up to 10 people per group, which means you get an exclusive, tailored experience without strangers.

Can I customize my route?
Yes, you can create your own sailing route, choosing the islands and spots you’d like to visit, making each trip unique.

What amenities are available onboard?
You’ll have private cabins with four bathrooms, linens and towels, snorkeling gear, safety equipment, and a dinghy boat for water excursions.

What is the cost per group?
The total price is approximately $8,558.73 for up to 10 people, offering a good value for a high-end, private experience.

Is WiFi available onboard?
No, WiFi is not included, so plan for disconnected relaxation or use your mobile data.

In summary, if you seek a luxurious, flexible, and private sailing experience in Greece, this seven-day catamaran cruise offers incredible value. With attentive crew, stunning views, and private accommodations, it caters perfectly to travelers who want to explore the Greek islands on their own terms, in comfort and style. Whether celebrating a special occasion or simply craving an authentic sea adventure, this trip promises unforgettable memories and a true taste of the Aegean.