Santorini: Private Cruise to Milos Polyaigos & Kimolos

If you’re eyeing a day out on the water around Santorini, this private cruise to Milos, Polyaigos, and Kimolos could be a compelling choice. While I haven’t personally taken this exact trip, I’ve gathered enough details to offer a thorough look at what you can expect—and whether it might be worth your time and money.

What immediately appeals is that this tour offers a personalized experience, with a private group of up to four people, and the chance to see some of the most stunning spots in the Aegean. The highlight for us? The opportunity to explore Kleftiko’s rock formations, swim in crystal-clear waters, and enjoy a leisurely few hours in Pollonia. On the flip side, the price tag of nearly $3,840 might put some travelers off, especially considering meals and extra activities aren’t included.

This cruise is well-suited for travelers who value privacy, flexibility, and a tailored itinerary. If you prefer small-group or private adventures over crowded tours, this could be a perfect fit. It’s also ideal if you’re comfortable with a full day on the water and are keen to explore lesser-visited islands beyond Santorini’s main hub.

Key Points

• Private group experience means personalized service and flexibility.
• Includes hotel transfers, making logistics smoother for travelers.
• Multiple stops for swimming, snorkeling, and sightseeing—great for water lovers.
• Scenic views and unique geological formations like Kleftiko and the pirate caves.
• No onshore meals included, so budget accordingly or plan to eat in Pollonia.
• Duration of around 10 hours, so you’re in for a full, adventure-packed day.

You can check availability for your dates here:

What You Can Expect from the Tour

This tour offers a blend of sightseeing, swimming, and relaxation, all with a dedicated crew guiding you through some of the most striking islands in the Aegean. The journey kicks off with a hotel pickup in Thera (Santorini’s main town), making the start seamless so you don’t have to worry about arranging transport. Once aboard a spacious, air-conditioned vessel, you’ll set out with a bilingual crew, ensuring clear communication whether you speak Greek or English.

The First Stop: Kleftiko in Milos

We loved the way the tour kicks off with a visit to Kleftiko, renowned for its otherworldly rock formations and vibrant sea colors. It’s a spot that’s famous among sailors and photographers alike. You’ll get to enjoy the scenery from the boat and, if the weather allows, explore the caves and sea tunnels by swimming or snorkeling. It’s a photographer’s dream, but also a real highlight for water lovers.

Next Up: Polyaigos for Snorkeling and Caves

After Kleftiko, the boat heads to Polyaigos, the largest uninhabited island in the Aegean. It’s a quiet, untouched paradise perfect for snorkeling and swimming in clear, inviting waters. You’ll have around 30 minutes here—enough time to cool off, explore the pirate caves, and soak in the seclusion. Be prepared for some rocky terrain if you decide to explore ashore, but most likely, you’ll be content with water-based exploration.

Visiting Kimolos

The third stop is Kimolos, a tiny island with distinctive white rocks and colorful doors carved into the rocks—an instantly picturesque scene. The white stone and colorful doors add a charming touch, recalling the island’s name, which means chalk. Here, you’ll have half an hour to swim or snorkel, and you might find the Syrmata—the traditional boat houses with bright doors—particularly photogenic. It’s a brief stop but one that adds character to the journey.

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Long Afternoon in Pollonia

The biggest chunk of the day is spent in Pollonia, a cute fishing village on Milos. You get about three hours here, which is plenty of time to wander its charming streets, enjoy the seaside views, and perhaps grab a bite in a local tavern. The village feels authentic, yet is well-developed enough for comfortable exploration. It’s an excellent opportunity to relax, take some photos, or just soak in the island vibe.

Sunset at Santorini’s Caldera

After all the island hopping, the tour returns to Santorini, with a special treat—the sunset over the Caldera. Watching the sun dip behind the cliffs is a classic experience, and well worth ending the day on a high note.

The Practicalities

The boat journey runs for about 10 hours in total, with starting times available depending on the day. The tour includes hotel transfers, making it easier to enjoy without worrying about logistics, and snacks, fruit, water, towels, and snorkeling gear are all provided, adding to the comfort.

What’s not included? You’ll need to plan for onshore meals, which you can buy in Pollonia or bring along. Extra costs may also apply for off-boat activities or souvenirs.

Price and Value

At $3,839 for up to four people, this tour is definitely on the higher end, but it reflects the private experience and all-inclusive convenience. For travelers craving exclusivity and personalized service, the cost might be justified. However, if budget is a concern, there are other tour options, but they might be less intimate or flexible.

Considerations

• Weather can impact the trip, especially for snorkeling and swimming, so check the forecast.
• Duration means you should be prepared for a full day. It’s ideal for active travelers who enjoy being on the water.
• Language support is available in English and Greek, so communication shouldn’t be an issue if you’re a speaker of either.

Why This Tour Might Be a Good Fit

If you’re someone who values privacy and personalized attention, this private cruise is likely to appeal. It’s great for couples, small groups, or friends who want a customized day out without the crowds. The stops at Kleftiko, Polyaigos, and Kimolos mean you’ll see some of the most photogenic and peaceful spots in the region—perfect for travelers who want to get away from the busy tourist areas.

It’s also ideal if you enjoy water activities—swimming, snorkeling, and exploring caves—since the tour’s stops are planned to maximize these experiences. Plus, the inclusion of hotel transfers simplifies planning, and the flexible booking policy (cancel up to 24 hours in advance) adds peace of mind.

Who Might Not Love It

If your priority is budget-friendly travel, this experience might stretch your budget. Also, if you’re not comfortable spending a good chunk of the day on a boat, or dislike water-based activities, this might not be the best fit. The trip also doesn’t include onshore meals, so you’ll need to plan for lunch or snacks in Pollonia.

Final Thoughts

This private cruise around Santorini and nearby islands offers a blend of stunning scenery, personalized service, and peaceful water-based exploration. While the price point reflects the exclusivity and convenience, many travelers who prioritize a tailored experience and the chance to visit less crowded spots find it worthwhile. The stops at Kleftiko, Polyaigos, and Kimolos are real highlights, offering striking landscapes and the chance to swim in some of the clearest waters you’ll find in the Aegean.

If you’re looking for a day that balances adventure, relaxation, and scenic beauty—all with a personal touch—this cruise could be just what you need. That said, if budget or onshore dining are priorities, you might want to consider other options or plan ahead for meals.

FAQ

Is this tour suitable for families?
While the tour is private and can be tailored, it’s primarily designed for adults comfortable with boat trips and water activities. If traveling with children, consider their comfort with sea travel and swimming.

What should I bring?
Bring your passport or ID, swimwear, sunscreen, weather-appropriate clothing, and any personal items needed for water activities.

Are meals included?
No, onshore meals are not included. You might want to bring snacks or plan to eat in Pollonia, where you’ll have three hours of free time.

What’s the duration of the tour?
The total experience lasts about 10 hours, including transfers, sightseeing, and free time.

Is snorkeling equipment provided?
Yes, snorkeling gear is included, so you can explore the waters comfortably.

Can I cancel the booking?
Yes, you can cancel up to 24 hours in advance for a full refund.

What are the starting times?
Starting times vary depending on the day; check availability when booking.

Is the tour bilingual?
Yes, the crew speaks both English and Greek, ensuring clear communication.

If you’re after a day of personalized island-hopping with scenic vistas and water fun, this cruise could be a highlight of your Santorini trip. Just weigh the cost against what’s included and consider whether a private, full-day experience fits your style and budget.

You can check availability for your dates here: