2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos

Two days at sea can change your view of the Cyclades. This private sailing trip links Milos, Kimolos, and Polyaigos with quiet bays, bright swimming spots, and some of the Aegean’s most memorable coastal scenery. I like the small private group, limited to your party of up to four, and I like the chance to reach places such as Gerakas Beach and Kleftiko by boat. The main drawback is the price: at $2,936.83 per group, this is a major expense unless you can share it with three other people.

You also need to accept the rhythm of a sailing trip. Wind and weather can change the plan, and dinner is not included during the overnight stop in Kimolos. Still, for a couple or small group wanting time on the water instead of a fast day trip, this offers a generous two-day taste of the islands.

Key points to know before you book

• Private sailing for up to four people: You share the boat only with your own group, giving you more space and a quieter pace than a large excursion.
• Three islands in two days: The route connects Milos, Kimolos, and uninhabited Polyaigos rather than staying around one harbor.
• Kleftiko cave visit by small boat or paddle board: Lunch follows the cave stop, making this one of the main highlights of the second day.
• Overnight in Psathi on Kimolos: You have time to walk about 15 minutes into the village and eat dinner at your own expense.
• Meals and boat costs are covered: Breakfast, two lunches, fuel, taxes, and berth fees are included.
• Weather matters: You can cancel up to three full days ahead for a refund, but poor conditions can also force a date change or cancellation.

Why this private sailing trip is different

The best feature is not one beach. It is the way the trip strings together several kinds of island scenery. You begin with Milos villages and famous rock formations, spend the night on Kimolos, then head toward Polyaigos and the western coast of Milos.

That variety matters. A standard beach outing can give you one attractive swimming stop and a few hours in the sun. Here, you get a moving view of the islands, time to swim in different waters, a port stay, a village walk, and a cave visit. The schedule also leaves room for long stops, including two hours at Goupa and about 90 minutes at Kleftiko.

The tour is private, but it is not a private yacht charter with unlimited flexibility clearly promised. The listed route is fairly full, and the captain still has to work with wind, waves, and safe anchoring. Think of it as a planned sailing journey with personal space, not a completely free-form day on the water.

Day one begins around Klima and Sarakiniko

The boat leaves from Adamantas at 10:00 a.m. The starting point is listed at PCFW+J2 Adamantas, and pickup is available for two people maximum. If more than two people need transport, you can hire a taxi on Milos and meet the boat there.

The first listed stop is Klima, the small seaside village on Milos. Its houses sit right by the water, with the typical Cycladic colors and a church adding to the postcard view. The scheduled visit is short, about 10 minutes, so this is more of a scenic introduction than a long village visit.

You may also see a sandy beach on the north side of Milos during this part of the route. The water is described as clear and suitable for a midday swim when the wind comes from the south. That detail is worth noting because wind direction affects the comfort of a swim and may affect how closely the boat follows the planned route.

Next comes Sarakiniko Beach, with about 45 minutes scheduled. Its pale volcanic rock and smooth, sculpted forms give it the famous moon-like appearance associated with Milos. From a boat, you get a useful view of the bright shoreline without having to arrive by road with the island’s other beachgoers.

The stop is also intended for swimming and cliff jumping. The description makes cliff jumping sound like the favorite way to enjoy the area, but you should treat that as a personal choice, not a requirement. If you prefer to stay in the water or on the boat, the stop still gives you time to enjoy one of Milos’s most unusual coastal settings.

Goupa and the Elephant Beach lunch stop

The boat then crosses toward Kimolos and stops at Goupa, also called Elephant Beach. This is the longest stop on the first day, with about two hours for lunch and swimming.

Goupa is known for its clear water and coastal setting. The relaxed timing is valuable here. You are not being hurried from a quick photo stop to the next attraction. You can swim before lunch, eat aboard the boat, and return to the water afterward.

Two lunches are included across the trip, and this is one of them. Breakfast is also included, along with fuel, taxes, and berth fees. Dinner is not included, so you should plan to pay for your evening meal in Kimolos.

The phrase extra fresh Mediterranean lunch appears in the tour details, but no exact menu is given. I would not book this expecting a specific dish or dietary arrangement unless you confirm it before departure. The clear value is that the main midday meal is handled while you are at a scenic stop.

An evening in Psathi, Kimolos

The first day ends at Psathi, the port of Kimolos. The boat remains here overnight for roughly 17 hours, giving you a proper evening ashore rather than another night at sea.

Psathi is described as small and charming, with a beach, restaurants, and patisseries near the waterfront. The village of Kimolos is about a 15-minute walk from the port. That short walk gives you a chance to see a more typical Cycladic settlement instead of spending the whole evening beside the boat.

This overnight stop is one of the tour’s strongest practical features. You get a break from the boat, a chance to stretch your legs, and time for a seafood dinner followed by a drink or dessert. Since the tour does not include dinner, budget separately for the meal.

The village visit also helps balance the water-based schedule. Two days of swimming and sailing can become tiring, especially in strong sun. Kimolos gives you a change of pace and a chance to experience an inhabited island after spending much of the day along the coast.

Polyaigos brings a quieter second morning

The second day begins with Myrsini Bay, where the boat stops for about 90 minutes. This is the swimming and sunbathing stop on the uninhabited island of Polyaigos.

Because Polyaigos has no permanent settlement, the appeal is its open, quiet setting and clean water. You are not coming here for a village, museum, or restaurant. You are coming to swim, relax, and see a more undeveloped side of the island group.

The length of this stop is generous enough for a proper swim rather than a quick dip. It also gives you time to stay aboard and enjoy the view if you have had enough sun. I would bring protection from the heat, since the schedule includes repeated outdoor stops and no land-based shelter is promised.

The visit to Polyaigos is also a good reason to choose this two-day trip instead of a shorter outing around Milos. The route reaches an island that is difficult to experience as part of an ordinary road itinerary. Your main access is by boat, and the trip builds that access into the day.

Gerakas Beach and the onboard mezze break

Gerakas Beach comes next, with about an hour scheduled. This sandy beach on Milos can be reached only by boat, according to the tour details. It has blue water, golden sand, and warm bathing conditions.

That combination makes Gerakas a classic swimming stop, but its boat-only access is the key point. You are not simply visiting a beach that you could reach by taxi. The sailing trip gives you access to a coastal section that would otherwise be left off a land itinerary.

An aperitif with Greek mezze is served aboard the sailboat here. This adds a local food touch without turning the trip into a formal dining tour. The mezze also gives you something to eat between the included lunches and the morning swimming stop.

The one-hour duration should be enough for a swim and a light snack, but it is not a long beach day. If you want hours on one stretch of sand, this schedule may feel busy. If you prefer several different settings, the pace works better.

Kleftiko is the grand finish

Kleftiko is the final major stop, with around 90 minutes for the bay, cave exploration, and lunch. It is the most famous part of the route, once associated with pirates and now known for bright water, pale rock, and sea caves.

The captain takes you to a cave in a dinghy boat or by paddle board. This is more interesting than simply looking at Kleftiko from the deck. You get a closer view of the rock formations and a chance to move through the water near the caves.

The phrase dingy boat appears in the supplied details, but the intended meaning is clearly a small tender or dinghy. If you prefer not to paddle, the small boat offers another way to reach the cave. If you enjoy being active, the paddle board adds a little more freedom, provided conditions allow it.

Lunch is served at Kleftiko. The schedule gives you enough time to combine a meal with the cave visit, though the exact order may depend on weather and anchoring conditions. This is another place where the boat’s private setup helps. Your group can enjoy the stop without being tied to a large crowd moving through the same cave at once.

Kleftiko is also the point where the tour’s two-day structure pays off. You are not rushing from Adamantas to one famous bay and back in a single day. You arrive after seeing Kimolos and Polyaigos, with a full day of sailing already behind you.

The price makes more sense with four people

At $2,936.83 for a group of up to four, the full cost works out to about $734 per person if four people share it. For two people, it is about $1,468 per person. Those figures make the group size very important.

The price includes breakfast, two lunches, fuel, taxes, and berth fees. It also covers the private boat and the overnight berth in Kimolos. You do not have to worry about splitting fuel or port charges during the trip, which makes the final cost easier to understand.

Dinner, drinks beyond the included food, and transport for groups of more than two from your accommodation are separate. The tour does not list hotel pickup for all four people. Confirm the meeting plan before you leave for Adamantas.

I see the best value for four people who want privacy and a two-day route. If you are a couple, the cost is harder to justify unless private sailing is a central part of your Milos visit. A large public cruise would likely cost less, but it would not offer the same private setting or overnight plan.

Who will enjoy this most

I would recommend this trip to people who want the boat to be the main part of their Milos holiday. You should enjoy swimming, sun, coastal views, and a schedule built around the sea.

It suits:

• Couples looking for a private two-day outing
• Families or friends who can share the cost among four people
• Visitors who want both Milos and Kimolos
• People who want to see Polyaigos by boat
• Anyone interested in Kleftiko cave access by dinghy or paddle board
• Visitors who prefer a slower overnight route instead of a single long cruise

It may be less suitable if you want detailed sightseeing in villages, long walks, or a low-cost excursion. Klima receives only a short stop, and the trip gives more time to swimming than to land-based exploration. You also need to be comfortable with the possibility of weather changes.

The experience has a perfect 5 rating from nine reviews, with the strongest praise focused on the crew, the destinations, and sailing as a way to see the islands. That matches the trip’s main strength: it is not just transportation between beaches. It makes the journey itself the central activity.

Practical details that affect your decision

The tour starts at 10:00 a.m. and returns to the same meeting point in Adamantas after the second day. Confirmation is sent at booking. Service animals are allowed, and most people can participate.

Good weather is required. If poor conditions cancel the trip, you are offered another date or a full refund. You can also cancel for a full refund if you do so at least three full days before the local start time. Cancellations or changes made inside that period are not refunded or accepted.

The tour is offered in English. Since the schedule includes swimming, beach time, and a small-boat cave visit, pack what you need for a full day outdoors. The supplied details do not specify equipment, cabin arrangements, or a menu, so ask Oscar Private Sailing those questions before paying if they matter to you.

Should you book this sailing tour?

Book it if you want a private, sea-focused introduction to Milos, Kimolos, and Polyaigos, especially if four people can share the cost. The route includes famous places such as Sarakiniko and Kleftiko, but it also reaches Kimolos’s Psathi port, Polyaigos, and boat-only Gerakas Beach.

Skip it if the price is too high for your group, if you want extensive time ashore, or if your schedule cannot handle a weather-related change. For the right group, though, the combination of quiet bays, a Kimolos overnight stay, included meals, and Kleftiko cave access makes this a strong splurge in the Cyclades.

FAQ

Where does the tour start?

The meeting point is in Adamantas, Milos, at PCFW+J2 Adamantas, Greece.

What time does the tour start?

The tour starts at 10:00 a.m.

Can the operator provide pickup?

Pickup is available for two people maximum. If more than two people need transport, you can hire a taxi on the island.

How many people can join the private tour?

The price covers a private group of up to four people. Only your group participates.

Which islands does the tour visit?

The route includes Milos, Kimolos, and the uninhabited island of Polyaigos.

Is dinner included?

No. Breakfast and two lunches are included, but dinner is not.

Are fuel and berth fees included?

Yes. Fuel, taxes, and berth fees are included in the tour price.

What happens if the weather is poor?

The experience requires good weather. If it is canceled because of poor conditions, you are offered a different date or a full refund.