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

The best part of this private two-day sailing trip is the route itself. You move between Milos, Kimolos, and the uninhabited island of Polyaigos by boat, reaching coves and beaches that are difficult to visit from land. The schedule mixes famous sights, such as Sarakiniko and Kleftiko, with quiet swimming stops.

I like the small-group setup, limited to your own party of up to four, and I like that fuel, taxes, berth fees, breakfast, and two lunches are covered. The main drawback is the price: at $2,936.83 per group, this makes the most sense when four people share the cost. Dinner in Kimolos is extra, and pickup is available for only two people.

Key points at a glance

• Two islands and one uninhabited island: Sail from Milos to Kimolos and Polyaigos over two days.
• A night in Psathi: Sleep ashore at Kimolos’ small port, with the village about 15 minutes away on foot.
• Swim-focused schedule: Allow time for Sarakiniko, Myrsini Bay, Gerakas Beach, Goupa, and Kleftiko.
• Kleftiko by small boat: Visit a sea cave by dinghy or paddle board, then eat lunch aboard.
• Private for up to four: You share the boat only with your own group.
• Weather matters: Poor conditions can lead to a new date or a full refund.

Why this two-day route works so well

Milos is a fine island to explore by road, but some of its best coastal scenery makes more sense from the water. White rock, small coves, sea caves, and beaches cut off from the road all come into view in one long circuit.

This trip also gives you something a standard boat outing usually cannot: an overnight stop. Rather than rushing back to Adamantas at the end of the day, you spend the night at Kimolos’ port of Psathi. That gives you time for dinner, a walk to the village, and a slower start the next morning.

The schedule is active, but not packed with a long list of land attractions. Most stops are built around swimming, sunbathing, a meal, or a short look at a coastal site. If you want a day filled with museums and guided walks, this is not the right choice. If your ideal Greek holiday includes warm water, salt on your skin, and very little time in a car, the format fits.

Day one: Klima, Sarakiniko, and Kimolos

The sailing begins at 10:00 a.m. at PCFW+J2 Adamantas in Adamantas. The boat first heads toward Klima, the small seaside settlement on Milos known for its colorful boat houses and waterfront setting. The stop is listed at about 10 minutes, so think of it as a quick coastal look rather than a long village visit.

From the boat, Klima gives you an early taste of Milos’ unusual shoreline. You can see the simple houses gathered close to the water, with a church adding to the scene. If the wind comes from the south, the nearby sandy beach can also work for a midday swim.

The short timing here is worth noting. You will not have much time to wander, shop, or sit over a coffee. The value is in seeing Klima from the sea, where its position along the coast is easiest to appreciate.

Sarakiniko from the water

Next comes Sarakiniko Beach, with about 45 minutes scheduled. The bright volcanic rock and smooth white surfaces make this one of Milos’ most recognizable coastal sights. From a boat, you get a different angle than from the road, with the pale rock dropping toward the water.

Swimming is the main reason for the stop. The trip information specifically points to cliff jumping as an option, but you should treat that as a personal choice, not a required part of the outing. A boat gives you access to the water without requiring a long walk across the shore.

Sarakiniko can attract many people, so arriving by boat may provide a welcome break from the land-based crowds. Still, 45 minutes passes quickly. You will have time for a swim and a look around, not an extended beach session.

Goupa and the Elephant Beach lunch stop

The boat then crosses to Kimolos for a two-hour lunch break at Goupa, also called Elephant Beach. This is one of the more generous stops on the first day, and it gives you time to swim before and after eating.

The water is described as clear, and the setting is especially suited to a long pause. You are not being hurried from one photo stop to the next. The included Mediterranean lunch adds real value here, since you do not need to arrange food while moving between islands.

Breakfast and two lunches are included in the overall trip. Dinner is not, so keep that distinction in mind when working out the total cost. At Goupa, you can expect the day’s main meal to be served aboard or as part of the sailing stop, but the supplied details do not specify a fixed menu.

This is also where the private format helps. With only your own group aboard, you can use the swimming time at your own pace within the captain’s schedule. A party of four can spread the cost while still keeping the outing personal.

Overnight at Psathi, Kimolos

The first day ends at Psathi, the small port of Kimolos. The planned stay is about 17 hours, allowing you to sleep on the island rather than sail back to Milos.

Psathi has a beach, restaurants, and patisseries close to the waterfront. The village of Kimolos is about a 15-minute walk away, which gives you a chance to see a typical Cycladic settlement instead of spending the whole night beside the boat.

I like this overnight because it changes the rhythm of the trip. You can have a seafood-focused dinner, order a cocktail afterward, and walk back to the port without needing to watch the clock for a return crossing. You pay for dinner separately, but you gain a full evening on Kimolos.

The supplied details do not state the accommodation arrangement, so you should confirm exactly where you sleep and whether lodging is part of the sailing package before paying. The port stay is clear, but the room or cabin details are not provided.

Day two: Polyaigos and Myrsini Bay

The second morning turns toward Polyaigos, an uninhabited island near Kimolos. The first listed stop is Myrsini Bay, with about an hour and a half for swimming and sunbathing.

This is the kind of stop that makes a private sailing trip worthwhile. There is no village schedule to follow and no land transport involved. You get time in a bay on an island without permanent residents, with the focus on the water and the coast.

Because the stop lasts 90 minutes, you can swim without feeling that you must get out immediately for the next departure. You might also prefer to stay aboard and enjoy the view if you have had enough sun. The trip is built around choice, but the captain’s timing still controls when the boat moves on.

The waters around Polyaigos are presented as a major part of the experience, but the exact facilities on the island are not listed. You should expect a natural stop rather than shops, changing rooms, or a developed beach service.

Gerakas Beach and an onboard mezze

The next stop is Gerakas Beach on Milos, where the boat spends about an hour. This sandy beach is accessible only by boat, with blue water, golden sand, and warm bathing water listed as the main attractions.

That restricted access gives this stop a different feel from Sarakiniko. Sarakiniko is famous for its striking rock and easy recognition. Gerakas is about reaching a beach that land vehicles cannot reach.

An hour is enough for a swim and a little time on the sand, but not a long beach day. An onboard Greek mezze is also part of the stop. This small spread is a useful touch because it turns a swim break into a light social meal rather than another pause where you need to find food.

The exact mezze items are not specified, so do not book this expecting a particular dish. If you have dietary needs, ask the operator before departure.

Kleftiko by dinghy or paddle board

The final major stop is Kleftiko, one of Milos’ best-known bays. It once served as a hideout for pirates, and its coastal rocks and sea caves create the kind of setting that is hard to understand from a road.

The planned time is about an hour and a half. The captain takes you into a cave by dinghy or paddle board, while lunch is served as part of the stop. This is more than a quick look from the sailboat. You get a chance to move closer to the rock formations and enter a cave on a small craft.

You should be comfortable around water to get the most from Kleftiko. The information says a dinghy or paddle board is used, but it does not spell out which option is available to each person or how long the cave visit lasts. Ask the crew if you have concerns about balance, paddling, or getting in and out of a small boat.

The second included lunch is another practical advantage. Kleftiko is remote by land, so having food aboard keeps the visit simple. You can focus on the cave, the water, and the rock formations instead of arranging a meal elsewhere.

What the private price really buys you

The cost is $2,936.83 per group for up to four people. Split four ways, that works out to about $734.21 per person. With only two people, the per-person cost becomes much higher, so this trip is best suited to a family or group of friends who can fill all four places.

The price includes:

• Breakfast
• Two lunches
• Fuel and other boat expenses
• Taxes
• Berth fees
• Private use of the activity for your group

Dinner is not included. You should also confirm the overnight accommodation details, since the supplied information names the port stay but does not list the lodging arrangement.

For the right group, the price buys more than transportation. You are paying for two days on a private route, an overnight island stop, fuel, docking, meals, and access to coastal sites that are not all easy to reach by road. That is a meaningful package, but it is not a budget excursion.

The strongest value comes when you care about privacy and flexibility. If you are happy on a larger shared boat, a lower-cost option may suit you better. If you want the boat to yourself and plan to swim at every possible stop, the premium is easier to justify.

Timing, pickup, and practical details

The meeting point is in Adamantas, and the tour starts at 10:00 a.m. Pickup can be arranged for a maximum of two people. If your party is larger, you can hire a taxi on Milos and meet at the starting point.

The activity ends back at the meeting point. Since the total duration is about two days, do not schedule a tight ferry connection or another major activity immediately afterward. The exact return time is not listed.

Confirmation is provided when you book. The activity is offered in English, and most people can participate. Service animals are allowed, and the meeting point is near public transportation.

The trip depends on good weather. If poor conditions force a cancellation, you can choose another date or receive a full refund. You can also cancel for a full refund if you do so at least three full days before the start time. Changes or cancellations made inside that window are not accepted.

Because wind and sea conditions affect the route, I would keep your schedule flexible around this outing. The weather rule is not a minor footnote for a sailing trip. It is part of planning one.

Who will enjoy this sailing trip most

I would choose this for you if you want to see several islands without packing and unpacking each day. It is also a strong match for swimmers, sun-seekers, couples, and small groups of friends who value a private boat.

The trip suits people who enjoy a relaxed but water-focused schedule. You need to be comfortable spending long stretches aboard, getting in and out for swims, and following the captain’s timing.

It may be less suitable if you want extensive time in each village. Klima receives only a short stop, and Kimolos village is explored independently during the overnight. The main emphasis is coastal scenery, swimming, meals, and the sea caves at Kleftiko.

The overnight also gives the trip more character than a simple day cruise. You get a short taste of Kimolos after the day boats have moved on, though dinner and any personal spending remain your responsibility.

Should you book the two-day Milos sailing?

Book it if your group can share the cost and your ideal Milos experience involves swimming, quiet coves, and a private route through three islands. The overnight in Kimolos, the Polyaigos stop, and the Kleftiko cave visit give the trip a strong sense of place.

Think twice if you are traveling alone, watching every euro, or hoping for a detailed guided tour of villages and monuments. The $2,936.83 group price is substantial, and dinner and lodging details need clarification.

For a group of four that wants a private boat, two lunches, breakfast, covered boat expenses, and a full night away from Milos, this is a well-targeted splurge. Just confirm the accommodation arrangement, ask about meal needs, and leave room in your schedule for weather changes.

FAQ

Where does the sailing tour start?

The tour starts at PCFW+J2 Adamantas in Adamantas, Milos.

What time does the tour begin?

The scheduled start time is 10:00 a.m.

Where does the tour end?

The activity ends back at the meeting point in Adamantas.

How many people can join the private tour?

The price covers one private group of up to four people.

Is hotel pickup available?

Pickup can be arranged for a maximum of two people. You can also hire a taxi on Milos to reach the meeting point.

Which islands does the tour visit?

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

What meals are included?

Breakfast and two lunches are included. Dinner is not included.

Is the trip offered in English?

Yes. The activity is offered in English.

What happens if the weather is poor?

If poor weather causes cancellation, you can choose a different date or receive a full refund.

When can I cancel for a full refund?

You must cancel at least three full days before the experience start time for a full refund. Changes made less than three full days before the start time are not accepted.