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

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

Outty Ranking 64 4.7 · 11 traveler reviews48 hoursFrom $2,785
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Outty Ranking

64/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

4.7/5

Based on 11 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos worth booking?

2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos is a 48-hour experience in Milos, Greece, from $2,785 per person. It scores 64 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.7/5 rating across 11 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
64 / 100
Rating
4.7/5 (11)
Duration
48 hours
From
$2,785 per person

This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and gets you to places mostly accessible only by boat. Breakfast, lunch and drinks are included. Notes: The company keeps the right to modify the itinerary and to adjust the swimming stops location depending on the weather conditions.

What you get

    About this experience

    This cruise is unique and a must when visiting Milos. It gives visitors the opportunity to experience a night on-board a 13m sailing boat and gets you to places mostly accessible only by boat. Breakfast, lunch and drinks are included. Notes: The company keeps the right to modify the itinerary and to adjust the swimming stops location depending on the weather conditions.

    What's included

    Included

    • all boat expenses ,fuel taxes, berth fees
    • Lunch
    • Breakfast

    Not included

    • Gratuities
    • Dinner

    Where it starts and ends

    Meeting point

    Milos

    The meeting point will be next to the ferries in the port of Adamas, Milos.

    Hotel pickup

    Pickup is available for selected locations. Pickup begins about 5 minutes before departure.

    Ends at

    The meeting point will be next to the ferries in the port of Adamas, Milos.

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    el, en, fr
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Oscar Private Sailing

    Know before you go

    • Infants are required to sit on an adult’s lap
    • Service animals allowed
    • Public transportation options are available nearby
    • Suitable for all physical fitness levels

    Photos

    2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos, photo 22-Day Private Sailing Tour around Milos, Kimolos and Polyaigos, photo 32-Day Private Sailing Tour around Milos, Kimolos and Polyaigos, photo 42-Day Private Sailing Tour around Milos, Kimolos and Polyaigos, photo 52-Day Private Sailing Tour around Milos, Kimolos and Polyaigos, photo 62-Day Private Sailing Tour around Milos, Kimolos and Polyaigos, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 11 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    3 mentions

    The tastings and food stops are a highlight for most reviewers.

    Small groups

    3 mentions

    The group size is repeatedly described as intimate rather than packed.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Traveler reviews

    11 verified traveler reviews for 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos. Ratings and reviews provided by Viator and Tripadvisor.

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    522alyssad · October 2026

    Not as advertised

    We did the two night/three day charter. We had some wonderful moments on our sailing trip, but overall the experience was not what we believed we were booking. Our biggest concern is with the company and the lack of transparency between what is advertised and what was actually provided. When we booked, we chose this charter based in large part on the specific boat and experience shown on the website. The boat we received, however, was completely different—the name, model, and photos did not match what had been advertised. We also had a different captain than expected, and we weren’t made aware of these changes until the day of our charter. For a multi-day private charter that we had planned and looked forward to for months, this felt misleading and was a significant disappointment. The departure logistics also changed at the last minute. We had specifically booked our hotel the night before in the town where we had been told we would meet the boat. The day before our charter, the meeting location was changed to a different town, leaving us to arrange additional transportation. Our captain himself was welcoming and did several things exceptionally well. He was fantastic with our son, made him feel included, and did a great job adjusting our itinerary based on weather and crowds. He brought us to some absolutely beautiful places, and we appreciated his knowledge of the area. However, the boat was also the captain’s liveaboard home, and it very much felt that way. Although he was welcoming, at times we felt more like guests in someone’s personal space than guests on a private charter. The boat also did not feel particularly well maintained or prepared to the standard we expected based on how the experience was advertised. The food was another disappointment. Our first mate was a very nice but quite shy 18-year-old who clearly tried his best, and we genuinely enjoyed having him with us. He even made us a great Greek salad! However, he did not seem to have much sailing or cooking experience, and much of the food seemed to be reheated or previously prepared and simply wasn’t very good. This is not a criticism of him—he was kind and did what he could. Rather, for a multi-day private charter, we expected the company to provide a crew with the experience needed to deliver the level of food and service that had been presented to us. We were also surprised by how little actual sailing we did during a multi-day sailing charter. There were absolutely highlights. We saw spectacular places, avoided some of the crowds, and our captain created some really special moments for our son. We did not have a bad trip. But this was something we had imagined as one of the highlights of our time in Greece, and it wasn’t the experience we had researched, booked, and paid for. Ultimately, our biggest concern is not with our captain or first mate, but with the company. A customer should be able to look at a charter company’s website, choose a particular boat and experience, and reasonably expect that to be what they receive—or, at minimum, be clearly informed well in advance if something significant has changed. That transparency was missing here, and unfortunately it left us feeling disappointed by an experience we had been incredibly excited about.

    via Tripadvisor

    N6201FHvictoriam · April 2026

    Unforgettable highlight of our family trip

    We travelled to Greece 🇬🇷 July 2024 for a family holiday. I was thrilled to find Oscar Private Sailing as an intro into a sailing holiday. Nikos made everything so enjoyable and perfect. From finding the best coves for swimming and relaxing, to creating amazingly delicious meals - everything was perfect. I would highly recommend Nikos for an authentic and fun sailing adventure. Thanks Nikos (sorry for the delayed review!).

    via Tripadvisor

    Culture767261 · July 2024

    Thanks Nikos from our heart

    Where to start...? We both love the water, swimming, snorkelling and diving. it was simply perfect. Nikos is a very professional and relaxed person it it was simply beautiful to have spend these days on his boat with him. Nikos is a real pro and knows how to read the sea, the wind and we had some proper sailing - there was one big problem: it was too short. .-)) we felt so sorry that we have to leave as it felt to stay longer as we had such a good time. Thanks Nikos for this beautiful experience from my heart- as we said we hope to be back very very soon and if possible this year. Take care. Aleksandra & Stephen

    via Tripadvisor

    jammies2022 · June 2024

    Amazing experience

    What an amazing experience! The waters at the stops along the way were so clear and blue. Nikos is a great capitan, knowledgeable, considerate, fun, attentive and a great cook as well. All while being respectful to allow you your space to enjoy the trip. I can't think how our experience could have been better. A wonderful memory for our family.

    via Tripadvisor

    nathaliew921 · May 2024

    Unforgettable experience

    Such a great adventure! Nikos took us to the most beautiful spots, and he was very knowledgeable, accommodating, and a great cook. Highly recommend for anyone looking to see Greece on the water

    via Tripadvisor

    Good to know

    Duration
    48 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    Available for selected locations
    Booked in 30 days
    4
    Verdict
    Solid Choice

    Who runs this experience

    Operated by Oscar Private Sailing, who run 3 experiences we rank across 1 city, with an average Outty Ranking of 60.6.

    See everything Oscar Private Sailing runs

    Why this scores 64

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)88
    Review evidence (18% weight)40
    Booking momentum (14% weight)31
    Value for money (12% weight)70
    Listing quality (10% weight)68
    Local standing (8% weight)41
    Booking flexibility (8% weight)100

    2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Milos.

    How much does 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos cost?

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    Prices start at $2,785 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Milos usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos take?

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    Plan for about 48 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Milos is not rushed.

    Is 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos worth it?

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    It holds an Outty Ranking of 64 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.7/5 across 11 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Milos, and how flexible the cancellation terms are.

    Can I cancel or reschedule 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos?

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    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 48-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos?

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    Around 4 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Milos can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

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    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Milos and add a light layer if any part of the 48-hour experience runs outdoors or after sunset.

    Where does 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos start and how do I get there?

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    The exact meeting point and directions are on your voucher once you book, and they sit in central Milos within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Milos?

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    On Outty we rank every Milos experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Milos Small-Group Full-Day Cruise with Snorkelling and Lunch, Best of Milos and Poliegos Catamaran snorkelling Cruise with BBQ, CATAMARAN Kleftiko Poliegos & Round of Milos Lunch with Openbar. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Milos?

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    Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Milos?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

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    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

    What is included in 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos?

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    Included: all boat expenses ,fuel taxes, berth fees; Lunch; and Breakfast. Not included: Gratuities; and Dinner. Always check the voucher for the final list before you travel.

    Does 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos include hotel pickup?

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    Yes, pickup is offered, or you can meet at the start point instead from 4 listed pickup locations in and around Milos. Be ready about 5 minutes before the start time.

    What languages is 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos offered in?

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    It is offered in Greek, English and French. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos?

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    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    Is 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos wheelchair or stroller accessible?

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    The operator notes: Infants are required to sit on an adult’s lap. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos if the weather is bad?

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    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    What do travelers say about 2-Day Private Sailing Tour around Milos, Kimolos and Polyaigos?

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    Across 11 reviews averaging 4.7 out of 5, recurring themes include knowledge and storytelling, food and drink, small groups. Reviewers describe the commentary as informative rather than scripted.

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