What are the best options for Cyclades Islands Sailing Trips?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Cyclades Islands Sailing Trips are: Private 2 Hours Sunset Cruise in Milos — Magical Klima Village Private Cruise West Side of Milo's & Kleftiko Private Boat Tour in Milos with Lunch Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch Santorini 3 Islands Trip Sailing Wooden Boat

What are the best kid-friendly options for Cyclades Islands Sailing Trips Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Cyclades Islands Sailing Trips are: Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers Milos and Polyaigos Full Day Cruise with Meals and Snorkelling Santorini Volcano Hot Springs View all kid-friendly Tours →

Which Cyclades Islands Sailing Trips have Instant Confirmation?

Cyclades Islands Sailing Trips with Instant Confirmation include: Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers Milos and Polyaigos Full Day Cruise with Meals and Snorkelling View all Tours with Instant Confirmation →

Which Cyclades Islands Sailing Trips have Free Cancellation?

Cyclades Islands Sailing Trips with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include: Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer Santorini Classic Catamaran Cruise with BBQ, Drinks and Transfers Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers Milos and Polyaigos Full Day Cruise with Meals and Snorkelling View all Tours with Free Cancellation →

I need a ride! Which Cyclades Islands Sailing Trips have Hotel Pickup?

No problem. These Cyclades Islands Sailing Trips include Hotel Pickup: Santorini Sunset Luxury Sailing Catamaran Cruise with BBQ, drinks, transfer Santorini: Caldera Classic Semi-Private Cruise with BBQ & Drinks Luxury Santorini Catamaran Cruise: Lunch, BBQ, Drinks, Transfers Santorini Oia:Small Group Sunset Cruise w BBQ Fresh Fish & Drinks Catamaran Day & Sunset Cruises with meals Drinks and transportation View all Tours with Hotel Pickup →

Got any more Cyclades Islands trip ideas?

We sure do. Check out our curated lists of hand-picked Cyclades Islands Tours. Top 10 Cyclades Islands 2026 Senior-friendly tours Cyclades Islands The best tours and activities for culture lovers in Cyclades Islands Top Day Trips from Cyclades Islands Things to do in Cyclades Islands this summer View all Cyclades Islands Trip Ideas →

What are the most popular styles of Tours and Activities in Cyclades Islands?

Based on our sales data over the past year, the most popular styles of tours and activities in Cyclades Islands are: Cyclades Islands Luxury & Special Occasions Cyclades Islands Luxury Tours Cyclades Islands Tours & Sightseeing Cyclades Islands Half-day Tours Cyclades Islands Cruises, Sailing & Water Tours View all tour styles in Cyclades Islands →

Top Cyclades Islands Sailing Trips 2026 (w/Prices)

Cool Rewards

Cool Rewards is a loyalty program operated by Cool Shore Excursions. Rewards may be earned by any eligible person holding a Cool Shore Excursions account, subject to the Cool Shore Excursions customer Terms of Use.
Your account and your rewards balance are shared across all our participating sites, including cooldestinations.com. Rewards earned on any participating site can be redeemed on any other participating site.

Earning rewards

Rewards can be earned by making bookings on Cool Shore Excursions or on any other participating site. You will see the value of the rewards you can earn during the booking process.
Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
Earned rewards will be available to redeem once they are no longer in a pending state.
For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

To redeem rewards, you must be logged into your Cool Shore Excursions account. You can redeem them on Cool Shore Excursions or on any other participating site.
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There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
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Miscellaneous

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Interpretation & Definitions

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The words of which the initial letter is capitalized have meanings defined under the following conditions.

Definitions
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We strongly advise You to read the terms and conditions and privacy policies of any third-party websites or services that You visit.

Cancellation Policies

Cool Shore Excursions uses three different cancellation policies, depending on your specific Tour or Activity. Please be sure to verify which one applies to your chosen experience before confirming your Booking.

This information can be found on every Experience we offer under the Cancellation Policy section, as well as on the checkout page.

Standard Cancellation Policy — A majority of our activity cancellations are free up to 24 hours before the activity commencement time (based on the local time of the activity).

All Sales Final — If any Goods or Services are designated as ‘All Sales Final’ or with materially similar messaging (which includes but is not limited to all group bookings booked through our Group Bookings Department), it is non-refundable, and it will not be possible to change or cancel it after making a Booking for any reason.

Non-Standard Cancellation Policy — A minority of Goods or Services have other, different cancellation policies. In all circumstances, you must check the cancellation policy contained in the applicable Product listing at the time of your Booking, which is the policy that will apply to and govern the terms of your cancellation and any refunds.

Cancelling Your Reservation

To cancel your Reservation you must contact Cool Shore Excursions as soon as possible.

Cancellation Due To Bad Weather
If your Activity Operator must cancel due to bad weather and cannot accommodate you on another day, you will be issued a refund. Please be aware before issuing a refund, Cool Shore Excursions will confirm if this is the case. Please note, this is only a valid reason if the Tour Operator cancels the tour.

If Tour Operator Cancels Tour or Excursion
If, for some reason, a Tour Operator cancels and cannot accommodate you on another day or at another time, you will be offered a refund and the option to take the trip. In the event of cancellation due to bad weather, Cool Shore Excursions will confirm this before authorizing a refund.

Refunds

No refunds are available once an Experience has commenced, or for any package components that have started to be utilized.
- If your Experience materially differed from its description, please contact us within 7 days. We investigate every report and, where warranted, will provide an appropriate remedy.
- Credit card disputes filed for services delivered as described are contested with full documentation, including redemption records, and this agreement.
Wherever possible, refunds are handled via our automated online system. In some cases, your refund request will require verification from various parties, and that work is done exclusively via email.
Approved refunds will be issued to your original method of payment within thirty (30 days) from the date of the approval.

Adjusting Your Reservation

Contact our office directly to make any adjustments to your reservations. If you call and reach voicemail, please leave a message including time, date, number of guests attending, and the name of the Tour or Excursion.
If you adjust your reservation, a voucher will be issued and applied to your new reservation date. Subsequently, a revised confirmation will be emailed to you.
If the newly adjusted Activity is canceled for any reason, a store credit will be issued. A non-refundable change fee of $25 per adult ticket will be applied at the time of reservation change.

Customer Responsibility

Showing Up Late
If you or a member of your party shows up late and are consequently not able to participate you will still be responsible for the full amount of the Tour, Activity, or Excursion.

No Shows
If you, or a member of your party, do not show up for your Tour, Activity, or Excursion you will be responsible for the full amount of reservation.

Unsatisfactory Activity Experience
If you experience an issue of any sort with a Tour, Activity, or Excursion you have booked via Cool Shore Excursions, immediately bring this to the attention of the Tour, Activity, or Excursion’s operator. Make your concerns and complaints heard with the person in charge so that you may reach an agreeable solution immediately. Do not wait until you return from your vacation. If, for some reason, you feel a partial or full refund is merited, you must make this known on the same day of your Tour or Excursion.

Payment Dispute Policy

If You have any concerns or disputes about the Service, You agree first to try to resolve the dispute informally by contacting the Company.

Termination

We may terminate or suspend Your Account immediately, without prior notice or liability, for any reason whatsoever, including without limitation if You breach these Terms and Conditions.

Upon termination, Your right to use the Service will cease immediately. If You wish to terminate Your Account, You may simply discontinue using the Service.

Limitation of Liability

Notwithstanding any damages that You might incur, the entire liability of the Company and any of its suppliers under any provision of this Terms and Your exclusive remedy for all of the foregoing shall be limited to the amount actually paid by You through the Service or 100 USD if You haven’t purchased anything through the Service.

To the maximum extent permitted by applicable law, in no event shall the Company or its suppliers be liable for any special, incidental, indirect, or consequential damages whatsoever (including, but not limited to, damages for loss of profits, loss of data or other information, for business interruption, for personal injury, loss of privacy arising out of or in any way related to the use of or inability to use the Service, third-party software and/or third-party hardware used with the Service, or otherwise in connection with any provision of this Terms), even if the Company or any supplier has been advised of the possibility of such damages and even if the remedy fails of its essential purpose.

Arrangements set forth in Your Booking are made solely for the convenience of the Ticket Holder and are at Ticket Holder’s risk. The Providers of such Services are independent contractors and are not acting as agents or representatives of Cool Shore Excursions, or their respective affiliates or subsidiaries. In no event shall Cool Shore Excursions be liable for any accident or harm to Ticket Holders, which occurs as a result of any acts, omissions, or negligence of any independent contractors.

Some states do not allow the exclusion of implied warranties or limitation of liability for incidental or consequential damages, which means that some of the above limitations may not apply. In these states, each party’s liability will be limited to the greatest extent permitted by law.

“AS IS” and “AS AVAILABLE” Disclaimer

The Service is provided to You “AS IS” and “AS AVAILABLE” and with all faults and defects without warranty of any kind. To the maximum extent permitted under applicable law, the Company, on its own behalf and on behalf of its Affiliates and its and their respective licensors and service providers, expressly disclaims all warranties, whether express, implied, statutory or otherwise, with respect to the Service, including all implied warranties of merchantability, fitness for a particular purpose, title and non-infringement, and warranties that may arise out of course of dealing, course of performance, usage or trade practice. Without limitation to the foregoing, the Company provides no warranty or undertaking, and makes no representation of any kind that the Service will meet Your requirements, achieve any intended results, be compatible or work with any other software, applications, systems or services, operate without interruption, meet any performance or reliability standards or be error free or that any errors or defects can or will be corrected.

Without limiting the foregoing, neither the Company nor any of the company’s provider makes any representation or warranty of any kind, express or implied: (i) as to the operation or availability of the Service, or the information, content, and materials or products included thereon; (ii) that the Service will be uninterrupted or error-free; (iii) as to the accuracy, reliability, or currency of any information or content provided through the Service; or (iv) that the Service, its servers, the content, or e-mails sent from or on behalf of the Company are free of viruses, scripts, trojan horses, worms, malware, timebombs or other harmful components.

Some jurisdictions do not allow the exclusion of certain types of warranties or limitations on applicable statutory rights of a consumer, so some or all of the above exclusions and limitations may not apply to You. But in such a case the exclusions and limitations set forth in this section shall be applied to the greatest extent enforceable under applicable law.

Governing Law

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For European Union (EU) Users

If You are a European Union consumer, you will benefit from any mandatory provisions of the law of the country in which you are resident in.

United States Federal Government End Use Provisions

If You are a U.S. federal government end user, our Service is a “Commercial Item” as that term is defined at 48 C.F.R. §2.101.

United States Legal Compliance

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Severability and Waiver

Severability
If any provision of these Terms is held to be unenforceable or invalid, such provision will be changed and interpreted to accomplish the objectives of such provision to the greatest extent possible under applicable law and the remaining provisions will continue in full force and effect.

Waiver
Except as provided herein, the failure to exercise a right or to require performance of an obligation under this Terms shall not effect a party’s ability to exercise such right or require such performance at any time thereafter nor shall be the waiver of a breach constitute a waiver of any subsequent breach.

Translation Interpretation

These Terms and Conditions may have been translated if We have made them available to You on our Service.

You agree that the original English text shall prevail in the case of a dispute.

Changes to These Terms and Conditions

We reserve the right, at Our sole discretion, to modify or replace these Terms at any time. If a revision is material We will make reasonable efforts to provide at least 30 days’ notice prior to any new terms taking effect. What constitutes a material change will be determined at Our sole discretion.

By continuing to access or use Our Service after those revisions become effective, You agree to be bound by the revised terms. If You do not agree to the new terms, in whole or in part, please stop using the website and the Service.

Top Cyclades Islands Sailing Trips

Cyclades Islands Tours

Attractions

Guides

Calendar

Private 2 Hours Sunset Cruise in Milos — Magical Klima Village

Private Cruise West Side of Milo's & Kleftiko

Private Boat Tour in Milos with Lunch

Milos Private Half-Day Catamaran Cruise to Kleftiko with Lunch

Santorini 3 Islands Trip Sailing Wooden Boat

3-Hour Mykonos Best Beaches Yacht Cruise

Private Mykonos Cruise: Rhenia Swim & Little Venice Sunset

Santorini Morning or Sunset Romance Private Sailing Volcano Tour

Santorini Sailing for Cruise Guests A Volcano and Beach Tour

Mykonos Half Day Cruise to Rhenia and Delos Islands with Meals

Half Day Catamaran Afternoon Cruise in Kleftiko

Santorini Sunset cruise

Shared Day Cruise to Little Venice & Agios Stefanos

Luxury cruise in Greece to the CYCLADES by sailboat with CHEF

EXPLORE - Tour Adventure Koufonisia & Naxos (Private max 10 Pax)

Private Caldera Cruise Santorini

5 HourS Blue Lagoon start 1530 - cliff jumping in TRIPITI

All inclusive Sunset Cruise Delos & Rhenia&swimming stop

3 Hours Private Sunset Tour in Greece with Free Drinks & Snacks

DREAM - Antiparos, Blue Lagoon & Despotiko (Private max 10 Pax)

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