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Set sail for adventure in the Aegean Sea on this Western Cyclades sailing adventure! Imagine waking up on your sailboat, with the sunshine on the sparkling water greeting you each morning. Best of all, you don’t need any experience, as each boat comes with an experienced skipper, who will also be your tour guide as you explore the best of Greece.
Starting in Athens, you will spend 8 incredible days sailing around Greece. Start each day with breakfast and a refreshing swim. Then spend your days relaxing on beaches, or add some adventure with snorkelling, dinghy tours, and island hikes.
Your group can personalize a tour that best suits your needs and preferences, so this trip is great for families, but can also be customized for groups that want more vigorous adventure.
End each day under the stars and let yourself be lulled to sleep each night by the gentle rocking of the boat and the sound of lapping waves. This sailing adventure in the Cyclades is everything you’ve ever dreamed that island hopping in Greece could be, with the luxury of a chartered sailboat and your own guide and skipper for the week. The dream trip of a lifetime is within your reach, and there’s no time like the present! Book your Western Cyclades sailing adventure today!
Greek Sailing Adventure








Set sail for adventure in the Aegean Sea on this Western Cyclades sailing adventure! Imagine waking up on your sailboat, with the sunshine on the sparkling water greeting you each morning. Best of all, you don’t need any experience, as each boat comes with an experienced skipper, who will also be your tour guide as you explore the best of Greece.
Starting in Athens, you will spend 8 incredible days sailing around Greece. Start each day with breakfast and a refreshing swim. Then spend your days relaxing on beaches, or add some adventure with snorkelling, dinghy tours, and island hikes.
Your group can personalize a tour that best suits your needs and preferences, so this trip is great for families, but can also be customized for groups that want more vigorous adventure.
End each day under the stars and let yourself be lulled to sleep each night by the gentle rocking of the boat and the sound of lapping waves. This sailing adventure in the Cyclades is everything you’ve ever dreamed that island hopping in Greece could be, with the luxury of a chartered sailboat and your own guide and skipper for the week. The dream trip of a lifetime is within your reach, and there’s no time like the present! Book your Western Cyclades sailing adventure today!
Sail between islands in the Cyclades archipelago of Greece and explore them with experienced guides.
View native wildlife, such as wild goats, Mediterranean seals, and dolphins, in their natural habitats.
Swim, snorkel, and explore sandy beaches and rocky coves in the clear waters of the Aegean Sea.
Experience the history and culture of the region, touring archaeological sites, meeting locals, and eating incredible local food.

Trip map

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Andrew C.
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We were well supported and route directions were easy to follow!
Beverly M.
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Bill B.
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10Adventures arranged everything for us, and what a trip it was!
Bipin J.
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We stayed in the best hotels, enjoyed delectable food, and hiked over 100km. Thanks to 10Adventures for making a memorable trip!
Bryn T.
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It's been superbly organized by 10Adventures all the way.
Carol L.
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Carol V.
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Thank you 10Adventures, it was indeed a buen camino!
Catharine T.
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We had an incredibly magical time that will stay with us for a lifetime.
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Chris N.
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10Adventures sorted out all of my accommodations and itinerary, and everything went as smooth as silk.
Christie O.
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It was perfect! I liked the fact knowing that I had somebody to call if I needed any assistance.
Colleen N.
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Craig and Ali C.
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Thank you so much 10Adventures! It was amazing and we're really looking forward to booking our next adventure with you.
Denise O.
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Dorian H.
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I had a great trip with 10Adventures!
Doug H.
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Drew S.
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10Adventures was awesome!
Eloise R.
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Euan D.
Cycling Dolomites to Lake Garda
Cycling Dolomites to Lake Garda
Gisèle S.
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We couldn't have done this trip without Nadine's help! We had a couple of challenges and she helped us out.
Guri-Lise H.
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Wonderful picnics!
Holly A.
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Jeanne G.
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Nadine was my travel guide and expert, and she was wonderful!
Jennifer W.
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10Adventures took care of everything!
Jillian R.
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Truly the trip of a lifetime!
Jinny M.
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Aisling G.
Picos de Europa
Really good value for the money, and having booked it I won't be doing any organizing myself any more.
Alexander R.
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We had a great time. The tour was very well organized, we stayed in nice places, and made some friends along the way.
John D.
Venice to Croatia Bike Tour
Great hotels, good breakfast every day, and good maps that always got us where we needed to go.
John O.
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The price was far better than all of the other companies we had looked at.
Julieanne M.
The Complete TMB
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Karen J.
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We're ready for our next adventure!
Katarina P.
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The trip was absolutely beautiful. I can't wait to go back!
Kate D.
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It was a dream. I can't think of a better way to see the world!
Kellie C.
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The experience was just so wonderful!
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It's an awesome adventure. Don't wait, take yours!
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It was a lot easier going through 10Adventures, I honestly don't think we could have booked our trip without that support.
Maureen W.
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Nadine was a great help in assisting us with some minor tweaks to the itinerary, and while we were there we found the organization, the planning, and support were brilliant.
Max W.
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Michael S.
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This was absolutely the trip of a lifetime!
Mei Ling H.
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Michelle H.
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Thanks 10Adventures!
Kellie C.
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Mike C.
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Nancy E.
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Thank you 10Adventures for some unforgettable experiences!
Nicole G.
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It was absolutely beautiful! We loved the service from 10Adventures.
Rachel D.
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Reid C.
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Renee H.
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Renee S.
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Rich G.
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Lesley C.
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Shahryar T.
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Shelley S.
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Stacey C.
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Sue W.
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Svetlana L.
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Sylvia F.
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Teresa B.
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Timothy K.
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Tony W.
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Uwe P.
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Why book with 10 Adventures?
We know adventure
Founded by experienced travellers, active and adventure vacations are all we do.
Experience the trip of a lifetime organized by a team of travel specialists who combine knowledge and passion for adventure travel.
Self-guided specialists
With over 600 tours across 30+ countries, we specialize in self-guided tours.
Combine the freedom of travelling on your own with the confidence that all of your logistics are taken care of.
Packed with value
Get everything you need for your next vacation with one easy booking.
We take care of accommodations, luggage transfers, gear rentals, and more - so you can focus on making memories.
World Class support
Get unbeatable support at every step of your journey.
Whether you are planning or travelling, no matter what your question, a real human is always a call or click away.
Hassle free bookings
Have peace of mind for when travel plans change.
Explore our flexible booking, payment, and cancellation options, as well as our Lifetime Deposits program.
Tours begin and end on Saturdays. Tours are typically available each Saturday between May and October, though custom bookings are available outside those months.
Pricing varies depending on the standard of boat you choose:
- Hanse 418 42’: from $14,575USD per boat (from $2,450USD per person)
- Hanse 508 51’: from $17,895USD per boat (from $2,250USD per person)
- Hanse 548 55’: from $19,895USD per boat (from $2,495USD per person)
Boat Details for Greek Sailing Tours
Beneteau Oceanis Sailboat– 46 feet
She sports 2 double cabins (2 in the stern) and 1 bathroom/shower for the guests. There is also one extra double cabin in the bow and 1 bathroom/shower for the crew. She also boasts a fully equipped kitchen and a very large dining room area in her galley, as well as an impressively large sundeck. She has a 57 hp motor engine that we use when there's not enough wind to power the sails. She comes equipped with snorkeling gear. br>
Total price for a group of up to 6 guests: from $14,575USD
Hanse 508 – 51 feet
Brand new 2020 model luxurious sailboat that includes 4 spacious double-bed cabins, one of which is reserved for the crew, all with en-suite toilets and showers. There is a fully-equipped kitchen and a large dining room. High-powered solar panels keep everything running smoothly and air conditioning will keep you cool even on the hottest day. This boat is larger, wider and has foldable water platform to make sunbathing and swimming in an open sea more entertaining.
Total price for a group of up to 8 guests: from $17,895USD
Hanse 548 – 55 feet
Brand new 2020 model luxurious sailboat that includes 4 spacious double-bed cabins, one of which is reserved for the crew, all with en-suite toilets and showers. All cabins have air conditioning thanks to a generator. There is a fully-equipped kitchen and a large dining room. High-powered solar panels keep everything running smoothly. This boat is larger, wider and has foldable water platform to make sunbathing and swimming in an open sea more entertaining.
Total price for a group of up to 8 guests: from $19,895USD
Meals
7 breakfasts on board are included typically consisting of seasonal fruit, peanut butter and jam, local bread, cheese, bacon, orange juice, coffee and tea.
Accommodations
Accommodations for 7 nights on the sailboat are included.
Transportation during the Tour
Sailboat charter and all related expenses (fuel, marina fees, etc.) are included in the price of the tour.
Also Included
- Services of a skipper for a week
- Services of a bilingual tour guide for a week
- Guided hiking, walking and sightseeing tours of all the places visited by a professional guide
- All taxes (including VAT)
Not included
- Airfare to/from Athens, Greece
- Transfers where needed (can be arranged for an extra fee)
- Meals not listed in inclusions (a shopping trip for supplies can be arranged free of charge in Athens). Dinners are typically in Greek tavernas in villages each night, and are not included.
- Personal expenses
- Gratuities to your guide and skipper
- Travel insurance (required)
Optional Extras
- Extra night in a hotel in Athens
- SUP or Paddleboard Rental
- Private cultural and culinary walking tour of Athens
- Private archaeological tour of Athens with a professional archaeologist
- Trip extensions to other parts of Greece
Accommodation for Greek Sailing Adventure
How hard is this tour?
We rate this tour as a 1 / 5, though it can be customized to more difficulty depending on your group. All activities and destinations can be customized to your interests and abilities. Guests should be able to swim.
Is this trip appropriate for families?
Yes! The sample itinerary is fine for families with children ages 4 and up. Arrangements can be made to accommodate families with children ages 3 and younger. Please make a note of this when booking your tour.
Will the tour company help me prepare for my trip?
Yes! The tour company will arrange 3 different video chats in preparation for your trip. By the time you arrive in Athens, you and your guide will have gotten to know each other, customized your tour to your preferences, and talked through everything you need to know to have a great trip!
What can I expect the tour company to provide prior to my tour?
The tour company offers access to online resources such as packing lists and interactive sightseeing maps. They can also offer advice and help booking extra hotel nights or transportation. If you would like to extend your trip to visit other parts of Greece, they can organize that as well.
What add-ons or additional services are available?
For an additional fee, guests can rent a paddleboard or SUP, arrange for a private cultural and culinary walking tour of Athens, take a private archaeological tour of Athens with a professional archaeologist, or extend their trip in other parts of Greece.
Do I need a Visa?
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
Are meals included?
7 breakfasts are included. Other meals and snacks are at your own expense. A shopping tour can be arranged to purchase supplies. Dinner will often be in a restaurant (at your expense).
Do I need insurance?
Yes, it is mandatory to have Health and Medical insurance to join this trip. Get your Travel Insurance.
Can you accommodate guests with disabilities?
Generally, it is expected that guests be able to get on and off of the sailboat unassisted by walking over a gangway. They should also be able to climb the 4 steps between the deck and the galley. However, arrangements can sometimes be made to accommodate guests with mobility challenges, so please reach out so we can learn more about your individual needs.
How do I get to Athens to start this tour?
Make your own way to Athens, flying to Athens International Airport (ATH). The tour begins at the Lavrion Marina, which can be reached from the airport via public transportation or by arranging a private transfer.
When and where should I arrive to begin my sailing adventure?
Please meet at the Lavrion Marina in Athens on the Saturday that your trip begins between 1-3 PM. If your travel plans require this time to be adjusted, please contact your tour guide. In the case of needing to change marinas, you will be contacted directly.
Where does the tour end?
The tour ends in Athens where it began. Checkout on the last day of your trip (Saturday) is at 9:00AM, which allows time to travel to the airport in time for most departing flights.
What can I expect from a typical day of sailing?
Your day begins with breakfast and time for a refreshing swim or a stroll on the island. By late morning, set sail toward the next destination. In the early afternoon, stop at point of interest along the way, or simply take a break to swim or snorkel in an uninhabited bay. Early in the evening, you’ll reach the place where you’ll spend the night, either dropping anchor in a bay or pulling into a marina. Spend the evening on the island sightseeing and end with an authentic Greek dinner in a local restaurant.
Do you sail at night?
Rarely. We only sail at night if the need arises, such as an unfavorable weather forecast or a guest’s need to leave later for a specific reason.
What if there’s bad weather?
Your guide and your skipper will monitor weather conditions and forecasts and choose an alternative itinerary if necessary.
Are the tours in English?
Yes, the tour guide is English speaking.
How much should I plan for food and personal expenses?
Compared with North America, Greece is relatively inexpensive. A budget of $40-60 USD per day will allow for a nice dinner (including alcohol) and personal snacks throughout the day.
Can I rent any water-sport equipment?
Yes, you can rent a paddleboard or SUP for an additional charge.
What is the weather like in Greece?
Expect summers in Greece to be hot and humid. In May and October, there is higher likelihood of cooler temperatures and occasional rain, but in July and August, temperatures range between 25-40°C. While open seas are always unpredictable, typically the seas are calm and ideal for sailing in the summer.
What should I pack?
Remember that space is limited on a sailboat, so please try to pack light. You’ll need clothes appropriate for the weather, and a water/windproof jacket in case of wet or cool weather. Bring sun protection such as a hat and sunscreen, swimwear, snorkelling gear and good walking shoes for hikes. Remember that wearing shorts is not permitted in monasteries and churches, so have at least one pair of long trousers or a long skirt. A flashlight and an umbrella may prove useful, and you can also consider bringing a camping mat and sleeping bag if you choose to sleep on deck.
Do I need vaccines?
Check with your family doctor.
Are there any travel restrictions for this country?
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview on the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provides advice on foreign travel. Note that the travel advice may change depending on your nationality.