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Cyclades Luxury Sailing Adventure (Catamaran)

8 days
•
Start and end in Athens
4.7
3 reviews
  • Sailboat with people in the clear blue waters near rocky cliffs.
  • A boat on clear blue water with a backdrop of rocky cliffs.
  • Group of people on a sailboat enjoying the view.
  • Rocky coastal cliffs with bright sunlight reflecting on the water.
  • Blue water with a sailboat and rocky coast in the background.
    View all
  • A boat on clear blue water with a backdrop of rocky cliffs.
  • Catamaran's bow navigating turquoise waters with a rocky coastline.
  • Rocky coastal cliffs with bright sunlight reflecting on the water.
  • Group of people hiking along a coastal landscape with blue water.
  • Person standing on rocky coast with yachts in the sea.
    View all
From
$2,876
-18%
US $2,359 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

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Best price guarantee Learn More

Trails Beyond

4.9(96 reviews)

Replies within 1 day •67% response rate

Gold Operator
Trails Beyond
Sailing
Catch the wind and set sail for new horizons
Group Tour
Join a group and forge lifelong friendships
Fully Guided
An experienced guide will be with you for the entire tour
Low Intensity
Travelers can expect some light physical activities
Guided in English
Group Size 5 - 10
All Ages Welcome
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Athens to Cape Sounio / Kythnos

    Start point
    Alimos Marina, Λεωφ. Ποσειδώνος, Alimos, Αττικη, Greece (Alimos marina - exact pier number TBA)
    Meals
    Snack (Welcome snacks & drinks)

    Included Activities

    • Boat orientation and check-in
    • Welcome snacks and drinks on board

    Optional Activities

    • Evening swim at Loutra hot springs (Kythnos option)
    • Dinner at seaside restaurants (Kythnos option)
    Landmarks
    Temple of Poseidon
    Loutra Hot Springs
    Itinerary Image 1Itinerary Image 2
  2. Day 2

    Cape Sounio / Kythnos to Serifos

    Meals
    Breakfast (Breakfast on board), Lunch (Lunch on board)

    Included Activities

    • Breakfast on board
    • Sailing to Serifos island
    • Walk to Chora and Venetian Fortress viewpoint
    • Lunch on board

    Optional Activities

    • Morning dive near Temple of Poseidon
    • Morning hike on Kythnos (if starting from Kythnos)
    • Dinner at traditional tavernas
    • Drinks at local bars
    Landmarks
    Temple of Poseidon
    Chora
    Venetian Fortress
  3. Day 3

    Serifos to Kimolos

    Meals
    Breakfast (Breakfast on board)

    Included Activities

    • Breakfast on board
    • Sailing to Kimolos island
    • Day anchored at pristine beach
    • Walk to Chora

    Optional Activities

    • Dining at local restaurants
    • Visits to local bars
    Landmarks
    Kimolos
    Itinerary Image 1
  4. Day 4

    Kimolos to Milos

    Meals
    Breakfast (Breakfast on board), Lunch (Lunch on board)

    Included Activities

    • Breakfast on board
    • Swimming and snorkeling stop at Polyegos
    • Sailing to Kleftiko
    • Swimming and cave exploration at Kleftiko
    • Lunch on board
    • Sailing to Milos port

    Optional Activities

    • Boat diving at Polyegos
    • Boat diving at Kleftiko
    Landmarks
    Polyegos Island
    Kleftiko Coves
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Milos to Sifnos

    Meals
    Breakfast (Breakfast on board)

    Included Activities

    • Breakfast on board
    • Sailing to Sifnos island

    Optional Activities

    • Morning tour of Milos highlights including Sarakiniko beach, catacombs, Venus de Milo discovery site, ancient theatre, and Klima fishing village (approximately 3 hours, extra cost)
    • Visit to Kastro village
    • Dining at local restaurants
    Landmarks
    Sarakiniko Beach
    Kastro
    Klima
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  6. Day 6

    Sifnos to Kythnos

    Meals
    Breakfast (Breakfast on board)

    Included Activities

    • Breakfast on board
    • Sailing to Kythnos island
    • Visit to Kolona beach
    • Swimming and snorkeling at Kolona

    Optional Activities

    • Lunch at tavern on Kolona beach
    • Walk to Agios Loukas islet summit for panoramic views
    • Evening at Merichas port or secluded beach
    Landmarks
    Kolona Beach
    Agios Loukas Islet
    Merichas Port
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  7. Day 7

    Kythnos to Athens

    Meals
    Breakfast (Breakfast on board), Lunch (Lunch on board)

    Included Activities

    • Breakfast on board
    • Sailing to Athens
    • Final swimming stop en route
    • Lunch on board

    Optional Activities

    • Evening exploration of Athens south suburbs
    • Seaside stroll
    • Dinner at seaside restaurants
    Landmarks
    Athens Marina
  8. Day 8

    Athens Departure

    End point
    Alimos Marina, Λεωφ. Ποσειδώνος, Alimos, Αττικη, Greece (Same drop off as pickup location)

    Optional Activities

    • Airport transfer arrangement

Want to read it later?

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What's Included

Expand All
  • Accommodation
  • Guide
  • Insurance
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights
  • Optional
  • Additional Services

Adventure Type

Choose the type of organized adventure that suits your preferences.
  • Group Adventures
    Join a group and forge lifelong friendships.
    What to expect
    • Group of 10 travelers max.
    • Fast booking confirmation
    • Carefully planned itineraries
    • Travel with like-minded people
    Starting at
    US $2,359 / traveler
    Check availability
  • Personalized Adventures
    Customize an existing itinerary or create your own.
    What to expect
    • Travel with your own group of min. 2 travelers
    • Choose your preferred dates and duration
    • Upgrade your accommodation
    • Customize the itineraries
    After requesting a quote, we will get back to you with a price based on your requirements.
    Request quote

Operated by

Trails Beyond

Gold Operator
Rating
4.9(96 reviews)
Response time
within 1 day
Response rate
67%
Cancellation policy

Traveler Moments

  • A person standing on a hill overlooking a scenic sunset over islands.
  • Rocks beside a clear blue sea.
  • Bell overlooking a panoramic sea view.
  • Rolling hills under a cloudy sky.
  • View from a boat looking at the sea and distant shores.
  • Coastal path with white buildings and mountains in the background.
  • Ancient temple ruins under clear blue skies.
  • Clear waters with rocky seabed visible.
  • Aerial view of a town with a church bell tower.
  • Turquoise waters with visible rock formations underneath.
  • A coastal area with rocky formations and a person swimming in clear blue water.
  • A seaside village scene with chairs and a view of the sea.
  • Rocky seaside with blue water and a small island formation.
  • A boat on clear blue water with a backdrop of rocky cliffs.
  • A sailing mast against a blue sky filled with clouds.
  • Rocky coastal cliffs with bright sunlight reflecting on the water.
  • A nighttime street scene with tables and chairs at a cafe.
  • Coastal cliffs meeting the deep blue sea under a clear sky.
  • A serene harbor with boats lit at night and a lone rowboat in the foreground.
  • A seascape with the sun setting over the horizon, casting reflections on the water.
  • A person standing on a hill overlooking a scenic sunset over islands.
  • Hiking trail with stone walls and a cloudy sky.
  • A view of the ocean with a boat's wake in the foreground.
  • A coastal walkway with white buildings and a stone wall.
  • Historical stone columns against a bright blue sky.
  • Close-up view of clear water with rocks underneath a boat.
  • View from a hill overlooking a town with white buildings.
  • Close-up view of clear water and underwater rocks.
  • A coastal area with rocky formations and a person swimming in clear blue water.
  • A seaside village scene with chairs and a view of the sea.
  • Rocky seaside with blue water and a small island formation.
  • A boat on clear blue water with a backdrop of rocky cliffs.
  • A sailing mast against a blue sky filled with clouds.
  • Rocky coastal cliffs with bright sunlight reflecting on the water.
  • A nighttime street scene with tables and chairs at a cafe.
  • Coastal cliffs meeting the deep blue sea under a clear sky.
  • A serene harbor with boats lit at night and a lone rowboat in the foreground.
  • A bell with ocean view in the background.
  • Close-up view of a rocky shoreline and clear water.
  • A seascape with the sun setting over the horizon, casting reflections on the water.

Traveler Reviews

4.7
Overall rating based on 3 Reviews
  • Itinerary
    4.7
  • Transport
    5.0
  • Guide
    5.0
  • Accommodation
    4.3
  • Food
    4.3
  • Tour Operator
    4.9

Sort by

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Most popular
Highest first
Lowest first

Sort by

Most Recent
Most Popular
Highest First
Lowest First
  • Cyclades Luxury Sailing Adventure (Catamaran) reviewer 1
    May 22nd, 2024
    It is impossible to express how much we loved our trip. By the end Mike and Andreas were like family. We stayed...
    Show more
    • Hiking trail with stone walls and a cloudy sky.
    • Close-up view of a rocky shoreline and clear water.
    • Turquoise waters with visible rock formations underneath.
    • A serene harbor with boats lit at night and a lone rowboat in the foreground.
    • A nighttime street scene with tables and chairs at a cafe.
    • Clear waters with rocky seabed visible.
    • A seaside village scene with chairs and a view of the sea.
    • A person standing on a hill overlooking a scenic sunset over islands.
    • A sailing mast against a blue sky filled with clouds.
    • A serene harbor with boats lit at night and a lone rowboat in the foreground.
    • A coastal walkway with white buildings and a stone wall.
    • A nighttime street scene with tables and chairs at a cafe.
    • Rocks beside a clear blue sea.
    • View from a boat looking at the sea and distant shores.
    • A sailing mast against a blue sky filled with clouds.
    • Rocky coastal cliffs with bright sunlight reflecting on the water.
    • Rolling hills under a cloudy sky.
    • A seascape with the sun setting over the horizon, casting reflections on the water.
    • Coastal cliffs meeting the deep blue sea under a clear sky.
    • A coastal area with rocky formations and a person swimming in clear blue water.
    • Rocky coastal cliffs with bright sunlight reflecting on the water.
    • A bell with ocean view in the background.
    • Coastal path with white buildings and mountains in the background.
    • Close-up view of clear water with rocks underneath a boat.
    • Historical stone columns against a bright blue sky.
    • A view of the ocean with a boat's wake in the foreground.
    • A coastal area with rocky formations and a person swimming in clear blue water.
    • Rocky seaside with blue water and a small island formation.
    • A seaside village scene with chairs and a view of the sea.
    • Coastal cliffs meeting the deep blue sea under a clear sky.
    • A person standing on a hill overlooking a scenic sunset over islands.
    • Bell overlooking a panoramic sea view.
    • Close-up view of clear water and underwater rocks.
    • A boat on clear blue water with a backdrop of rocky cliffs.
    • View from a hill overlooking a town with white buildings.
    • A seascape with the sun setting over the horizon, casting reflections on the water.
    • A boat on clear blue water with a backdrop of rocky cliffs.
    • Aerial view of a town with a church bell tower.
    • Ancient temple ruins under clear blue skies.
    • Rocky seaside with blue water and a small island formation.
    Traveled in May 2024
  • M
    July 13th, 2023
    It was an awesome experience! Having done something similar in Croatia, we were hoping this tour would have more...
    Show more
    Traveled in July 2023
  • K
    September 21st, 2022
    Trip was amazing and defiantly the trip of a lifetime. Mike and Danae were fantastic! We had such a great time and...
    Show more
    Traveled in August 2022

Dates & Availability

Select departure month and travellers

Select Date

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Upcoming departures
Hurry, deals only available for a limited time!
Ends in2d2h1m27s
  • Instant Confirmation
    -18%
    From Saturday
    13 Jun, 2026
    To Saturday
    20 Jun, 2026
    English
    Filling Fast
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,876
    US $2,359 per person
    Multiple Room Types
  • Instant Confirmation
    From Saturday
    11 Jul, 2026
    To Saturday
    18 Jul, 2026
    English
    From:
    US $3,062 per person
    Multiple Room Types
  • Instant Confirmation
    From Saturday
    5 Sep, 2026
    To Saturday
    12 Sep, 2026
    English
    From:
    US $3,062 per person
    Multiple Room Types

Want to read it later?

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More benefits

What our customers ask about this tour

The content in our FAQ section is subject to change.
All questions
We couldn't find results
Try a different search term or ask a question to this adventure's experts
  • M

    Mike

    Asked on April 7th, 2025

    What are the demographics for this sailing trip? Is it mostly families? couples? retirees? My friend and I are both in our 30s and want to understand the current makeup of other passengers.

    Age Range
    Tour Details
    • Trails BeyondOperator•Written April 2025

      The average ages that usually join our tours are 40's-50's and they are travellers who appreciate nature, love the sea (i.e swimming, board paddling), enjoy tranquility and local food, cultural tours on islands and definitely don't throw a party on board! But, if you're looking for a little fun, that's something that you can experience on the islands we will disembark on.

  • X

    Xavier

    Asked on March 29th, 2025

    What is included in the standard yacht sailing package?

    Meals
    Tour Details
    • Trails BeyondOperator•Written March 2025

      The standard yacht sailing package includes yacht charter, skipper, tour leader, cleaning fee, fuel, port fees, water and electricity costs, all breakfasts and some lunches, liability insurance, bed linen and towels (one set per person), and taxes.

  • L

    Lauren

    Asked on February 22nd, 2025

    What is not included in the sailing package?

    Meals
    Tour Details
    • Trails BeyondOperator•Written February 2025

      A few lunches and dinners are not included in the sailing package. It's recommended to budget for simple meals from local supermarkets or bakeries during the tour.

  • H

    Heather

    Asked on February 18th, 2025

    Am I able to help sail the boat (sails, anchorage, steering at the helm) or are we just Along for the ride?

    Tour Details
    Transport
    • Trails BeyondOperator•Written February 2025

      It sounds great that you have an ASA Sailing Certification and you will be more than welcomed if you wish to help our captain on board. Please note that normally that's not mandatory and the tours we offer are basically for entertaiment and relaxation. Kindly be informed that the captain is on charge for any damage and group's safety, so we all follow strictly his instructions on board.

  • A

    Aaron

    Asked on December 28th, 2024

    Could you kindly advise which of the 2 departures has more guaranteed chance of departure? What's the best discount you can offer for the single occupancy? And what is included and what is not included? Do we have our own toilet bathroom in our cabin? Do we have internet on the catamaran? How big is the cabin? Could you kindly show the picture of a cabin? Where is the boarding port / leaving port?

    Accommodation
    Price / Availability
    Tour Details
    Transport
    • Trails BeyondOperator•Written January 2025

      There is an ensuite private bathroom in your cabin. There is no wifi on board, so if you wish to include it there is an extra charge of 70€ in total for the whole week. Otherwise, you will be able to find wifi spots on the islands. The boarding/leaving port will be Alimos Marina, Alimos (10 km south of the center of Athens).

    • A

      Aaron

      Traveler•Written January 2025

      The most important is having own toilet in own room

      • A
      1 more answer
  • M

    Mathias

    Asked on December 17th, 2024

    Is there a security deposit required for yacht charter?

    Price / Availability
    • Trails BeyondOperator•Written December 2024

      Yes, a fully refundable security deposit is required at the time of embarkation, the amount may vary depending on the yacht. It is refunded at the end of the charter unless there is damage caused to the yacht.

  • S

    Sergio

    Asked on December 14th, 2024

    Is travel insurance required for joining a sailing tour?

    Travel Support
    • Trails BeyondOperator•Written December 2024

      Travel insurance is not mandatory but is strongly recommended for coverage against unforeseen events like illness, robbery, or document loss during travel.

  • A

    Audrey

    Asked on December 1st, 2024

    Do you have anything available for solo travelers? I would like to spend June & July 2025 in and round the Greek Islands. Im 61 and healthy.

    Age Range
    Tour Details
    • Trails BeyondOperator•Written December 2024

      Since you are a solo traveller, you can choose your own cabin in the boat to have your own space because the rooms are small due to boat construction.

  • W

    Wilo

    Asked on November 28th, 2024

    How does the yachting industry in Greece operate?

    Other
    • Trails BeyondOperator•Written November 2024

      Sailing charters in Greece typically run on a week-long basis, starting and ending on Saturdays. Yachts must return to base the evening before the last day.

  • T

    Traveling

    Asked on November 23rd, 2024

    Are there specific recommendations for places to visit in Greece after the yacht tour?

    Other
    Tour Details
    • Trails BeyondOperator•Written November 2024

      Tour operators can provide recommendations for additional travel within Greece, including popular destinations like the Peloponnese peninsula and cultural sites like Meteora.

Can’t find the answer to your question?
Reach out to the experts at Trails Beyond with your enquiry, they usually respond within 1 day.
From
$2,876
-18%
US $2,359 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Best price guarantee Learn More

Trails Beyond

4.9(96 reviews)

Replies within 1 day •67% response rate

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With TourRadar RISE, you can earn commission when someone books a tour through a link you share — like this one.

Good to Know

Tour ID: 137530

  • Currency
    €
    Euro
    Greece
  • Plugs & Adapters

  • Vaccines
    • These are only indications, so please visit your doctor before you travel to be 100% sure.
    • Hepatitis A - Recommended for Greece. Ideally 2 weeks before travel.
    • Hepatitis B - Recommended for Greece. Ideally 2 months before travel.
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before July 10th, 2026 a full payment is necessary. For tours departing after July 10th, 2026, a minimum payment of 10% is required to confirm your booking with Trails Beyond. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 60 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Trails Beyond will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Trails Beyond" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.
  • People also viewed

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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec