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Greece Sailing Adventure: Cyclades Islands

10 days
•
Start and end in Santorini
4.6 (21 reviews)
  • Hilltop town with white buildings in a mountainous area.
  • Traditional white Greek buildings with a windmill against a blue sky.
  • Picturesque harbor with colorful boats and traditional Greek architecture.
    View all

  • Lots of time spent on the boat, beautiful swimming spots and a great way to spend a short time at lots of islands.

    Shannah•traveled in September5.0
  • People talking near an ancient stone structure overlooking the sea.
  • Person sitting and enjoying a panoramic view of a coastal town at sunset.
  • Beautiful sunset over the ocean with silhouetted mountains.
  • Scenic harbor with boats docked and white buildings on a hill.
  • Illuminated hilltop town at dusk with colorful lights.
  • Outdoor dining area with people enjoying meals under string lights.
    View all
From
$2,563
-14%
US $2,198 per person
+ $127 Kitty

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

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2026

Jan
Feb
Mar
Apr
May
Jun
Jul
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Sep
Oct
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2027

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Jul
Aug
Sep
Oct
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2028

Jan
Feb
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

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Best price guarantee Learn More

Plan your adventure:
Platinum Operator
Intrepid Travel
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
Medium Intensity
Travelers should be comfortable with somewhat-demanding activities
Guided in English
Group Size 12 - 11
Ages 15+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Santorini to Ios

    Santorini to Ios

    Included Activities

    • Yacht accommodation and sailing to Ios
    • Skipper-led orientation and trip coordination

    Optional Activities

    • Pre-tour exploration of Thira, Santorini (arriving early)
    • Volcanic beaches visit
    • Walk along caldera rim to Firostefani, Imerovigli and Oia
    • Explore Ios beaches
    • Visit Hora shops, restaurants and bars
    Landmarks
    Athinios Port
    Thira
    Firostefani
    Imerovigli
    Oia
    Ios Port
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  2. Day 2

    Amorgos

    Amorgos

    Included Activities

    • Sailing to Amorgos
    • Stop for swimming at Paradisi Beach

    Optional Activities

    • Explore Katapola waterfront restaurants and cafes
    • Visit ancient Minoan Settlement
    • Trip to 11th-century Moni Hozoviotissis monastery
    • Explore village of Hora
    • Visit Amorgos Archaeological Collection at Gavros Tower
    Landmarks
    Paradisi Beach
    Katapola Port
    Minoan Settlement
    Moni Hozoviotissis
    Hora
    Byzantine churches of Hora
    Amorgos Archaeological Collection
    Gavros Tower
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 3

    Small Cyclades

    Small Cyclades

    Included Activities

    • Sailing to Small Cyclades
    • Swimming and beach time

    Optional Activities

    • Explore fishing villages
    • Dine at waterfront taverna with fresh seafood
    Landmarks
    Koufonisia
    Iraklia
    Schinoussa
    Donousa
  4. Day 4

    Naxos

    Naxos

    Included Activities

    • Sailing to Naxos

    Optional Activities

    • Daytrip around Naxos island
    • Swimming and water sports at southern beaches
    • Hike to Kastro neighbourhood
    • Visit Roman Catholic Cathedral
    • Explore Archaeological Museum
    • Optional countryside trip with temple visit and family tavern lunch
    • Sample local Kitron lemon liquor
    Landmarks
    Kastro
    Roman Catholic Cathedral
    Archaeological Museum of Naxos
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Syros

    Syros

    Included Activities

    • Sailing to Syros
    • Stop for swimming at Bay of Gaidharos

    Optional Activities

    • Bus trip to Ano Syros
    • Explore Ano Syros stone archways and narrow alleys
    • Visit Ermoupoli town hall
    • Sample authentic Greek food and culture in Ermoupoli
    • Optional group dinner at neighbourhood family home with homemade cuisine and seafront views
    Landmarks
    Bay of Gaidharos
    Ano Syros
    Ermoupoli
    Itinerary Image 1
  6. Day 6

    Syros

    Syros
  7. Day 7

    Mykonos

    Mykonos

    Included Activities

    • Sailing to Mykonos

    Optional Activities

    • Browse galleries and boutiques in Mykonos town
    • Visit Church of Panagia Paraportiani
    • Relax on white beaches
    • Visit Little Venice
    • Enjoy cocktail and sunset at Little Venice
    • Explore Mykonos nightlife
    Landmarks
    Church of Panagia Paraportiani
    Little Venice
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  8. Day 8

    Sifnos

    Sifnos

    Included Activities

    • Sailing to Sifnos

    Optional Activities

    • Swim at Kamares beach
    • Explore Apollonia village
    • Visit whitewashed houses, churches and chapels
    • Visit Museum of Popular Art
    • Climb headland for panoramic views
    • See medieval Kastro fortress
    Landmarks
    Kamares Beach
    Apollonia
    Museum of Popular Art
    Kastro
  9. Day 9

    Folegandros

    Folegandros

    Included Activities

    • Sailing to Folegandros

    Optional Activities

    • Relax at Karavostasis pebbly beach
    • Dine at waterfront tavernas
    • Explore Hora village
    • Visit Kastro area
    • Visit Church of the Panagia for sunset views
    Landmarks
    Karavostasis
    Hora
    Kastro
    Church of the Panagia
  10. Day 10

    Folegandros to Santorini

    Folegandros to Santorini

    Included Activities

    • Ferry transfer from Ios to Santorini

    Optional Activities

    • Taxi arrangement to hotel or airport (with skipper assistance)
    Landmarks
    Athinios Port

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What's Included

Expand All
  • Accommodation
  • Guide
  • Transport

What's Not Included

  • Flights
  • Insurance
  • Meals
  • Optional
  • Additional Services

Operated by

Intrepid Travel

Platinum Operator
Rating
4.5 (12,103 reviews)
Response time
4 hours
Response rate
100%
Cancellation policy

Traveler Moments

  • A person steering a boat on the water.
  • A bustling street at night with people and shops.
  • A sun setting over a mountainous island seascape.
  • People swimming in clear blue waters near rocky shores.
  • Traditional white Greek buildings with a windmill against a blue sky.
  • A charming cafe in a narrow alley with colorful chairs.

Traveler Reviews

4.6
Overall rating based on 21 Reviews
  • Itinerary
    4.8
  • Transport
    4.7
  • Guide
    5.0
  • Accommodation
    4.2
  • Food
    4.5
  • Tour Operator
    4.5

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Highest First
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  • Ruth
    Ruth5.0•July 2026
    They can't do much better than our trip with Jiorgos
    Traveled in June 2026
    Reply from: Intrepid Travel
    Thank you for taking the time to post a review and for your 5-star rating. We're delighted to hear that you had such a great time on our Greece Sailing Adventure. We'll be sure to pass your kind words on to Jiorgos. We hope to welcome you on another adventure soon.
    Show more
  • Fiona
    Fiona5.0•October 2025
    The actual trip was amazing. The skipper was very knowledgeable and safety conscious. You have to allow 2 days for...
    Show more
    Traveled in September 2025
    Reply from: Intrepid Travel
    Thank you for letting us know how much you enjoyed your sailing trip. It is true that sailing is it's own pace and can take some adjustments, but now that you have experienced it, we hope that this turns into one of many sailing trips with Intrepid in your future.
    Show more
  • Elliot5.0•September 2025
    Amazing captain. He made this trip a fantastic sailing experience
    • A person steering a boat on the water.
    • A bustling street at night with people and shops.
    Traveled in August 2025
    Reply from: Intrepid Travel
    Thanks so much Elliot for sharing your thoughts on this trip with us. We are thrilled to hear that you had a great time sailing through this beautiful part of the world and we look forward to many more adventures!
    Show more
  • Deborah5.0•July 2024
    This was on my bucket list and it has exceeded my expectations,loved every minute of it and it was all down to our...
    Show more
    Traveled in June 2024
    Reply from: Intrepid Travel
    Hi Deborah, thank you for your lovely review. We are always excited to know when we have been able to host a traveller on their bucket list journey!! It is amazing to hear that everything met your expectations and that your time with your skipper was well spent. We look forward to seeing what other adventures you have in mind- stay well.
    Show more
  • Shannah5.0•September 2023
    Did the 10 day sailing trip around greece! Had an amazing time. Lots of time spent on the boat, beautiful swimming...
    Show more
    Traveled in August 2023
  • Susan5.0•May 2023
    Outstanding organization. Amazing visits to the islands, each unique. Daily very helpful briefings.with island info,...
    Show more
    Traveled in May 2023
  • Kornelia5.0•October 2022
    Great way to see and experience the cyclades.
    Traveled in September 2022
    Reply from: Intrepid Travel
    Hi there! Thank you so much for sharing your experience with us. We are so glad you enjoyed this sailing adventure in Greece. We look forward to welcoming you back on another tour soon!
    Show more
  • CateCotterell3.0•May 2021
    The tour leader for this tour was exceptional - incredibly knowledgeable, professional and did all he could to make...
    Show more
    Traveled in May 2021
    Reply from: Intrepid Travel
    Hi Cate, thank you for your detailed review about your Ningaloo Reef & Pilbara Adventure. We are delighted to read that you found your leader to be exceptional and did all he could, we are proud of our local leaders and their intimate knowledge of the area really enhancing your experience. Despite it, we are truly sorry that we have let you down, with the optional activity in Exmouth. It is through feedback like yours and the others that we are able to review and make improvements where necessary. A Customer Care consultant will be in contact with you directly to learn and answer your direct concerns you have brought to our attention.
    Show more
  • Carmen5.0•September 2019
    This is the fourth Intrepid trip I've taken.I've already gotten a few friends to use Intrepid as well.There are many...
    Show more
    Traveled in May 2019
  • Kaja4.7•September 2019
    Amazing Tour with an amazing skipper
    Traveled in May 2019

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Dates & Availability

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2026

Jan
Feb
Mar
Apr
May
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Sep
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2027

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Jul
Aug
Sep
Oct
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2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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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 in0d0h2m22s
  • From Monday
    10 Aug, 2026
    To Wednesday
    19 Aug, 2026
    Check the availability with the operator
    Departure on request
    From:
    US $2,563 per person
    Kitty
    $127
  • From Friday
    14 Aug, 2026
    To Sunday
    23 Aug, 2026
    Check the availability with the operator
    Departure on request
    From:
    US $2,693 per person
    Kitty
    $127
  • 1 Other Unavailable Departure
  • -14%
    From Thursday
    20 Aug, 2026
    To Saturday
    29 Aug, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    $2,563
    US $2,198 per person
    Multiple Room Types
    Kitty
    $127
  • From Monday
    24 Aug, 2026
    To Wednesday
    2 Sep, 2026
    Check the availability with the operator
    Departure on request
    From:
    US $2,968 per person
    Kitty
    $127
  • -14%
    From Sunday
    30 Aug, 2026
    To Tuesday
    8 Sep, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    $2,848
    US $2,440 per person
    Multiple Room Types
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  • -14%
    From Thursday
    3 Sep, 2026
    To Saturday
    12 Sep, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    $2,848
    US $2,440 per person
    Multiple Room Types
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    $127
  • -14%
    From Wednesday
    9 Sep, 2026
    To Friday
    18 Sep, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    $2,848
    US $2,440 per person
    Multiple Room Types
    Kitty
    $127
  • -10%
    From Sunday
    13 Sep, 2026
    To Tuesday
    22 Sep, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    $2,848
    US $2,576 per person
    Multiple Room Types
    Kitty
    $127
  • From Saturday
    19 Sep, 2026
    To Monday
    28 Sep, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    US $2,848 per person
    Multiple Room Types
    Kitty
    $127
  • From Wednesday
    23 Sep, 2026
    To Friday
    2 Oct, 2026
    Check the availability with the operator
    Departure on request
    From:
    US $3,138 per person
    Kitty
    $127

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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
  • N

    Nick

    Asked on July 15th, 2025

    Could she share her room with another female traveller and if this date is guaranteed?

    Accommodation
    Group size
    • Intrepid TravelOperator•Written July 2025

      We can confirm that if you choose our twin share option, you'll be paired with another traveler from the same group and of the same gender. The minimum group requirement is just one person, so even if you're the only one booked, the trip will still go ahead as planned.

  • K

    Karen

    Asked on June 28th, 2025

    I am imteresting to see cyclade islands for 11 days in full. Do you have the toure what is included what is the price from where you start

    Price / Availability
    Tour Details
    • Intrepid TravelOperator•Written June 2025

      Our "Greece Sailing Adventure: Cyclades Islands" is a full 10 day tour around the islands starting and ending in Santorini. The cost listed is the full price for the tour excluding airfare. We do not offer inclusive tours with airfare at this time, we do apologize.

  • C

    Christopher

    Asked on June 25th, 2025

    Catamaran type sail boat??

    Tour Details
    • Intrepid TravelOperator•Written June 2025

      The boat for this trip would be, The Ocean Star 56 is a classic sailboat, combining timeless design, exceptional seaworthiness and unmatched comfort. Fashioned with a traditional wood interior, the Ocean Star 56 has an impressive saloon and offers spacious [for a sailing boat] cabins. Equipped with 2 double cabins, 2 twin cabins and 1 triple cabin, the Ocean Star 56 is the perfect yacht for novices to learn the 'ropes'.

    • C

      Christopher

      Traveler•Written June 2025

      we did a cat trip with intrepid out of Thailand 10y ago - great captain / crew

      • C
      1 more answer
  • S

    Samuel

    Asked on March 18th, 2025

    Would like to see the Yatch. Do you have any pictures please.

    Tour Details
    • Intrepid TravelOperator•Written March 2025

      You can check out detailed information about the boat and some picture in the Intrepid trip website.

  • M

    Maya

    Asked on January 23rd, 2025

    Are meals included in the tour?

    Meals
    • Intrepid TravelOperator•Written January 2025

      No meals are included. A contribution to a kitty is required for some meals, which are then managed and prepared by the group.

  • L

    Lori

    Asked on November 29th, 2024

    How do I book the tour?

    Payments
    • Intrepid TravelOperator•Written December 2024

      You can book the tour by proceeding to the 'Book Now' section of the tour page and completing the required details.

  • K

    Katie

    Asked on October 12th, 2024

    Will there be a window in the cabin on the boat?

    Accommodation
    • Intrepid TravelOperator•Written October 2024

      The features of the cabins, including the availability of windows, can vary based on the boat assigned to your tour.

  • V

    Vicky

    Asked on August 26th, 2024

    we are looking for a private yacht charter for 2 adults that hops around the greek islands

    Accommodation
    Tour Details
    • Intrepid TravelOperator•Written August 2024

      We are able to put together a private charter on our boat however the minimum numbers that we need are usually 5+ people. Anything under 5 people tends to be 5x the online cost maybe more depending on time of year. If you are looking to do a private group charter then we can defiantly assist.

  • J

    Jan

    Asked on August 26th, 2024

    Are there group size restrictions on the tour?

    Group size
    • Intrepid TravelOperator•Written August 2024

      The maximum group size for the tour is typically limited to 11 travelers to ensure a personal and enjoyable experience.

  • M

    Maureen

    Asked on June 10th, 2024

    Can I bring a laptop on the tour?

    Other
    Tour Details
    • Intrepid TravelOperator•Written June 2024

      You are welcome to bring a laptop, but please be aware that our sailing boats do not have Wi-Fi. Connection opportunities are available when visiting towns.

Can’t find the answer to your question?
Reach out to the experts at Intrepid Travel with your enquiry, they usually respond within 4 hours.
From
$2,563
-14%
US $2,198 per person
+ $127 Kitty

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

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Good to Know

Tour ID: 22857

  • 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 October 4th, 2026 a full payment is necessary. For tours departing after October 4th, 2026, a minimum payment of $400 is required to confirm your booking with Intrepid Travel. 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 Intrepid Travel will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Intrepid Travel" 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.
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May
Jun
Jul
Aug
Sep
Oct
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2027

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2028

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