Escape Sale•Organized adventures  Up to 70% OFF

Sale ends: 23 Sep, 2026

Switch to the app and book faster and easier!

Where?
When?
2
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

Where to?

Traveling when?

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

Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
$2,883
US $2,470 per person

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
$2,883
-14%
US $2,470 per person
+ $126 Kitty

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select departure month

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

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. Intro

    Introduction

  2. Day 1

    Santorini to Ios

    Santorini to Ios

    Included Activities

    • Ferry from Santorini to Ios
    • Board yacht at Ios

    Optional Activities

    • Explore Thira's restaurants, shops and bars
    • Visit volcanic beaches
    • Walk along caldera's rim to Firostefani, Imerovigli and Oia (scenic at sunset)
    • Explore Hora's beaches, shops, restaurants and bars
    Landmarks
    Athinios Port
    Thira
    Firostefani
    Imerovigli
    Oia
    Hora, Ios
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. 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
  4. 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
  5. Day 4

    Naxos

    Naxos

    Included Activities

    • Access to Naxos island

    Optional Activities

    • Daytrip around the island
    • Visit southern beaches with water sports
    • Hike to Kastro (Roman Catholic neighbourhood)
    • Visit Roman Catholic Cathedral in Kastro square
    • Visit Archaeological Museum (former Jesuit School of Commerce)
    • Countryside excursion to observe rural life and visit ancient temple
    • Lunch at family tavern in the hills
    • Taste kitron (lemon liqueur)
    Landmarks
    Naxos
    Kastro, Naxos
    Roman Catholic Cathedral, Naxos
    Archaeological Museum, Naxos
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  6. 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
  7. Day 6

    Syros

    Syros
  8. Day 7

    Mykonos

    Mykonos

    Included Activities

    • Access to Mykonos island

    Optional Activities

    • Browse galleries and boutiques
    • Visit Church of Panagia Paraportiani
    • Relax on white beaches
    • Visit Little Venice
    • Enjoy cocktails and sunset at Little Venice
    • Experience Mykonos nightlife
    Landmarks
    Church of Panagia Paraportiani
    Little Venice, Mykonos
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  9. 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
  10. 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
  11. Day 10

    Ios to Santorini

    Ios to Santorini

    Included Activities

    • Ferry from Ios to Santorini

    Optional Activities

    • Taxi arrangement to hotel or airport
    Landmarks
    Athinios Port

Want to read it later?

Download this tour’s PDF brochure and start tour planning offline

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 (12,143 reviews)
Response time
7 hours
Response rate
92%
Cancellation policy
Learn more

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

Sort by

Most recent
Most popular
Highest first
Lowest first

Sort by

Most Recent
Most Popular
Highest First
Lowest First
  • 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 bustling street at night with people and shops.
    • A person steering a boat on the water.
    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

Sign up or log in to access your TourRadar+ savings

Dates & Prices

Select departure month

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 on 23 Sep, 2026
  • From Wednesday
    23 Sep, 2026
    To Friday
    2 Oct, 2026
    This departure date is not available or sold out
    Sold out
    From:
    US$2,848 per person
    Kitty
    $126
  • From Tuesday
    29 Sep, 2026
    To Thursday
    8 Oct, 2026
    English
    Almost Sold Out
    Check the availability with the operator
    Departure on request
    From:
    US$2,848 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Saturday
    1 May, 2027
    To Monday
    10 May, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,963
    US$2,538 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Tuesday
    11 May, 2027
    To Thursday
    20 May, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,963
    US$2,538 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Friday
    21 May, 2027
    To Sunday
    30 May, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,963
    US$2,538 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Monday
    31 May, 2027
    To Wednesday
    9 Jun, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,963
    US$2,538 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Friday
    4 Jun, 2027
    To Sunday
    13 Jun, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,883
    US$2,470 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Thursday
    10 Jun, 2027
    To Saturday
    19 Jun, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,883
    US$2,470 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Monday
    14 Jun, 2027
    To Wednesday
    23 Jun, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,883
    US$2,470 per person
    Price based on Shared Room
    Kitty
    $126
  • Instant Confirmation
    -14%
    From Sunday
    20 Jun, 2027
    To Tuesday
    29 Jun, 2027
    English
    Almost Sold Out
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    $2,883
    US$2,470 per person
    Price based on Shared Room
    Kitty
    $126

Want to read it later?

Download this tour’s PDF brochure and start tour planning offline

Why book with TourRadar?

    • Trusted and vetted operators
    • Rated excellent on
    • Best price guarantee
    • 24/7 customer support
    • Unlock exclusive TourRadar+ member savings

    To protect your payment and ensure your booking will be processed in United States, never transfer or communicate outside of the TourRadar website or app.

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
  • L

    Lisa

    Asked on July 18th, 2026

    how does accomodations work for 3 people could we fly from santorini to palermo

    Accommodation
    Flights / Transfers
    • Intrepid TravelOperator•Written July 2026

      We have triple bunk cabins available so if there is space on your chosen departure this would be the best way to keep you all roomed together. Otherwise booking into twin cabins would be the next available and one person in your group would be sharing with another solo traveller of the same gender.

      Intrepid does not book flights so you are welcome to fly wherever you would like that works for your trip.

  • 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.

Can’t find the answer to your question?
Reach out to the experts at Intrepid Travel with your enquiry, they usually respond within 7 hours.
From
$2,883
-14%
US $2,470 per person
+ $126 Kitty

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select departure month

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

Plan your adventure:

Earn while you share

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: 22857

  • Currency
    €
    Euro
    Greece
  • Plugs & Adapters

    As a traveler from USA, Canada, England, Australia, New Zealand, South Africa you will need an adaptor for types C, F.

    Type C
    Greece
    Type F
    Greece
  • 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 November 18th, 2026 a full payment is necessary. For tours departing after November 18th, 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

    • Cancellation terms may vary per tour. Please check for the full cancellation policy here.

      Checking the cancellation terms for this tour…
    • Your money is protected.
      TourRadar is an authorized agent of Intrepid Travel, and we handle payments so you don't have to. Payment is securely transferred to the Operator based on your departure date.
  • Insurance

    Our travel protection from our award-winning partner, XCover, means you and your travel companions can book with peace of mind knowing there’s protection available in case your trip doesn’t go to plan. At checkout you will be able to select between different options in case you or the tour are eligible for insurance. In case no option is available, you are always able to purchase travel insurance outside of TourRadar.

    Checking which travel protection options are available for you…
  • 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

Videos

  • Europe
  • Western Europe Travel Guide
  • Main Page Video
Europe

Keep Exploring Greece

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