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

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.

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

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.

Catamaran type sail boat??

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'.

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

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

Are meals included in the tour?

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

How do I book the tour?

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

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

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

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

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.

Are there group size restrictions on the tour?

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

Can I bring a laptop on the tour?

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.

From

US $2,840 per person

Greece Sailing Adventure: Cyclades Islands

10 days

•

From Santorini to Ios

4.6

20 traveler reviews

View all
Varied and interesting itinerary. Got the whole group to bond together really well.
S
Stephen T, traveled in September
4.5
View all

From

US $2,840 per person

+ $131 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

1 Adult2 Adults, 1 Child2 Children

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

Day 1
Santorini
Optional Activities
- Arrive early to explore Santorini's restaurants, shops and bars
- Visit volcanic beaches
- Walk along the caldera's rim to Firostefani, Imerovigli and Oia
- Explore Ios beaches
- Browse Hora's shops, restaurants and bars
Landmarks
Athinios Port
Thira
Firostefani
Imerovigli
Oia
Ios Port
Day 2
Ios to Amorgos
Optional Activities
- Swim at Paradisi Beach
- Explore Katapola waterfront restaurants, cafes and bars
- Visit the ancient Minoan Settlement
- Visit Moni Hozoviotissis monastery (11th-century)
- Explore the village of Hora
- Visit Amorgos Archaeological Collection in Gavros Tower
Landmarks
Amorgos
Paradisi Beach
Katapola
Moni Hozoviotissis
Hora
Gavros Tower
Day 3
Small Cyclades
Optional Activities
- Swim and relax on the islands' beaches
- Explore fishing villages
- Sample fresh seafood at waterfront taverna
Landmarks
Koufonisia
Iraklia
Schinoussa
Donousa
Day 4
Naxos
Optional Activities
- Day trip around Naxos
- Visit southern beaches
- Try water sports
- Hike to Kastro neighborhood
- Visit Roman Catholic Cathedral
- Visit Archaeological Museum
- Optional countryside trip to observe rural life and ancient temples
- Lunch at family tavern in the hills
- Taste local Kitron (lemon liquor)
Landmarks
Kastro
Roman Catholic Cathedral
Archaeological Museum
Day 5
Syros
Optional Activities
- Swim at Bay of Gaidharos
- Bus trip to Ano Syros village
- Explore stone archways and narrow alleys
- Sample authentic Greek food and culture in Ermoupoli
- Visit town hall in main square
- Optional group dinner at neighborhood family's home
Landmarks
Bay of Gaidharos
Ano Syros
Ermoupoli
Day 6
Syros
Day 7
Mykonos
Optional Activities
- Browse galleries and boutiques
- Visit Church of Panagia Paraportiani
- Relax on white beaches
- Visit Little Venice
- Enjoy sunset cocktails at Little Venice
- Experience Mykonos nightlife
Landmarks
Church of Panagia Paraportiani
Little Venice
Day 8
Sifnos
Optional Activities
- Swim at Kamares beach
- Explore Apollonia village
- Visit Museum of Popular Art
- Climb headland for panoramic ocean views
- Visit medieval fortress of Kastro
Landmarks
Kamares
Apollonia
Museum of Popular Art
Kastro
Day 9
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
Day 10
Return to Santorini
Optional Activities
- Extend your stay in Santorini
Landmarks
Athinios Port

Landmarks
Athinios Port
Thira
Firostefani
Imerovigli
Oia
Ios Port

Landmarks
Amorgos
Paradisi Beach
Katapola
Moni Hozoviotissis
Hora
Gavros Tower

Landmarks
Koufonisia
Iraklia
Schinoussa
Donousa

Landmarks
Kastro
Roman Catholic Cathedral
Archaeological Museum

Landmarks
Bay of Gaidharos
Ano Syros
Ermoupoli

Landmarks
Church of Panagia Paraportiani
Little Venice

Landmarks
Kamares
Apollonia
Museum of Popular Art
Kastro

Landmarks
Karavostasis
Hora
Kastro
Church of the Panagia

Landmarks
Athinios Port

What's Included

Expand All

Accommodation
Guide
Transport
Free eSIM
TourRadar offers the lead traveler (the person who booked) a free 1GB eSIM for the trip. The eSIM is redeemable only through the TourRadar app 72 hours before departure.

What's Not Included

Flights
Insurance
Meals
Optional
Additional Services

Operated by

Intrepid Travel

4.5

(12,109 reviews)

Number of tours

876

Age Range

5 to 99 years old

Response time

10 hours

Response rate

84%

Back in 1989, two guys from Melbourne, Australia by the names of Darrell and...

Sustainability Initiatives

Reduce Carbon Emissions

Animal Welfare

Supporting Destinations

Sustainability Programs

Your Peace of Mind Options

Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Traveler Moments

Traveler Reviews

4.6

Overall rating based on 20 Reviews

Itinerary
4.8
Transport
4.7
Guide
5.0
Accommodation
4.2
Food
4.5
Tour Operator
4.5

Fiona Alison
October 3rd, 2025
5.0
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
E
Elliot
September 21st, 2025
5.0
Amazing captain. He made this trip a fantastic sailing experience
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
D
Deborah
July 17th, 2024
5.0
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
S
Shannah
September 27th, 2023
5.0
Did the 10 day sailing trip around greece! Had an amazing time. Lots of time spent on the boat, beautiful swimming...
Did the 10 day sailing trip around greece! Had an amazing time. Lots of time spent on the boat, beautiful swimming spots and a great way to spend a short time at lots of islands. Spent most of the day out on the water and afternoon/nights exploring different greek islands. We had the most amazing skippers (George and Orestis). They mad the trip so fun and we’re full of information about Greece and the history. Definitely recommend this trip! Best skippers ever!Show more
Traveled in August 2023
S
Susan Merida
May 26th, 2023
5.0
Outstanding organization. Amazing visits to the islands, each unique. Daily very helpful briefings.with island info,...
Outstanding organization. Amazing visits to the islands, each unique. Daily very helpful briefings.with island info, and great links sent to us, highlighted and enhanced the odyssey. Skipper highly experienced, congenial, friendly and always ready to answer our questions. Flexibility with departure, according to our needs and the daily activities. Great recommendations for dining, museum visits, extra excursion options. As a native English speaker living in Germany I did luck out with a marvelous lively mix of native speakers on our boat. I celebrated my birthday with this energetic group. The trip surpassed my expectations. I highly recommend this trip.Show more
Traveled in May 2023
K
Kornelia
October 8th, 2022
5.0
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
C
CateCotterell
May 29th, 2021
3.0
The tour leader for this tour was exceptional - incredibly knowledgeable, professional and did all he could to make...
The tour leader for this tour was exceptional - incredibly knowledgeable, professional and did all he could to make this the most awesome adventure for all members of the Tour. UNFORTUNATELY whilst the Pilbara experiences were fantastic and not to be missed, Intrepid tours failed to reserve places for the Optional Activity for Sunday 22 May - this being the Ningaloo Whale Shark swim. It is high season here in Exmouth for whale Shark swims - there were simply no places reserved by Intrepid , nothing in our intrepid travel documents alerting us and others to the need to book in advance. Subsequently 4 of the group have missed out entirely on this experience - and when you’ve spent the amount of money we have to travel to Exmouth from Sydney, accomodation, flights , car rental , tour costs then we , along with others in this group have been left feeling completely ripped off in having missed out on this once in a lifetime experience Not ok IntrepidShow 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
A
Carmen M
September 18th, 2019
5.0
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
A
Kaja R
September 18th, 2019
4.7
Amazing Tour with an amazing skipper
Traveled in May 2019
A
Donald L
September 18th, 2019
4.3
I don't have friends to whom I make recommendations.
Traveled in May 2019

Dates & Availability

Select departure month and travellers

Select Date

1 Adult2 Adults, 1 Child2 Children

Upcoming departures

From Saturday
2 May, 2026
To Monday
11 May, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $3,040 per person
Multiple Room Types
Kitty
$131
From Friday
22 May, 2026
To Sunday
31 May, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $3,040 per person
Multiple Room Types
Kitty
$131
From Tuesday
26 May, 2026
To Thursday
4 Jun, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $3,040 per person
Multiple Room Types
Kitty
$131
From Monday
1 Jun, 2026
To Wednesday
10 Jun, 2026
Check the availability with the operator
Departure on request
From:
US $3,040 per person
Kitty
$131
See Similar Tours For These Dates
From Friday
5 Jun, 2026
To Sunday
14 Jun, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $3,040 per person
Multiple Room Types
Kitty
$131
From Thursday
11 Jun, 2026
To Saturday
20 Jun, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $3,040 per person
Multiple Room Types
Kitty
$131
From Monday
15 Jun, 2026
To Wednesday
24 Jun, 2026
Check the availability with the operator
Departure on request
From:
US $2,980 per person
Kitty
$131
See Similar Tours For These Dates
From Sunday
21 Jun, 2026
To Tuesday
30 Jun, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $2,840 per person
Multiple Room Types
Kitty
$131
From Thursday
25 Jun, 2026
To Saturday
4 Jul, 2026
English
Almost Sold Out
Check the availability with the operator
Departure on request
From:
US $2,840 per person
Multiple Room Types
Kitty
$131
From Wednesday
1 Jul, 2026
To Friday
10 Jul, 2026
Check the availability with the operator
Departure on request
From:
US $2,840 per person
Kitty
$131
See Similar Tours For These Dates

Why book with TourRadar?

Trusted and vetted operators
Rated excellent on
Best price guarantee

24/7 customer support
Earn $50 in travel credits
Free eSim with every purchase

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

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
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.

From

US $2,840 per person

+ $131 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

1 Adult2 Adults, 1 Child2 Children

Best price guarantee Learn More

Plan your adventure:

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 April 14th, 2026 a full payment is necessary. For tours departing after April 14th, 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
- Your money is safe with TourRadar, as we only pay the tour operator after your tour has departed.
- TourRadar is an authorized Agent of Intrepid Travel. Please familiarize yourself with the Intrepid Travel payment, cancellation and refund conditions.
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
Colorado Vacation Packages
Kilimanjaro climbing rongai route 7 days
Israel & Jordan in 15 days
Taste of Scotland
Private Taj Mahal Agra Overnight Tour from De…
Islands of New England (Providence, RI to Ca…
11-Day Exotic Southeast Asia: Thailand, Singa…

Videos

Europe
Western Europe Travel Guide
Main Page Video

Greece Sailing Adventure: Cyclades Islands

Itinerary

Santorini

Optional Activities

Ios to Amorgos

Optional Activities

Small Cyclades

Optional Activities

Naxos

Optional Activities

Syros

Optional Activities

Syros

Mykonos

Optional Activities

Sifnos

Optional Activities

Folegandros

Optional Activities

Return to Santorini

Optional Activities

Want to read it later?

What's Included

What's Not Included

Sustainability Initiatives

Your Peace of Mind Options

Cancellation Policy

Travel Insurance

Traveler Moments

Traveler Reviews

Dates & Availability

Want to read it later?

Why book with TourRadar?

What our customers ask about this tour

Good to Know

Videos

Similar Tours

Keep Exploring Greece