Where?
When?
2

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
US $4,903 per person

Southern Cyclades Sailing Cruise 2026

8 days
Start and end in Athens
5.0
1 traveler review
From
US $4,903 per person
+ $425 Port fee per guest

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
Save and compare this adventure

Best price guarantee Learn More

Plan your adventure:
Sailing
Catch the wind and set sail for new horizons
Partially Guided
Independent travel, featuring selected guided excursions
Low Intensity
Travelers can expect some light physical activities
Guided in English
Group Size 20 - 41
Ages 8+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Piraeus Departure

    Start point
    Pireas, Attica, Greece (port Piraeus, 20:00 - 22:00)
    Meals
    Dinner (Full board - Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies. Accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Explore Zea Marina harbour
    • Explore Mikrolimano harbour
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board
    Landmarks
    Zea Marina
    Mikrolimano
  2. Day 2

    Milos

    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Dinner (Full board - Decadent dinner accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Explore Sarakiniko beach
    • Visit picturesque fishing villages
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board

    Optional Activities

    • Visit Venus of Milo statue location
    • Explore island caves
    • Visit island catacombs
    Landmarks
    Sarakiniko Beach
    Milos Island
  3. Day 3

    Mountainous Island

    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Dinner (Full board - Decadent dinner accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Explore cliff-top towns
    • Visit deserted beaches
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board
    Itinerary Image 1
  4. Day 4

    Santorini

    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Afternoon Tea (Full board - Afternoon tea service available.), Dinner (Full board - Decadent dinner accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Visit Fira town
    • Explore volcanic beaches
    • Witness Santorini sunset
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board

    Optional Activities

    • Climb 687 steps to caldera edge
    • Drive mountain road to caldera viewpoint
    • Take funicular to caldera viewpoint
    Landmarks
    Fira
    Santorini Caldera
    Itinerary Image 1
  5. Day 5

    Astypalaia

    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Afternoon Tea (Full board - Afternoon tea service available.), Dinner (Full board - Decadent dinner accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Explore Chora
    • Visit Venetian Castle
    • View traditional windmills
    • Access Kaminakia beach by boat
    • Access Vatses beach by boat
    • Explore Vatses cave with stalactites and stalagmites
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board

    Optional Activities

    • Dine at Kaminakia tavern (boiled goat stew specialty)
    Landmarks
    Venetian Castle Chora
    Kaminakia Beach
    Vatses Beach
    Itinerary Image 1
  6. Day 6

    Ios

    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Afternoon Tea (Full board - Afternoon tea service available.), Dinner (Full board - Decadent dinner accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Explore golden beaches
    • Visit Ios Chora
    • Explore whitewashed houses and narrow alleys
    • Experience picturesque cliff-top villages
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board

    Optional Activities

    • Ios nightlife and bars
    • Ios restaurants
    Landmarks
    Ios Chora
    Itinerary Image 1
  7. Day 7

    Serifos

    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Afternoon Tea (Full board - Afternoon tea service available.), Dinner (Full board - Decadent dinner accompanied with wines from extensive collection and desserts. Coffee, tea, still water and crackers available at bar counter throughout the day.)

    Included Activities

    • Walk scenic trail from Livadi port to Hora
    • Explore Hora capital
    • Visit Castle complex
    • Visit Town Hall
    • Explore Square of the Windmills
    • Visit Archaeological Collection
    • Visit Church of Agios Ioannis Theologos
    • View Lighthouse of Serifos
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board

    Optional Activities

    • Explore island beaches
    Landmarks
    Hora (Serifos)
    Castle Complex Serifos
    Church of Agios Ioannis Theologos
    Lighthouse of Serifos
  8. Day 8

    Athens Return

    End point
    Pireas, Attica, Greece (port Piraeus, 08:00 - 08:00)
    Meals
    Breakfast (Full board - Ample breakfast with fresh juices, smoothies and beverages. Coffee, tea, still water and crackers available at bar counter throughout the day.), Lunch (Full board - Hearty lunch. Buffet or à la carte Mediterranean cuisine with Greek traditions, fresh seafood, finest ingredients and local delicacies.), Afternoon Tea (Full board - Afternoon tea service available.)

    Included Activities

    • Explore Piraeus waterfront
    • Explore Zea Marina
    • Explore Mikrolimano
    • Visit cafes and restaurants in Mikrolimano
    • Kayaking (equipment provided)
    • Windsurfing (equipment provided)
    • Snorkeling with fins and masks (equipment provided)
    • On-board entertainment and animation programs
    • Yoga classes on board
    • Karaoke on board

    Optional Activities

    • Explore Athens city centre
    • Visit metro stations with ancient necropolis remnants
    • Visit archaeological sites in Athens
    Landmarks
    Zea Marina
    Mikrolimano
    Athens
Want to read it later?

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

What's Included

Expand All
  • Accommodation
  • Meals
  • Additional Services
  • 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
  • Optional

Operated by

Running On Waves

5.0
(5 reviews)

Number of tours

15

Age Range

8 to 99 years old

Response time

within 3 days

Response rate

50%

Our Ship-owning company owns and operates a 64-meter-long three-mast luxury...

Read more

Your Peace of Mind Options

Cancellation Policy

A transparent overview of applicable fees.

Travel Insurance

Be covered for any unforseen circumstances.

Traveler Reviews

5.0
Overall rating based on 1 Reviews
  • Itinerary
    5.0
  • Transport
    5.0
  • Guide
    5.0
  • Accommodation
    5.0
  • Food
    5.0
  • 5.0

Sort by

Most recent
Most popular
Highest first
Lowest first

Sort by

Most Recent
Most Popular
Highest First
Lowest First
  • Southern Cyclades Sailing Cruise 2026 reviewer 1
    May 9th, 2025
    5.0
    cozy tour that i would like to repeat next year
    Traveled in May 2025

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
  • Instant Confirmation
    From Saturday
    20 Jun, 2026
    To Saturday
    27 Jun, 2026
    English
    This departure date is available and will 100% depart
    Guaranteed departure
    From:
    US $4,903 per person
    Multiple Room Types
    Port fee per guest
    $425
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
    • 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
Can’t find the answer to your question?
From
US $4,903 per person
+ $425 Port fee per guest

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
Save and compare this adventure

Best price guarantee Learn More

Plan your adventure:

Good to Know

Tour ID: 308353

  • 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 18th, 2026 a full payment is necessary. For tours departing after April 18th, 2026, a minimum payment of 25% is required to confirm your booking with Running On Waves. 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 Running On Waves will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Running On Waves" 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.

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