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2026

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Who is travelling?

AdultsAges 18 or above

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ChildrenUnder 18

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Fully guided Sailing adventure in the Cyclades Islands

8 days
Start and end in Lavrion

No departure dates available

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Plan your adventure:
Sailing
Catch the wind and set sail for new horizons
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
Max Group Size 6
Ages 8+
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Lavrion to Kythnos

    Start point
    Olympic Marine, Attica, Greece (Our office, 14:00 - 15:00)
    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Included Activities

    • Guided orientation on the sailing boat
    • Sailing past Temple of Poseidon at Cape Sounion
    • Overnight anchorage at Kolona beach, Kythnos

    Optional Activities

    • Dinner at local seafood restaurant on northern cliffs of Kolona beach
    Landmarks
    Temple of Poseidon
    Kolona Beach
    Itinerary Image 1Itinerary Image 2
  2. Day 2

    Kythnos to Serifos

    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Included Activities

    • Swimming at Kolona beach
    • Sailing to Serifos island
    • Swim stop in turquoise bays on eastern side of Serifos
    • Private 2-hour guided walking tour of Serifos main town including old town and Venetian castle

    Optional Activities

    • Short hike to whitewashed chapel overlooking Aegean Sea
    • Dinner at local seafood restaurant on the beach
    Landmarks
    Serifos Venetian Castle
    Serifos Main Town
    Itinerary Image 1Itinerary Image 2
  3. Day 3

    Serifos to Milos

    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Included Activities

    • Sailing to Milos island
    • Sail past bay of Sarakiniko
    • Private 2-hour guided walking tour of Milos castle, main town, and catacombs

    Optional Activities

    • Cocktails on terrace overlooking sunset
    Landmarks
    Sarakiniko Bay
    Milos Castle
    Itinerary Image 1Itinerary Image 2
  4. Day 4

    Polyaigos - Sifnos

    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen), Lunch (Quick lunch onboard)

    Included Activities

    • Sailing to bay of Kleftiko, Milos
    • Swimming and cave exploration in Kleftiko
    • Sailing around Milos viewing sulfur and obsidian mines
    • Sailing to Polyaigos island
    • Swimming and snorkeling at Polyaigos
    • Sailing to Sifnos island

    Optional Activities

    • Snorkeling at Kleftiko
    • Paddleboarding at Kleftiko (150 euros per paddleboard per tour)
    • Dinner at local restaurants on Sifnos
    Landmarks
    Bay of Kleftiko
    Polyaigos Island
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 5

    Sifnos to Loutra, Kythnos

    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Included Activities

    • Sailing to Loutra, Kythnos
    • Swimming at Loutra beach
    • Access to natural hot springs at Loutra
    • Private guided walking tour of Kythnos main town including medieval chapels and whitewashed houses

    Optional Activities

    • Beer and relaxation in natural pool under moonlight
    • Local taxi transport to main settlement (paid by guests)
    • Dinner at local eateries in main town
    Landmarks
    Loutra Beach
    Loutra Hot Springs
  6. Day 6

    Kythnos to Kea

    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Included Activities

    • Sailing to Kea island
    • Archaeological site of Afaia exploration (Temple of Athena, Temple of Poseidon, ancient shipyard, ancient theater)
    • Dinghy transport to Afaia
    • Local bus transport to Ioulida main town
    • Private guided walking tour of Ioulida
    • Hike to Lion of Kea

    Optional Activities

    • Dinner at local restaurant in Ioulida
    Landmarks
    Afaia Archaeological Site
    Temple of Athena
    Temple of Poseidon
    Lion of Kea
  7. Day 7

    Kea to Cape Sounion

    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Included Activities

    • Sailing toward Athens
    • Stop at Temple of Poseidon at Cape Sounion
    • Dinghy transport to beach
    • Exploration of Temple of Poseidon

    Optional Activities

    • Swimming at Temple of Poseidon beach
    Landmarks
    Temple of Poseidon
  8. Day 8

    Departure

    End point
    Olympic Marine, Attica, Greece (Our office, 08:30 - 09:00)
    Meals
    Breakfast (Daily self service breakfast onboard: free range eggs, bacon, peanut butter, jam, coffee and tea, fresh seasonal fruit and vegetables, milk and cereal, local cheeses and cold cuts, bread, and access to fully equipped galley kitchen)

    Optional Activities

    • Transportation to airport or downtown Athens

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What's Included

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

What's Not Included

  • Flights
  • Optional
  • Additional Services
Response time
less than 1 hour
Cancellation policy

What our customers ask about this tour

The content in our FAQ section is subject to change.
All questions
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  • C

    Carla

    Asked on February 20th, 2023

    Can you tell me the name of the boat, and what type of boat?

    Tour Details
    • Bearing True SouthOperatorWritten February 2023

      The sailboats available for this specific tour are either an Elan Impression 45.1 (2020), a Hanse 458 (2019) or Bavaria 46 (2020) or similar.

Can’t find the answer to your question?
Reach out to the experts at Bearing True South with your enquiry, they usually respond in less than 2 hours.

No departure dates available

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Good to Know

Tour ID: 183362

  • 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 June 16th, 2026 a full payment is necessary. For tours departing after June 16th, 2026, a minimum payment of 50% is required to confirm your booking with Bearing True South. 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 45 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 Bearing True South will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Bearing True South" 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