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2026

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2027

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2028

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Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
US $1,195 per person

Dodecanese Sailing Explorer

8 days
Start and end in Rhodes
4.5
906 traveler reviews
From
US $1,195 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select Date

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2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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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
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Plan your adventure:
Sailing
Catch the wind and set sail for new horizons
Guided in English
Group Size 2 - 25
All Ages Welcome
Image of a map showing the route of the tour

Itinerary

  1. Day 1

    Rhodes

    Meals
    Dinner (Welcome dinner)

    Included Activities

    • Explore Rhodes Harbour waterfront
    • Visit UNESCO World Heritage Old Town

    Optional Activities

    • Shop at local markets for spices and olive oil
    • Dine at authentic Greek tavernas
    • Browse antique shops
    Landmarks
    Old Town of Rhodes
    Rhodes Harbour
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  2. Day 2

    Rhodes to Symi

    Meals
    Breakfast, Lunch

    Included Activities

    • Swimming and snorkeling at Nanou Bay
    • Arrival at Symi Port

    Optional Activities

    • Dinner at waterfront tavernas in Symi
    Landmarks
    Nanou Bay
    Symi Port
  3. Day 3

    Symi

    Meals
    Breakfast, Lunch (Lunch served on deck at St. George Bay)

    Included Activities

    • Swimming and snorkeling at St. George Bay
    • Lunch on deck at St. George Bay
    • Visit Monastery of the Archangel Michael Panormitis
    Landmarks
    St. George Bay
    Monastery of the Archangel Michael Panormitis
  4. Day 4

    Symi to Tilos

    Meals
    Breakfast, Lunch

    Included Activities

    • Swimming and snorkeling at Akrogiali Bay

    Optional Activities

    • Visit Mikro Chorio ghost village
    • Dinner at traditional taverna in harbor with farm-to-table approach and local goat dishes
    Landmarks
    Akrogiali Bay
    Tilos Harbor (Livadia)
    Mikro Chorio
  5. Day 5

    Tilos to Chalki

    Meals
    Breakfast, Lunch

    Included Activities

    • Swimming and snorkeling at Trakhia Bay

    Optional Activities

    • Visit village church for traditional mass between 7:30-8:00 PM
    • Dinner at family-run waterfront taverna with seafood meze
    Landmarks
    Trakhia Bay
    Nimporio
  6. Day 6

    Chalki to Rhodes (Kalithea)

    Meals
    Breakfast, Lunch, Dinner (Special dinner)

    Included Activities

    • Visit Anthony Quinn Bay
    • Explore Kalithea coves
    • Swimming at Kalithea
    Landmarks
    Anthony Quinn Bay
    Kalithea
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  7. Day 7

    Rhodes

    Meals
    Breakfast, Lunch

    Included Activities

    • Return to Rhodes Port

    Optional Activities

    • Visit Palace of the Grand Master
    • Explore Street of the Knights
    • Wander Medieval Old Town
    • Farewell Dinner at traditional taverna
    Landmarks
    Palace of the Grand Master
    Street of the Knights
    Old Town of Rhodes
  8. Day 8

    Rhodes

    Meals
    Breakfast

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What's Included

Expand All
  • Accommodation
  • Meals
  • Additional Services
  • Transport

What's Not Included

  • Flights
  • Insurance
  • Additional Services
Gold Operator
Rating
4.5(906 reviews)
Response time
11 hours
Response rate
94%
Cancellation policy

Reviews from other tours by Encounters Travel

  • Jaime
    September 14th, 2024
    Excellent introduction to Classical Greece. Our guide, Georgina, was super knowledgeable , capable, and friendly.
  • Anthony
    September 24th, 2023
    These tours start with the itinerary, but are made or busted with the guide. Ours was Dominique (sp?). She was...
    Show more
  • Paula
    December 28th, 2024
    Operated by Fez travel, an all round wonderful experience, our tour guide Halil and driver were excellent. Highly...
    Show more

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
  • From Saturday
    18 Jul, 2026
    To Saturday
    25 Jul, 2026
    English
    From:
    US $1,400 per person
  • From Saturday
    25 Jul, 2026
    To Saturday
    1 Aug, 2026
    English
    From:
    US $1,400 per person
  • From Saturday
    15 Aug, 2026
    To Saturday
    22 Aug, 2026
    English
    From:
    US $1,400 per person
  • From Saturday
    10 Oct, 2026
    To Saturday
    17 Oct, 2026
    English
    From:
    US $1,195 per person
  • From Saturday
    17 Oct, 2026
    To Saturday
    24 Oct, 2026
    English
    From:
    US $1,195 per person
  • From Saturday
    1 May, 2027
    To Saturday
    8 May, 2027
    English
    From:
    US $1,195 per person
    Multiple Room Types
  • From Saturday
    8 May, 2027
    To Saturday
    15 May, 2027
    English
    From:
    US $1,195 per person
    Multiple Room Types
  • From Saturday
    15 May, 2027
    To Saturday
    22 May, 2027
    English
    From:
    US $1,265 per person
    Multiple Room Types
  • From Saturday
    22 May, 2027
    To Saturday
    29 May, 2027
    English
    From:
    US $1,265 per person
    Multiple Room Types
  • From Saturday
    29 May, 2027
    To Saturday
    5 Jun, 2027
    English
    From:
    US $1,265 per person
    Multiple Room Types

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What our customers ask about this tour

The content in our FAQ section is subject to change.
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  • P

    Pauline

    Asked on January 29th, 2026

    Are the cabins en-suite with a shower?

    Accommodation
    • Encounters TravelOperatorWritten January 2026

      Where premium cabins are offered, these are the same as standard level cabins, the difference relates to the bathroom facilities, where standard cabins have a wet-room and premium cabins have a separate shower cubicle.
      The gulets we use are motorised pleasure craft with sails, and while they can manoevre under sail, the majority of the time the motor will be used. This is particularly the case during July and August when winds are very low. Strong winds also cause them to bank steeply and so time actually under sail is generaly very limited. These are not sailing vessels where you are expected to help with the rigging or take part in sailing as an activity.
      The gulets come with facilities for both outdoor and indoor dining. There are freezers to keep drinks cold, a CD/cassette player (so bring your music!), snorkels and masks, fishing lines and some board games. You will need to bring your own beach towel and other personal items with you. Charging points are available for your electronic devices in your cabin (you will need to bring an adapter).

    • P

      Pauline

      TravelerWritten January 2026

      The price advertised on TourRadar does specify premium cabin with the word PRIVATE next to it. Does that guarantee us a en-suite with shower?

    • Encounters TravelOperatorWritten January 2026

      If you book a premium cabin, then you have a private cabin with an ensuite shower and toilet, yes.

    • P
      2 more answers
Can’t find the answer to your question?
Reach out to the experts at Encounters Travel with your enquiry, they usually respond within 11 hours.
From
US $1,195 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

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

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Good to Know

Tour ID: 334393

  • 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 August 3rd, 2026 a full payment is necessary. For tours departing after August 3rd, 2026, a minimum payment of $250 is required to confirm your booking with Encounters 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 65 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 Encounters Travel will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Encounters 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.

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