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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

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From
US $1,195 per person

Dodecanese Sailing Explorer

8 days
•
Start and end in Rhodes
2.0 (1 review)
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 departure month

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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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
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Pay only $250 today. The rest is due 65 days before departure. Learn more

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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

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Image of a map showing the route of the tour

Itinerary

  1. Intro

    Introduction

  2. Day 1

    Rhodes

    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
  3. Day 2

    Rhodes to Symi

    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
  4. Day 3

    Symi

    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
  5. Day 4

    Symi to Tilos

    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
  6. Day 5

    Tilos to Chalki

    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
  7. Day 6

    Chalki to Rhodes (Kalithea)

    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
  8. Day 7

    Rhodes

    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
  9. Day 8

    Rhodes

    Rhodes
    Meals
    Breakfast

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

What's Not Included

  • Flights
  • Insurance
  • Additional Services
Gold Operator
Rating
4.5 (897 reviews)
Response time
within 1 day
Response rate
96%
Cancellation policy
Learn more

Traveler Reviews

2.0
Overall rating based on 1 Reviews

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  • George2.0•October 2026
    First I must say, our entire vacation was planned around this tour. We are profoundly disappointed. The tour was...
    Show more
    Traveled in October 2026

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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
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  • From Saturday
    1 May, 2027
    To Saturday
    8 May, 2027
    English
    From:
    US$1,195 per person
    Price based on Private Double Room
  • From Saturday
    8 May, 2027
    To Saturday
    15 May, 2027
    English
    From:
    US$1,195 per person
    Price based on Private Double Room
  • From Saturday
    15 May, 2027
    To Saturday
    22 May, 2027
    English
    From:
    US$1,265 per person
    Price based on Private Double Room
  • From Saturday
    22 May, 2027
    To Saturday
    29 May, 2027
    English
    From:
    US$1,265 per person
    Price based on Private Double Room
  • From Saturday
    29 May, 2027
    To Saturday
    5 Jun, 2027
    English
    From:
    US$1,265 per person
    Price based on Private Double Room
  • From Saturday
    5 Jun, 2027
    To Saturday
    12 Jun, 2027
    English
    From:
    US$1,265 per person
    Price based on Private Double Room
  • From Saturday
    12 Jun, 2027
    To Saturday
    19 Jun, 2027
    English
    From:
    US$1,265 per person
    Price based on Private Double Room
  • From Saturday
    3 Jul, 2027
    To Saturday
    10 Jul, 2027
    English
    From:
    US$1,400 per person
    Price based on Private Double Room
  • From Saturday
    10 Jul, 2027
    To Saturday
    17 Jul, 2027
    English
    From:
    US$1,400 per person
    Price based on Private Double Room
  • From Saturday
    17 Jul, 2027
    To Saturday
    24 Jul, 2027
    English
    From:
    US$1,400 per person
    Price based on Private Double Room

Want to read it later?

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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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  • B

    Bryan

    Asked on June 3rd, 2026

    1 person in own cabin July 18th ok? How much please?

    Price / Availability
    Single supplement
    • Encounters TravelOperator•Written June 2026

      There is 1 cabin remaining on the 18th July departure it is a premium cabin. The total price for 1 person including supplement in GBP is £1484.

    • B

      Bryan

      Traveler•Written June 2026

      Is that price gbp for solo and can you send image of premium cabin and gulet please?

    • Encounters TravelOperator•Written June 2026

      The only difference between standard and premium cabins is the bathroom layout, Standard cabins have an open wetroom style whereas premium cabins have an enclosed en suite.

    • B
      2 more answers
  • P

    Pauline

    Asked on January 29th, 2026

    Are the cabins en-suite with a shower?

    Accommodation
    • Encounters TravelOperator•Written 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

      Traveler•Written 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 TravelOperator•Written 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 1 day.

Good to know

Tour ID: 334393

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  • Pay in installments

    Spread the cost in interest-free biweekly installments of $47.

  • Deposit only

    Book now with just a $250 deposit. The remaining balance is due 65 days before departure.

  • € - Euro

    You’ll encounter Euro in Greece.

  • Plug types C, F

    You’ll need an adapter for these sockets in Greece.

  • 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

      Used in Greece

    • Type F

      Used in Greece

  • Visa

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  • Payment information

    Pay now
    A $250 deposit
    Balance due
    65 days before departure
    Installments
    Interest-free, every two weeks
    Currency
    USD
    Booking fee
    None

    Book now with just a $250 deposit and pay the rest later. The remaining balance is due 65 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $47 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before January 8th, 2027 will need to be paid in full at checkout.

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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 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
Pay only $250 today. The rest is due 65 days before departure. Learn more

Best price guarantee Learn More

Plan your adventure:

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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